[ CAS No. 614750-81-1 ] {[proInfo.proName]}

Name: 614750-81-1|[1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde|95%
Brand: Ambeed
SKU: A299352
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Quality Control of [ 614750-81-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 614750-81-1 ]

Product Details of [ 614750-81-1 ]

CAS No. :	614750-81-1	MDL No. :	MFCD11112116
Formula :	C₇H₅N₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SYLGZKAGHAOGFM-UHFFFAOYSA-N
M.W :	147.13	Pubchem ID :	45083592
Synonyms :

Calculated chemistry of [ 614750-81-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.37
TPSA :	47.26 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.16
Log Po/w (XLOGP3) :	0.21
Log Po/w (WLOGP) :	0.54
Log Po/w (MLOGP) :	0.39
Log Po/w (SILICOS-IT) :	0.6
Consensus Log Po/w :	0.58

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.42
Solubility :	5.54 mg/ml ; 0.0377 mol/l
Class :	Very soluble
Log S (Ali) :	-0.76
Solubility :	25.5 mg/ml ; 0.173 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.64
Solubility :	3.37 mg/ml ; 0.0229 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.46

Safety of [ 614750-81-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 614750-81-1 ]

* 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.

Upstream synthesis route of [ 614750-81-1 ]
Downstream synthetic route of [ 614750-81-1 ]

[ 614750-81-1 ] Synthesis Path-Upstream 1~3

1
[ 68-12-2 ]
[ 614750-81-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With isopropylmagnesium bromide In tetrahydrofuran at 0℃; for 1 h; Stage #2: at 0 - 20℃; for 4 h;	(a) [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde To a solution of 6-iodo-[1,2,4]triazolo[1,5-a]pyridine (5.0 g, 20 mmol; prepared from 2-amino-5-iodopyridine (Aldrich-Sigma, St. Louis, Mo.) according to WO 01/62756) in anhydrous THF (300 mL) at 0° C. was slowly added a solution of isopropylmagnesium bromide in THF (1 M, 31 m]L, 31 mmol). The resulting milky suspension was stirred at 0° C. After an hour, DMF (6 mL, 50 mmol) was added to the suspension at 0° C. and the suspension was allowed to warm up to room temperature and stirred for 4 additional hours. 100 mL of water was then added at room temperature and stirred for 1 hour. The resulting mixture was extracted with diethylether and washed with saturated Na₂CO₃. The extracts were dried over MgSO₄ and concentrated. The residue was purified on a short silica gel cake with EtOAc to give [1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde as a light yellow solid (3 g, 100percent). ESP+ m/e 148.0. ¹H NMR (CDCl₃, 300 MHz), δ 10.03 (s, 1H), 9.10 (s, 1H), 8.49 (s, 1H), 8.02 (d, 1H), 7.82 (d, 1H).

Reference： [1] Patent: US2006/63809, 2006, A1, . Location in patent: Page/Page column 17

2
[ 614750-84-4 ]
[ 68-12-2 ]
[ 614750-81-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With isopropylmagnesium bromide In tetrahydrofuran at 0℃; for 1 h; Stage #2: at 0 - 20℃; Stage #3: With water In tetrahydrofuran	To a solution of 6-iodo[l,2,4]triazolo[l,5-a]pyridme (5 g, 0.02 mol, prepared according to literature procedure) in anhydrous THF (300 mL), was slowly added IM of isopropylmagnesium bromide in THF (31 mL, 0.03 mol) at 0 oC. It was stirred at OoC for 1 hour and then was added anhydrous DMF (6 mL, 0.05 mol). It was allowed to warm to room temperature and stirred for overnight. It was then quenched with 100 mL of water and worked up with diethyl ether and saturated NaHCO3. Dried over MgSO4 and concentrated. The residue was purified on silica gel column with EtOAc to give the desire product as a tan solid (3g, 100percent). LC-MS/ES+: M+l: 148.0.

