8-(17β-[tert-butyldimethylsilyl]oxy-5α-androstan-3-on-7α-yl)oct-6-enoic acid methyl ester | 326858-65-5

• 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: 8-(17β-[tert-butyldimethylsilyl]oxy-5α-androstan-3-on-7α-yl)oct-6-enoic acid methyl ester
• 英文别名: methyl 8-[(5S,7R,8R,9S,10S,13S,14S,17S)-17-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-7-yl]oct-6-enoate
• CAS: 326858-65-5
• 化学式: C₃₄H₅₈O₄Si
• 分子量: 558.918
• InChiKey: SVAYNZTYCXMOLZ-IWYAQQHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.89
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(17β-[tert-butyldimethylsilyl]oxy-5α-androstan-3-on-7α-yl)oct-6-enoic acid methyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 30.0h， 生成 17β-hydroxy-7α-(7-carboxyheptyl)-5α-androstan-3-one
  参考文献：
  名称：

  Discovery of 7α-substituted dihydrotestosterones as androgen receptor pure antagonists and their structure–activity relationships

  摘要：

  A series of 7 alpha-substituted dihydrotestosterone derivatives were synthesized and evaluated for androgen receptor (AR) pure antagonistic activity. From reporter gene assay (RGA), the compound with a side chain containing N-n-butyl-N-methyl amide (19a) showed pure antagonistic activity (IC50 = 340 nM, FI5 > 10,000 nM), whereas known AR antagonists showed partial agonistic activities. The optimization of 19a led to compound 23 (CH4892280), which showed more potent pure antagonistic activity (IC50 = 190 nM, FI5 > 10,000 nM). The SARs of tested compounds suggested that the length of the side chain and the substituents on the amide nitrogen are important for pure antagonistic activities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.072
• 作为产物：
  描述：

  7α-allyl-17β-[(tert-butyldimethylsilyl)oxy]androst-4-en-3-one 在 Grubbs catalyst first generation 氨 、 lithium 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 5.33h， 生成 8-(17β-[tert-butyldimethylsilyl]oxy-5α-androstan-3-on-7α-yl)oct-6-enoic acid methyl ester
  参考文献：
  名称：

  Discovery of 7α-substituted dihydrotestosterones as androgen receptor pure antagonists and their structure–activity relationships

  摘要：

  A series of 7 alpha-substituted dihydrotestosterone derivatives were synthesized and evaluated for androgen receptor (AR) pure antagonistic activity. From reporter gene assay (RGA), the compound with a side chain containing N-n-butyl-N-methyl amide (19a) showed pure antagonistic activity (IC50 = 340 nM, FI5 > 10,000 nM), whereas known AR antagonists showed partial agonistic activities. The optimization of 19a led to compound 23 (CH4892280), which showed more potent pure antagonistic activity (IC50 = 190 nM, FI5 > 10,000 nM). The SARs of tested compounds suggested that the length of the side chain and the substituents on the amide nitrogen are important for pure antagonistic activities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.072