3α-hydroxy-3β-methyl-5-androsten-17-one | 1195795-76-6

• 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: 3α-hydroxy-3β-methyl-5-androsten-17-one
• 英文别名: (3R,8R,9S,10R,13S,14S)-3-hydroxy-3,10,13-trimethyl-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 1195795-76-6
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: GCNLMVCMFQLZRM-YZOVGUKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  17,17-ethylenodioxy-3β-methyl-5-androsten-3α-ol 在 盐酸 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 12.0h， 以87%的产率得到3α-hydroxy-3β-methyl-5-androsten-17-one
  参考文献：
  名称：

  Novel Dehydroepiandrosterone Derivatives with Antiapoptotic, Neuroprotective Activity

  摘要：

  DHEA analogues with modifications at positions C3 or 07 were synthesized and evaluated for neuroprotective activity against the neural-crest-derived PC12 cell model of serum deprivation-induced apoptosis. The most potent compounds were the spiro-epoxy derivatives 17 beta-spiro[5-androstene-17, 2'-oxiran]-3 beta-ol (20), (20S)-3 beta,21-dihydroxy-17 beta,20-epoxy-5-pregnene (23), and (20R)-3 beta,21-dihydroxy-17 alpha,20-epoxy-5-pregnene (27) with IG(50) values of 0.19 +/- 0.01, 99.0 +/- 4.6, and 6.4 +/- 0.3 nM, respectively. Analogues 20, 23, and 27, up to the micromolar range of concentrations, were unable to activate estrogen receptor alpha and beta (ER alpha and ER beta) or to interfere with ER-dependent gene expression significantly. In addition, they were unable to stimulate the growth of Ishikawa, MCF-7, and LNCaP cells. Our results suggest that the spiro-epoxyneurosteroid derivatives 20, 23, and 27 may prove to be lead molecules for the synthesis of novel neuroprotective agents.

  DOI：

  10.1021/jm900468p

文献信息

• [EN] CYP11B, CYP17, AND/OR CYP21 INHIBITORS<br/>[FR] INHIBITEURS DE CYP11B, CYP17 ET/OU CYP21
  申请人：BIOMARIN PHARM INC

  公开号：WO2012083112A2

  公开（公告）日：2012-06-21

  Provided herein are inhibitors of CYP11B, CYP17, and/or CYP21 enzymes of Formula (Z), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), or (XVII). Also described herein are pharmaceutical compositions that include at least one compound described herein and the use of a compound or pharmaceutical composition described herein to treat androgen-dependent diseases, disorders and conditions. Formula (Z)
• Novel Dehydroepiandrosterone Derivatives with Antiapoptotic, Neuroprotective Activity
  作者：Theodora Calogeropoulou、Nicolaos Avlonitis、Vassilios Minas、Xanthippi Alexi、Athanasia Pantzou、Ioannis Charalampopoulos、Maria Zervou、Varvara Vergou、Efrosini S. Katsanou、Iakovos Lazaridis、Michael N. Alexis、Achille Gravanis

  DOI：10.1021/jm900468p

  日期：2009.11.12

  DHEA analogues with modifications at positions C3 or 07 were synthesized and evaluated for neuroprotective activity against the neural-crest-derived PC12 cell model of serum deprivation-induced apoptosis. The most potent compounds were the spiro-epoxy derivatives 17 beta-spiro[5-androstene-17, 2'-oxiran]-3 beta-ol (20), (20S)-3 beta,21-dihydroxy-17 beta,20-epoxy-5-pregnene (23), and (20R)-3 beta,21-dihydroxy-17 alpha,20-epoxy-5-pregnene (27) with IG(50) values of 0.19 +/- 0.01, 99.0 +/- 4.6, and 6.4 +/- 0.3 nM, respectively. Analogues 20, 23, and 27, up to the micromolar range of concentrations, were unable to activate estrogen receptor alpha and beta (ER alpha and ER beta) or to interfere with ER-dependent gene expression significantly. In addition, they were unable to stimulate the growth of Ishikawa, MCF-7, and LNCaP cells. Our results suggest that the spiro-epoxyneurosteroid derivatives 20, 23, and 27 may prove to be lead molecules for the synthesis of novel neuroprotective agents.