(5R,8S,11R,13S,14S,17S)-13-methyl-11-(2-methylbenzo[d]oxazol-5-yl)-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolane]-5,17(4H)-diol | 1360818-03-6

• 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: (5R,8S,11R,13S,14S,17S)-13-methyl-11-(2-methylbenzo[d]oxazol-5-yl)-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolane]-5,17(4H)-diol
• CAS: 1360818-03-6
• 化学式: C₃₁H₃₇NO₅
• 分子量: 503.638
• InChiKey: RYLSWJXSARPYCC-OWBSLNRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  37.0
• 可旋转键数：
  1.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  84.95
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5R,8S,11R,13S,14S,17S)-13-methyl-11-(2-methylbenzo[d]oxazol-5-yl)-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolane]-5,17(4H)-diol 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-(2-methyl-1,3-benzoxazol-5-yl)-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
  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：

  diallylamino-2-allyloxy-5-bromobenzene 在 copper(l) iodide 、 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5R,8S,11R,13S,14S,17S)-13-methyl-11-(2-methylbenzo[d]oxazol-5-yl)-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolane]-5,17(4H)-diol
  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