(20S)-20-hydroxycholestane-3,16-dione | 257904-93-1

• 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-hydroxycholestane-3,16-dione
• 英文别名: 20S-Hydroxy-5-alpha-cholestane-3,16-dione；(5S,8R,9S,10S,13S,14S,17S)-17-[(2S)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-dione
• CAS: 257904-93-1
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: RJXRRUHNMZQRFL-LVXDJYSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-(2-hydroxy-6-methylheptan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (20S)-20-hydroxycholestane-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

• 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.