de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane | 189102-76-9

分子结构分类

有机化合物 - 有机金属化合物 - 有机类金属化合物

中文名称

——

中文别名

——

英文名称

de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane

英文别名

——

de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane化学式

CAS

189102-76-9

化学式

C₂₅H₅₂O₂Si₂

mdl

——

分子量

440.858

InChiKey

GSXSZWXWEBVUKE-SHNSKLSNSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

425.0±18.0 °C(Predicted)
密度：

0.90±0.1 g/cm3(Predicted)
溶解度：

溶于氯仿

计算性质

辛醇/水分配系数(LogP)：

8.25
重原子数：

29.0
可旋转键数：

6.0
环数：

2.0
sp3杂化的碳原子比例：

1.0
拓扑面积：

18.46
氢给体数：

0.0
氢受体数：

2.0

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
(1R,3AR,4S,7AR)-1-[(2S)-1-羟基丙-2-基]-7A-甲基-1,2,3,3A,4,5,6,7-八氢茚-4-醇	(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol	64190-52-9	C₁₃H₂₄O₂	212.332

下游产品

中文名称	英文名称	CAS号	化学式	分子量
骨化醇杂质DCP	(20R)-de-A,B-8β-[(tert-butyldimethylsilyl)oxy]-20-(hydroxymethyl)pregnane	171011-48-6	C₁₉H₃₈O₂Si	326.595
(BETAS,1R,3AR,4S,7AR)-4-[[(叔丁基)二甲基硅烷基]氧基]八氢-BETA,7A-二甲基-1H-茚-1-乙醇	(S)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol	100928-03-8	C₁₉H₃₈O₂Si	326.595
——	(2S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)hex-5-yn-3-ol	1361587-87-2	C₂₂H₄₀O₂Si	364.644
——	(S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal	104651-47-0	C₁₉H₃₆O₂Si	324.579
艾地骨化醇起始原料杂质1	de-A,B-8β-<(tert-butyldimethylsilyl)oxy>-23,24-dinor-23-iodocholane	100928-05-0	C₁₉H₃₇IOSi	436.492
——	(S)-5-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)-1-ethoxyhex-1-ene	1235544-62-3	C₂₄H₄₆O₂Si	394.714
——	(S)-5-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)-1-ethoxyhex-1-ene	957214-08-3	C₂₄H₄₆O₂Si	394.714
——	[(1R,3aR,4S,7aR)-7a-methyl-1-[(2R)-1-(4-methyl-4-trimethylsilyloxypentoxy)propan-2-yl]-1,2,3,3a,4,5,6,7-octahydroinden-4-yl]oxy-tert-butyl-dimethylsilane	1026545-21-0	C₂₈H₅₈O₃Si₂	498.938
艾地骨化醇起始物料杂质2	[1R-(1β,3aα,7aβ)]-[1S-(4β)]-(1,1-dimethylethyl)dimethyl{[octahydro-7a-methyl-1-(1-methylethenyl)-1H-inden-4-yl]oxy}silane	215257-72-0	C₁₉H₃₆OSi	308.58
——	(4E,6E,8R)-8-[(1R,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]-3-ethylnona-4,6-dien-3-ol	189102-32-7	C₂₇H₅₀O₂Si	434.778
——	ethyl (2E,4E,6R)-6-[(1R,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]hepta-2,4-dienoate	189102-31-6	C₂₅H₄₄O₃Si	420.708
——	8β-[(tert-butyldimethylsilyl)oxy]de-A,B-androstan-17β-one	140659-26-3	C₁₆H₃₀O₂Si	282.498
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl isonicotinate	1454816-56-8	C₂₅H₄₁NO₃Si	431.691
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-chlorobenzoate	1454816-54-6	C₂₆H₄₁ClO₃Si	465.148
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 2-naphthoate	1454816-59-1	C₃₀H₄₄O₃Si	480.763
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl furan-2-carboxylate	1454816-57-9	C₂₄H₄₀O₄Si	420.665
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-methoxybenzoate	1454816-53-5	C₂₇H₄₄O₄Si	460.729
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl nicotinate	1454816-55-7	C₂₅H₄₁NO₃Si	431.691
——	(20R)-de-A,B-8β-[(tert-butyldimethylsilyl)oxy]-20-[(p-tolylsulfonyl)oxymethyl]pregnane	183506-75-4	C₂₆H₄₄O₄SSi	480.784
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 1-naphthoate	1454816-58-0	C₃₀H₄₄O₃Si	480.763
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 3-methoxybenzoate	1454816-52-4	C₂₇H₄₄O₄Si	460.729
——	tert-butyl(((1R,3aR,4S,7aR)-1-((S)-1-(furan-2-yl)ethyl)-7a-methyloctahydro-1H-inden-4-yl)oxy)dimethylsilane	1361587-89-4	C₂₂H₃₈O₂Si	362.628
——	(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 2-methoxybenzoate	1454816-51-3	C₂₇H₄₄O₄Si	460.729

反应信息

作为反应物：

描述：

de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane 在 4-二甲氨基吡啶、四丁基氟化铵、 N,N'-二环己基碳二亚胺作用下，以四氢呋喃、二氯甲烷为溶剂，生成 (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 2-methoxybenzoate

参考文献：

名称：

Analogues of the Inhoffen–Lythgoe diol with anti-proliferative activity

摘要：

The anti-proliferative activity of a series of ester-and amide-linked Inhoffen-Lythgoe side chain analogues is reported. Whereas the Inhoffen-Lythgoe diol was inactive in these studies, a number of aromatic and aliphatic ester-linked side chains demonstrated modest in vitro growth inhibition in two human cancepar cell lines, U87MG (glioblastoma) and HT-29 (colorectal adenocarcinoma). Structureactivity relationship (SAR) studies demonstrated the most active aromatic (13) and aliphatic (25 and 29) substituted analogues were approximately equipotent in U87MG and HT-29 cells. Further evaluation of 13, 25, and 29 indicated these analogues do not activate canonical vitamin D signaling nor antagonize Hedgehog (Hh) signaling. Thus, the cellular mechanism(s) that govern the anti-proliferative activity for this class of truncated vitamin D-based structures appears to be different from classical mechanisms previously identified for these scaffolds. (C) 2013 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.bmcl.2013.07.054