N-(olean-3β-hydroxy-18-en-28-oyl)-(1-hydroxymethyl-3-methyl)-butylamide | 872584-89-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(olean-3β-hydroxy-18-en-28-oyl)-(1-hydroxymethyl-3-methyl)-butylamide
• 英文别名: (4aS,6aR,6aR,6bR,8aR,10S,12aR,14aS)-10-hydroxy-N-[(2S)-1-hydroxy-4-methylpentan-2-yl]-2,2,6a,6b,9,9,12a-heptamethyl-3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a-tetradecahydropicene-4a-carboxamide
• CAS: 872584-89-9
• 化学式: C₃₆H₆₁NO₃
• 分子量: 555.885
• InChiKey: JWSWWOJOMRUBOW-UNKIKOFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(olean-3β-hydroxy-18-en-28-oyl)-(1-hydroxymethyl-3-methyl)-butylamide 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 N-[3β-(3',3'-dimethylsuccinoxy)olean-18-en-28-oyl]-(1-hydroxy-methyl-3-methyl-butyl)-amide
  参考文献：
  名称：

  Anti-AIDS Agents 69. Moronic Acid and Other Triterpene Derivatives as Novel Potent Anti-HIV Agents

  摘要：

  In a continuing structure-activity relationship study of potent anti-HIV agents, seven new triterpene derivatives were designed, synthesized, and evaluated for in vitro antiviral activity. Among them, moronic acid derivatives 19, 20, and 21 showed significant activity in HIV-1 infected H9 lymphocytes. Compounds 19 and 20 were also evaluated against HIV-1 NL4-3 and drug resistant strains in the MT-4 cell line. Compounds 19 and 20 showed better antiviral profiles than the betulinic acid analogue 8 (PA-457), which has successfully completed a Phase IIa clinical trial. Compound 20 showed potent anti-HIV activity with EC50 values of 0.0085 mu M against NL4-3, 0.021 mu M against PI-R (a multiple protease inhibitor resistant strain), and 0.13 mu M against FHR-2 (an HIV strain resistant to 8). Promising compound 20 has become a new lead for modification, and further development of 20-related compounds as clinical trial candidates is warranted.

  DOI：

  10.1021/jm0601912
• 作为产物：
  描述：

  黄莲木酸 在 sodium tetrahydroborate 、 草酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(olean-3β-hydroxy-18-en-28-oyl)-(1-hydroxymethyl-3-methyl)-butylamide
  参考文献：
  名称：

  Anti-AIDS Agents 69. Moronic Acid and Other Triterpene Derivatives as Novel Potent Anti-HIV Agents

  摘要：

  In a continuing structure-activity relationship study of potent anti-HIV agents, seven new triterpene derivatives were designed, synthesized, and evaluated for in vitro antiviral activity. Among them, moronic acid derivatives 19, 20, and 21 showed significant activity in HIV-1 infected H9 lymphocytes. Compounds 19 and 20 were also evaluated against HIV-1 NL4-3 and drug resistant strains in the MT-4 cell line. Compounds 19 and 20 showed better antiviral profiles than the betulinic acid analogue 8 (PA-457), which has successfully completed a Phase IIa clinical trial. Compound 20 showed potent anti-HIV activity with EC50 values of 0.0085 mu M against NL4-3, 0.021 mu M against PI-R (a multiple protease inhibitor resistant strain), and 0.13 mu M against FHR-2 (an HIV strain resistant to 8). Promising compound 20 has become a new lead for modification, and further development of 20-related compounds as clinical trial candidates is warranted.

  DOI：

  10.1021/jm0601912

文献信息

• Anti-retroviral moronic acid derivatives
  申请人：Lee Kuo-Hsiung

  公开号：US20060004097A1

  公开（公告）日：2006-01-05

  The present invention provides moronic acid derivatives of the general formula: which have antiviral activity, along with compositions containing the same and methods of use thereof.

  本发明提供了一种具有抗病毒活性的莫罗酸衍生物，其一般式为：，以及含有该衍生物的组合物和使用方法。