1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oic acid (O¹-ethyl-β-alanino)amide | 1416254-26-6

• 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: 1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oic acid (O¹-ethyl-β-alanino)amide
• 英文别名: ethyl 3-[[(3R,4R,5R,8R,9R,10R,13S,14R,15R)-4-(cyanomethyl)-4,9,10-trimethyl-3-(2-methyl-1-oxopropan-2-yl)-15-prop-1-en-2-yl-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carbonyl]amino]propanoate
• CAS: 1416254-26-6
• 化学式: C₃₅H₅₄N₂O₄
• 分子量: 566.825
• InChiKey: YWFNMJSLXXXZOB-KAZOPDRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oic acid 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-cyano-2,3-seco-2-norlup-20(29)-en-3-al-28-oic acid (O¹-ethyl-β-alanino)amide
  参考文献：
  名称：

  Synthesis and biological activity of mono- and diamides of 2,3-secotriterpene acids

  摘要：

  Amides of four types were synthesized derived from 2,3-seco-18 alpha H-oleanane and 2,3-secolupane mono- and dicarboxylic acids. The spectrum of diamide derivatives was expanded with C3-C3' and C28-C28' biscondensed amides with two A-secotriterpene backbones obtained by the interaction of monocarboxylic A-seco acids with lysine. Among the synthesized monoand diamide derivatives, potential inhibitors of herpes simplex virus type 1 replication were found, namely, some compounds with an ethyl beta-alaninate fragment (EC50 8.7 and 4.1 mu M). The ethyl beta-alaninate diamide was shown to combine antiherpetic and anti-HIV activity (EC50 5.1 mu M). For the active compounds, the ratios of maximum tolerable concentrations to EC50 ranged from 9.7 to 40.8. The synthesized amides did not show any marked cytotoxic effects against human rabdomiosarcoma RD TE32, A549 lung carcinoma, and melanoma MS cell lines.

  DOI：

  10.1134/s1068162013020143

文献信息

• Synthesis and biological activity of mono- and diamides of 2,3-secotriterpene acids
  作者：I. A. Tolmacheva、E. V. Igosheva、Yu. B. Vikharev、V. V. Grishko、O. V. Savinova、E. I. Boreko、V. F. Eremin

  DOI：10.1134/s1068162013020143

  日期：2013.3

  Amides of four types were synthesized derived from 2,3-seco-18 alpha H-oleanane and 2,3-secolupane mono- and dicarboxylic acids. The spectrum of diamide derivatives was expanded with C3-C3' and C28-C28' biscondensed amides with two A-secotriterpene backbones obtained by the interaction of monocarboxylic A-seco acids with lysine. Among the synthesized monoand diamide derivatives, potential inhibitors of herpes simplex virus type 1 replication were found, namely, some compounds with an ethyl beta-alaninate fragment (EC50 8.7 and 4.1 mu M). The ethyl beta-alaninate diamide was shown to combine antiherpetic and anti-HIV activity (EC50 5.1 mu M). For the active compounds, the ratios of maximum tolerable concentrations to EC50 ranged from 9.7 to 40.8. The synthesized amides did not show any marked cytotoxic effects against human rabdomiosarcoma RD TE32, A549 lung carcinoma, and melanoma MS cell lines.