4-bromo-5-(3-chlorophenyl)-N-cyclopentylisoxazole-3-carboxamide | 1273029-86-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-bromo-5-(3-chlorophenyl)-N-cyclopentylisoxazole-3-carboxamide
• 英文别名: 4-bromo-5-(3-chlorophenyl)-N-cyclopentyl-1,2-oxazole-3-carboxamide
• CAS: 1273029-86-9
• 化学式: C₁₅H₁₄BrClN₂O₂
• 分子量: 369.645
• InChiKey: RCPHTZSHFQKRLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(3-氯苯基)-异噁唑-3-羧酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 4-bromo-5-(3-chlorophenyl)-N-cyclopentylisoxazole-3-carboxamide
  参考文献：
  名称：

  Structure–activity studies of a novel series of isoxazole-3-carboxamide derivatives as TRPV1 antagonists

  摘要：

  Optimisation of a screening hit incorporating both TRPV1 activity and solubility was conducted. Substitution of the isoxazole-3-carboxamide with the bespoke 1S, 3R-3-aminocyclohexanol motif afforded the requisite balance of potency and solubility. Compounds 32 and 40 were found to have antihyperalgesic effects in the rat CFA Hg assay and induce a mechanism based hyperthermia. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.092

文献信息

• Structure–activity studies of a novel series of isoxazole-3-carboxamide derivatives as TRPV1 antagonists
  作者：Ronald Palin、Lynn Abernethy、Nasrin Ansari、Kenneth Cameron、Tom Clarkson、Maureen Dempster、David Dunn、Anna-Marie Easson、Darren Edwards、John Maclean、Katy Everett、Helen Feilden、Koc-Kan Ho、Steve Kultgen、Peter Littlewood、Duncan McArthur、Deborah McGregor、Hazel McLuskey、Irina Neagu、Stuart Neale、Lesley-Anne Nisbet、Michael Ohlmeyer、Quynhchi Pham、Paul Ratcliffe、Yajing Rong、Andrew Roughton、Melanie Sammons、Robert Swanson、Heather Tracey、Glenn Walker

  DOI：10.1016/j.bmcl.2010.12.092

  日期：2011.2

  Optimisation of a screening hit incorporating both TRPV1 activity and solubility was conducted. Substitution of the isoxazole-3-carboxamide with the bespoke 1S, 3R-3-aminocyclohexanol motif afforded the requisite balance of potency and solubility. Compounds 32 and 40 were found to have antihyperalgesic effects in the rat CFA Hg assay and induce a mechanism based hyperthermia. (C) 2010 Elsevier Ltd. All rights reserved.