Name: 1244-78-6|2-(3,4-Dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-chromen-4-one|97%
Brand: Ambeed
SKU: A435852
Rating: 98 (27 reviews)

1
[ 1247-97-8 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
47%	With aluminum tri-bromide In acetonitrile at 0℃; for 1h;
	With aluminium trichloride; diethyl ether

Reference： [1]De La Torre, Maria D.L.; Tomé, Augusto C.; Silva, Artur M.S.; Cavaleiro, José A.S. [Tetrahedron Letters, 2002, vol. 43, # 26, p. 4617 - 4620]
[2]Briggs; Locker [Journal of the Chemical Society, 1951, p. 3131,3134]

2
[ 908094-01-9 ]
isorhamnetin-3-O-glucoside [ No CAS ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 5℃; Yield given;

Reference： [1]Ishida; Umino; Tsuji; Kosuge [Chemical and Pharmaceutical Bulletin, 1988, vol. 36, # 11, p. 4414 - 4420]

3
3-O-stearyl-3',4',5,7-tetra-O-methylquercetin [ No CAS ]
[ 1244-78-6 ]
[ 57-11-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In water Ambient temperature;

Reference： [1]Ghosal, Shibnath; Biswas, Kanika; Jaiswal, Dinesh K. [Phytochemistry, 1980, vol. 19, p. 123 - 126]

4
5-Hydroxy-2-phenyl-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-chromen-4-one [ No CAS ]
[ 74-88-4 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide

Reference： [1]Waage, Susan K.; Hedin, Paul A. [Phytochemistry, 1985, vol. 24, # 2, p. 243 - 246]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; dihydrogen peroxide

6
[ 627-32-7 ]
[ 1244-78-6 ]
[ 461391-95-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;

Reference： [1]De La Torre, Maria D.L.; Tomé, Augusto C.; Silva, Artur M.S.; Cavaleiro, José A.S. [Tetrahedron Letters, 2002, vol. 43, # 26, p. 4617 - 4620] De La Torre, Maria D. L.; Rodrigues, Andrea G. P.; Tomé, Augusto C.; Silva, Artur M. S.; Cavaleiro, José A. S. [Tetrahedron, 2004, vol. 60, # 16, p. 3581 - 3592]

7
[ 1244-78-6 ]
[ 108-24-7 ]
[ 7678-40-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 20℃;

Reference： [1]Manthey, John A.; Guthrie, Najla [Journal of Agricultural and Food Chemistry, 2002, vol. 50, # 21, p. 5837 - 5843]

8
[ 855-97-0 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 3,3-dimethyldioxirane In dichloromethane; acetone at 0 - 20℃; for 0.5h;
	With Oxone; sodium hydrogencarbonate; sodium carbonate In dichloromethane; acetone
	With potassium peroxymonosulfate; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid In dichloromethane; acetone at 25℃; for 72h;

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]
[2]Wang, Gang-Qiang; Yan, Li-Li; Wang, Qiu-An [Heterocyclic Communications, 2018, vol. 24, # 2, p. 119 - 124]
[3]Yang, Hao-Jie; Li, Ya-Nan; Yan, Chen; Yang, Jue; Zeng, Yan-Rong; Yi, Ping; Li, Yan-Mei; Hao, Xiao-Jiang; Yuan, Chun-Mao [Fitoterapia, 2021, vol. 151]

9
[ 1244-78-6 ]
[ 77-78-1 ]
[ 1247-97-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate In acetone for 1h; Heating;

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]

10
[ 1244-78-6 ]
[ 117-39-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With boron tribromide In dichloromethane for 6h; Heating;
	With trimethylsilyl iodide In methanol at 35℃; for 96h; Inert atmosphere;

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]
[2]Location in patent: experimental part Hasan, Aurangzeb; Sadiq; Abbas; Mughal; Khan, Khalid M.; Ali, Muhammad [Natural Product Research, 2010, vol. 24, # 11, p. 995 - 1003]

11
[ 1247-97-8 ]
[ 1244-78-6 ]
[ 1245-15-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 47% 2: 26%	With aluminum tri-bromide In acetonitrile at 0℃; for 1.5h;

Reference： [1]De La Torre, Maria D. L.; Rodrigues, Andrea G. P.; Tomé, Augusto C.; Silva, Artur M. S.; Cavaleiro, José A. S. [Tetrahedron, 2004, vol. 60, # 16, p. 3581 - 3592]

12
[ 1244-78-6 ]
[ 461391-96-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / K₂CO₃ / dimethylformamide / 3 h / 60 °C 2: 83 percent / triethylamine / CH₂Cl₂ / 2 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: 82 percent / K₂CO₃ / dimethylformamide / 3 h / 60 °C 2: 83 percent / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

Reference： [1]De La Torre, Maria D. L.; Rodrigues, Andrea G. P.; Tomé, Augusto C.; Silva, Artur M. S.; Cavaleiro, José A. S. [Tetrahedron, 2004, vol. 60, # 16, p. 3581 - 3592]
[2]De La Torre, Maria D.L.; Tomé, Augusto C.; Silva, Artur M.S.; Cavaleiro, José A.S. [Tetrahedron Letters, 2002, vol. 43, # 26, p. 4617 - 4620]

13
2'-hydroxy-3,4,4',6'-tetramethoxychalcone [ No CAS ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 97 percent / K₂CO₃ / acetone / 2 h / Heating 2: 86 percent / dimethyl dioxirane / acetone; CH₂Cl₂ / 0.5 h / 0 - 20 °C

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]

14
[ 76650-20-9 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 90 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C 2: 97 percent / K₂CO₃ / acetone / 2 h / Heating 3: 86 percent / dimethyl dioxirane / acetone; CH₂Cl₂ / 0.5 h / 0 - 20 °C

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]

15
[ 29080-58-8 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 97 percent / K₂CO₃ / acetone / 2 h / Heating 2: 86 percent / dimethyl dioxirane / acetone; CH₂Cl₂ / 0.5 h / 0 - 20 °C

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]

16
[ 1244-78-6 ]
[ 1245-15-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 96 percent / K₂CO₃ / acetone / 1 h / Heating 2: 99 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]

17
[ 1244-78-6 ]
[ 7380-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 96 percent / K₂CO₃ / acetone / 1 h / Heating 2: 99 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C 3: 89 percent / dimethyl dioxirane / acetone; CH₂Cl₂ / 0.83 h / 0 - 20 °C

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]

18
[ 1244-78-6 ]
[ 14965-12-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 96 percent / K₂CO₃ / acetone / 1 h / Heating 2: 99 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C 3: 89 percent / dimethyl dioxirane / acetone; CH₂Cl₂ / 0.83 h / 0 - 20 °C 4: 94 percent / K₂CO₃ / acetone / 4 h / Heating

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]