Reference： [1] Patent: WO2006/26305, 2006, A1, . Location in patent: Page/Page column 30-31

3
[ 1075260-64-8 ]
[ 614750-81-1 ]

Reference： [1] Patent: WO2008/128953, 2008, A1, . Location in patent: Page/Page column 114-115

[ 614750-81-1 ] Synthesis Path-Downstream 1~75

1
[ 68-12-2 ]
[ 614750-81-1 ]

Yield	Reaction Conditions	Operation in experiment
100%		(a) [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde To a solution of 6-iodo-[1,2,4]triazolo[1,5-a]pyridine (5.0 g, 20 mmol; prepared from 2-amino-5-iodopyridine (Aldrich-Sigma, St. Louis, Mo.) according to WO 01/62756) in anhydrous THF (300 mL) at 0° C. was slowly added a solution of isopropylmagnesium bromide in THF (1 M, 31 m]L, 31 mmol). The resulting milky suspension was stirred at 0° C. After an hour, DMF (6 mL, 50 mmol) was added to the suspension at 0° C. and the suspension was allowed to warm up to room temperature and stirred for 4 additional hours. 100 mL of water was then added at room temperature and stirred for 1 hour. The resulting mixture was extracted with diethylether and washed with saturated Na2CO3. The extracts were dried over MgSO4 and concentrated. The residue was purified on a short silica gel cake with EtOAc to give [1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde as a light yellow solid (3 g, 100percent). ESP+ m/e 148.0. 1H NMR (CDCl3, 300 MHz), delta 10.03 (s, 1H), 9.10 (s, 1H), 8.49 (s, 1H), 8.02 (d, 1H), 7.82 (d, 1H).

Reference： [1]Patent: US2006/63809,2006,A1 .Location in patent: Page/Page column 17

2
[ 614750-85-5 ]
[ 614750-81-1 ]
[ 614750-82-2 ]

Yield	Reaction Conditions	Operation in experiment
80%		To a stirred solution of <strong>[614750-81-1][1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde</strong> (2.50 g, 17.01 mmol) (prepared according to the method described in WO 03/087304 A2) and diphenyl (6-methylpyridin-2-yl)(phenylamino)methylphosphonate (7.32 g, 17.01 mmol) in a mixture of THF (40 mL) and i-PrOH (10 mL) was added Cs2CO3 (7.20 g, 22.11 mmol), and the mixture was stirred at room temperature overnight. A solution of 3 N HCl (25 mL) was added dropwise to the reaction mixture, and the mixture was stirred for 1 h. It was then diluted with tert-butyl methyl ether (40 mL) and extracted with 1 N HCl (2.x.35 mL). The aqueous extracts were neutralized with 50percent KOH until pH 7-8 was reached. The precipitates were collected by filtration, washed with water, and dried over P2O5 in vacuo to give the titled compound (3.41 g, 80percent) as an off-white solid. 1H NMR (400 MHz, CDCl3): delta 8.61 (d, 1H, J=0.8 Hz), 8.31 (s, 1H), 7.88 (dd, 1H, J=7.6, 1.6 Hz), 7.73 (t, 1H, overlapped, J=7.6 Hz), 7.71 (dd, 1H, overlapped, J=9.2, 0.8 Hz), 7.54 (dd, 1H, J=9.2, 1.6 Hz), 7.37 (dd, 1H, J=7.6, 1.6 Hz), 4.62 (s, 2H), 2.67 (s, 3H).
		(b) 1-(6-Methyl-pyridin-2-yl)-2-[1,2,4]triazolo[1,5-a]pyridin-6-yl-ethanone To a solution of <strong>[614750-81-1][1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde</strong> (3 g, 20 mmol; see subpart (a) above) and [(6-methyl-pyridin-2-yl)-phenylamino-methyl]-phosphonic acid diphenyl ester (8.8 g, 20 mmol; prepared from 6-methyl-pyridine-2-carboxaldehyde (Aldrich-Sigma, St. Louis, Mo.) according to Tetrahedron Lett. 39:1717-1720 (1998)) in a mixture of THF (40 mL) and iPrOH (10 mL) was added Cs2CO3 (8.6 g, 26 mmol) and the mixture was stirred at room temperature for overnight. A solution of 3N HCl (30 mL) was added dropwise to the above mixture and stirred for 1 hour. It was then diluted with MTBE (methyl t-butyl ether) and extracted with 1N HCl twice. The aqueous extracts were neutralized with ca. 50percent KOH until pH 7-8 was reached and precipitates formed. The precipitates were collected, washed with water, and dried to yield 1-(6-methyl-pyridin-2-yl)-2-[1,2,4]triazolo[1,5-a]pyridin-6-yl-ethanone as an off white solid (2.9 g). The filtrates were extracted with EtOAc and dried over MgSO4 and concentrated. The residue was recrystallized with iPrOH/H2O to yield more desired product (0.6 g). ESP+, m/e 253. 1H NMR (CDCl3, 300 MHz), delta 8.6 (s, 1H), 8.29 (s, 1H), 7.87 (d, 1H), 7.72 (t, 1H), 7.70 (d, 1H), 7.53 (dd, 1H), 7.36 (d, 1H), 4.61 (s, 2H), 2.66 (s, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6049 - 6053
[2]Patent: US8080568,2011,B1 .Location in patent: Page/Page column 18
[3]Patent: US2006/63809,2006,A1 .Location in patent: Page/Page column 17
[4]European Journal of Medicinal Chemistry,2012,vol. 57,p. 74 - 84

