A-108835

分子结构分类

有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物

中文名称

——

中文别名

——

英文名称

A-108835

英文别名

2-deoxyintegracide A；Integracide A；[(2R,3R,5R,10S,11R,12R,13R,17R)-2,11-dihydroxy-4,4,10,13-tetramethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-3-sulfooxy-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-12-yl] acetate

CAS

——

化学式

C₃₂H₅₀O₈S

mdl

——

分子量

594.81

InChiKey

BGABDSBXSCYPTK-PGHPLGCHSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

5.3
重原子数：

41
可旋转键数：

9
环数：

4.0
sp3杂化的碳原子比例：

0.78
拓扑面积：

139
氢给体数：

3
氢受体数：

8

上下游信息

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	integracide A	126348-77-4	C₃₂H₅₀O₅	514.746
——	(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-2,11-dihydroxy-4,4,10,13-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-aminoacetate 2,2,2-trifluoroacetate	——	C₃₄H₅₃NO₆	571.798
——	(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-3,11-dihydroxy-4,4,10,13-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-2-yl 2-aminoacetate 2,2,2-trifluoroacetate	——	C₃₄H₅₃NO₆	571.798
——	[(2S,4S,6R,8R,15R,16R,17R,18R)-18-hydroxy-2,7,7,16-tetramethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadeca-1(11),12-dien-17-yl] acetate	——	C₃₂H₄₈O₄	496.731
——	[(2R,3R,5R,10S,11R,12R,13R,17R)-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-3,11-dihydroxy-2-(methoxymethoxy)-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-12-yl] acetate	——	C₃₄H₅₄O₆	558.799
——	[(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-3-(2-aminoacetyl)oxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-11-hydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-2-yl] 2-aminoacetate	——	C₃₆H₅₆N₂O₇	628.85
——	4-((2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-2,11-dihydroxy-4,4,10,13-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)-4-oxobutanoic acid	——	C₃₆H₅₄O₈	614.82
——	[(2R,3R,5R,10S,11R,12R,13R,17R)-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-2,11-dihydroxy-3-(methoxymethoxy)-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-12-yl] acetate	——	C₃₄H₅₄O₆	558.799
——	O4-[(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-2,11-dihydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-yl] O1-methyl butanedioate	——	C₃₇H₅₆O₈	628.847
——	4-((2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-3,11-dihydroxy-4,4,10,13-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-2-yloxy)-4-oxobutanoic acid	276703-81-2	C₃₆H₅₄O₈	614.82
——	[(2R,3R,5R,10S,11R,12R,13R,17R)-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-11-hydroxy-2,3-bis(methoxymethoxy)-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-12-yl] acetate	——	C₃₆H₅₈O₇	602.852
——	[(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-3,11-dihydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-2-yl] 4-(hydroxyamino)-4-oxo-butanoate	——	C₃₆H₅₅NO₈	629.835
——	[(2S,4R,8R,10R,17R,18R,19R,20R)-20-hydroxy-2,6,6,9,9,18-hexamethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icosa-1(13),14-dien-19-yl] acetate	——	C₃₅H₅₄O₅	554.811
——	[(2R,3R,5R,10S,11R,12R,13R,17R)-3,11,12-triacetoxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-2-yl] acetate	——	C₃₈H₅₆O₈	640.858
——	(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-3,11-dihydroxy-4,4,10,13-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-2-yl 2-(tert-butoxycarbonylamino)acetate	——	C₃₉H₆₁NO₈	671.915
——	[(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-3-[2-(tert-butoxycarbonylamino)acetyl]oxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-11-hydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-2-yl] 2-(tert-butoxycarbonylamino)acetate	——	C₄₆H₇₂N₂O₁₁	829.084
——	(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-3,11-dihydroxy-4,4,10,13-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-2-yl benzoate	——	C₃₉H₅₄O₆	618.854
——	(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-2,11-dihydroxy-4,4,10,13-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl benzoate	——	C₃₉H₅₄O₆	618.854
——	[(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-3-benzoyloxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-11-hydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-2-yl] benzoate	——	C₄₆H₅₈O₇	722.962
——	(2R,3R,5R,10S,11R,12R,13R,17R)-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthrene-2,3,11,12-tetrol	126348-84-3	C₃₀H₄₈O₄	472.709
——	(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-3,11-dihydroxy-4,4,10,13-tetramethyl-17-((R)-6-methyl-5-methyleneheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-2-yl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)acetate	276703-92-5	C₄₉H₆₃NO₈	794.041
——	[(2R,3R,5R,10S,11R,12R,13R,17R)-12-acetoxy-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-3-[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]oxy-11-hydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-2-yl] 2-(9H-fluoren-9-ylmethoxycarbonylamino)acetate	——	C₆₆H₇₆N₂O₁₁	1073.34
——	[(2R,3R,5R,10S,12R,13R,17R)-2,3-dihydroxy-4,4,10,13-tetramethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-11-oxo-2,3,5,6,7,12,16,17-octahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate	——	C₃₂H₄₈O₅	512.73

