7α-allyl-17β-[(tert-butyldimethylsilyl)oxy]-5α-androstan-3-one | 326856-26-2

• 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: 7α-allyl-17β-[(tert-butyldimethylsilyl)oxy]-5α-androstan-3-one
• 英文别名: 7alpha-Allyl-17beta-(tert-butyldimethylsilyloxy)-5alpha-androstan-3-one；(5S,7R,8R,9S,10S,13S,14S,17S)-17-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-7-prop-2-enyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 326856-26-2
• 化学式: C₂₈H₄₈O₂Si
• 分子量: 444.773
• InChiKey: SVMIKINKTYXGOR-OWFWVCCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.79
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7α-allyl-17β-[(tert-butyldimethylsilyl)oxy]-5α-androstan-3-one 在 palladium on activated charcoal 、 Grubbs catalyst first generation 盐酸 、 氢气 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 51.0h， 生成 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：

  7α-allyl-17β-[(tert-butyldimethylsilyl)oxy]androst-4-en-3-one 在 氨 、 lithium 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 0.33h， 以64%的产率得到7α-allyl-17β-[(tert-butyldimethylsilyl)oxy]-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

文献信息

• Novel antiandrogenic agent
  申请人：——

  公开号：US20030158164A1

  公开（公告）日：2003-08-21

  A compound pf general formula (I): 1 wherein, for example, X 1 and X 2 independently represent a hydrogen atom. R a represents a hydrogen atom or a protecting group for a hydroxyl group. R b and R c form an optionally protected —(C═O)— together with the 3-position carbon atom attached to R b and R c , and the broken line forms a single bond or double bond together with the solid line, or a pharmaceutically acceptable salt of the compound or a prodrug thereof.

  一种通式为(I)的化合物：其中，例如，X1和X2独立地表示氢原子。Ra表示氢原子或羟基的保护基。Rb和Rc与连接到Rb和Rc的3-位置碳原子一起形成一个可选的受保护的—(C═O)—，而断裂的线与实线一起形成单键或双键，或者其药物可接受的盐或前药。
• Antiandrogenic agent
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US07018993B2

  公开（公告）日：2006-03-28

  A compound pf general formula (I): wherein, for example, X1 and X2 independently represent a hydrogen atom. Ra represents a hydrogen atom or a protecting group for a hydroxyl group. Rb and Rc form an optionally protected —(C═O)— together with the 3-position carbon atom attached to Rb and Rc, and the broken line forms a single bond or double bond together with the solid line, or a pharmaceutically acceptable salt of the compound or a prodrug thereof.

  通式（I）的化合物：其中，例如X1和X2独立地表示氢原子。Ra表示氢原子或保护羟基的保护基。Rb和Rc与连接它们的3位碳原子一起形成可选的保护—（C═O）—，而断裂的线与实线一起形成单键或双键，或该化合物的药学上可接受的盐或前药。
• 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.