19
[ 1244-78-6 ]
[ 7741-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 96 percent / K₂CO₃ / acetone / 1 h / Heating 2: 99 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C 3: 89 percent / dimethyl dioxirane / acetone; CH₂Cl₂ / 0.83 h / 0 - 20 °C 4: 87 percent / K₂CO₃ / acetone; CH₂Cl₂ / 4 h / Heating

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]

20
[ 120-14-9 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 99 percent / KOH / ethanol / 3 h / 20 °C 2: 90 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C 3: 97 percent / K₂CO₃ / acetone / 2 h / Heating 4: 86 percent / dimethyl dioxirane / acetone; CH₂Cl₂ / 0.5 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: potassium hydroxide / ethanol / 6 h / 35 °C 1.2: 3 h / 120 °C 2.1: potassium peroxymonosulfate; toluene-4-sulfonic acid; sodium carbonate; sodium hydrogencarbonate / dichloromethane; acetone / 72 h / 25 °C

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]
[2]Yang, Hao-Jie; Li, Ya-Nan; Yan, Chen; Yang, Jue; Zeng, Yan-Rong; Yi, Ping; Li, Yan-Mei; Hao, Xiao-Jiang; Yuan, Chun-Mao [Fitoterapia, 2021, vol. 151]

21
[ 832-58-6 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 99 percent / KOH / ethanol / 3 h / 20 °C 2: 90 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C 3: 97 percent / K₂CO₃ / acetone / 2 h / Heating 4: 86 percent / dimethyl dioxirane / acetone; CH₂Cl₂ / 0.5 h / 0 - 20 °C

Reference： [1]Chu, Han-Wei; Wu, Huan-Ting; Lee, Yean-Jang [Tetrahedron, 2004, vol. 60, # 11, p. 2647 - 2655]

22
[ 55368-24-6 ]
[ 1244-78-6 ]
[ 851133-85-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 3h;	3 Preparation 3: 1- (4- {2- [2- (3, 4-Dimethoxyphenyl)-5, 7-dimethoxy-4-oxo-4H-3-chromenyloxy] ethoxy} phenyl)-1-ethanone A mixture of compound obtained in preparation 2 (25 g, 69.6 mmol), a compound obtained in preparation 1 (21.5 g, 88.4 mmol) and potassium carbonate (77 g, 557 mmol) was placed in a 1 L round bottomed flask and DMF (400 mL) was added to the reaction mixture. The reaction mixture was heated to 80 °C with stirring for 3 h sunder nitrogen atmosphere. The reaction mixture was then cooled to 25 °C and poured slowly into ice-cold water (1 L). The. separated solid was filtered and washed with water (2 x 500 mL). It was triturated with methanol and filtered to afford the title compound (31.5 g, 87 %), as a pale brown solid, after drying under vacuum.

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2005/40163, 2005, A1 Location in patent: Page/Page column 57

23
[ 41386-38-3 ]
[ 1244-78-6 ]
[ 851133-89-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 9h;	16 Preparation 16: 4-{2-[2-(3, 4-Dimethoxy-phenyl)-5, 7-dimethoxy-4-oXo-4H-chromen-3-yloxy] - ethoxy}-benzoic acid ethyl ester A mixture of 2- (3, 4-dimethoxyphenyl) -3-hydroxy-5, 7-dimethoxy-4H-4-chromenone (4 g, 11.17 mmol) obtained in preparation 2, 4- (2-Bromo-ethoxy)-benzoic acid ethyl ester (3.66 g, 13.40 mmol) obtained in preparation 15 and K2CO3 (4.62 g, 33.51 mmol) in DMF (20 mL) was stirred at 80 °C for 9 hrs under Nitrogen atmosphere. The mixture was then poured into water (60 rail) and stirred for 30 min. The separated solid was filtered, washed with water (2 x 20 mL) and dried under vacuum to give the desired product in 68 % yield (4.2 g).

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2005/40163, 2005, A1 Location in patent: Page/Page column 65

24
3-[(6-O-(deoxy-α-L-manopyranosyl)-β-glucopyranosyl)oxy]-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-1-benzopyran-4-one [ No CAS ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With hydrogenchloride In water at 25 - 100℃; for 2h;	2.ii Step (ii): 2- (3, 4-dimethoxyphenyl) -3-hydroxy-5, 7-dimethoxy-4H-4-chromenone The compound obtained in step (i) (80 g, 110 mmol) was placed in a 2 L single neck round bottom flask and hydrochloric acid (20 %, 1 L) was added at 25 °C. The reaction mixture was allowed to reflux at 100 °C for 2 h and then cooled to 25 °C. The solid that separated was filtered, washed with isopropanol (200 mL) and dried under vacuum to affording the title compound (27. 5g, 70%) as a pale yellow solid.

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2005/40163, 2005, A1 Location in patent: Page/Page column 57

25
[ 120-14-9 ]
[ 177578-58-4 ]
[ 1055316-78-3 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 8% 2: 2%	With sodium methylate In methanol; toluene at 20℃; for 0.75h;

Reference： [1]Ottersbach, Philipp A.; Bolek, David; Lepicova, Eva; Nieger, Martin; Guetschow, Michael [Journal of Heterocyclic Chemistry, 2008, vol. 45, # 4, p. 1149 - 1153]

26
[ 58528-03-3 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
92.2%	With hydrogenchloride In water for 1h; Reflux;	3.2.2. Preparation of Quercetin 5,7,3',4'-tetramethyl Ether (QTME, 4) The above product was refluxed with aqueous hydrochloric acid (0.5%, 300 mL) for 1 h. The solvent was removed after cooling and the residue obtained was washed with distilled water to neutral to give QTME (4, 0.99 g, 92.2%), yellow solid, mp 195-197 °C (lit [34]: mp 194 °C). 1H-NMR (500 MHz, CDCl3) δ: 6.33 (1H, d, J = 2.01 Hz, C-6-H), 6.53 (1H, d, J = 2.01 Hz, C-8-H), 7.53 (1H, d, J = 8.50 Hz, C-5'-H), 7.72 (1H, dd, J = 8.50 Hz, J = 2.50 Hz, C-6'-H), 7.79 (1H, d, J = 2.50 Hz, C-2'-H), 9.47 (s, 1H, 3-OH), 3.87-3.97 (s, 12H, 4 × -OCH3). 13C-NMR (DMSO-d6) δ: 172.658 (C-4), 164.147 (C-9), 160.528 (C-7), 156.572 (C-2), 150.338 (C-5), 146.608 (C-4'), 142.148 (C-3'), 138.030 (C-3), 123.705(C-1'), 120.666 (C-6'), 110.995 (C-2'), 110.341 (C-5'), 106.302 (C-1'), 96.198 (C-6), 95.555 (C-8), 56.581, 56.086, 55.831, 55.627 (4-OCH3). Anal. calcd. for C19H18O7: C, 63.68; H, 5.06; O, 31.25. Found: C, 63.81; H, 5.11. HRMS (ESI) m/z: 359.11804 [M+H]+, calcd. for C19H19O7 359.11253. Spectroscopic data of the compound was consistent with those in the literatures [35-37].
9 g	With hydrogenchloride In water at 100℃; for 3h;
0.8 g	With sulfuric acid In ethanol for 2h; Reflux;

