3β-<(dimethyl-tert-butylsilyl)oxy>lup-20(29)-en-28-al | 173106-51-9

• 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: 3β-<(dimethyl-tert-butylsilyl)oxy>lup-20(29)-en-28-al
• 英文别名: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[tert-butyl(dimethyl)silyl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbaldehyde
• CAS: 173106-51-9
• 化学式: C₃₆H₆₂O₂Si
• 分子量: 554.973
• InChiKey: JJJDXIWDHGIMDW-WHONGPPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.23
• 重原子数：
  39
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-<(dimethyl-tert-butylsilyl)oxy>lup-20(29)-en-28-al 在 sodium hydroxide 、 三氯化铁 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 180.0h， 生成 11-(((3beta-羟基羽扇-20(29)-烯-28-酰基)甲基)氨基)氨基十一烷酸
  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：

  (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(tert-Butyl-dimethyl-silanyloxy)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 88.25h， 生成 3β-<(dimethyl-tert-butylsilyl)oxy>lup-20(29)-en-28-al
  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