3
[ 614750-81-1 ]
[ 878760-44-2 ]
[ 878760-46-4 ]

Yield	Reaction Conditions	Operation in experiment
97%		To a solution of [l,2,4]triazolo[l,5-a]pyridine-6-carbaldehyde (2.5 g, 0.0169 mol) in a mixed solvent of THF (40 mL) and iPrOH (10 mL), was added (phenylamino-(2-methyl- pyrimidin-4-yl)-methyl)-phosphonic acid diphenyl ester (7.33 g, 0.0169 mol; see Example l(b) above) and Cs2CO3 (7.26 g, 0.022 mol). It was stirred at room temperature for 48 hours and then treated with 3N HCl (10 mL) for 1 hour. The reaction mixture was then diluted with methyl t-butyl ether and extracted with IN HCl twice. The combined aqueous layers were neutralized with 30percent aqueous KOH to pH of ca. 8, then extracted with ethyl acetate (3x). Organic layers were dried over MgSO4 and concentrated to yield a dark orange oil, which was purified on silica gel column with EtOAc/hexane (4:1) to give l-(2-methyl-pyrimidin-4-yl)-2- [l,2,4]triazolo[l,5-a]pyridin-6-yl-ethanone (4.15 g, 97percent) as a yellow solid. 1H NMR (300 MHz, CDCl3), delta 8.94 (d, IH), 8.62 (s, IH), 8.34 (s, IH), 7.76 (d, IH), 7.75 (s, IH), 7.51 (d, IH), 4.61 (s, 2H), 2.90 (s, 3H).

Reference： [1]Patent: WO2006/26305,2006,A1 .Location in patent: Page/Page column 31

4
[ 614750-81-1 ]
[ 878760-48-6 ]
[ 878760-49-7 ]

Yield	Reaction Conditions	Operation in experiment
57%		To a solution of [l,2,4]triazolo[l,5-a]pyridine-6-carbaldehyde (0.91 g, 6.1 mmol; see Example 2a) in a mixed solvent of THF (40 mL) and iPrOH (10 mL), was added (phenylamino- (2-trifluoromethyl-pyrimidin-4-yl)-methyl)-phosphonic acid diphenyl ester (3.0 g, 6.1 mmol) and Cs2CO3 (2.64 g, 8 mmol). It was stirred at room temperature for 16 hours and then treated with 3N HCl (10 mL) for 1 hour. The reaction mixture was then diluted with methyl t-butyl ether and extracted with IN HCl twice. The combined aqueous layers were neutralized with 30percent aqueous KOH to pH of ca. 8, and yellow precipitation was collected and dried to give 2- [l,2,4]triazolo[l,5-a]pyridin-6-yl-l-(2-trifluoromethyl-pyrimidin-4-yl)-ethanone (1.08 g, 57percent) as a yellow solid. LC-MS/ES+: M+l : 308.3. 1H NMR (300 MHz, CDCl3), delta 9.38 (s, IH), 8.89 (d, IH), 8.59-8.31 (m, 2H), 7.87-7.50 (m, 3H), 6.43 (s, IH).

Reference： [1]Patent: WO2006/26305,2006,A1 .Location in patent: Page/Page column 32-33

5
[ 79-24-3 ]
[ 614750-81-1 ]
[ 1043907-94-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; at 0 - 20℃;	Preparation 1 : l-([l,2,4]triazolo[l,5-a]pyridin-6-yl)-2-nitropropan-l-ol.; [0131] Into a Vial was added 0.50 M of Sodium methoxide in methanol (130 mL). This was cooled at 0 °C and nitroethane (50 mL, 0.7 mol.) was added followed by [l,2,4]triazolo[l,5- a]pyridine-6-carbaldehyde (3.35 g, 0.0228 mol.). The reaction was allowed to warm to room temperature with stirring overnight. LCMS shows conversion to a new peak consistent with <n="33"/>the product (RT=0.51 min, m/z=223.20 M+H). The reaction was concentrated and then dissolved in EA and rinsed with 5 percent citric acid then dried and concentrated to give a white powder that was taken on directly into the next step. MS (ESI (+) m/z): 223.20 (M+H+)

