methyl 3β-(tert-butyldimethylsilyloxy)-5α-pregnan-21-oate | 1227043-65-3

• 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 3β-(tert-butyldimethylsilyloxy)-5α-pregnan-21-oate
• 英文别名: methyl 2-[(3S,5S,8S,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]acetate
• CAS: 1227043-65-3
• 化学式: C₂₈H₅₀O₃Si
• 分子量: 462.789
• InChiKey: QRBDQFLYPRPWRF-CMRFFYFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-溴戊烷 、 methyl 3β-(tert-butyldimethylsilyloxy)-5α-pregnan-21-oate 在 lithium diisopropyl amide 、 4-羟甲基-3-甲氧基苯氧基乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以70%的产率得到methyl (20R)-20-pentyl-3β-(tert-butyldimethylsilyloxy)-5α-pregnan-21-oate
  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 3β-Hydroxy-5α-pregnan-21-oate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以98%的产率得到methyl 3β-(tert-butyldimethylsilyloxy)-5α-pregnan-21-oate
  参考文献：
  名称：

  具有强抗肿瘤活性的新型类固醇海绵酸甲酯的立体选择性合成

  摘要：

  海绵酸甲酯是一种天然存在的新型类固醇衍生物，具有不寻常的 C-20 甲氧基羰基和有效的抗肿瘤活性，其立体选择性合成是从市售的孕烯醇酮醋酸酯开始以 11% 的总产率实现的。

  DOI：

  10.1055/s-0029-1218567

文献信息

• Stereoselective Synthesis of Methyl Spongoate, a New Steroid with Potent Antitumor Activities
  作者：Yue-Wei Guo、Jing-Xu Gong、Ze-Hong Miao、Li-Gong Yao、Jian Ding、Tibor Kurtán

  DOI：10.1055/s-0029-1218567

  日期：2010.2

  The stereoselective synthesis of methyl spongoate, a naturally occurring new steroid derivative with an unusual C-20 methoxycarbonyl group and potent antitumor activities, was achieved starting from the commercially available pregnenolone acetate in 11% overall yield.

  海绵酸甲酯是一种天然存在的新型类固醇衍生物，具有不寻常的 C-20 甲氧基羰基和有效的抗肿瘤活性，其立体选择性合成是从市售的孕烯醇酮醋酸酯开始以 11% 的总产率实现的。
• Synthesis and antitumor evaluation of methyl spongoate analogs
  作者：Cheng-Shi Jiang、Cai-Guo Huang、Bo Feng、Jia Li、Jing-Xu Gong、Tibor Kurtán、Yue-Wei Guo

  DOI：10.1016/j.steroids.2010.08.002

  日期：2010.12

  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.