反应信息

作为反应物：

描述：

A-108835 在 lithium hydroxide 作用下，以 1,4-二氧六环为溶剂，反应 0.08h，生成 (2R,3R,5R,10S,11R,12R,13R,17R)-17-[(1R)-1,5-dimethyl-4-methylene-hexyl]-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthrene-2,3,11,12-tetrol

参考文献：

名称：

HIV-1整合酶抑制剂整合剂B和相关天然产物的化学和构效关系。

摘要：

4，4-二甲基麦角锡烷三萜类化合物，Integracides是HIV-1整合酶（一种在HIV-1复制中的关键酶）的抑制剂。描述了杀虫剂B和相关天然产物的化学和结构-活性关系。HIV-1整合酶活性需要带电荷的基团，例如硫酸根，羧基或氨基。这些化合物显示出HIV-1整合酶活性，IC（50）值在4.8-15μM之间，并且在病毒扩散试验中显示出抗病毒活性，但是只有很小的治疗窗口或没有治疗窗口。

DOI：

10.1021/np030211s

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文献信息

A new mild PTSA-catalyzed method for sulfate ester hydrolysis and acid-catalyzed rearrangement of 12-acetyl-diene-11-ol tetracyclic triterpenoids involving an angular methyl migration

作者：Sheo B Singh

DOI：10.1016/s0040-4039(00)01190-4

日期：2000.9

mechanisms for the rearrangement have been elucidated and conditions have been developed to give high yields of the rearrangement products. A new and general PTSA·H2O and PPTS-catalyzed sulfate hydrolysis method has been developed.

含有12-乙酰基-Δ8,14-二烯-11-ol部分的四环三萜类化合物经历了一系列的酸催化重排。已经对重排产物进行了表征，已经阐明了用于重排的合理机制，并且已经开发了条件以提供高产率的重排产物。开发了一种新的，通用的PTSA·H 2 O和PPTS催化的硫酸盐水解方法。
Integracides: tetracyclic triterpenoid inhibitors of HIV-1 integrase produced by Fusarium sp.

作者：Sheo B Singh、Deborah L Zink、Anne W Dombrowski、Jon D Polishook、John G Ondeyka、Jorden Hirshfield、Peter Felock、Daria J Hazuda

DOI：10.1016/s0968-0896(02)00529-1

日期：2003.4

HIV-1 integrase is a critical enzyme in the replication of HIV-1. It is absent in the host cells and therefore is a good target for treatment of HIV-1 infections. Integracides are members of the tetracyclic triterpenoids family that were isolated from the fermentation broth of a Fusarium sp. Integracide A, a sulfated ester, exhibited significant inhibitory activity against strand transfer reaction of HIV-1 integrase. The discovery, structure elucidation including single crystal X-ray structure and HIV-1 inhibitory activity of these compounds are described. (C) 2003 Elsevier Science Ltd. All rights reserved.

A-108835

分子结构分类

计算性质

上下游信息

反应信息

文献信息

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