3-{4-[3-(4-oxo-3,4-dihydroquinazolin-2-yl)propionyl]piperazine-1-carbonyl}piperidine-1-carboxylic acid allyl ester | 1537890-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-{4-[3-(4-oxo-3,4-dihydroquinazolin-2-yl)propionyl]piperazine-1-carbonyl}piperidine-1-carboxylic acid allyl ester
• 英文别名: prop-2-enyl 3-[4-[3-(4-oxo-3H-quinazolin-2-yl)propanoyl]piperazine-1-carbonyl]piperidine-1-carboxylate
• CAS: 1537890-86-0
• 化学式: C₂₅H₃₁N₅O₅
• 分子量: 481.552
• InChiKey: XGRSSEKYHKHWFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-{4-[3-(4-oxo-3,4-dihydroquinazolin-2-yl)propionyl]piperazine-1-carbonyl}piperidine-1-carboxylic acid allyl ester 在 吗啉 、 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 生成 2-{3-oxo-3-[4-(piperidine-3-carbonyl)piperazin-1-yl]propyl}-3H-quinazolin-4-one 、 2-{3-[4-(1-allyl-piperidine-3-carbonyl)piperazin-1-yl]-3-oxopropyl}-3H-quinazolin-4-one
  参考文献：
  名称：

  Novel PARP-1 inhibitors based on a 2-propanoyl-3H-quinazolin-4-one scaffold

  摘要：

  Poly(ADP-ribose) polymerase-I (PARP-1) enzyme is involved in maintaining DNA integrity and programmed cell death. A virtual screening of commercial libraries led to the identification of five novel scaffolds with inhibitory profile in the low nanomolar range. A hit-to-lead optimization led to the identification of a group of new potent PARP-1 inhibitors, acyl-piperazinylamides of 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-propionic acid. Molecular modeling studies highlighted the preponderant role of the propanoyl side chain. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.048
• 作为产物：
  描述：

  C₁₉H₃₁N₃O₅ 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-{4-[3-(4-oxo-3,4-dihydroquinazolin-2-yl)propionyl]piperazine-1-carbonyl}piperidine-1-carboxylic acid allyl ester
  参考文献：
  名称：

  Novel PARP-1 inhibitors based on a 2-propanoyl-3H-quinazolin-4-one scaffold

  摘要：

  Poly(ADP-ribose) polymerase-I (PARP-1) enzyme is involved in maintaining DNA integrity and programmed cell death. A virtual screening of commercial libraries led to the identification of five novel scaffolds with inhibitory profile in the low nanomolar range. A hit-to-lead optimization led to the identification of a group of new potent PARP-1 inhibitors, acyl-piperazinylamides of 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-propionic acid. Molecular modeling studies highlighted the preponderant role of the propanoyl side chain. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.048