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CAS No. : | 55837-20-2 | MDL No. : | MFCD09834143 |
Formula : | C16H17BrClN3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 414.68 | Pubchem ID : | - |
Synonyms : |
RU-19110
|
Num. heavy atoms : | 24 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.44 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 99.59 |
TPSA : | 84.22 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.84 cm/s |
Log Po/w (iLOGP) : | 2.59 |
Log Po/w (XLOGP3) : | 1.4 |
Log Po/w (WLOGP) : | 1.5 |
Log Po/w (MLOGP) : | 1.92 |
Log Po/w (SILICOS-IT) : | 2.73 |
Consensus Log Po/w : | 2.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.34 |
Solubility : | 0.191 mg/ml ; 0.00046 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.77 |
Solubility : | 0.7 mg/ml ; 0.00169 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.95 |
Solubility : | 0.00466 mg/ml ; 0.0000112 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Representative examples include, but are not limited to: ... dinitolmide ethopabate furaltadone furazolidone halofuginone ipronidazole levamisole hydrochloride melengestrol acetate ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With trifluoroacetic acid In dichloromethane at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: (2S,3R)-3-benzyloxy-2-[2-oxo-3-(7-bromo-6-chloro-4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester With hydrogenchloride; water for 0.666667h; Reflux; Stage #2: With potassium carbonate In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / 0 °C / Inert atmosphere 2: N-Bromosuccinimide / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C 4: hydrogen bromide; acetic acid / 3 h / 20 °C 5: potassium carbonate / water / pH 10 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C 3: hydrogen bromide; acetic acid / 3 h / 20 °C 4: potassium carbonate / water / pH 10 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C 2: hydrogen bromide; acetic acid / 3 h / 20 °C 3: potassium carbonate / water / pH 10 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogen bromide; acetic acid / 3 h / 20 °C 2: potassium carbonate / water / pH 10 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate In water | 4.19. (-)-Halofuginone 3 The salt (-)-32HBr was basified topH 10 with 0.1Maq. K2CO3 and extracted with DCM (5 5 mL). Thecombined organic layers were washed with brine (25 mL), driedover MgSO4, filtered, and concentrated in vacuo (without heating) to afford (-)-3 (14 mg, 93%) as a white solid. Mp 143e145 C;{lit.,9 Mp 160 C (decomp.)}; [a]D20 5.4 (c 0.50, EtOH); {lit.,9[a]D2010 (c 0.5, DMF)}; IR (neat): 3128, 2926, 2852, 1722, 1674,1607, 1448, 1382, 1309, 1223, 1106, 1075, 1043, 900 cm1; HRMS(ESI): calcd. for [C16H1779Br35ClN3O3 H] 414.0220, found 414.0212;1H NMR ((CD3)2SO, 500 MHz): d 1.16e1.42 (m, 2H), 1.52e1.61 (m,1H), 1.84e1.95 (m, 1H), 2.32e2.40 (m, 1H), 2.45 (dd, J 15.5, 9.0 Hz,1H), 2.64 (td, J 9.0, 4.0 Hz, 1H), 2.75e2.84 (m, 1H), 2.93e3.03 (m,2H), 4.76 (d, J 6.0 Hz, 1H), 4.94e5.06 (m, 2H), 8.16 (s, 1H), 8.22 (s,1H), 8.24 (s, 1H) ppm (OH not visible by 1H NMR spectroscopy); 13CNMR ((CD3)2SO, 125 MHz): d 26.3 (CH2), 34.7 (CH2), 44.1 (CH2), 46.0(CH2), 55.3 (CH2), 60.5 (CH), 71.2 (CH), 122.2 (C), 127.4 (CH), 128.8(C), 132.2 (C), 132.8 (CH), 147.8 (C), 150.2 (CH), 159.1 (C), 203.9 (C)ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In chloroform-d1 for 15h; Reflux; | 4.21. (-)-Isohalofuginone 14 In an identical procedure to that described above for (+)-2,(-)-3 (11.0 mg, 0.027 mmol) was heated to reflux in CDCl3 (1 mL)for 24 h affording, after purification by flash column chromatography(CHCl3/MeOH; 4:1), ()-14 (7.5 mg, 68%) as an off-whitesolid. Rf 0.1 (CHCl3/MeOH; 4:1); Mp 142e145 C; {lit.,15Mp 137e141 C, (±)-14}; [a]D20 20.2 (c 0.50, CHCl3); IR(neat): 3307, 2923, 2853, 1676, 1603, 1446, 1378, 1365, 1305, 1261,1098, 1009 cm1; HRMS (ESI): calcd. for [C16H1779Br35ClN3O3 H]414.0220, found 414.0220; 1H NMR (CDCl3, 500 MHz): d 1.50e1.62(m, 2H), 1.76e1.91 (m, 2H), 2.00e2.18 (m, 2H), 2.50e2.59 (m, 1H),2.95e3.04 (m, 1H), 3.28e3.35 (m, 1H), 3.86e3.94 (m, 1H), 4.18 (d,J 14.0 Hz, 1H), 4.37 (d, J 14.0 Hz, 1H), 8.02 (s, 1H), 8.28 (s, 1H),8.36 (s, 1H) ppm; 13C NMR (CDCl3, 125 MHz): d 20.0 (CH2), 26.8(CH2), 43.5 (CH2), 44.5 (CH2), 50.2 (CH2), 55.7 (CH), 77.8 (CH), 105.2(C), 121.9 (C), 127.8 (CH), 129.3 (C), 132.6 (CH), 133.3 (C), 147.1 (C),149.4 (CH), 160.0 (C) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: boron trifluoride diethyl etherate / acetonitrile / 0.17 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / 0 °C / Inert atmosphere 3: N-Bromosuccinimide / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C 5: hydrogen bromide; acetic acid / 3 h / 20 °C 6: potassium carbonate / water / pH 10 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.2% | With pyridine; dmap; water; triethylamine In ethanol for 2.5h; Reflux; | 6.a-6.b; 7.a-7.b; 8.a-8.b A method for preparing Changshanone succinic acid monoester arginine salt includes the following steps Dissolve 1 mol of Changshanone in 75% ethanol aqueous solution,And stir at 50 into a homogeneous phase to obtain Changshan copper solution;b. Mix 4mol of succinic anhydride and the catalyst uniformly and then add it to the Changshan copper solution obtained in step a in batches, then stir under reflux for 2.5 hoursAfter that, it was acidified with hydrochloric acid to pH=6, and naturally cooled to room temperature,Obtained Changshanone succinic acid monoester solid; wherein the catalyst is 0.6molA mixture of 4-dimethylaminopyridine DMAP, 0.1 mol of triethylamine and 0.9 mol of pyridine; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.52% | Stage #1: succinic acid anhydride; (2S,3R)-halofuginone With dicyclohexyl-carbodiimide In ethanol for 5h; Reflux; Stage #2: With sodium hydroxide In ethanol | 1.a-1.c; 2.a-2.c; 3.a-3.c The preparation method of the sodium salt of Changsanone succinic acid monoester includes the following steps Dissolve 1 mol of Changshanone in 50% ethanol solution,And stir at 80 into a homogeneous phase to obtain Changshan copper solution;b. Mix 5 mol of succinic anhydride and 1.2 mol of dicyclohexylcarbodiimide DCC uniformly, and then add it to the Changshan copper solution obtained in step a in batches, and then stir at reflux for 5 hours.After that, it was acidified with hydrochloric acid to pH=6, and naturally cooled to room temperature,Obtained Changshanone succinic acid monoester solid;c. Place the solid of the ketone succinate obtained in step b in ethanol to reflux to dissolve the ketone succinate monoester, and then add 1 mol of sodium hydroxide to the ketone succinate monoester in batches Stir and cool to obtain the sodium salt of Changsanone succinic acid monoester.c. Place the solid of the ketone succinate obtained in step b in ethanol to reflux to dissolve the ketone succinate monoester, and then add 1 mol of sodium hydroxide to the ketone succinate monoester in batches Stir and cool to obtain the sodium salt of Changsanone succinic acid monoester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.2% | Stage #1: succinic acid anhydride; (2S,3R)-halofuginone With triethylamine In 1,2-dimethoxyethane for 5h; Reflux; Stage #2: With potassium hydroxide In N,N-dimethyl-formamide | 4.a-4.c; 5.a-5.c The preparation method of the potassium salt of Changshanone succinic acid monoester includes the following steps Dissolve 1mol of Changshanone in 60% ethylene glycol solution,And stirred at 45 into a homogeneous phase to obtain Changshan copper solution;b. Mix 3 mol of succinic anhydride and 4 mol of triethylamine uniformly and add them in batches to the Changshan copper solution obtained in step a, and then reflux and stir for 5 hours,After that, it was acidified with hydrochloric acid to pH=6, and naturally cooled to room temperature,Obtained Changshanone succinic acid monoester solid;c. Place the solid of the ketone succinate obtained in step b in N,N-dimethylformamide and reflux to dissolve the ketone succinate monoester,Then add 1.5mol to the Changshanone succinic acid monoester in batchesPotassium hydroxide was stirred and cooled to obtain the potassium salt of Changsanone succinic acid monoester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With dmap; triethylamine In dichloromethane at 20℃; for 36h; | 1 Halofuginone (50 mg, 0.12 mmol), succinic anhydride (18 mg, 0.18 mmol), DMAP (1.5 mg, 0.01 mmol) and Et3N (0.025 mL, 0.18 mmol) were dissolved in 20 mL of DCM and the reaction mixture was stirred this was continued for 36 hours until the starting material was consumed, which was monitored by TLC analysis. Then, the solvent was pumped out, and the residue was separated by flash column to obtain compound 2 (45 mg, 73%). |