4-(((3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-((S)-1-oxopropan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-4-oxobutanoic acid | 1214884-94-2

• 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: 4-(((3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-((S)-1-oxopropan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-4-oxobutanoic acid
• CAS: 1214884-94-2
• 化学式: C₂₆H₃₈O₅
• 分子量: 430.585
• InChiKey: CMBOBIWSUQHTHK-ZHRHZKROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(((3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-((S)-1-oxopropan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-4-oxobutanoic acid 、 4-氨基丁酸甲酯盐酸盐 在 三乙胺 、 sodium cyanoborohydride 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到4-[[(3S,8S,9S,10R,13S,14S,17R)-17-[(2S)-1-[(4-methoxy-4-oxobutyl)amino]propan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid
  参考文献：
  名称：

  SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents

  摘要：

  There is an urgent need for the development of new drugs for the treatment of neglected tropical diseases such as human African trypanosomiasis, Chagas disease and leishmaniasis. Azasterols, have been shown to have activity against the parasites which cause these diseases. In this paper we report synthesis of new azasterols and subsequent analysis of the SAR. The chemistry focused on variations in the ester at the 3 beta-position of the sterol and the position of the nitrogen in the side chain. The data allowed us to derive preliminary pharmacophore models for the activity of the azasterols against the parasites which cause these diseases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.062
• 作为产物：
  描述：

  丁二酸酐 、 (3beta,20S)-20-甲酰基-3-羟基-5-孕烯 在 4-二甲氨基吡啶 、 1,2-二氯乙烷 作用下， 以 二氯甲烷 为溶剂， 以24%的产率得到4-(((3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-((S)-1-oxopropan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-4-oxobutanoic acid
  参考文献：
  名称：

  SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents

  摘要：

  There is an urgent need for the development of new drugs for the treatment of neglected tropical diseases such as human African trypanosomiasis, Chagas disease and leishmaniasis. Azasterols, have been shown to have activity against the parasites which cause these diseases. In this paper we report synthesis of new azasterols and subsequent analysis of the SAR. The chemistry focused on variations in the ester at the 3 beta-position of the sterol and the position of the nitrogen in the side chain. The data allowed us to derive preliminary pharmacophore models for the activity of the azasterols against the parasites which cause these diseases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.062