	With hydrogenchloride; water In ethanol for 2h; Reflux;
9.97 g	With hydrogenchloride; water at 100℃; for 2h;	4.2. General procedure for the preparation of intermediates 6x The intermediate 3x was placed in a 500 mL three-necked round-bottomed flask, and hydrochloric acid (36%, 40 mL) was added into the mixture. The reaction mixture was allowed to reflux at 100 °C for 2 h and then cooled to room temperature. The solid was filtered, washed with water and recrystallized by ethanol. It was then filtered to obtain compound 4x (9.97 g) with the following properties: yield, 69.6%; m.p. 192e194 C; 1H NMR (500 MHz,DMSO-d6, ppm) d:7.78 (d, J 8.6 Hz, 1H, AreH); 7.72 (s, 1H, AreH);7.10 (d, J 8.6 Hz, 1H, AreH); 6.82 (s, 1H, AreH), 6.43 (s, 1H, AreH);3.86 (s, 3H, AreOCH3); 3.82 (s, 3H, AreOCH3); 3.81 (s, 3H,AreOCH3); 3.80 (s, 3H, AreOCH3); 13C NMR (125 MHz, DMSO-d6,ppm) d: 171.56,164.25,160.60,158.57,150.40,148.92,142.21,138.44,124.07, 121.24, 112.02, 110.87, 106.74, 96.17, 93.37, 56.68, 56.53,56.17, 56.08; Formula: C19H18O7; ESI-MS m/z: 359.3 [M H].
	With sulfuric acid In ethanol for 2h; Reflux;	Step 2: Synthesis of quercetin 5, 7, 30, 40 tetramethyl ether : To a fine solution of rutin hydrate (1b) (2 g,0.003 M) in dry acetone (20 ml), anhydrous potassiumcarbonate (8 g, 0.056 M) and dimethyl sulfate (8 ml,0.059 M) were added and the reaction mixture wasrefluxed for 60 h. The solution was filtered, and insolublepotassium salts were washed with acetone. The washingswere combined with the filtrate, and the solvent wasremoved under reduced pressure to obtain methylatedglycoside as semisolid residue. The product was refluxedwith ethanolic sulfuric acid (2 %, 50 ml) for 2 h. Thesolvent was removed under reduced pressure, and theresidue obtained was recrystallized from ethanol to givequercetin 5, 7, 30, 40 tetramethyl ether (QTME) (1d).
	With hydrogenchloride In water at 70℃; for 3h;	6.1 Preparation of 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-benzopyran-4-one Take a clean and dry 500 mL round bottom flask.Weighed with an analytical balancetakeRutin (6g, 9.828mmoL) and K2CO3 (20g, 144.7mmoL) were placed one after another.The mixture was dissolved by adding 15 mL of acetone.Add 30 tubes of dimethyl sulfate,Stir at 60 ° C under reflux. once in a while,Adding dimethyl sulfate 5-10 tube to the reaction solution,Add a total of two times.When the reaction proceeds to 12h,Add 10 tubes of dimethyl sulfate,Continue to react for 12 h. After the reaction is over,Adding ammonia water(dropped from above the condenser),Until it is no longer boiling (alkaline, this step is mainly to remove dimethyl sulfate).Spin the above reaction mixture,Add water and add dichloromethane (ρ=1.325g/mL) for extraction.The mixture was separated by a separating funnel to obtain a dichloromethane extract.Spin the extract,Add 10% HCl solution to dissolve,Then add a small amount of ethanol around the inner wall of the flask.Dissolve the solid on the inner wall.After the treatment, heating, refluxing at 70 ° C for 3 h, hydrolysis, to obtain a flocculent solid, suction filtration, to obtain a crude product, the crude product was separated and purified by silica gel column chromatography (200 mesh silica gel).The eluent is (petroleum ether/ethyl acetate),Get the desired product (2.16g, 36.0%),The product was obtained as a pale yellow solid in 36% yield.
	With sulfuric acid In ethanol for 4h; Reflux;
	With hydrogenchloride; water In ethanol for 2h; Reflux;

Reference： [1]Wang, Zhonglei; Yang, Liyan; Cui, Shuai; Liang, Yingxi; Zhang, Xiaohua [Molecules, 2014, vol. 19, # 4, p. 4791 - 4801]
[2]Location in patent: experimental part Roschek Jr., Bill; Fink, Ryan C.; McMichael, Matthew D.; Li, Dan; Alberte, Randall S. [Phytochemistry, 2009, vol. 70, # 10, p. 1255 - 1261]
[3]Location in patent: experimental part Madhukar, Mamta; Sawraj, Shruti; Sharma, Pritam Dev [European Journal of Medicinal Chemistry, 2010, vol. 45, # 6, p. 2591 - 2596]
[4]Location in patent: scheme or table Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]
[5]Han, Yu; Ding, Yan; Xie, Dandan; Hu, Deyu; Li, Pei; Li, Xiangyang; Xue, Wei; Jin, Linhong; Song, Baoan [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 732 - 737]
[6]Rasheed, Arun; Lathika; Raju, Y. Prasanna; Mansoor; Azeem; Balan, Nija [Medicinal Chemistry Research, 2016, vol. 25, # 1, p. 70 - 82]
[7]Current Patent Assignee: TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108276374, 2018, A Location in patent: Paragraph 0039
[8]Rajaram, Pravien; Jiang, Ziran; Chen, Guanglin; Rivera, Alyssa; Phasakda, Alison; Zhang, Qiang; Zheng, Shilong; Wang, Guangdi; Chen, Qiao-Hong [Bioorganic Chemistry, 2019, vol. 87, p. 227 - 239]
[9]Han, Xu; Liu, Xin Hua; Ma, Duo; Yu, Yun Long; Zhang, Zhao Yan [Journal of Enzyme Inhibition and Medicinal Chemistry, 2021, vol. 36, # 1, p. 344 - 360]

27
[ 1244-78-6 ]
[ 39889-69-5 ]
[ 1227615-20-4 ]

Yield	Reaction Conditions	Operation in experiment
25.4%	With dmap; triethylamine In dichloromethane at -10℃;

Reference： [1]Location in patent: experimental part Madhukar, Mamta; Sawraj, Shruti; Sharma, Pritam Dev [European Journal of Medicinal Chemistry, 2010, vol. 45, # 6, p. 2591 - 2596]

28
[ 10496-67-0 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; sodium hydroxide In methanol; water at 0℃;

Reference： [1]Location in patent: experimental part Hasan, Aurangzeb; Sadiq; Abbas; Mughal; Khan, Khalid M.; Ali, Muhammad [Natural Product Research, 2010, vol. 24, # 11, p. 995 - 1003]

29
[ 211752-02-2 ]
[ 1244-78-6 ]
[ 1393734-55-8 ]

Yield	Reaction Conditions	Operation in experiment
84.6%	With potassium carbonate In N,N-dimethyl-formamide at 60℃;	4.1.11. 3-(2-(6-Amino-9H-purin-9-yl)ethoxy)-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one (19) General procedure: A mixture of compound 6 (200 mg, 0.48 mmol), 9-(2-bromoethyl)-9H-purin-6-amine 18 (140 mg, 0.58 mmol), K2CO3 (133 mg, 0.96 mmol) in anhydrous DMF (20 mL) was stirred at 60 °C for overnight. The solution was poured into ice-water, and the precipitate was filtrated, and purified by flash chromatography to afford the title compound 19 (203 mg, 81.4%).

