methyl (2R)-2-[(2R,5S,8R,9S,10S,13S,14S,17R)-2-bromo-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-3-(2-chloro-1,3-thiazol-5-yl)propanoate | 1256093-39-6

• 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
• 英文名称: methyl (2R)-2-[(2R,5S,8R,9S,10S,13S,14S,17R)-2-bromo-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-3-(2-chloro-1,3-thiazol-5-yl)propanoate
• CAS: 1256093-39-6
• 化学式: C₂₆H₃₅BrClNO₃S
• 分子量: 556.992
• InChiKey: NANQVDAIKAKCKL-BEWKCTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-[(2R,5S,8R,9S,10S,13S,14S,17R)-2-bromo-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-3-(2-chloro-1,3-thiazol-5-yl)propanoate 在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以60%的产率得到methyl (2R)-3-(2-chloro-1,3-thiazol-5-yl)-2-[(5S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]propanoate
  参考文献：
  名称：

  Synthesis and antitumor evaluation of methyl spongoate analogs

  摘要：

  A series of novel methyl spongoate (1) analogs has been synthesized and evaluated for their in vitro cytotoxic properties. It was found that the nature of the C-20 side chain had significant effects on their bioactivities and some analogs showed higher cytotoxicity than 1 against A549, HCT-116, HepG2, SW-1990, MCF-7 and NCl-H460 tumor cell lines. The pharmacological results confirmed that the alpha,beta-unsaturated carbonyl moiety, a Michael acceptor in ring A, plays a pivotal role in the cytotoxic effect of these derivatives. The compiled pharmacological data may be useful for the design of novel analogous anticancer drugs. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.08.002
• 作为产物：
  描述：

  methyl (20S)-20-(2'-chlorothiazolyl-5'-methenyl)-3-oxo-5α-pregnan-21-oate 在 pyridinium hydrobromide perbromide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到methyl (2R)-2-[(2R,5S,8R,9S,10S,13S,14S,17R)-2-bromo-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-3-(2-chloro-1,3-thiazol-5-yl)propanoate
  参考文献：
  名称：

  Synthesis and antitumor evaluation of methyl spongoate analogs

  摘要：

  A series of novel methyl spongoate (1) analogs has been synthesized and evaluated for their in vitro cytotoxic properties. It was found that the nature of the C-20 side chain had significant effects on their bioactivities and some analogs showed higher cytotoxicity than 1 against A549, HCT-116, HepG2, SW-1990, MCF-7 and NCl-H460 tumor cell lines. The pharmacological results confirmed that the alpha,beta-unsaturated carbonyl moiety, a Michael acceptor in ring A, plays a pivotal role in the cytotoxic effect of these derivatives. The compiled pharmacological data may be useful for the design of novel analogous anticancer drugs. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.08.002