(8S,13S,14S,17S)-N,N-diallyl-13-methyl-17-(prop-1-yn-1-yl)-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-amine | 1360817-90-8

• 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: (8S,13S,14S,17S)-N,N-diallyl-13-methyl-17-(prop-1-yn-1-yl)-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-amine
• CAS: 1360817-90-8
• 化学式: C₂₉H₃₉NO₂
• 分子量: 433.634
• InChiKey: QUXAKGFKZPBEHL-UNFRKHOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (8S,13S,14S,17S)-N,N-diallyl-13-methyl-17-(prop-1-yn-1-yl)-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-amine 在 disodium hydrogenphosphate 、 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 双氧水 、 六氟丙酮 作用下， 以 二氯甲烷 为溶剂， 生成 N-((5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-yl)formamide
  参考文献：
  名称：

  Synthesis and antihormonal properties of novel 11β-benzoxazole-substituted steroids

  摘要：

  Early studies led to the identification of 11 beta-aryl-4',5'-dihydrospiro[estra-4,9-diene-17 beta,4'-oxazole] analogs with potent and more selective antiprogestational activity compared to antiglucocorticoid activity than mifepristone. In the present study, we replaced the 4'-dimethylaminophenyl group of mifepristone with the benzoxazol group to give 5a-d. We also prepared the 17 beta-formamido analogs 6a,b using a new synthetic strategy via the intermediate epoxide 21. These compounds were evaluated for their antagonist hormonal properties using the T47D cell-based alkaline phosphatase assay and the A549 cell-based functional assay. Compound 5c showed potent antagonist activity at GR with better selectivity for GR versus PR than mifepristone and is a promising lead for further development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.110
• 作为产物：
  描述：

  N-allyl-N-((8S,13S,14S)-13-methyl-1,4,6,7,8,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17(2H)-ylidene)prop-2-en-1-aminium bromide 在 potassium cyanide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (8S,13S,14S,17S)-N,N-diallyl-13-methyl-17-(prop-1-yn-1-yl)-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-amine
  参考文献：
  名称：

  Synthesis and antihormonal properties of novel 11β-benzoxazole-substituted steroids

  摘要：

  Early studies led to the identification of 11 beta-aryl-4',5'-dihydrospiro[estra-4,9-diene-17 beta,4'-oxazole] analogs with potent and more selective antiprogestational activity compared to antiglucocorticoid activity than mifepristone. In the present study, we replaced the 4'-dimethylaminophenyl group of mifepristone with the benzoxazol group to give 5a-d. We also prepared the 17 beta-formamido analogs 6a,b using a new synthetic strategy via the intermediate epoxide 21. These compounds were evaluated for their antagonist hormonal properties using the T47D cell-based alkaline phosphatase assay and the A549 cell-based functional assay. Compound 5c showed potent antagonist activity at GR with better selectivity for GR versus PR than mifepristone and is a promising lead for further development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.110