5-androsten-3β,7β-diol-17-one ethylene ketal 3-tert-butyldimethylsilyl ether | 202415-78-9

• 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: 5-androsten-3β,7β-diol-17-one ethylene ketal 3-tert-butyldimethylsilyl ether
• 英文别名: 3β-(t-butyldimethylsilyloxy)-17,17-ethylenedioxyandrost-5-en-7β-ol；(3S,7R,8R,9S,10R,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethylspiro[1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-7-ol
• CAS: 202415-78-9
• 化学式: C₂₇H₄₆O₄Si
• 分子量: 462.745
• InChiKey: GKVRHZWMMBMJMO-AMKJHPCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-androsten-3β,7β-diol-17-one ethylene ketal 3-tert-butyldimethylsilyl ether 在 硼烷 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.5h， 生成 5α-androstan-17-one-3β,6α,7β-triol ethylene ketal 3-tert-butyldimethylsilyl ether
  参考文献：
  名称：

  有效合成IPL576,092：新型抗哮喘药。

  摘要：

  描述了新型抗哮喘药IRL576,092（2）的对映体合成。所开发的合成途径涉及关键步骤，即立体选择性地还原6的烯酮羰基官能团，然后进行硼氢化。从市售的5-androsten-3beta-ol-17-one 3开始，采用有限数量的色谱步骤，该方法分9个步骤提供IPL576,092（2），总产率为25％。

  DOI：

  10.1021/jo0108717
• 作为产物：
  描述：

  去氢表雄酮 在 咪唑 、 ruthenium trichloride 、 sodium tetrahydroborate 、 cerium(III) chloride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 环己烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 20.0h， 生成 5-androsten-3β,7β-diol-17-one ethylene ketal 3-tert-butyldimethylsilyl ether
  参考文献：
  名称：

  有效合成IPL576,092：新型抗哮喘药。

  摘要：

  描述了新型抗哮喘药IRL576,092（2）的对映体合成。所开发的合成途径涉及关键步骤，即立体选择性地还原6的烯酮羰基官能团，然后进行硼氢化。从市售的5-androsten-3beta-ol-17-one 3开始，采用有限数量的色谱步骤，该方法分9个步骤提供IPL576,092（2），总产率为25％。

  DOI：

  10.1021/jo0108717

文献信息

• Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines
  作者：Shigemasa Yoshida、Akira Honda、Yasushi Matsuzaki、Sugano Fukushima、Naomi Tanaka、Aya Takagiwa、Yoshinori Fujimoto、Hiroshi Miyazaki、Gerald Salen

  DOI：10.1016/s0039-128x(02)00117-4

  日期：2003.1

  Dehydroepiandrosterone (DHEA) is a naturally occurring steroid synthesized in the adrenal cortex, gonads, brain, and gastrointestinal tract, and it is known to have chemopreventive and anti-proliferative actions on tumors. These effects are considered to be induced by the inhibition of glucose-6-phosphate dehydrogenase (G6PD) and/or HMG-CoA reductase (HMGR) activities. The present study was undertaken to investigate whether endogenous DHEA metabolites, i.e. DHEA-sulfate, 7-oxygenated DHEA derivatives, androsterone, epiandrosterone, and etiocholanolone, have anti-proliferative effects on cancer cells and to clarify which enzyme, G6PD or HMGR, is responsible for growth inhibition. Growth of Hep G2, Caco-2, and HT-29 cells, evaluated by 3-[4,5-dimethylthiazol]-2yl-2,5-diphenyl tetrazolium bromide (MTT) and bromodeoxyuridine incorporation assays, was time- and dose-dependently inhibited by addition of all DHEA-related steroids we tested. In particular, the growth inhibition due to etiocholanolone was considerably greater than that caused by DHEA in all cell lines. The suppression of growth of the incubated steroids was not correlated with the inhibition of G6PD (r = -0.031, n = 9, NS) or HMGR (r = 0.219, n = 9, NS) activities. The addition of deoxyribonucleosides or mevalonolactone to the medium did not overcome the inhibition of growth induced by DHEA or etiocholanolone, while growth suppression by DHEA was partially prevented by the addition of ribonucleosides. These results demonstrate that endogenous DHEA metabolites also have an anti-proliferative action that is not induced by inhibiting G6PD or HMGR activity alone. These non-androgenic DHEA metabolites may serve as chemopreventive or anti-proliferative therapies. (C) 2002 Elsevier Science Inc. All rights reserved.
• J. Org. Chem. 2002, 67, 3908-3910
  作者：

  DOI：——

  日期：——
• Efficient Synthesis of IPL576,092:  A Novel Anti-Asthma Agent
  作者：Yaping Shen、David L. Burgoyne

  DOI：10.1021/jo0108717

  日期：2002.5.1

  of the novel anti-asthma agent IRL576,092 (2) is described. The synthetic route developed involves stereoselective 1,2-reduction of the enone carbonyl functionality of 6 and subsequent hydroboration as the key steps. Starting from the commercially available 5-androsten-3beta-ol-17-one 3, this approach affords IPL576,092 (2) in nine steps with overall yields of 25%, employing a limited number of chromatographic

  描述了新型抗哮喘药IRL576,092（2）的对映体合成。所开发的合成途径涉及关键步骤，即立体选择性地还原6的烯酮羰基官能团，然后进行硼氢化。从市售的5-androsten-3beta-ol-17-one 3开始，采用有限数量的色谱步骤，该方法分9个步骤提供IPL576,092（2），总产率为25％。