2-fluoro-5-[(1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]benzonitrile | 1111085-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡嗪类
• 英文名称: 2-fluoro-5-[(1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]benzonitrile
• CAS: 1111085-63-2
• 化学式: C₁₅H₁₀FN₃O
• 分子量: 267.262
• InChiKey: IETQBHPIGQIQAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-fluoro-5-[(1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]benzonitrile 在 水 、 sodium hydroxide 作用下， 生成 2-fluoro-5-[(1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-4-yl)methyl]benzoic acid
  参考文献：
  名称：

  Identification and SAR of novel pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1)

  摘要：

  Herein we describe the discovery of a novel series of pyrrolo[1,2-a]pyrazin-1(2H)-one PARP inhibitors. Optimization led to compounds that display excellent PARP-1 enzyme potency and inhibit the proliferation of BRCA deficient cells in the low double-digit nanomolar range showing excellent selectivity over BRCA proficient cancer cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.026
• 作为产物：
  描述：

  N-[3-(3-cyano-4-fluorophenyl)prop-2-yn-1-yl]-N-(2,4-dimethoxybenzyl)-1H-pyrrole-2-carboxamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.28h， 以42 mg的产率得到2-fluoro-5-[(1-oxo-2H-pyrrolo[1,2-a]pyrazin-4-yl)methyl]benzonitrile
  参考文献：
  名称：

  A novel base-mediated intramolecular hydroamination to build fused heteroaryl pyrazinones

  摘要：

  Functionalized fused heteroaryl pyrazinones were built up through a novel DBU-catalyzed intramolecular hydroamination reaction of aryl(prop-2-yn-1-yl)-1H-heteroaryl-2-carboxamides. The nucleophilic addition afforded three isomers; two with an exo-cyclic double bond [cis (Z), trans (E)], and a third one with an endo-cyclic double bond. After the carboxamide deprotection, isomerization of the mixture under acidic conditions resulted in a unique isomer. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.116

文献信息

• Identification and SAR of novel pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1)
  作者：Giovanna Pescatore、Danila Branca、Fabrizio Fiore、Olaf Kinzel、Laura Llauger Bufi、Ester Muraglia、Federica Orvieto、Michael Rowley、Carlo Toniatti、Caterina Torrisi、Philip Jones

  DOI：10.1016/j.bmcl.2009.12.026

  日期：2010.2

  Herein we describe the discovery of a novel series of pyrrolo[1,2-a]pyrazin-1(2H)-one PARP inhibitors. Optimization led to compounds that display excellent PARP-1 enzyme potency and inhibit the proliferation of BRCA deficient cells in the low double-digit nanomolar range showing excellent selectivity over BRCA proficient cancer cells. (C) 2009 Elsevier Ltd. All rights reserved.
• A novel base-mediated intramolecular hydroamination to build fused heteroaryl pyrazinones
  作者：Laura Llauger、Costanza Bergami、Olaf D. Kinzel、Samuele Lillini、Giovanna Pescatore、Caterina Torrisi、Philip Jones

  DOI：10.1016/j.tetlet.2008.10.116

  日期：2009.1

  Functionalized fused heteroaryl pyrazinones were built up through a novel DBU-catalyzed intramolecular hydroamination reaction of aryl(prop-2-yn-1-yl)-1H-heteroaryl-2-carboxamides. The nucleophilic addition afforded three isomers; two with an exo-cyclic double bond [cis (Z), trans (E)], and a third one with an endo-cyclic double bond. After the carboxamide deprotection, isomerization of the mixture under acidic conditions resulted in a unique isomer. (C) 2008 Elsevier Ltd. All rights reserved.