3β,16α-dihydroxy-17,17-dimethoxyandrost-5-ene | 10459-30-0

• 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: 3β,16α-dihydroxy-17,17-dimethoxyandrost-5-ene
• 英文别名: 17,17-dimethoxy-5-androstene-3β,16α-diol；17,17-dimethoxyandrost-5-ene-3β,16α-diol；(3S,8R,9S,10R,13S,14S,16R)-17,17-dimethoxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,16-diol
• CAS: 10459-30-0
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: UFMDBLHVCUKJLU-CUPSPLGBSA-N

物化性质

• 熔点：
  177-179 °C
• 沸点：
  464.5±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β,16α-dihydroxy-17,17-dimethoxyandrost-5-ene 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 氢氧化钾 、 L-Selectride 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 57.0h， 生成 17,17-dimethoxyandrost-5-ene-3β,7α,16α-triol
  参考文献：
  名称：

  Derivatives of 16α-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: Synthesis and gas chromatography/mass spectrometry analysis

  摘要：

  Derivatives of 16 alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3 beta, 16 alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by L-Selectride (R) or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7 alpha-hydroxy and 7 beta-hydroxy derivatives of 16 alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by H-1 and C-13 NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.04.002
• 作为产物：
  描述：

  androsta-5,16-diene-3β,17-diyl diacetate 在 溴 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 0.5h， 生成 3β,16α-dihydroxy-17,17-dimethoxyandrost-5-ene
  参考文献：
  名称：

  C19-Steroids as androgen receptor modulators: Design, discovery, and structure-activity relationship of new steroidal androgen receptor antagonists

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2006.05.022

文献信息

• Numazawa, Mitsuteru; Mutsumi, Ayako; Ogata, Mieko, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 9, p. 3381 - 3386
  作者：Numazawa, Mitsuteru、Mutsumi, Ayako、Ogata, Mieko

  DOI：——

  日期：——
• NUMAZAWA, MITSUTERU;MUTSUMI, AYAKO;OGATA, MIEKO, CHEM. AND PHARM. BULL., 36,(1988) N 9, C. 3381-3386
  作者：NUMAZAWA, MITSUTERU、MUTSUMI, AYAKO、OGATA, MIEKO

  DOI：——

  日期：——