7α-(13-bromo-2-tridecen-1-yl)-3,3-ethylenedioxy-17β-methoxymethoxy-5α-androstane | 326858-78-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7α-(13-bromo-2-tridecen-1-yl)-3,3-ethylenedioxy-17β-methoxymethoxy-5α-androstane
• 英文别名: (5S,7R,8R,9S,10S,13S,14S,17S)-7-(13-bromotridec-2-enyl)-17-(methoxymethoxy)-10,13-dimethylspiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]
• CAS: 326858-78-0
• 化学式: C₃₆H₆₁BrO₄
• 分子量: 637.782
• InChiKey: AIXRCPZAYSDXJG-JFAAMXBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7α-(13-bromo-2-tridecen-1-yl)-3,3-ethylenedioxy-17β-methoxymethoxy-5α-androstane 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 13.0h， 以86%的产率得到7α-(13-bromotridecyl)-3,3-ethylenedioxy-17β-methoxymethoxy-5α-androstane
  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：

  17β-hydroxy-7α-(2-propen-1-yl)-5α-androstan-3-one 在 Grubbs catalyst first generation 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 7α-(13-bromo-2-tridecen-1-yl)-3,3-ethylenedioxy-17β-methoxymethoxy-5α-androstane
  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

文献信息

• Discovery of 7α-substituted dihydrotestosterones as androgen receptor pure antagonists and their structure–activity relationships
  作者：Kazutaka Tachibana、Ikuhiro Imaoka、Hitoshi Yoshino、Takashi Emura、Hirohumi Kodama、Yoshiyuki Furuta、Nobuaki Kato、Mitsuaki Nakamura、Masateru Ohta、Kenji Taniguchi

  DOI：10.1016/j.bmc.2006.09.072

  日期：2007.1.1

  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.