Reference： [1]Location in patent: experimental part Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

30
6-(2-bromoethoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxy-3,4-dihydroquinazolin-4-amine [ No CAS ]
[ 1244-78-6 ]
[ 1393734-56-9 ]

Yield	Reaction Conditions	Operation in experiment
64.5%	With potassium carbonate In N,N-dimethyl-formamide at 60℃;	4.1.11. 3-(2-(6-Amino-9H-purin-9-yl)ethoxy)-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one (19) General procedure: A mixture of compound 6 (200 mg, 0.48 mmol), 9-(2-bromoethyl)-9H-purin-6-amine 18 (140 mg, 0.58 mmol), K2CO3 (133 mg, 0.96 mmol) in anhydrous DMF (20 mL) was stirred at 60 °C for overnight. The solution was poured into ice-water, and the precipitate was filtrated, and purified by flash chromatography to afford the title compound 19 (203 mg, 81.4%).

Reference： [1]Location in patent: experimental part Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

31
[ 1835-02-5 ]
[ 1244-78-6 ]
[ 1393734-48-9 ]

Yield	Reaction Conditions	Operation in experiment
76.8%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	4.1.6. 2-(3,4-Dimethoxyphenyl)-3-(2-(3,4-dimethoxyphenyl)-2-oxoethoxy)-5,7-dime- thoxy-4H-chromen-4-one (13) A solution of compound 6 (200 mg, 0.56 mmol), 2-bromo-1-(3,4-dimethoxy- phenyl)ethanone (217 mg, 0.84 mmol), K2CO3 (154.6 mg, 1.12 mmol) in DMF (10 mL) was stirred at room temperature for overnight, the solution was poured into ice-water (30 mL). The precipitate was filtrated, and purified by flash chromatography to afford the title compound 13 (231 mg, 76.8% yield). Mp 222-224 °C; 1H NMR (CDCl3, 600 MHz) δ: 7.88 (s, 1H), 7.76 (d, J = 8.3 Hz, 1H), 7.73 (d, J = 8.3 Hz, 1H), 7.54 (s, 1H), 6.92 (d, J = 8.22 Hz, 1H), 6.84 (d, J = 8.82 Hz, 1H), 6.50 (s, 1H), 6.33 (s, 1H), 5.44 (s, 2H), 3.94, 3.91, 3.89 (3s, 18H, 6 × OCH3); 13C NMR (CDCl3, 150 MHz) δ: 193.1, 173.9, 164.0, 160.9, 158.8, 153.6, 152.7, 151.0, 149.1, 148.6, 139.5, 127.9, 123.3, 123.0, 121.7, 111.8, 110.6, 110.2, 110.1, 109.2, 95.9, 92.5, 73.9, 56.5, 56.2, 56.1, 55.9, 55.9; HRMS calcd for (C29H28O10 + H)+ 537.1760, found 537.1777.

Reference： [1]Location in patent: experimental part Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

32
[ 1244-78-6 ]
[ 1393734-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 60 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

Reference： [1]Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

33
[ 1244-78-6 ]
[ 1393734-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 60 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

Reference： [1]Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

34
[ 1244-78-6 ]
[ 1393734-51-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 60 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

Reference： [1]Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

35
[ 1244-78-6 ]
[ 68217-74-3 ]
[ 1393734-54-7 ]

Yield	Reaction Conditions	Operation in experiment
81.4%	With potassium carbonate In N,N-dimethyl-formamide at 60℃;	4.1.11. 3-(2-(6-Amino-9H-purin-9-yl)ethoxy)-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one (19) General procedure: A mixture of compound 6 (200 mg, 0.48 mmol), 9-(2-bromoethyl)-9H-purin-6-amine 18 (140 mg, 0.58 mmol), K2CO3 (133 mg, 0.96 mmol) in anhydrous DMF (20 mL) was stirred at 60 °C for overnight. The solution was poured into ice-water, and the precipitate was filtrated, and purified by flash chromatography to afford the title compound 19 (203 mg, 81.4%). Mp 267-269 °C; 1H NMR (CD3COOD, 600 MHz) δ: 8.47 (s, 1H), 8.34 (s, 1H), 7.32 (d, J = 2.22 Hz, 1H), 7.29 (dd, J = 2.16, 8.76 Hz, 1H), 6.73 (d, J = 8.82 Hz, 1H), 6.63 (d, J = 2.16 Hz, 1H), 6.44 (d, J = 2.22 Hz, 1H), 4.61-4.59 (m, 2H), 4.56-4.54 (m, 2H), 3.90, 3.88, 3.86, 3.78 (4s, 12H, 4 × OCH3); 13C NMR (CD3COOD, 150 MHz) δ: 174.7, 165.3, 160.8, 155.1, 152.8, 151.5, 148.6, 148.0, 143.6, 138.8, 122.2, 122.1, 111.2, 110.6, 108.4, 96.2, 92.7, 68.9, 55.7, 55.6, 55.4, 55.3, 44.7; HRMS calcd for (C25H25N5O7 + H)+ 520.1832, found 520.1817.

Reference： [1]Location in patent: experimental part Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

36
[ 1244-78-6 ]
[ 78358-08-4 ]
[ 1393734-47-8 ]

Yield	Reaction Conditions	Operation in experiment
86.7%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	4.1.5. 2-(3,4-Dimethoxyphenyl)-5,7-dimethoxy-3-((3,4,5-trimethoxybenzyl)oxy)-4H-chromen-4-one (12) A solution of compound 6 (200 mg, 0.54 mmol), 3,4,5-trimethoxybenzyl methanesulfonate (232 mg, 0.81 mmol), K2CO3 (149 mg, 1.1 mmol) in DMF (10 mL) was stirred in room temperature for 12 h. The solution was poured into ice-water, and the precipitate was filtrated, and purified by flash chromatography to afford the title compound 12 (252 mg, 86.7%). Mp 90-92 °C; 1H NMR (CDCl3, 600 MHz) δ: 7.64 (d, J = 2.22 Hz, 1H), 7.58 (dd, J = 2.16, 8.76 Hz, 1H), 6.89 (d, J = 8.82 Hz, 1H), 6.57 (s, 2H), 6.46 (d, J = 2.22 Hz, 1H), 6.31 (d, J = 2.16 Hz, 1H), 4.99 (s, 2H), 3.94, 3.90, 3.86, 3.77, 3.75, 3.71 (6s, 21H, 7 × OCH3); 13C NMR (CDCl3, 150 MHz) δ: 174.1, 163.9, 158.9, 153.3, 153.0, 150.7, 148.4, 139.5, 137.7, 132.7, 123.5, 121.8, 111.9, 110.5, 109.4, 106.1, 106.0, 95.8, 92.5, 74.2, 60.8, 56.5, 56.0, 55.8; HRMS calcd for (C29H30O10 + H)+ 539.1917, found 539.1931.

