2-amino-4-methoxycarbonylmethyl-oxazole-5-carboxylic acid methyl ester | 6496-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-amino-4-methoxycarbonylmethyl-oxazole-5-carboxylic acid methyl ester
• 英文别名: Methyl 2-amino-5-methoxycarbonyl-4-oxazoleacetate；methyl 2-amino-4-(2-methoxy-2-oxoethyl)-1,3-oxazole-5-carboxylate
• CAS: 6496-99-7
• 化学式: C₈H₁₀N₂O₅
• 分子量: 214.178
• InChiKey: ZPFYRBJUUPMGPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.24
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104.65
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-amino-4-methoxycarbonylmethyl-oxazole-5-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 反应 0.5h， 以56%的产率得到2-amino-4-(carboxymethyl)-1,3-oxazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of sulfonamidooxazoles and β-keto sulfones: selective inhibitors of 11β-hydroxysteroid dehydrogenase type I

  摘要：

  The design, synthesis, and biological evaluation of arylsulfonamidooxazoles as 11 beta-HSD1 inhibitors and the serendipitous discovery of beta-keto sulfones as potent 11 beta-HSD1 inhibitors are described here. These two classes of compounds are not active against 11 beta-HSD2 and therefore may have significant therapeutic potential for metabolic syndrome, type 2 diabetes and related metabolic dysfunctions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.093
• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 在 溴 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-amino-4-methoxycarbonylmethyl-oxazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of sulfonamidooxazoles and β-keto sulfones: selective inhibitors of 11β-hydroxysteroid dehydrogenase type I

  摘要：

  The design, synthesis, and biological evaluation of arylsulfonamidooxazoles as 11 beta-HSD1 inhibitors and the serendipitous discovery of beta-keto sulfones as potent 11 beta-HSD1 inhibitors are described here. These two classes of compounds are not active against 11 beta-HSD2 and therefore may have significant therapeutic potential for metabolic syndrome, type 2 diabetes and related metabolic dysfunctions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.093