(3S,10R,13S,17S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol | 191677-74-4

• 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: (3S,10R,13S,17S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol
• 英文别名: 3β-(tert-butyldiphenylsilyloxy)-17-β-hydroxy-5-androstene；(3S,8R,9S,10R,13S,14S,17S)-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
• CAS: 191677-74-4
• 化学式: C₃₅H₄₈O₂Si
• 分子量: 528.85
• InChiKey: YGVFRBQXDBNUET-LWVFPSBSSA-N

物化性质

• 熔点：
  161-164 °C
• 沸点：
  583.8±50.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,10R,13S,17S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol 在 盐酸 、 甲醇 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.17h， 生成 (3S,10R,13S,17R)-10,13-dimethyl-17-(4-phenyl-1H-1,2,3-triazol-1-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  CONTRACEPTIVE AGENTS

  摘要：

  这项发明提供了式I、II、III或IV的化合物： 其中R1至R11、X和Y具有规范中定义的任何值。这些化合物抑制Na、K-ATPase α4，并可用作避孕剂。

  公开号：

  US20140005132A1
• 作为产物：
  描述：

  (3S,10R,13S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到(3S,10R,13S,17S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  CONTRACEPTIVE AGENTS

  摘要：

  这项发明提供了式I、II、III或IV的化合物： 其中R1至R11、X和Y具有规范中定义的任何值。这些化合物抑制Na、K-ATPase α4，并可用作避孕剂。

  公开号：

  US20140005132A1

文献信息

• 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.
• A direct stereoselective synthesis of 7β-hydroxytestosterone
  作者：David Labaree、Robert M. Hoyte、Richard B. Hochberg

  DOI：10.1016/s0039-128x(97)00018-4

  日期：1997.6

  Although 7 beta-hydroxytestosterone is a known product androgen metabolism, there are no published methods for its chemical synthesis except from the equally difficult to obtain 7 beta-hydroxy-4-androstene-3,17-dione. We found that several seemingly straightforward routes for its synthesis failed. Consequently, we tried to produce 7 beta-hydroxytestosterone by enzymatic oxidation of 5-androstene-3 beta,7 beta,17 beta-triol with cholesterol oxidase (Brevibacterium sp.), a procedure previously used to synthesize 7 beta-hydroxy-4-cholesten-3-one from 3 beta,7 beta-dihydroxycholesterol (Alexander and Fisher 1995). However, 5-androstene-3 beta,7 beta,17 beta-triol was, at best, a very poor substrate for the enzyme leading to the production of 7 beta-hydroxytestosterone in only trace amounts. Thus, we explored a strategy for the enzymatic synthesis in which a C-8-ester at C-17 (5-androstene-3 beta,7 beta,17 beta-triol 17-caprylate) would serve to mimic the bulky and hydrophobic side chain of cholesterol and thus allow the C-19-steroid to act as an effective substrate. When this ester was incubated with cholesterol oxidase, it was converted efficiently to 7 beta-hydroxytestosterone-17-caprylate. Attempts to remove the ester group by several mild hydrolytic procedures caused elimination of the 7 beta-hydroxyl group; we, therefore, obtained 7 beta-hydroxy-testosterone by incubation of the intermediate ester with porcine lipase. (C) 1997 by Elsevier Science Inc.