Reference： [1]Location in patent: experimental part Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

37
[ 1244-78-6 ]
[ 540-51-2 ]
[ 1393734-45-6 ]

Yield	Reaction Conditions	Operation in experiment
86.5%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃;	4.1.1. 2-(3,4-Dimethoxyphenyl)-3-(2-hydroxyethoxy)-5,7-dimethoxy-4H-chromen-4-one (7) A mixture of compound 6 (1.00 g, 2.80 mmol), 2-bromoethanol (600 mg, 4.20 mmol), anhydrous K2CO3 (773 mg, 5.60 mmol) and KI (100 mg, 0.60 mmol) in DMF (20 mL) was heated with stirring at 60 °C for overnight. Then H2O (100 mL) was added and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated to dryness, and the resulting residue was purified by flash chromatography to afford the title compound 7 (974 mg, 86.5% yield). Mp 120-122 °C; 1H NMR (CDCl3, 600 MHz) δ: 7.71-7.69 (m, 2H), 6.98 (d, J = 8.8 Hz, 1H, H), 6.52 (d, J = 2.2 Hz, 1H), 6.37 (d, J = 2.2 Hz, 1H), 4.65 (br s, 1H, -OH), 3.98 (t, J = 3.8 Hz, 2H), 3.97, 3.96, 3.95, 3.91 (4 s, 12H, 4 × OCH3), 3.79 (t, J = 3.8 Hz, 2H); 13C NMR (CDCl3, 150 MHz) δ: 174.9, 164.3, 161.0, 158.9, 153.7, 151.1, 148.9, 139.8, 129.9, 121.8, 111.1, 110.9, 109.0, 96.1, 92.5, 75.0, 61.7, 56.5, 55.9; HRMS calcd for (C21H22O8 + H)+ 403.1393, found 403.1372.

Reference： [1]Location in patent: experimental part Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

38
[ 1244-78-6 ]
[ 118-41-2 ]
[ 1393734-46-7 ]

Yield	Reaction Conditions	Operation in experiment
85.4%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	4.1.4. 2-(3,4-Dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl 3,4,5-trime-thoxybenzoate (11) A mixture of compound 6 (200 mg, 0.56 mmol), 3,4,5-trimethoxycinnamic acid (178 mg, 0.84 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl, 161 mg, 0.84 mmol), 4-dimethylaminopyridine (DMAP, 102 mg, 0.84 mmol) in anhydrous CH2Cl2 (20 mL) was stirred at room temperature for overnight. Then the solution was washed by saturated aqueous Na2CO3, saturated aqueous NH4Cl, and brine in sequence. The organic layer was dried by anhydrous MgSO4. The solvent was evaporated to dryness, and the residue was purified by flash chromatography to afford the title compound 11 (264 mg, 85.4% yield). Mp 108-110 °C; 1H NMR (CDCl3, 600 MHz) δ: 7.52 (dd, J = 2.22, 8.82 Hz, 1H), 7.45 (s, 1H), 7.41 (d, J = 1.68 Hz, 1H), 6.91 (d, J = 8.82 Hz, 1H), 6.54 (d, J = 2.22 Hz, 1H), 6.35 (d, J = 2.22 Hz, 1H), 3.92, 3.90, 3.89, 3.88, 3.79 (5s, 21H, 7 × OCH3); 13C NMR (CDCl3, 150 MHz) δ: 170.6, 164.4, 163.9, 161.3, 159.2, 153.3, 153.0, 151.3, 148.8, 142.9, 134.0, 123.9, 122.4, 121.7, 110.9, 110.7, 108.8, 107.8, 96.1, 92.7, 61.0, 56.3, 56.0, 55.9; HRMS calcd for (C29H28O11 + H)+ 553.1710, found 553.1701.

Reference： [1]Location in patent: experimental part Yuan, Jian; Wong, Iris L.K.; Jiang, Tao; Wang, Si Wen; Liu, Tao; Jin Wen, Bin; Chow, Larry M.C.; Wan Sheng, Biao [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 413 - 422]

39
[ 1244-78-6 ]
[ 20260-53-1 ]
[ 1638526-44-9 ]

Yield	Reaction Conditions	Operation in experiment
89.5%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Reflux;	3.2.4. Synthesis of VB3-QTME (1) QTME (0.050 g, 0.14 mmol) and nicotinoyl chloride hydrochloride (0.027 g, 0.15 mmol) were dissolved in dichloromethane (30 mL) containing DCC (0.173 g, 0.84 mmol) and DMAP (0.149 g,0.84 mmol). The reaction mixture was stirred at reflux for 12 h. After reaction, the solvent wasremoved under reduced pressure. After washing with saturated Na2CO3 and NH4Cl, successively, the solid product obtained was chromatographed on silica gel column using petroleum ether/ethylacetate/acetone/methyl alcohol (200:100:30:40) as eluent and the solvent was removed under reduced pressure to obtain light yellow needle-like crystals of VB3-QTME (1); yield (0.058 g, 89.5%), mp 168-170 °C. 1H-NMR (500 MHz, CDCl3) δ: 6.40 (1H, d, J = 2.02 Hz, C-6-H), 6.59 (1H, d, J = 2.02 Hz, C-8-H), 6.94 (1H, d, J = 2.50 Hz, C-2'-H), 7.53 (2H, ABq, J = 8.50 Hz, C-5'-H, C-6'-H), 9.47 (1H, s, PyC-2-H), 8.90 (1H, d, PyC-6-H), 8.47 (1H, d, PyC-4-H), 7.41 (1H, t, PyC-5-H), 3.84-3.94 (s, 12H,4 × -OCH3). 13C-NMR (DMSO-d6) δ: 172.519 (C-4), 164.505 (C-7), 163.295 (ester C=O), 160.528 (C-5), 159.294 (C-9), 155.294 (C-2), 152.526 (PyC-3'), 151.293 ((PyC-2'), 142.148 (C-3'), 141.171 (C-4'),138.005 (C-3), 135.028 (PyC-5'), 125.521 (PyC-1'), 124.677 (PyC-4'), 121.511 (C-1'), 120.666 (C-6'), 110.995 (C-2'), 110.341 (C-5'), 108.087 (C-1'), 96.198 (C-6), 93.908 (C-8), 56.577, 56.093, 55.826, 55.622 (4 -OCH3). Anal. calcd. for C25H21NO8: C, 64.79; H, 4.57; N, 3.02; O, 27.62. Found: C, 64.83; H, 4.59; N, 2.97. HRMS (ESI) m/z: 464.13925 [M+H]+, calcd. for C25H22NO8 464.13400.

