5-(4-氰基苯基)烟酸 | 845885-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-(4-氰基苯基)烟酸
• 英文名称: 5-(4-Cyanophenyl)nicotinic acid
• 英文别名: 5-(4-cyanophenyl)pyridine-3-carboxylic acid
• CAS: 845885-80-5
• 化学式: C₁₃H₈N₂O₂
• 分子量: 224.219
• InChiKey: YCOSFPRPICBYHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-氰基苯基)烟酸 、 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 5-(4-cyanophenyl)-N-(3,5-dimethylphenyl)nicotinamide
  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：

  5-(4-氰基苯基)烟酸乙酯 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-(4-氰基苯基)烟酸
  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

• Discovery of Potent Antimalarial Type II Kinase Inhibitors with Selectivity over Human Kinases
  作者：Lushun Wang、Monica J. Bohmer、Jinhua Wang、Flore Nardella、Jaeson Calla、Mariana Laureano De Souza、Kyra A. Schindler、Lukas Montejo、Nimisha Mittal、Frances Rocamora、Mayland Treat、Jordan T. Charlton、Patrick K. Tumwebaze、Philip J. Rosenthal、Roland A. Cooper、Ratna Chakrabarti、Elizabeth A. Winzeler、Debopam Chakrabarti、Nathanael S. Gray

  DOI：10.1021/acs.jmedchem.3c02046

  日期：2024.1.25

  urging a need for the development of novel antimalarial agents. Repurposing human kinase inhibitors provides a potential expedited route given the availability of a diverse array of kinase-targeting drugs that are approved or in clinical trials. Phenotypic screening of a library of type II human kinase inhibitors identified compound 1 as a lead antimalarial, which was initially developed to target human

  尽管根除疟疾的努力取得了进展，但该疾病仍然对全球健康构成重大威胁。非洲正在出现对一线治疗的获得性耐药，这迫切需要开发新型抗疟药物。鉴于已批准或正在进行临床试验的多种激酶靶向药物的可用性，重新利用人类激酶抑制剂提供了一条潜在的快速途径。对 II 型人类激酶抑制剂库的表型筛选将化合物1鉴定为一种主要抗疟药，该药物最初是针对人类肝配蛋白 A 型受体 2 (EphA2) 开发的。在这里，我们报告了化合物1的构效关系研究和先导化合物优化，最终得到了具有改善的抗疟活性和选择性的化合物33 。
• 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.