(20S)-20-hydroxycholest-4-ene-3,16-dione | 257904-96-4

• 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: (20S)-20-hydroxycholest-4-ene-3,16-dione
• 英文别名: cholest-4-en-20ξ-ol-3,16-dione；20S-Hydroxycholest-4-en-3,16-dione；(8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,6,7,8,9,11,12,14,15,17-decahydro-1H-cyclopenta[a]phenanthrene-3,16-dione
• CAS: 257904-96-4
• 化学式: C₂₇H₄₂O₃
• 分子量: 414.629
• InChiKey: NQUDYEUBQSNKOA-YYSUUBOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (20S)-20-hydroxycholestane-3,16-dione 在 meta-iodoxybenzoic acid 、 二苯基二硒醚 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以30%的产率得到(20S)-20-hydroxycholest-1-ene-3,16-dione
  参考文献：
  名称：

  First synthesis of 3,16,20-polyoxygenated cholestanes, new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa

  摘要：

  Using tigogenin as starting material, (20S)-20-hydroxycholestane-3,6-dione (1), (16S, 20S)-16,20-dihydroxycholestan-3-one (2), (20S)-20-hydroxycholest-1-ene-3,16-dione (3) and (20S)-20-hydroxycholest-4-ene-3,16-dione (4), natural polyoxygenated Steroids from the gorgonian, Leptogorgia sarmentosa, were synthesized in four steps. Antitumor activity against three tumor cell lines (breast cancer, MCF7, lung cancer NCI and oral cancer KB) was evaluated. Two compounds (3 and 4) showed strong activity against NCI (IC50 6.16 and 10.51 mu M) and moderate activity against MCF7 and KB, the IC50 being in the range 30.6S-47.22 mu M. Compound 2 showed moderate activity against NCI (IC50 42.68 mu M) but was inactive against MCF7 and KB whereas compound 1 showed no activity against all tested cells. (c) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.04.013

文献信息

• Further study on synthesis and evaluation of 3,16,20-polyoxygenated steroids of marine origin and their analogs as potent cytotoxic agents
  作者：Potjamarn Bunyathaworn、Suthinee Boonananwong、Boonsong Kongkathip、Ngampong Kongkathip

  DOI：10.1016/j.steroids.2010.02.011

  日期：2010.6

  A series of new polyoxygenated steroid derivatives with various steroid skeleton moieties were synthesized. Antitumor activity of the compounds against three tumor cell lines (Breast cancer MCF7, lung cancer NCl and oral cancer KB) were evaluated. Compounds with aromatic A ring of this series exhibited the most potent cytotoxicities in all tested cells. The absence of OH at C-16 or lack of cholesterol like side chain at C-20 in the steroid skeleton apparently result in decreased cytotoxicity. The compound became inactive when the side chain contains double bond at C-24-C-25. When hydroxyl group at C-3 was protected no cytotoxicities against MCF7 and NCl and considerable low cytotoxicity against KB cell lines were observed. (C) 2010 Elsevier Inc. All rights reserved.
• First synthesis of 3,16,20-polyoxygenated cholestanes, new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa
  作者：Suthinee Boonananwong、Boonsong Kongkathip、Ngampong Kongkathip

  DOI：10.1016/j.steroids.2008.04.013

  日期：2008.10

  Using tigogenin as starting material, (20S)-20-hydroxycholestane-3,6-dione (1), (16S, 20S)-16,20-dihydroxycholestan-3-one (2), (20S)-20-hydroxycholest-1-ene-3,16-dione (3) and (20S)-20-hydroxycholest-4-ene-3,16-dione (4), natural polyoxygenated Steroids from the gorgonian, Leptogorgia sarmentosa, were synthesized in four steps. Antitumor activity against three tumor cell lines (breast cancer, MCF7, lung cancer NCI and oral cancer KB) was evaluated. Two compounds (3 and 4) showed strong activity against NCI (IC50 6.16 and 10.51 mu M) and moderate activity against MCF7 and KB, the IC50 being in the range 30.6S-47.22 mu M. Compound 2 showed moderate activity against NCI (IC50 42.68 mu M) but was inactive against MCF7 and KB whereas compound 1 showed no activity against all tested cells. (c) 2008 Elsevier Inc. All rights reserved.