Reference： [1]Patent: WO2008/94556,2008,A2 .Location in patent: Page/Page column 31-32

6
[ 614750-81-1 ]
[ 1043902-96-0 ]
[ 1043902-98-2 ]
[ 1043902-97-1 ]

Yield	Reaction Conditions	Operation in experiment
50%; 22%		Step 4: 1 - [1 ,2,4] Triazolo [1 ,5-a] pyridin-6-yl-3-(8-trimethylsiIanyloxy-l ,4-dioxa- spiro[4.5]dec-8-yl)-prop-2-yn-l-ol; <n="44"/>[00166] To a solution of N,N-diisopropylamine (4.6 mL, 0.033 mol; Aldrich) in anhydrous THF (10OmL, Acros) was added dropwise 1.6 M n-butyllithium in hexane (19.0 mL; Aldrich) at -78 °C and the mixture stirred for Ih. To the above solution was added dropwise a solution of (8-ethynyl-l,4-dioxa-spiro[4.5]dec-8-yloxy)-trimethylsilane (6.5 g, 0.026 mol) in anhydrous THF (5OmL, Acros) at -78 °C and the mixture stirred for Ih. To the above solution was added dropwise a solution of [l,2,4]triazolo[l,5-a]pyridine-6-carbaldehyde (4.1 g, 0.028 mol) in anhydrous THF (15OmL, Acros) at -78 °C and the mixture stirred for Ih. The mixture was allowed to warm to room temperature then quenched with water and extracted with ethyl acetate (3x). The combined organic phases were washed with saturated ammonium chloride dried over MgSO4, concentrated and the residue purified on CombiFlash silica gel column with 0-100percent ethyl acetate in methylene chloride to give the desired product (2.4g, 22percent) and the desilyated product (4.2g, 50percent). ES+/330.42

Reference： [1]Patent: WO2008/94574,2008,A2 .Location in patent: Page/Page column 42-43

7
[ 1075260-64-8 ]
[ 614750-81-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium periodate; osmium(VIII) oxide; water; In 1,4-dioxane; at 20℃; for 0.5h;	(c) Title Compound; A solution of 6-ethenyl[l,2,4]triazolo[l,5-alpha]pyridine (340mg,2.34mmol) in 1,4- dioxane/water (10/5mL) was treated with sodium periodate (1.25g, 5.85mmol) and 4percent osmium tetroxide solution in water(0.45mL) at room temperature for 30 minutes. <n="116"/>The dioxane was evaporated and the aqueous was extracted with 20percent methanol in dichloromethane (2x10OmL). The combined organics were dried on magnesium sulphate, filtered and evaporated to give 330mg of the desired product.MS (ES+) m/z 148 (MH+)1H NMR(250MHz) delta(CDC13) 10.1 (IH, s), 9.12 (IH, m), 8.51 (IH, s), 8.04 (IH, d,), 7.79(IH, d).

Reference： [1]Patent: WO2008/128953,2008,A1 .Location in patent: Page/Page column 114-115

8
[ 614750-81-1 ]
[ 1132610-60-6 ]
[ 1132610-47-9 ]

Yield	Reaction Conditions	Operation in experiment
87%		General procedure: To a stirred solution of<strong>[614750-81-1][1,2,4]-triazolo[1,5-a]pyridine-6-carbaldehyde</strong>(1.77 g, 12.04 mmol) in a mixture of THF (48 mL) and i-PrOH (12 mL), 13a, 13b, or 13c (5.40 g, 12.04 mmol) and Cs2CO3 (5.10 g, 15.65mmol) were added. The mixture was stirred at room temperature for 24 h, and toit, 3 N HCl (20 mL) was added dropwise and stirred for an additional 1 h. Thereaction mixture was diluted with tert-butylmethyl ether (50 mL) and extracted with 1 N HCl (2 × 50 mL). The combined aqueous layer was neutralizedwith 2 N NaOH at 0 oC while a lot of yellow precipitates wereformed. The mixture was stirred at 0 oC for an additional 2 h andthen filtered. The filtered precipitates were washed with water (2 × 50 mL), and the solid was dissolved in CH2Cl2(200 mL). The CH2Cl2 solution was washed with brine (50mL), dried over anhydrous Na2SO4, filtered, and then evaporatedto dryness under reduced pressure to afford the titled compounds as an off-whitesolid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 5228 - 5231
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 912 - 916

