piperazin-1-yl(thiophen-2-yl)methanonetrifluoroacetate salt | 477204-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: piperazin-1-yl(thiophen-2-yl)methanonetrifluoroacetate salt
• 英文别名: 1-(2-Thienylcarbonyl)piperazine trifluoroacetate；piperazin-1-yl(thiophen-2-yl)methanone;2,2,2-trifluoroacetic acid
• CAS: 477204-94-7
• 化学式: C₂HF₃O₂*C₉H₁₂N₂OS
• 分子量: 310.297
• InChiKey: BLRUMSYYHSFSKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  97.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  piperazin-1-yl(thiophen-2-yl)methanonetrifluoroacetate salt 、 3-(4-氧代-3,4-二氢-2-喹唑啉)-丙酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92 mg的产率得到2-{3-oxo-3-[4-(thiophen-2-ylcarbonyl)piperazin-1-yl]propyl}quinazolin-4(3H)-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：

  2-噻吩甲酸 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 piperazin-1-yl(thiophen-2-yl)methanonetrifluoroacetate salt
  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.