5-Chloro-N-(5-chloro-pyridin-2-yl)-2-(4-{[methyl-(2-methylamino-ethyl)-amino]-methyl}-benzoylamino)-benzamide | 679426-68-7

• 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: 5-Chloro-N-(5-chloro-pyridin-2-yl)-2-(4-{[methyl-(2-methylamino-ethyl)-amino]-methyl}-benzoylamino)-benzamide
• 英文别名: 5-chloro-N-(5-chloropyridin-2-yl)-2-[[4-[[methyl-[2-(methylamino)ethyl]amino]methyl]benzoyl]amino]benzamide
• CAS: 679426-68-7
• 化学式: C₂₄H₂₅Cl₂N₅O₂
• 分子量: 486.401
• InChiKey: HVZQBAZMFIUZBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1H-吡唑-1-甲脒盐酸盐 、 5-Chloro-N-(5-chloro-pyridin-2-yl)-2-(4-{[methyl-(2-methylamino-ethyl)-amino]-methyl}-benzoylamino)-benzamide 在 TEA 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-[[4-[[2-[carbamimidoyl(methyl)amino]ethyl-methylamino]methyl]benzoyl]amino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide
  参考文献：
  名称：

  Design, synthesis, and SAR of anthranilamide-based factor Xa inhibitors with improved functional activity

  摘要：

  Compound 2 containing an aminomethylbenzoyl moiety as the S4 binding motif was synthesized in order to modulate hydrophlicity of anthranilamide-based factor Xa inhibitors with substituted biphenyl P4 groups. Structure-activity relationship studies around 2 have led to a series of potent factor Xa inhibitors which are highly active in the human plasma-based thrombin generation assay with 2XTG values less than 1 muM. Compound 55 shows strong antithrombotic activity in our rabbit deep vein thrombosis model, and also exhibits good oral bioavailability and a long half life in rats. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2003.11.080
• 作为产物：
  描述：

  5-氯-2-硝基苯甲酸 在 吡啶 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.08h， 生成 5-Chloro-N-(5-chloro-pyridin-2-yl)-2-(4-{[methyl-(2-methylamino-ethyl)-amino]-methyl}-benzoylamino)-benzamide
  参考文献：
  名称：

  Design, synthesis, and SAR of anthranilamide-based factor Xa inhibitors with improved functional activity

  摘要：

  Compound 2 containing an aminomethylbenzoyl moiety as the S4 binding motif was synthesized in order to modulate hydrophlicity of anthranilamide-based factor Xa inhibitors with substituted biphenyl P4 groups. Structure-activity relationship studies around 2 have led to a series of potent factor Xa inhibitors which are highly active in the human plasma-based thrombin generation assay with 2XTG values less than 1 muM. Compound 55 shows strong antithrombotic activity in our rabbit deep vein thrombosis model, and also exhibits good oral bioavailability and a long half life in rats. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2003.11.080

文献信息

• Design, synthesis, and SAR of anthranilamide-based factor Xa inhibitors with improved functional activity
  作者：Penglie Zhang、Liang Bao、Jingmei F. Zuckett、Zhaozhong J. Jia、John Woolfrey、Ann Arfsten、Susan Edwards、Uma Sinha、Athiwat Hutchaleelaha、Joseph L. Lambing、Stanley J. Hollenbach、Robert M. Scarborough、Bing-Yan Zhu

  DOI：10.1016/j.bmcl.2003.11.080

  日期：2004.2

  Compound 2 containing an aminomethylbenzoyl moiety as the S4 binding motif was synthesized in order to modulate hydrophlicity of anthranilamide-based factor Xa inhibitors with substituted biphenyl P4 groups. Structure-activity relationship studies around 2 have led to a series of potent factor Xa inhibitors which are highly active in the human plasma-based thrombin generation assay with 2XTG values less than 1 muM. Compound 55 shows strong antithrombotic activity in our rabbit deep vein thrombosis model, and also exhibits good oral bioavailability and a long half life in rats. (C) 2004 Published by Elsevier Ltd.