9
[ 614750-81-1 ]
[ 40061-55-0 ]
[ 937279-48-6 ]

Yield	Reaction Conditions	Operation in experiment
		Step 10A: 3-Hydroxy-2-m-tolyl-3-[1,2,4]triazolo[1,5-a]pyridin-6-yl-propionic acid ethyl ester To a solution of 2.0 M lithium diisopropylamide in tetrahydrofuran (2.8 mL; Aldrich) and tetrahydrofuran (THF) (3.0 mL; Acros) at -40° C. was added ethyl meta-tolylacetate (1.00 mL, 5.61 mmol; Aldrich) in THF (6.0 mL). The mixture was stirred for 15 minutes at -40° C. To this was added <strong>[614750-81-1][1,2,4]triazolo[1,5-a]pyridine-6-carbaldehyde</strong> (0.830 g, 5.64 mol) in THF (9.0 mL). The material is very insoluble, so additional tetrahydrofuran (4.5 mL; Acros;) was used to transfer the aldehyde. The mixture was stirred for 30 minutes at -40° C. and then for 3 hours at room temperature. The reaction was cooled in an ice bath, then quenched carefully with 1.00 M hydrogen chloride in water (10. mL; Fisher). The solvents were evaporated, and the residue taken up in DMSO. The DMSO solution was purified using preparative HPLC chromatography to yield 883 mg of the title compound. m/z=326.15 (M+H).

Reference： [1]Patent: US2010/56505,2010,A1 .Location in patent: Page/Page column 32

10
[ 614750-84-4 ]
[ 68-12-2 ]
[ 614750-81-1 ]

Yield	Reaction Conditions	Operation in experiment
100%		To a solution of 6-iodo[l,2,4]triazolo[l,5-a]pyridme (5 g, 0.02 mol, prepared according to literature procedure) in anhydrous THF (300 mL), was slowly added IM of isopropylmagnesium bromide in THF (31 mL, 0.03 mol) at 0 oC. It was stirred at OoC for 1 hour and then was added anhydrous DMF (6 mL, 0.05 mol). It was allowed to warm to room temperature and stirred for overnight. It was then quenched with 100 mL of water and worked up with diethyl ether and saturated NaHCO3. Dried over MgSO4 and concentrated. The residue was purified on silica gel column with EtOAc to give the desire product as a tan solid (3g, 100percent). LC-MS/ES+: M+l: 148.0.

Reference： [1]Patent: WO2006/26305,2006,A1 .Location in patent: Page/Page column 30-31

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[ 614750-81-1 ]
[ 1338072-76-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6049 - 6053

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[ 614750-81-1 ]
[ 1338072-78-8 ]

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[ 614750-81-1 ]
[ 1338072-80-2 ]

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[ 614750-81-1 ]
[ 1338072-81-3 ]

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[ 614750-81-1 ]
[ 1338072-83-5 ]

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[ 614750-81-1 ]
[ 1338072-87-9 ]

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[ 614750-81-1 ]
[ 1338072-89-1 ]

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[ 614750-81-1 ]
[ 1338072-93-7 ]

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[ 614750-81-1 ]
[ 1338072-95-9 ]

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[ 614750-81-1 ]
[ 1338072-97-1 ]

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[ 614750-81-1 ]
[ 1338072-99-3 ]

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[ 614750-81-1 ]
[ 1338073-00-9 ]

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[ 614750-81-1 ]
[ 1338073-02-1 ]

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[ 614750-81-1 ]
[ 1338073-03-2 ]

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[ 614750-81-1 ]
[ 1338073-05-4 ]

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[ 614750-81-1 ]
[ 1338072-36-8 ]

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[ 614750-81-1 ]
[ 1338072-43-7 ]

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[ 614750-81-1 ]
[ 746667-09-4 ]

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[ 614750-81-1 ]
[ 1338072-63-1 ]

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[ 614750-81-1 ]
[ 1338072-64-2 ]

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[ 614750-81-1 ]
[ 1338072-65-3 ]

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[ 614750-81-1 ]
[ 1338072-68-6 ]

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[ 1338072-70-0 ]

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[ 1415663-75-0 ]