11-[((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-1,2,3,4,5,5a,5b,6,7,7a,8,9,11a,11b,12,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-undecanoic acid methyl ester | 173106-23-5

• 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,11aR,11bR,13aR,13bR)-10-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-1,2,3,4,5,5a,5b,6,7,7a,8,9,11a,11b,12,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-undecanoic acid methyl ester
• 英文别名: methyl 11-[[(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysene-3a-carbonyl]amino]undecanoate
• CAS: 173106-23-5
• 化学式: C₄₂H₆₇NO₅
• 分子量: 665.998
• InChiKey: IVOTWPPVNYKDFK-OUYBJUHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11-[((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-1,2,3,4,5,5a,5b,6,7,7a,8,9,11a,11b,12,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-undecanoic acid methyl ester 在 四氯化钛 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以32.3%的产率得到11-[((1R,3aS,5aR,5bR,7aR,9R,10S,11aR,11bR,13aR,13bR)-9,10-Dihydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-undecanoic acid methyl ester
  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
• 作为产物：
  描述：

  2-hydroxy-3-oxolupa-1,20(29)-dien-28-oic acid 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成 11-[((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-1,2,3,4,5,5a,5b,6,7,7a,8,9,11a,11b,12,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-undecanoic acid methyl ester
  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