(3S,3aR,8S,8aS)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-6-dodecanoyloxy-8-isopropyl-8-methyl-1-oxo-3,3a,8,8a-tetrahydro-1H-indeno[1,2-c]pyrrole-2-carboxylic acid tert-butyl ester | 348642-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (3S,3aR,8S,8aS)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-6-dodecanoyloxy-8-isopropyl-8-methyl-1-oxo-3,3a,8,8a-tetrahydro-1H-indeno[1,2-c]pyrrole-2-carboxylic acid tert-butyl ester
• CAS: 348642-94-4
• 化学式: C₃₉H₆₅NO₆Si
• 分子量: 672.034
• InChiKey: CZNZQXFEUGEEAC-MLMRVGIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.31
• 重原子数：
  47.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,3aR,8S,8aS)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-6-dodecanoyloxy-8-isopropyl-8-methyl-1-oxo-3,3a,8,8a-tetrahydro-1H-indeno[1,2-c]pyrrole-2-carboxylic acid tert-butyl ester 在 氢氟酸 作用下， 以 乙腈 为溶剂， 以95%的产率得到(3S,8S,9S,10R)-6-dodecanoyloxyl-3-hydroxymethyl-8-isopropyl-8-methyl-3,3a,8,8a-tetrahydro-2H-2-aza-cyclopenta[a]inden-1-one
  参考文献：
  名称：

  Rational design, synthesis, and biological evaluation of rigid pyrrolidone analogues as potential inhibitors of prostate cancer cell growth

  摘要：

  In view of its role in tumor promotion and signal transduction, protein kinase C (PKC) has proven to be an exciting target for cancer therapy. With the aid of molecular modeling, we rationally designed and stereoselectively synthesized a new class of rigidified pyrrolidone-based PKC activators. Pyrrolidone 15 was found to exhibit reasonable affinity for PKC delta, with lower affinity for the other isozymes tested. Pyrrolidone 2 causes the dose-dependent induction of apoptosis in LNCaP prostate cancer cells. This apoptotic effect could be markedly potentiated by the use of LNCaP cells overexpressing the PKC alpha or delta isozymes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00097-x
• 作为产物：
  描述：

  2-溴-5-羟基苯甲醛 在 palladium on activated charcoal 吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三氟化硼乙醚 、 氢气 、 三正丁基氢锡 、 sodium hydride 、 magnesium 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (3S,3aR,8S,8aS)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-6-dodecanoyloxy-8-isopropyl-8-methyl-1-oxo-3,3a,8,8a-tetrahydro-1H-indeno[1,2-c]pyrrole-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Rational design, synthesis, and biological evaluation of rigid pyrrolidone analogues as potential inhibitors of prostate cancer cell growth

  摘要：

  In view of its role in tumor promotion and signal transduction, protein kinase C (PKC) has proven to be an exciting target for cancer therapy. With the aid of molecular modeling, we rationally designed and stereoselectively synthesized a new class of rigidified pyrrolidone-based PKC activators. Pyrrolidone 15 was found to exhibit reasonable affinity for PKC delta, with lower affinity for the other isozymes tested. Pyrrolidone 2 causes the dose-dependent induction of apoptosis in LNCaP prostate cancer cells. This apoptotic effect could be markedly potentiated by the use of LNCaP cells overexpressing the PKC alpha or delta isozymes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00097-x