3β-acetoxy-5,6β-dibromo-17a-oxa-D-homo-5α-androstan-17-one | 94965-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3β-acetoxy-5,6β-dibromo-17a-oxa-D-homo-5α-androstan-17-one
• 英文别名: 3β-acetoxy-5,6β-dibromo-17a-oxa-D-homo-5α-androstan-17-one；3β-Acetoxy-5,6β-dibrom-17a-oxa-D-homo-5α-androstan-17-on
• CAS: 94965-28-3
• 化学式: C₂₁H₃₀Br₂O₄
• 分子量: 506.275
• InChiKey: VMXYTCZASWNLEA-FFIVAJFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3α,6β-dibromo-3β-acetoxyandrostan-17-one 在 过氧乙酸 、 对甲苯磺酸 、 溶剂黄146 作用下， 生成 3β-acetoxy-5,6β-dibromo-17a-oxa-D-homo-5α-androstan-17-one
  参考文献：
  名称：

  Levy; Jacobsen, Journal of Biological Chemistry, 1947, vol. 171, p. 71,76

  摘要：

  DOI：

文献信息

• C19-Steroids as androgen receptor modulators: Design, discovery, and structure-activity relationship of new steroidal androgen receptor antagonists
  作者：Padma Marwah、Ashok Marwah、Henry A. Lardy、Hiroshi Miyamoto、Chawnshang Chang

  DOI：10.1016/j.bmc.2006.05.022

  日期：2006.9

  Dehydroepiandrosterone (DHEA), the most abundant steroid in human circulating blood, is metabolized to sex hormones and other C-19-steroids. Our previous collaborative study demonstrated that androst-5-ene-3 beta,17 beta-diol (Adiol) and androst-4-ene-3,17-dione (Adione), metabolites of DHEA, can activate androgen receptor (AR) target genes. Adiol is maintained at a high concentration in prostate cancer tissue; even after androgen deprivation therapy and its androgen activity is not inhibited by the antiandrogens currently used to treat prostate cancer patients. We have synthesized possible metabolites of DHEA and several synthetic analogues and evaluated their role in androgen receptor transactivation to identify AR modulators. Steroids with low androgenic potential in PC-3 cell lines were evaluated for anti-dihydrotestosterone (DHT) and anti-Adiol activity. We discovered three potent antiandrogens: 3 beta-acetoxyandrosta-1,5-diene-17-one 17-ethylene ketal (ADEK), androsta-1,4-diene-3,17-dione 17-ethylene ketal (OAK), and 3 beta-hydroxyandrosta-5,16-diene (HAD) that antagonized the effects of DHT as well as of Adiol on the growth of LNCaP cells and on the expression of prostate-specific antigen (PSA). In vivo tests of these compounds will reveal their potential as potent antiandrogens for the treatment of prostate cancer. (c) 2006 Elsevier Ltd. All rights reserved.