tert-butyl 3-((2E)-3-[2,5-dihydro-4-(5-methoxy-1H-indol-3-yl)-2,5-dioxo-1H-pyrrol-3-yl]acrylamidomethyl) benzoate | 1258285-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 3-((2E)-3-[2,5-dihydro-4-(5-methoxy-1H-indol-3-yl)-2,5-dioxo-1H-pyrrol-3-yl]acrylamidomethyl) benzoate
• CAS: 1258285-79-8
• 化学式: C₂₈H₂₇N₃O₆
• 分子量: 501.539
• InChiKey: PQTXYBSVKMDTNA-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  126.59
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-((2E)-3-[2,5-dihydro-4-(5-methoxy-1H-indol-3-yl)-2,5-dioxo-1H-pyrrol-3-yl]acrylamidomethyl) benzoate 在 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以73%的产率得到5-[(3-tert-butoxycarbonyl)benzylaminocarboyl]-9-methoxy-1,3-dihydropyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
  参考文献：
  名称：

  Synthesis and evaluation of 5-substituted 9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones as check point 1 kinase inhibitors

  摘要：

  The structure-activity relationship (SAR) of 5-substituted pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione derivatives 5 was investigated for their potential as Chk1 inhibitors for possible chemo- and radio-potentiators in anticancer chemotherapies. In silico virtual screening helped to optimize the substituent on the phenyl ring, and led to identification of the m-carbamoyl group among the 117 analogues tested. Further optimization studies focusing on the docking model of 15 in the active site of Chk1 revealed that 32b (IC50 = 2.8 nM) was a more potent inhibitor than UNC-01. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.042
• 作为产物：
  描述：

  tert-butyl 3-(acrylamidomethyl)benzoate 、 3-bromo-4-(5-methoxy-3-indolyl)-1H-pyrrole-2,5-dione 在 三正丁胺 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以83%的产率得到tert-butyl 3-((2E)-3-[2,5-dihydro-4-(5-methoxy-1H-indol-3-yl)-2,5-dioxo-1H-pyrrol-3-yl]acrylamidomethyl) benzoate
  参考文献：
  名称：

  Synthesis and evaluation of 5-substituted 9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-diones as check point 1 kinase inhibitors

  摘要：

  The structure-activity relationship (SAR) of 5-substituted pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione derivatives 5 was investigated for their potential as Chk1 inhibitors for possible chemo- and radio-potentiators in anticancer chemotherapies. In silico virtual screening helped to optimize the substituent on the phenyl ring, and led to identification of the m-carbamoyl group among the 117 analogues tested. Further optimization studies focusing on the docking model of 15 in the active site of Chk1 revealed that 32b (IC50 = 2.8 nM) was a more potent inhibitor than UNC-01. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.042