(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-5-methoxy-5-oxopentan-2-yl)-10,13-dimethyl-3-(nitrooxy)hexadecahydro-1H-cyclopenta[a]phenanthrene-7,12-diyl diacetate | 936215-28-0

• 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: (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-5-methoxy-5-oxopentan-2-yl)-10,13-dimethyl-3-(nitrooxy)hexadecahydro-1H-cyclopenta[a]phenanthrene-7,12-diyl diacetate
• CAS: 936215-28-0
• 化学式: C₂₉H₄₅NO₉
• 分子量: 551.678
• InChiKey: RVFYMZAULQOYAM-CXFLVZIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  131.27
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-5-methoxy-5-oxopentan-2-yl)-10,13-dimethyl-3-(nitrooxy)hexadecahydro-1H-cyclopenta[a]phenanthrene-7,12-diyl diacetate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (R)-4-((3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-3-(nitrooxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
  参考文献：
  名称：

  Novel liver-specific nitric oxide (NO) releasing drugs with bile acid as both NO carrier and targeting ligand

  摘要：

  Novel liver-specific nitric oxide (NO) releasing drugs with bile acid as both the NO carrier and targeting ligand were designed and synthesized by direct nitration of the hydroxyl group in bile acids or the 3-O-hydroxyl alkyl derivatives, with the intact 24-COOH being preserved for hepatocyte specific recognition. Preliminary biological evaluation revealed that oral administrated targeted conjugates could protect mice against acute liver damage induced by acetaminophen or carbon tetrachloride. The nitrate level in the liver significantly increased after oral administration of 1e while nitrate level in the blood did not significantly change. Co-administration of ursodeoxycholic acid (UDCA) significantly antagonized the increase of nitrate in the liver resulted by administration of 1e. (C) 2014 Hui-Fen Wang and Bo-Hua Zhong. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.04.001
• 作为产物：
  描述：

  胆酸甲酯 在 盐酸 、 4-二甲氨基吡啶 、 硝酸 作用下， 以 吡啶 、 甲醇 、 乙酸酐 为溶剂， 反应 7.0h， 生成 (3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-((R)-5-methoxy-5-oxopentan-2-yl)-10,13-dimethyl-3-(nitrooxy)hexadecahydro-1H-cyclopenta[a]phenanthrene-7,12-diyl diacetate
  参考文献：
  名称：

  Novel liver-specific nitric oxide (NO) releasing drugs with bile acid as both NO carrier and targeting ligand

  摘要：

  Novel liver-specific nitric oxide (NO) releasing drugs with bile acid as both the NO carrier and targeting ligand were designed and synthesized by direct nitration of the hydroxyl group in bile acids or the 3-O-hydroxyl alkyl derivatives, with the intact 24-COOH being preserved for hepatocyte specific recognition. Preliminary biological evaluation revealed that oral administrated targeted conjugates could protect mice against acute liver damage induced by acetaminophen or carbon tetrachloride. The nitrate level in the liver significantly increased after oral administration of 1e while nitrate level in the blood did not significantly change. Co-administration of ursodeoxycholic acid (UDCA) significantly antagonized the increase of nitrate in the liver resulted by administration of 1e. (C) 2014 Hui-Fen Wang and Bo-Hua Zhong. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.04.001