7α-allyl-17β-[(tert-butyldimethylsilyl)oxy]androst-4-en-3-one | 115814-80-7

• 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]androst-4-en-3-one
• 英文别名: 17β-(t-Butyldimethylsilyloxy)-7α-allyl-4-androsten-3-one；17beta-(t-Butyldimethylsilyloxy)-7alpha-allyl-4-androsten-3-one；(7R,8R,9S,10R,13S,14S,17S)-17-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-7-prop-2-enyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 115814-80-7
• 化学式: C₂₈H₄₆O₂Si
• 分子量: 442.758
• InChiKey: AYLFDISXWYNINT-UCSHBLHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.71
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 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]androst-4-en-3-one 在 palladium on activated charcoal 、 Grubbs catalyst first generation 盐酸 、 氨 、 氢气 、 lithium 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 丙酮 、 叔丁醇 为溶剂， 反应 51.33h， 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：

  17β-<(tert-butyldimethylsilyl)oxy>androsta-4,6-dien-3-one 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 7α-allyl-17β-[(tert-butyldimethylsilyl)oxy]androst-4-en-3-one
  参考文献：
  名称：

  立体定向合成von7α-烯丙基和7α-丙基甾体

  摘要：

  DOI：

  10.1016/s0040-4039(00)80344-5

文献信息

• Discovery and structure–activity relationships of new steroidal compounds bearing a carboxy-terminal side chain as androgen receptor pure antagonists
  作者：Kazutaka Tachibana、Ikuhiro Imaoka、Hitoshi Yoshino、Nobuaki Kato、Mitsuaki Nakamura、Masateru Ohta、Hiromitsu Kawata、Kenji Taniguchi、Nobuyuki Ishikura、Masahiro Nagamuta、Etsuro Onuma、Haruhiko Sato

  DOI：10.1016/j.bmcl.2007.07.090

  日期：2007.10

  was investigated. Compounds 6 and 7, which have a carboxylic acid at the end of the side chain at the position 7alpha of dihydrotestosterone (DHT), showed partial agonistic activities in reporter gene assay (RGA). Conversion of the steroidal core structure to 17alpha-methyltestosterone gave compound 14, which showed weak pure antagonistic activity. Optimization of the side chain by the insertion of

  研究了CH4892280（4）（一种雄激素受体（AR）纯拮抗剂）的前导优化。在二氢睾酮（DHT）7α位的侧链末端具有羧酸的化合物6和7在报告基因测定（RGA）中显示出部分激动活性。甾体核心结构向17α-甲基睾丸酮的转化得到化合物14，其显示出弱的纯拮抗活性。通过插入苯环优化侧链产生化合物22和28-30，其在亚微摩尔浓度下显示出纯的拮抗活性。阐明了结构-活性关系。
• Androstane derivative having substituent in 7- abd 17--positions
  申请人：Nakamura Mitsuaki

  公开号：US20050009797A1

  公开（公告）日：2005-01-13

  A compound of Formula (I): [wherein R 1 represents a lower alkyl group, X represents an oxygen atom or a methylene group, m represents an integer of 1 to 10, and n represents an integer of 0 to 5] or a salt or ester thereof; a medicament and a pharmaceutical composition comprising one or more such compounds; a method for preventing or treating a disease closely related to androgen, which comprises administering an effective amount of one or more such compounds; a kit used for such prevention or treatment; and the use of one or more such compounds for the manufacture of the medicament.

  化合物公式（I）：[其中R1代表低碳基，X代表氧原子或亚甲基基团，m表示1至10的整数，n表示0至5的整数]或其盐或酯；一种药物和包括一种或多种此类化合物的制药组合物；一种预防或治疗与雄激素密切相关的疾病的方法，包括给予一种或多种此类化合物的有效量；一种用于此类预防或治疗的工具箱；以及一种用于制造药物的一种或多种此类化合物的用途。
• 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.
• Stereoselektive synthese von 7α-allyl- und 7α-propylsteroiden
  作者：Klaus Nickisch、Henry Laurent

  DOI：10.1016/s0040-4039(00)80344-5

  日期：——