Reference： [1]Wang, Zhonglei; Yang, Liyan; Cui, Shuai; Liang, Yingxi; Zhang, Xiaohua [Molecules, 2014, vol. 19, # 4, p. 4791 - 4801]

40
[ 153-18-4 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.5 h / 58 °C 1.2: 62 h / 20 - 100 °C 2.1: water; hydrogenchloride / 2 h / 100 °C
	Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 60 h / Reflux 2: sulfuric acid / ethanol / 2 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 24 h / 60 °C 2: hydrogenchloride / water / 3 h / 70 °C

	Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 60 h / Reflux 2: sulfuric acid / ethanol / 4 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 48 h / Reflux 2: water; hydrogenchloride / ethanol / 2 h / Reflux

Reference： [1]Han, Yu; Ding, Yan; Xie, Dandan; Hu, Deyu; Li, Pei; Li, Xiangyang; Xue, Wei; Jin, Linhong; Song, Baoan [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 732 - 737]
[2]Rasheed, Arun; Lathika; Raju, Y. Prasanna; Mansoor; Azeem; Balan, Nija [Medicinal Chemistry Research, 2016, vol. 25, # 1, p. 70 - 82]
[3]Current Patent Assignee: TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108276374, 2018, A
[4]Rajaram, Pravien; Jiang, Ziran; Chen, Guanglin; Rivera, Alyssa; Phasakda, Alison; Zhang, Qiang; Zheng, Shilong; Wang, Guangdi; Chen, Qiao-Hong [Bioorganic Chemistry, 2019, vol. 87, p. 227 - 239]
[5]Han, Xu; Liu, Xin Hua; Ma, Duo; Yu, Yun Long; Zhang, Zhao Yan [Journal of Enzyme Inhibition and Medicinal Chemistry, 2021, vol. 36, # 1, p. 344 - 360]

41
[ 1244-78-6 ]
[ 105-39-5 ]
ethyl 2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.5%	With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 6h;	4.2. General procedure for the preparation of intermediates 6x A mixture of 4x (9.97 g, 27.82 mmol) and potassium carbonate (5.77 g, 41.73 mmol) were dissolved in 40 mL DMF and added into a 100 mL three-necked round-bottomed flask. The reaction mixture was heated to 40 °C, then ethyl chloroacetate (6.82 g, 55.65 mmol) was added dropwise into the mixture. The reaction mixture was stirred for 6 h at 40 °C and then cooled to room temperature. A totalof 500 mL of cold water was added to the mixture. The solid that separated was filtered, washed with water and dried to obtain 11.56 g of compound ethyl 2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetate (5x) with the following properties: yield, 93.5%; yellow powder; m.p.145-147 °C; 1H NMR (500 MHz, DMSO-d6, ppm) d: 7.92 (d,J 8.6 Hz, 1H, AreH),7.64 (s, 1H, AreH), 7.22 (d, J 8.6 Hz, 1H,AreH), 6.73 (s, 1H, AreH), 6.43 (s, 1H, AreH), 4.92 (s, 2H,AreOeCH2e), 4.10e4.14 (m, 2H, eOeCH2eCH3), 3.92 (s, 3H,AreOCH3), 3.88 (s, 3H, AreOCH3), 3.85 (s, 3H, AreOCH3), 3.84 (s,3H, AreOCH3), 1.29 (t, J1 8.0 Hz, J2 9.2 Hz, 3H, eOeCH2eCH3); 13C NMR (125 MHz, DMSO-d6, ppm) d: 172.23, 169.28, 162.28,161.10, 158.57, 152.03, 147.62, 142.21, 139.34, 125.58, 120.31, 112.08,110.93, 107.76, 96.13, 93.62, 65.08, 62.33, 56.72, 56.58, 56.23, 56.11, 14.16; Formula: C23H24O9; ESI-MS m/z: 445.4 [M+H]+.

Reference： [1]Han, Yu; Ding, Yan; Xie, Dandan; Hu, Deyu; Li, Pei; Li, Xiangyang; Xue, Wei; Jin, Linhong; Song, Baoan [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 732 - 737]

42
[ 1244-78-6 ]
2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C 2: water; sodium hydroxide / methanol / 2 h / 20 °C

Reference： [1]Han, Yu; Ding, Yan; Xie, Dandan; Hu, Deyu; Li, Pei; Li, Xiangyang; Xue, Wei; Jin, Linhong; Song, Baoan [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 732 - 737]

43
[ 1244-78-6 ]
2-((1E,4E)-3-oxo-5-phenylpenta-1,4-dien-1-yl)phenyl-2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C 2: water; sodium hydroxide / methanol / 2 h / 20 °C 3: dicyclohexyl-carbodiimide; dmap / dichloromethane / 10 h / 0 °C

Reference： [1]Han, Yu; Ding, Yan; Xie, Dandan; Hu, Deyu; Li, Pei; Li, Xiangyang; Xue, Wei; Jin, Linhong; Song, Baoan [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 732 - 737]

44
[ 1244-78-6 ]
4-((1E,4E)-3-oxo-5-phenylpenta-1,4-dien-1-yl)phenyl-2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C 2: water; sodium hydroxide / methanol / 2 h / 20 °C 3: dicyclohexyl-carbodiimide; dmap / dichloromethane / 10 h / 0 °C

Reference： [1]Han, Yu; Ding, Yan; Xie, Dandan; Hu, Deyu; Li, Pei; Li, Xiangyang; Xue, Wei; Jin, Linhong; Song, Baoan [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 732 - 737]

45
[ 1244-78-6 ]
2-((1E,4E)-5-(2-methoxyphenyl)-3-oxopenta-1,4-dien-1-yl)phenyl-2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C 2: water; sodium hydroxide / methanol / 2 h / 20 °C 3: dicyclohexyl-carbodiimide; dmap / dichloromethane / 10 h / 0 °C

Reference： [1]Han, Yu; Ding, Yan; Xie, Dandan; Hu, Deyu; Li, Pei; Li, Xiangyang; Xue, Wei; Jin, Linhong; Song, Baoan [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 732 - 737]

46
[ 1244-78-6 ]
4-((1E,4E)-5-(2-methoxyphenyl)-3-oxopenta-1,4-dien-1-yl)phenyl-2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C 2: water; sodium hydroxide / methanol / 2 h / 20 °C 3: dicyclohexyl-carbodiimide; dmap / dichloromethane / 10 h / 0 °C

Reference： [1]Han, Yu; Ding, Yan; Xie, Dandan; Hu, Deyu; Li, Pei; Li, Xiangyang; Xue, Wei; Jin, Linhong; Song, Baoan [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 732 - 737]

