3-(4-Trifluoromethoxy-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid | 1258269-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-Trifluoromethoxy-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid
• 英文别名: 3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole-5-carboxylic acid
• CAS: 1258269-11-2
• 化学式: C₁₀H₅F₃N₂O₄
• 分子量: 274.156
• InChiKey: VPNVUWCQIRUJLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-(4-Trifluoromethoxy-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid 、 1-氨基-3,5-二甲苯 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3,5-dimethylphenyl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxamide
  参考文献：
  名称：

  Subtype-selective Nav1.8 sodium channel blockers: Identification of potent, orally active nicotinamide derivatives

  摘要：

  A series of aryl-substituted nicotinamide derivatives with selective inhibitory activity against the Na(v)1.8 sodium channel is reported. Replacement of the furan nucleus and homologation of the anilide linker in subtype-selective blocker A-803467 (1) provided potent, selective derivatives with improved aqueous solubility and oral bioavailability. Representative compounds from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.121
• 作为产物：
  描述：

  ethyl 3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxylate 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(4-Trifluoromethoxy-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid
  参考文献：
  名称：

  Subtype-selective Nav1.8 sodium channel blockers: Identification of potent, orally active nicotinamide derivatives

  摘要：

  A series of aryl-substituted nicotinamide derivatives with selective inhibitory activity against the Na(v)1.8 sodium channel is reported. Replacement of the furan nucleus and homologation of the anilide linker in subtype-selective blocker A-803467 (1) provided potent, selective derivatives with improved aqueous solubility and oral bioavailability. Representative compounds from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.121

文献信息

• HETEROCYCLIC MODULATORS OF HIF ACTIVITY FOR TREATMENT OF DISEASE
  申请人：Institute For Applied Cancer Science/The University of Texas MD Anderson Cancer Center

  公开号：US20140057914A1

  公开（公告）日：2014-02-27

  The present invention relates to compounds and methods which may be useful as inhibitors of HIF pathway activity for the treatment or prevention of cancer and other hypoxia-mediated diseases.

  本发明涉及化合物和方法，可能用作HIF通路活性的抑制剂，用于治疗或预防癌症和其他缺氧介导的疾病。
• US9115120B2
  申请人：——

  公开号：US9115120B2

  公开（公告）日：2015-08-25
• [EN] HETEROCYCLIC MODULATORS OF HIF ACTIVITY FOR TREATMENT OF DISEASE<br/>[FR] MODULATEURS HÉTÉROCYCLIQUES DE L'ACTIVITÉ DU FACTEUR HIF UTILISÉS POUR LE TRAITEMENT DE MALADIES
  申请人：JONES PHILIP

  公开号：WO2014031933A2

  公开（公告）日：2014-02-27

  The present invention relates to compounds and methods which may be useful as inhibitors of HIF pathway activity for the treatment or prevention of cancer and other hypoxia-mediated diseases.
• Subtype-selective Nav1.8 sodium channel blockers: Identification of potent, orally active nicotinamide derivatives
  作者：Michael E. Kort、Robert N. Atkinson、James B. Thomas、Irene Drizin、Matthew S. Johnson、Matthew A. Secrest、Robert J. Gregg、Marc J.C. Scanio、Lei Shi、Ahmed H. Hakeem、Mark A. Matulenko、Mark L. Chapman、Michael J. Krambis、Dong Liu、Char-Chang Shieh、XuFeng Zhang、Gricelda Simler、Joseph P. Mikusa、Chengmin Zhong、Shailen Joshi、Prisca Honore、Rosemarie Roeloffs、Stephen Werness、Brett Antonio、Kennan C. Marsh、Connie R. Faltynek、Douglas S. Krafte、Michael F. Jarvis、Brian E. Marron

  DOI：10.1016/j.bmcl.2010.08.121

  日期：2010.11

  A series of aryl-substituted nicotinamide derivatives with selective inhibitory activity against the Na(v)1.8 sodium channel is reported. Replacement of the furan nucleus and homologation of the anilide linker in subtype-selective blocker A-803467 (1) provided potent, selective derivatives with improved aqueous solubility and oral bioavailability. Representative compounds from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.