N-(olean-3-oxo-18-en-28-oyl)-aminoundecanoic acid methyl ester | 912271-67-1

• 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-3-oxo-18-en-28-oyl)-aminoundecanoic acid methyl ester
• 英文别名: methyl 11-[[(4aS,6aR,6aR,6bR,8aR,12aR,14aS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-4,5,6,6a,7,8,8a,11,12,13,14,14a-dodecahydro-3H-picene-4a-carbonyl]amino]undecanoate
• CAS: 912271-67-1
• 化学式: C₄₂H₆₉NO₄
• 分子量: 652.014
• InChiKey: GHWBGTNEURREBM-PWIHYUTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(olean-3-oxo-18-en-28-oyl)-aminoundecanoic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 11-[[(4aS,6aR,6aR,6bR,8aR,10S,12aR,14aS)-10-(3-carboxy-2,2-dimethylpropanoyl)oxy-2,2,6a,6b,9,9,12a-heptamethyl-3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a-tetradecahydropicene-4a-carbonyl]amino]undecanoic acid
  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：

  methyl 11-aminoundecanoate 、 黄莲木酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以51%的产率得到N-(olean-3-oxo-18-en-28-oyl)-aminoundecanoic acid methyl ester
  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