17β-Acetoxy-7α-methyl-androst-4-en-3-on | 7100-33-6

• 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: 17β-Acetoxy-7α-methyl-androst-4-en-3-on
• 英文别名: 7α-Methyl-3-oxo-17β-acetoxy-Δ⁴-androsten；6α-Methyltestosteronacetat；17β-acetoxy-7α-methyl-androst-4-en-3-one；17β-acetoxy-7α-methyltestosterone；Androst-4-en-3-one, 17-(acetyloxy)-7-methyl-, (7alpha,17beta)-；[(7R,8R,9S,10R,13S,14S,17S)-7,10,13-trimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 7100-33-6
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: SFECWQWNBHMGCT-JTIIFYKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17β-Acetoxy-7α-methyl-androst-4-en-3-on 在 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 (7S,8R,9S,10R,13S,14S,17S)-3-Chloro-7,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  甾体3,5-二烯。

  摘要：

  DOI：

  10.1021/jm00234a009
• 作为产物：
  描述：

  在 水 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 17β-Acetoxy-7α-methyl-androst-4-en-3-on
  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

• The Synthesis and Myotrophic Activity of 1-Halo-4-methylestra-1,3,5(10)-trienes
  作者：G. W. Moersch、T. P. Culbertson、D. F. Morrow、E. L. Wittle、R. R. Humphrey、W. A. Neuklis、M. E. Butler、M. M. Creger

  DOI：10.1021/jm00336a014

  日期：1964.11
• Steroidal 3,5-dienes
  作者：Philip M. Weintraub、Paul L. Tiernan、Harvey D. Benson、Joyce F. Grunwell、J. O'Neal Johnston、V. Petrow

  DOI：10.1021/jm00234a009

  日期：1976.12
• 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.