11-{[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-(1-bromomethyl-vinyl)-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl]-amino}-undecanoic acid methyl ester | 173106-29-1

• 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: 11-{[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-(1-bromomethyl-vinyl)-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl]-amino}-undecanoic acid methyl ester
• 英文别名: methyl 11-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-acetyloxy-1-(3-bromoprop-1-en-2-yl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]amino]undecanoate
• CAS: 173106-29-1
• 化学式: C₄₄H₇₂BrNO₅
• 分子量: 774.963
• InChiKey: GWPYBSIRKBHTPS-VYXZDGRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  11-{[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-(1-bromomethyl-vinyl)-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl]-amino}-undecanoic acid methyl ester 在 sodium hydroxide 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 216.0h， 生成 11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-[1-(2-Diethylamino-ethylsulfanylmethyl)-vinyl]-9-hydroxy-5a,5b,8,8,11a-pentamethyl-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
• 作为产物：
  描述：

  3Beta-乙酰氧基白桦酸 在 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 氯仿 为溶剂， 反应 106.0h， 生成 11-{[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-(1-bromomethyl-vinyl)-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