ethyl 2-(3-chlorophenyl)-5-methyloxazole-4-carboxylate | 1144520-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(3-chlorophenyl)-5-methyloxazole-4-carboxylate
• 英文别名: 4-Oxazolecarboxylic acid, 2-(3-chlorophenyl)-5-methyl-, ethyl ester；ethyl 2-(3-chlorophenyl)-5-methyl-1,3-oxazole-4-carboxylate
• CAS: 1144520-63-7
• 化学式: C₁₃H₁₂ClNO₃
• 分子量: 265.696
• InChiKey: FTIWHQXXBRDBOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-chlorophenyl)-5-methyloxazole-4-carboxylate 、 胍 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-carbamimidoyl-2-(3-chlorophenyl)-5-methyl-1,3-oxazole-4-carboxamide
  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
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 3-氯苄胺 在 叔丁基过氧化氢 、 碘 、 copper(II) acetate monohydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到ethyl 2-(3-chlorophenyl)-5-methyloxazole-4-carboxylate
  参考文献：
  名称：

  Facile Synthesis of Polysubstituted Oxazoles via A Copper-Catalyzed Tandem Oxidative Cyclization

  摘要：

  A highly efficient synthesis of polysubstituted oxazoles was developed via a copper-catalyzed tandem oxidative cyclization. The desired products can be obtained from readily available starting materials under mild conditions. This is an attractive alternative method for the synthesis of oxazole derivatives.

  DOI：

  10.1021/ol100688c

文献信息

• Facile Synthesis of Polysubstituted Oxazoles via A Copper-Catalyzed Tandem Oxidative Cyclization
  作者：Changfeng Wan、Jintang Zhang、Sujing Wang、Jinmin Fan、Zhiyong Wang

  DOI：10.1021/ol100688c

  日期：2010.5.21

  A highly efficient synthesis of polysubstituted oxazoles was developed via a copper-catalyzed tandem oxidative cyclization. The desired products can be obtained from readily available starting materials under mild conditions. This is an attractive alternative method for the synthesis of oxazole derivatives.
• (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.