4-(((3-chlorophenyl)(pyridin-4-yl)amino)methyl)-7,8-difluoroquinolin-2(1H)-one | 1125862-18-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(((3-chlorophenyl)(pyridin-4-yl)amino)methyl)-7,8-difluoroquinolin-2(1H)-one
• 英文别名: 4-[(3-chloro-N-pyridin-4-ylanilino)methyl]-7,8-difluoro-1H-quinolin-2-one
• CAS: 1125862-18-1
• 化学式: C₂₁H₁₄ClF₂N₃O
• 分子量: 397.811
• InChiKey: HSXXFRQLNFQLQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(2,3-二氟苯基)-3-氧代丁酰胺 在 硫酸 、 溴 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-(((3-chlorophenyl)(pyridin-4-yl)amino)methyl)-7,8-difluoroquinolin-2(1H)-one
  参考文献：
  名称：

  Heteroaromatic-aminomethyl quinolones: Potent and selective iNOS inhibitors

  摘要：

  The overproduction of nitric oxide during the biological response to inflammation by the nitric oxide synthase (NOS) enzymes have been implicated in the pathology of many diseases. By removal of the amide core from uHTS-derived quinolone 4, a new series highly potent heteroaromatic-aminomethyl quinolone iNOS inhibitors 8 were identified. SAR studies led to identification of piperazine 22 and pyrimidine 32, both of which reduced plasma nitrates following oral dosing in a mouse lipopolysaccharide challenge assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.073

文献信息

• [EN] DIARYLAMINE-SUBSTITUTED QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] QUINOLONES SUBSTITUÉES PAR DIARYLAMINE UTILES COMME INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE INDUCTIBLE.
  申请人：KALYPSYS INC

  公开号：WO2009029617A1

  公开（公告）日：2009-03-05

  Novel diarylamine-substituted quinolone compounds and pharmaceutical compositions, certain of which have been found to inhibit inducible NOS synthase have been discovered, together with methods of synthesizing and using the compounds including methods for the treatment of iNOS-mediated diseases in a patient by administering the compounds.

  已发现新的含有二芳胺基取代喹诺酮化合物和药物组合物，其中一些已被发现能抑制诱导型NOS合成酶，还包括合成和使用这些化合物的方法，包括通过给患者施用这些化合物治疗iNOS介导的疾病的方法。
• Heteroaromatic-aminomethyl quinolones: Potent and selective iNOS inhibitors
  作者：Sergio G. Durón、Andrew Lindstrom、Céline Bonnefous、Hui Zhang、Xiaohong Chen、Kent T. Symons、Marciano Sablad、Natasha Rozenkrants、Yan Zhang、Li Wang、Nahid Yazdani、Andrew K. Shiau、Stewart A. Noble、Peter Rix、Tadimeti S. Rao、Christian A. Hassig、Nicholas D. Smith

  DOI：10.1016/j.bmcl.2011.11.073

  日期：2012.1

  The overproduction of nitric oxide during the biological response to inflammation by the nitric oxide synthase (NOS) enzymes have been implicated in the pathology of many diseases. By removal of the amide core from uHTS-derived quinolone 4, a new series highly potent heteroaromatic-aminomethyl quinolone iNOS inhibitors 8 were identified. SAR studies led to identification of piperazine 22 and pyrimidine 32, both of which reduced plasma nitrates following oral dosing in a mouse lipopolysaccharide challenge assay. (C) 2011 Elsevier Ltd. All rights reserved.