[5-(2-aminophenyl)furan-2-ylcarbonyl]guanidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: [5-(2-aminophenyl)furan-2-ylcarbonyl]guanidine
• 英文别名: 5-(2-aminophenyl)-N-carbamimidoylfuran-2-carboxamide
• 化学式: C₁₂H₁₂N₄O₂
• 分子量: 244.253
• InChiKey: HZBCBUSCPHAICY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 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：
  121
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴-2-糠酸甲酯 在 palladium on activated charcoal 四(三苯基膦)钯 、 氢气 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0 ℃ 、303.98 kPa 条件下， 反应 10.0h， 生成 [5-(2-aminophenyl)furan-2-ylcarbonyl]guanidine
  参考文献：
  名称：

  (5-Arylfuran-2-ylcarbonyl)guanidines as Cardioprotectives through the Inhibition of Na⁺/H⁺ Exchanger Isoform-1

  摘要：

  A series of (5-arylfuran-2-ylcarbonyl)guanidines was synthesized and evaluated for the NHE-1 inhibitory activity and cardiprotective efficacy against ischemia-reperfusion injury. Starting with (5-phenylfuran-2-ylcarbonyl)guanidine 47 with a moderate inhibitory effect on NHE-1, the compounds with various substituents at the phenyl ring were investigated with the aim to optimize the potency. In this study, the 2,5-disubstituted compounds appeared to have better activities than the other analogues, and the 2-methoxy-5-chlorophenyl compound 85 was found as a potent inhibitor of NHE-1 (IC50 = 0.081 mu M). Furthermore, 85 showed a marked reduction of infarct size in the rat myocardial infarction model in vivo and significant improvement of cardiac contractile function in the isolated rat heart ischemia model in vitro.

  DOI：

  10.1021/jm0492305

文献信息

• Furancarbonylguanidine Derivatives, Their Preparation and Pharmaceutical Compositions Containing Them
  申请人：Yi Yang Kyu

  公开号：US20070299131A1

  公开（公告）日：2007-12-27

  The present invention relates to furancarbonylguanidine derivatives, a preparation method thereof and a pharmaceutical composition comprising the same. Furancarbonylguanidine derivatives of the present invention inhibit NHE-1 (sodium-hydrogen exchanger isoform 1), which helps recovery of heart function damaged from ischemia/reperfusion and decreases myocardial infarction rate, indicating that they have protective effect on myocardial cells. Thus, furancarbonylguanidine derivatives of the present invention can be effectively used for the prevention and the treatment of ischemic heart diseases such as myocardial infarction, arrhythmia, angina pectoris, etc, and also a promising candidate for a heart protecting agent applied to reperfusion therapy including thrombolytics or cardiac surgery including coronary artery bypass graft, percutaneous transluminal coronary angioplasty, etc.

  本发明涉及呋喃羰基胍衍生物、其制备方法和包含它们的药物组合物。本发明的呋喃羰基胍衍生物抑制NHE-1（钠-氢交换体型1），有助于恢复因缺血/再灌注而受损的心脏功能，并降低心肌梗死率，表明它们对心肌细胞具有保护作用。因此，本发明的呋喃羰基胍衍生物可有效用于预防和治疗缺血性心脏病，如心肌梗死、心律失常、心绞痛等，并且是再灌注治疗（包括溶栓治疗）或冠状动脉搭桥手术、经皮冠状动脉成形术等心脏手术的心脏保护剂的有前途的候选物。
• US7351843B2
  申请人：——

  公开号：US7351843B2

  公开（公告）日：2008-04-01
• (5-Arylfuran-2-ylcarbonyl)guanidines as Cardioprotectives through the Inhibition of Na⁺/H⁺ Exchanger Isoform-1
  作者：Sunkyung Lee、Kyu Yang Yi、Sun Kyung Hwang、Byung Ho Lee、Sung-eun Yoo、Kyunghee Lee

  DOI：10.1021/jm0492305

  日期：2005.4.1

  A series of (5-arylfuran-2-ylcarbonyl)guanidines was synthesized and evaluated for the NHE-1 inhibitory activity and cardiprotective efficacy against ischemia-reperfusion injury. Starting with (5-phenylfuran-2-ylcarbonyl)guanidine 47 with a moderate inhibitory effect on NHE-1, the compounds with various substituents at the phenyl ring were investigated with the aim to optimize the potency. In this study, the 2,5-disubstituted compounds appeared to have better activities than the other analogues, and the 2-methoxy-5-chlorophenyl compound 85 was found as a potent inhibitor of NHE-1 (IC50 = 0.081 mu M). Furthermore, 85 showed a marked reduction of infarct size in the rat myocardial infarction model in vivo and significant improvement of cardiac contractile function in the isolated rat heart ischemia model in vitro.