1-[(8S,9S,13S,14S,16R,17S)-3-methoxy-13,16-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethanone | 100978-10-7

• 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: 1-[(8S,9S,13S,14S,16R,17S)-3-methoxy-13,16-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 100978-10-7
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: FRQOMYHLAWAOAG-OCLNOYLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  、 碘甲烷 在 四丁基碘化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以97%的产率得到1-[(8S,9S,13S,14S,16R,17S)-3-methoxy-13,16-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethanone
  参考文献：
  名称：

  Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803

  摘要：

  A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe(3) reacted with four steroid dienone precursors to afford either the corresponding et-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of 43 was up to alpha/beta. No beta-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15 beta-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7 alpha and C-15 beta positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.05.008

文献信息

• Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803
  作者：Chun Li、Wenwei Qiu、Zhengfeng Yang、Jian Luo、Fan Yang、Mingyao Liu、Juan Xie、Jie Tang

  DOI：10.1016/j.steroids.2010.05.008

  日期：2010.12

  A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe(3) reacted with four steroid dienone precursors to afford either the corresponding et-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of 43 was up to alpha/beta. No beta-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15 beta-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7 alpha and C-15 beta positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803. (C) 2010 Elsevier Inc. All rights reserved.