47
[ 1244-78-6 ]
2-((1E,4E)-5-(3-nitrophenyl)-3-oxopenta-1,4-dien-1-yl)phenyl-2-((2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yl)oxy)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 40 °C 2: water; sodium hydroxide / methanol / 2 h / 20 °C 3: dicyclohexyl-carbodiimide; dmap / dichloromethane / 10 h / 0 °C

Reference： [1]Han, Yu; Ding, Yan; Xie, Dandan; Hu, Deyu; Li, Pei; Li, Xiangyang; Xue, Wei; Jin, Linhong; Song, Baoan [European Journal of Medicinal Chemistry, 2015, vol. 92, p. 732 - 737]

48
[ 1227857-41-1 ]
[ 1244-78-6 ]
C₃₅H₂₉Cl₂NO₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38.77%	With dmap; triethylamine In dichloromethane at -10℃;	Step 3: Aceclofenac-QTME mutual prodrug (ACF-Q): QTME (1.74 g, 0.005 M) was dissolved in dichloromethane(20 ml) containing triethyl amine (5 drops) and4-dimethyl amino pyridine (1 pinch). The reaction mixturewas cooled to -10 C, and aceclofenac acid chloride(2.057 g, 0.01 M) dissolved in dichloromethane (30 ml)was added dropwise over a period of 1 h. The reactionmixture was stirred overnight, and the solvent was removedunder reduced pressure and recrystallized from ethanol toobtain ACF-Q.

Reference： [1]Rasheed, Arun; Lathika; Raju, Y. Prasanna; Mansoor; Azeem; Balan, Nija [Medicinal Chemistry Research, 2016, vol. 25, # 1, p. 70 - 82]

49
[ 1244-78-6 ]
[ 106-96-7 ]
C₂₂H₂₀O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In acetone for 2h; Reflux;
	Stage #1: 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 3h;	4.2.1 General procedure for the preparation of the compounds 1-2 General procedure: Dissolve the raw materials myricitrin (20mmol) and K2CO3 (300mmol) in acetone, reflux stirring for 0.5h, slowly add dimethyl sulfate (300mmol) and stir at room temperature for 48h. Filtered precipitate, dissolve in absolute ethanol (100mL), reflux, add concentrated hydrochloric acid dropwise (20mL), yellow solid precipitate, and continue the reaction for 2h, filtration Purification to give compound 1. Compound 1 (10mmol) was dissolved with K2CO3 (30mmol) in DMF and stirred at room temperature for 0.5h. 3-bromopropyne (30mmol) was slowly added and reacted at room temperature for 3h, disperse with water (150mL), precipitate white solid, filter and dry to obtain compound 2.
	Stage #1: 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 3h;	4.2.1 General procedure for the preparation of the compounds 1-2 General procedure: Dissolve the raw materials myricitrin (20mmol) and K2CO3 (300mmol) in acetone, reflux stirring for 0.5h, slowly add dimethyl sulfate (300mmol) and stir at room temperature for 48h. Filtered precipitate, dissolve in absolute ethanol (100mL), reflux, add concentrated hydrochloric acid dropwise (20mL), yellow solid precipitate, and continue the reaction for 2h, filtration Purification to give compound 1. Compound 1 (10mmol) was dissolved with K2CO3 (30mmol) in DMF and stirred at room temperature for 0.5h. 3-bromopropyne (30mmol) was slowly added and reacted at room temperature for 3h, disperse with water (150mL), precipitate white solid, filter and dry to obtain compound 2.

Reference： [1]Wang, Gang-Qiang; Yan, Li-Li; Wang, Qiu-An [Heterocyclic Communications, 2018, vol. 24, # 2, p. 119 - 124]
[2]Du, Jun Cheng; Han, Xu; Liu, Xin Hua; Yan, Yaoyao; Zhang, Famin; Zhu, Rende [Bioorganic Chemistry, 2022, vol. 120]
[3]Du, Jun Cheng; Han, Xu; Liu, Xin Hua; Yan, Yaoyao; Zhang, Famin; Zhu, Rende [Bioorganic Chemistry, 2022, vol. 120]

50
[ 1244-78-6 ]
[ 100-44-7 ]
3-(benzyloxy)-2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxy-4H-benzopyran-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32.6%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 3h;	8 Preparation of 3-(benzyloxy)-2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxy-4H-benzopyran-4-one Take a clean and dry 50 mL round bottom flask.Analytical balance weighing completelyMethylationCrude quercetin (0.5000g),K2CO3 (1.000g, 7.235mmoL), adding a small amount of KI as a catalyst,Add 3mL DMF,Add 3 tubes of benzyl chloride,Heat at 70 ° C for 3 h. After the reaction was completed, the reaction mixture was transferred to a 250 mL separatory funnel, 100 mL of water was added, and an appropriate amount of dichloromethane was added for extraction.After standing for a while, layering to obtain an organic layer. The crude product was separated and purified by silica gel column chromatography (200 mesh silica gel) elutingThe solvent was (petroleum ether/ethyl acetate) to give the desired product (0.163 g, 32.60%).

Reference： [1]Current Patent Assignee: TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108276374, 2018, A Location in patent: Paragraph 0043

51
[ 95360-33-1 ]
[ 1244-78-6 ]
C₂₉H₂₈O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29.6%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70℃; for 3h;	9 Take a clean and dry 250 mL round bottom flask and analyze the balance to weigh the complete methylated quercetin.(0.500g),Ethyl 2-chloromethyl phenylacetate(0.6800g, 4.246mmoL), adding K2CO3 (1.000g, 7.235mmoL),Add a small amount of KI (0.05g, 3.012mmoL) as a catalyst,Add 3 mL of DMF to dissolve the solid powder at 70 ° CThe mixture was stirred under reflux for 3 h, and was completely observed by TLC. After the reaction was completed, the reaction solution was transferred to a 250 mL separatory funnel.100 mL of water was added, and an appropriate amount of dichloromethane was added for extraction, allowed to stand for a while, and layered to obtain an organic layer. Crude product with silica gel columnChromatography and separation and purification (200 mesh silica gel), the eluent was (petroleum ether / ethyl acetate) to give the desired product (0.1480 g,29.60%);

Reference： [1]Current Patent Assignee: TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN108276374, 2018, A Location in patent: Paragraph 0045; 0046

