2-{3-[4-(3-methylbenzofuran-2-carbonyl)piperazin-1-yl]-3-oxo-propyl}-3H-quinazolin-4-one | 1537890-84-8

• 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: 2-{3-[4-(3-methylbenzofuran-2-carbonyl)piperazin-1-yl]-3-oxo-propyl}-3H-quinazolin-4-one
• 英文别名: 2-[3-[4-(3-methyl-1-benzofuran-2-carbonyl)piperazin-1-yl]-3-oxopropyl]-3H-quinazolin-4-one
• CAS: 1537890-84-8
• 化学式: C₂₅H₂₄N₄O₄
• 分子量: 444.49
• InChiKey: HPXHWIPGJAHDJI-UHFFFAOYSA-N

物化性质

• 沸点：
  718.9±70.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  C₁₉H₂₄N₂O₄ 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 2-{3-[4-(3-methylbenzofuran-2-carbonyl)piperazin-1-yl]-3-oxo-propyl}-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

文献信息

• Novel PARP-1 inhibitors based on a 2-propanoyl-3H-quinazolin-4-one scaffold
  作者：Giuseppe Giannini、Gianfranco Battistuzzi、Loredana Vesci、Ferdinando M. Milazzo、Francesca De Paolis、Marcella Barbarino、Mario Berardino Guglielmi、Valeria Carollo、Grazia Gallo、Roberto Artali、Sabrina Dallavalle

  DOI：10.1016/j.bmcl.2013.12.048

  日期：2014.1

  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.