(3S,3aS,5aS,9aS,9bS)-3a-Methyl-7-oxo-3-phenylamino-dodecahydro-6-aza-cyclopenta[a]naphthalene-6-carboxylic acid tert-butyl ester | 477904-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3S,3aS,5aS,9aS,9bS)-3a-Methyl-7-oxo-3-phenylamino-dodecahydro-6-aza-cyclopenta[a]naphthalene-6-carboxylic acid tert-butyl ester
• CAS: 477904-24-8
• 化学式: C₂₄H₃₄N₂O₃
• 分子量: 398.546
• InChiKey: ORKSDTUPKXXZOZ-HPGFDKJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,3aS,5aS,9aS,9bS)-3a-Methyl-7-oxo-3-phenylamino-dodecahydro-6-aza-cyclopenta[a]naphthalene-6-carboxylic acid tert-butyl ester 在 三氟甲磺酸三甲基硅酯 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.25h， 生成 (+)-17β-(N-phenylamino)-(5β)-10-azaestr-1-en-3-one
  参考文献：
  名称：

  Synthesis of 17β-N-Substituted 19-Nor-10-azasteroids as Inhibitors of Human 5α-Reductases I and II

  摘要：

  The synthesis of 17beta-[N-(phenyl)methyl/phenyl-amido] substituted 10-azasteroids has been accomplished by either the TiCl4- or TMSOTf-catalysed reaction of carbamates 11 and 12 with Danishefsky's diene. The reaction provided 5alpha-H isomers 3a-5a and 5beta-H isomers 3b-5b depending on the reaction conditions. Both epimers of each compound were tested against human 5alpha-reductase types I and II. Unexpectedly, 5beta-H compounds were found more active than their 5a-H counterparts, the best inhibitors being 3b (IC50=279 and 2000 nM toward isoenzyme I and II, respectively) and 5b (IC50=913 and 247 nM toward isoenzymes I and II, respectively). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00254-7
• 作为产物：
  描述：

  (3aS,9aS,9bS)-3a-Methyl-1,2,4,6,8,9,9a,9b-octahydro-3aH-6-aza-cyclopenta[a]naphthalene-3,7-dione 在 盐酸 、 4-二甲氨基吡啶 、 sodium cyanoborohydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 40.5h， 生成 (3S,3aS,5aS,9aS,9bS)-3a-Methyl-7-oxo-3-phenylamino-dodecahydro-6-aza-cyclopenta[a]naphthalene-6-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of 17β-N-Substituted 19-Nor-10-azasteroids as Inhibitors of Human 5α-Reductases I and II

  摘要：

  The synthesis of 17beta-[N-(phenyl)methyl/phenyl-amido] substituted 10-azasteroids has been accomplished by either the TiCl4- or TMSOTf-catalysed reaction of carbamates 11 and 12 with Danishefsky's diene. The reaction provided 5alpha-H isomers 3a-5a and 5beta-H isomers 3b-5b depending on the reaction conditions. Both epimers of each compound were tested against human 5alpha-reductase types I and II. Unexpectedly, 5beta-H compounds were found more active than their 5a-H counterparts, the best inhibitors being 3b (IC50=279 and 2000 nM toward isoenzyme I and II, respectively) and 5b (IC50=913 and 247 nM toward isoenzymes I and II, respectively). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00254-7