11-{[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-(1-pyrrolidin-1-ylmethyl-vinyl)-icosahydro-cyclopenta[a]chrysene-3a-carbonyl]-amino}-undecanoic acid | 150840-87-2

• 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: 11-{[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-(1-pyrrolidin-1-ylmethyl-vinyl)-icosahydro-cyclopenta[a]chrysene-3a-carbonyl]-amino}-undecanoic acid
• 英文别名: N-(3beta-Hydroxy-30-pyrrolidinolup-20(29)-en-28-oyl)-11-aminoundecanoic acid；11-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(3-pyrrolidin-1-ylprop-1-en-2-yl)-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]amino]undecanoic acid
• CAS: 150840-87-2
• 化学式: C₄₅H₇₆N₂O₄
• 分子量: 709.109
• InChiKey: HKTYZRFGHVZYAO-PIGSMCEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  89.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-O-acetylbetulinic acid chloride 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 244.0h， 生成 11-{[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-(1-pyrrolidin-1-ylmethyl-vinyl)-icosahydro-cyclopenta[a]chrysene-3a-carbonyl]-amino}-undecanoic acid
  参考文献：
  名称：

  Betulinic Acid Derivatives:  A New Class of Human Immunodeficiency Virus Type 1 Specific Inhibitors with a New Mode of Action

  摘要：

  A series of omega-undecanoic amides of lup-20(29)-en-28-oic acid derivatives were synthesized and evaluated for activity in CEM 4 and MT-4 cell cultures against human immunodeficiency virus type 1 (HIV-1) strain IIIB/LAI. The potent HIV inhibitors which emerged, compounds 5a, 16a, and 17b, were all derivatives of betulinic acid (3 beta-hydroxylup-20(29)-en-28-oic acid). No activity was found against HIV-2 strain ROD. Compound 5a showed no inhibition of HIV-1 reverse transcriptase activity with poly(C). oligo(dG) as template/primer, nor did it inhibit HIV-1 protease. Additional mechanistic studies revealed that this class of compounds interfere with HIV-1 entry in the cells at a postbinding step.

  DOI：

  10.1021/jm950670t

文献信息

• Betulinic Acid Derivatives:  A New Class of Human Immunodeficiency Virus Type 1 Specific Inhibitors with a New Mode of Action
  作者：Michel Evers、Christèle Poujade、Françoise Soler、Yves Ribeill、Claude James、Yves Lelièvre、Jean-Christophe Gueguen、Daniel Reisdorf、Isabelle Morize、Rudi Pauwels、Erik De Clercq、Yvette Hénin、Anne Bousseau、Jean-François Mayaux、Jean-Bernard Le Pecq、Norbert Dereu

  DOI：10.1021/jm950670t

  日期：1996.1.1

  A series of omega-undecanoic amides of lup-20(29)-en-28-oic acid derivatives were synthesized and evaluated for activity in CEM 4 and MT-4 cell cultures against human immunodeficiency virus type 1 (HIV-1) strain IIIB/LAI. The potent HIV inhibitors which emerged, compounds 5a, 16a, and 17b, were all derivatives of betulinic acid (3 beta-hydroxylup-20(29)-en-28-oic acid). No activity was found against HIV-2 strain ROD. Compound 5a showed no inhibition of HIV-1 reverse transcriptase activity with poly(C). oligo(dG) as template/primer, nor did it inhibit HIV-1 protease. Additional mechanistic studies revealed that this class of compounds interfere with HIV-1 entry in the cells at a postbinding step.