N-carbamimidoyl-2-(3,5-dimethylphenyl)-5-methyl-1H-imidazole-4-carboxamide;methanesulfonic acid | 1144520-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-carbamimidoyl-2-(3,5-dimethylphenyl)-5-methyl-1H-imidazole-4-carboxamide;methanesulfonic acid
• CAS: 1144520-18-2
• 化学式: CH₄O₃S*C₁₄H₁₇N₅O
• 分子量: 367.429
• InChiKey: NIQHYJKINBMOBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  173
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲烷磺酸 、 以 丙酮 为溶剂， 生成 N-carbamimidoyl-2-(3,5-dimethylphenyl)-5-methyl-1H-imidazole-4-carboxamide;methanesulfonic acid
  参考文献：
  名称：

  (2-Aryl-5-methylimidazol-4-ylcarbonyl)guanidines and (2-aryl-5-methyloxazol-4-ylcarbonyl)guanidines as NHE-1 inhibitors

  摘要：

  A series of (2-aryl-5-methylimidazol-4-ylcarbonyl)guanidines and (2-aryl-5-methyloxazol-4-ylcarbonyl)guanidines were synthesized and evaluated as NHE-1 inhibitors. The structure-activity relationships well matched those of furan derivatives, which were previously investigated. The (2,5-disubstituted) phenyl compounds showed better activities than the other analogues in both imidazole and oxazole compounds. Especially, 2-(2,5-dichlorophenyl)imidazole 52, and 2-(2-methoxy-5-chlorophenyl) imidazole 54 compounds exhibited potent cardioprotective efficacy both in vitro and in vivo as well as high NHE-1 inhibitory activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.060

文献信息

• [EN] 4-METHYLIMIDAZOL-5-YLCARBONYLGUANIDINE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PREPARATION METHOD, AND PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF THE ISCHEMIC HEART DISEASES CONTAINING THE SAME AS AN ACTIVE INGRED<br/>[FR] DÉRIVÉS DE 4-MÉTHYLIMIDAZOL-5-YLCARBONYLGUANIDINE, LEURS SELS PHARMACEUTIQUEMENT ACCEPTABLES, PROCÉDÉS DE PRÉPARATION ET COMPOSITIONS PHARMACEUTIQUES POUR LA PRÉVENTION ET LE TRAITEMENT DES MALADIES CARDIAQUES ISCHÉMIQUES CONTENANT CEUX-CI COMME INGR
  申请人：KOREA RESERACH INST OF CHEMICA

  公开号：WO2008111794A1

  公开（公告）日：2008-09-18

  [EN] Disclosed are novel 4-methylimidazol-5- ylcarbonylguanidine derivatives, pharmaceutically acceptable salts thereof, preparation methods thereof, and pharmaceutical composition for the prevention and treatment of ischemic heart diseases, comprising the same as an active ingredient. Having potent inhibitory activity against NHE-I and excellent protective effects on the heart against ischemia/reperfusion, the novel 4-methylimidazol-5- ylcarbonylguanidine derivatives can be used for the prophylaxis and treatment of ischemic cardiac diseases such as myocardiac infarction, arrhythmia, and angina pectoris and can serve as a cardioprotective agent applicable for coronary reperfusion therapy with coronary artery bypass, percutaneous transluminal coronary angioplasty, and/or thrombolytics for myocardiac infarction.
  [FR] L'invention concerne de nouveaux dérivés de 4-méthylimidazol-5- ylcarbonylguanidine, leurs sels pharmaceutiquement acceptables, des procédés de préparation de ceux-ci et une composition pharmaceutique pour la prévention et le traitement des maladies cardiaques ischémiques, comprenant ceux-ci comme ingrédients actifs. Ayant une puissante activité inhibitrice contre NHE-I et des effets protecteurs excellents sur le coer, contre les ischémies/lésions de reperfusion, les nouveaux dérivés de 4-méthylimidazol-5-ylcarbonylguanidine peuvent être utilisés pour la prophylaxie et le traitement des maladies cardiaques ischémiques telles que l'infarctus du myocarde, l'arythmie et l'angine de poitrine et peuvent servir d'agents cardioprotecteurs utilisables pour le traitement de reperfusion coronaire associée au pontage coronarien, angioplastie coronarienne transluminale percutanée et/ou comme thrombolytiques pour l'infarctus du myocarde.
• (2-Aryl-5-methylimidazol-4-ylcarbonyl)guanidines and (2-aryl-5-methyloxazol-4-ylcarbonyl)guanidines as NHE-1 inhibitors
  作者：Sunkyung Lee、Kyu Yang Yi、Sung Jun Youn、Byung Ho Lee、Sung-eun Yoo

  DOI：10.1016/j.bmcl.2009.01.060

  日期：2009.3

  A series of (2-aryl-5-methylimidazol-4-ylcarbonyl)guanidines and (2-aryl-5-methyloxazol-4-ylcarbonyl)guanidines were synthesized and evaluated as NHE-1 inhibitors. The structure-activity relationships well matched those of furan derivatives, which were previously investigated. The (2,5-disubstituted) phenyl compounds showed better activities than the other analogues in both imidazole and oxazole compounds. Especially, 2-(2,5-dichlorophenyl)imidazole 52, and 2-(2-methoxy-5-chlorophenyl) imidazole 54 compounds exhibited potent cardioprotective efficacy both in vitro and in vivo as well as high NHE-1 inhibitory activities. (C) 2009 Elsevier Ltd. All rights reserved.