52
[ 111-24-0 ]
[ 1244-78-6 ]
C₂₄H₂₇BrO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 1,5-dibromo-pentane In N,N-dimethyl-formamide at 20℃; for 12h;	3 4.3. The general procedure for the synthesis of 3-O-dialkylaminoalkyl-3′,4′,5,7-O-tetramethylquercetins (11-34) General procedure: The solution of 3′,4′,5,7-O-tetramethylquercetin (6, 60 mg, 0.17 mmol) and potassium carbonate (70 mg, 0.51 mmol, 3 equiv.) in DMF (0.5 mL, 0.3 M) was stirred at room temperature for 10 min before an appropriate alkyl dibromide (0.51 mmol, 3 equiv.) was added through a syringe. The reaction was stirred at room temperature for 12 h until the starting material was fully consumed as indicated by TLC. The reaction mixture was diluted with a mixture of ethyl acetate and diethyl ether (100 mL, 1:1, v/v), which was rinsed with water (10 mL×1) and brine (10 mL×4). The subsequent organic layer wasdried over anhydrous sodium sulfate and concentrated in vacuo to generate a crude product (8, 9, or 10). To the solution of this crude product in DMF (0.5 mL, 0.3 M) was added potassium carbonate (70 mg, 0.51 mmol, 3 equiv.), and the mixture was stirred for 10 min. The appropriate amine (0.51 mmol, 3 equiv.) was added to the reaction mixture through a syringe, and the subsequent reaction mixture was stirred at room temperature over 12 h until no starting material was detected by TLC. The reaction mixture was diluted with a mixture of ethyl acetate and diethyl ether (100 mL, 1:1, v/v), which was rinsed with water (10 mL×1) and brine (10 mL×4). The subsequent organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to generate a crude product, which was subjected to PTLC purification using dichloromethane/methanol (90/10, v/v) as eluent. The respective 3-O-dialkylaminoalkyl-3′,4′,5,7-O-tetramethylquercetin was retrieved from PTLC silica gel by washing with dichloromethane/diethylamine(100/3, v/v).

Reference： [1]Rajaram, Pravien; Jiang, Ziran; Chen, Guanglin; Rivera, Alyssa; Phasakda, Alison; Zhang, Qiang; Zheng, Shilong; Wang, Guangdi; Chen, Qiao-Hong [Bioorganic Chemistry, 2019, vol. 87, p. 227 - 239]

53
[ 1244-78-6 ]
[ 109-64-8 ]
C₂₂H₂₃BrO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 1,3-dibromo-propane In N,N-dimethyl-formamide at 20℃; for 12h;	1 4.3. The general procedure for the synthesis of 3-O-dialkylaminoalkyl-3′,4′,5,7-O-tetramethylquercetins (11-34) General procedure: The solution of 3′,4′,5,7-O-tetramethylquercetin (6, 60 mg, 0.17 mmol) and potassium carbonate (70 mg, 0.51 mmol, 3 equiv.) in DMF (0.5 mL, 0.3 M) was stirred at room temperature for 10 min before an appropriate alkyl dibromide (0.51 mmol, 3 equiv.) was added through a syringe. The reaction was stirred at room temperature for 12 h until the starting material was fully consumed as indicated by TLC. The reaction mixture was diluted with a mixture of ethyl acetate and diethyl ether (100 mL, 1:1, v/v), which was rinsed with water (10 mL×1) and brine (10 mL×4). The subsequent organic layer wasdried over anhydrous sodium sulfate and concentrated in vacuo to generate a crude product (8, 9, or 10). To the solution of this crude product in DMF (0.5 mL, 0.3 M) was added potassium carbonate (70 mg, 0.51 mmol, 3 equiv.), and the mixture was stirred for 10 min. The appropriate amine (0.51 mmol, 3 equiv.) was added to the reaction mixture through a syringe, and the subsequent reaction mixture was stirred at room temperature over 12 h until no starting material was detected by TLC. The reaction mixture was diluted with a mixture of ethyl acetate and diethyl ether (100 mL, 1:1, v/v), which was rinsed with water (10 mL×1) and brine (10 mL×4). The subsequent organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to generate a crude product, which was subjected to PTLC purification using dichloromethane/methanol (90/10, v/v) as eluent. The respective 3-O-dialkylaminoalkyl-3′,4′,5,7-O-tetramethylquercetin was retrieved from PTLC silica gel by washing with dichloromethane/diethylamine(100/3, v/v).

Reference： [1]Rajaram, Pravien; Jiang, Ziran; Chen, Guanglin; Rivera, Alyssa; Phasakda, Alison; Zhang, Qiang; Zheng, Shilong; Wang, Guangdi; Chen, Qiao-Hong [Bioorganic Chemistry, 2019, vol. 87, p. 227 - 239]

54
[ 110-52-1 ]
[ 1244-78-6 ]
C₂₃H₂₅BrO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 12h;	2 4.3. The general procedure for the synthesis of 3-O-dialkylaminoalkyl-3′,4′,5,7-O-tetramethylquercetins (11-34) General procedure: The solution of 3′,4′,5,7-O-tetramethylquercetin (6, 60 mg, 0.17 mmol) and potassium carbonate (70 mg, 0.51 mmol, 3 equiv.) in DMF (0.5 mL, 0.3 M) was stirred at room temperature for 10 min before an appropriate alkyl dibromide (0.51 mmol, 3 equiv.) was added through a syringe. The reaction was stirred at room temperature for 12 h until the starting material was fully consumed as indicated by TLC. The reaction mixture was diluted with a mixture of ethyl acetate and diethyl ether (100 mL, 1:1, v/v), which was rinsed with water (10 mL×1) and brine (10 mL×4). The subsequent organic layer wasdried over anhydrous sodium sulfate and concentrated in vacuo to generate a crude product (8, 9, or 10). To the solution of this crude product in DMF (0.5 mL, 0.3 M) was added potassium carbonate (70 mg, 0.51 mmol, 3 equiv.), and the mixture was stirred for 10 min. The appropriate amine (0.51 mmol, 3 equiv.) was added to the reaction mixture through a syringe, and the subsequent reaction mixture was stirred at room temperature over 12 h until no starting material was detected by TLC. The reaction mixture was diluted with a mixture of ethyl acetate and diethyl ether (100 mL, 1:1, v/v), which was rinsed with water (10 mL×1) and brine (10 mL×4). The subsequent organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to generate a crude product, which was subjected to PTLC purification using dichloromethane/methanol (90/10, v/v) as eluent. The respective 3-O-dialkylaminoalkyl-3′,4′,5,7-O-tetramethylquercetin was retrieved from PTLC silica gel by washing with dichloromethane/diethylamine(100/3, v/v).

Reference： [1]Rajaram, Pravien; Jiang, Ziran; Chen, Guanglin; Rivera, Alyssa; Phasakda, Alison; Zhang, Qiang; Zheng, Shilong; Wang, Guangdi; Chen, Qiao-Hong [Bioorganic Chemistry, 2019, vol. 87, p. 227 - 239]

55
C₉H₁₀O₅ [ No CAS ]
[ 120-14-9 ]
[ 1244-78-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyrrolidine; oxygen In water at 50℃;

Reference： [1]Xiong, Wei; Wang, Xiaohong; Shen, Xianyan; Hu, Cuifang; Wang, Xin; Wang, Fei; Zhang, Guolin; Wang, Chun [Journal of Organic Chemistry, 2020, vol. 85, # 20, p. 13160 - 13176]

56
[ 1244-78-6 ]
C₁₂H₁₀ClN₃O₄ [ No CAS ]
N-(5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3,4-oxadiazol-2-yl)-2-(2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4-oxo-4H-chromen-3-yloxy)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.6%	With potassium carbonate; potassium iodide In acetone for 12h; Reflux;