2-(2-chloroacetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-chloroacetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide
• 英文别名: 2-[[2-[(2-chloroacetyl)amino]pyridin-4-yl]methylsulfanyl]-N-(3,5-dimethylphenyl)pyridine-3-carboxamide
• 化学式: C₂₂H₂₁ClN₄O₂S
• 分子量: 440.953
• InChiKey: AXAJKTPIBWELEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-chloroacetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide 、 N,N-二甲基乙二胺 反应 0.17h， 以37%的产率得到2-[2-(2-dimethylaminoethyl)aminoacetylaminopyridin-4-ylmethylthio]-N-(3,5-dimethylphenyl)pyridine-3-carboxamide
  参考文献：
  名称：

  Pyridylmethylthio derivatives as VEGF inhibitors: Part 2

  摘要：

  Optimization of compounds 5 and 6 led to the discovery of VEGF inhibitor 10g which reduced CYP inhibition. It was highly active in vitro (VEGF induced HUVEC proliferation assay) and showed efficacies in three disease models in vivo (cancer, RA, and AMD). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.071
• 作为产物：
  描述：

  2-巯基烟酸 在 氯化亚砜 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.75h， 生成 2-(2-chloroacetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide
  参考文献：
  名称：

  Pyridylmethylthio derivatives as VEGF inhibitors: Part 2

  摘要：

  Optimization of compounds 5 and 6 led to the discovery of VEGF inhibitor 10g which reduced CYP inhibition. It was highly active in vitro (VEGF induced HUVEC proliferation assay) and showed efficacies in three disease models in vivo (cancer, RA, and AMD). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.071

文献信息

• Novel cyclic compound having 4-pyridylalkylthio group having substituted or unsubstituted amino group introduced therein
  申请人：Honda Takahiro

  公开号：US20070149574A1

  公开（公告）日：2007-06-28

  A novel cyclic compound having a 4-pyridylalkylthio group having an (un)substituted amino group introduced therein or a salt thereof. They are useful as a medicine. The cyclic compound is a compound represented by the following formula (1), which is useful for the treatment of diseases in which angiogenesis participates. In the following formula (1), ring A represents a benzene ring or a 5- or 6-membered aromatic heterocycle optionally fused with a cycloalkane ring; B represents alkylene; R 1 and R 2 each represents H, (substituted) aryl, (substituted) heterocyclic group, etc.; R 3 and R 4 each represents H, (substituted) alkyl, (substituted) cycloalkyl, -Z-R 5 , etc.; R 5 represents (substituted) alkyl, (substituted) aryl, (substituted) heterocyclic group, etc.; X and Y each represents H, etc.; Z represents —CO—, —COO—, —CONR 6 —, —SO 2 —, etc.; R 6 represents H, etc.; p is 0, 1, or 2; and q is 0 or 1.

  一种具有4-吡啶基烷基硫基团的新型环状化合物，其中引入了（未）取代氨基或其盐。它们可用作药物。环状化合物是由以下式（1）表示的化合物，可用于治疗参与血管生成的疾病。在下式（1）中，环A表示苯环或5-或6-成员芳香杂环，可选择地与环烷环融合；B表示烷基；R1和R2各表示H，（取代）芳基，（取代）杂环基等；R3和R4各表示H，（取代）烷基，（取代）环烷基，-Z-R5等；R5表示（取代）烷基，（取代）芳基，（取代）杂环基等；X和Y各表示H等；Z表示-CO-，-COO-，-CONR6-，-SO2-等；R6表示H等；p为0、1或2；q为0或1。
• US7544703B2
  申请人：——

  公开号：US7544703B2

  公开（公告）日：2009-06-09
• Pyridylmethylthio derivatives as VEGF inhibitors: Part 2
  作者：Hisashi Tajima、Takahiro Honda、Kenji Kawashima、Yoshimasa Sasabuchi、Minoru Yamamoto、Masakazu Ban、Kazuyoshi Okamoto、Kenji Inoue、Takaaki Inaba、Yuriko Takeno、Takashi Tsuboi、Asaka Tonouchi、Hiroyuki Aono

  DOI：10.1016/j.bmcl.2010.12.071

  日期：2011.2

  Optimization of compounds 5 and 6 led to the discovery of VEGF inhibitor 10g which reduced CYP inhibition. It was highly active in vitro (VEGF induced HUVEC proliferation assay) and showed efficacies in three disease models in vivo (cancer, RA, and AMD). (C) 2010 Elsevier Ltd. All rights reserved.