甲基5-甲酰基-4-甲基-2-噻吩羧酸酯 | 391936-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 甲基5-甲酰基-4-甲基-2-噻吩羧酸酯
• 英文名称: 5-formyl-4-methylthiophene-2-carboxylic acid methyl ester
• 英文别名: Methyl 5-formyl-4-methylthiophene-2-carboxylate
• CAS: 391936-75-7
• 化学式: C₈H₈O₃S
• mdl: MFCD04972647
• 分子量: 184.216
• InChiKey: SKMVXVNHOBFLNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25

反应信息

• 作为反应物：
  描述：

  甲基5-甲酰基-4-甲基-2-噻吩羧酸酯 在 盐酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 (+)-3-MATIDA
  参考文献：
  名称：

  Stereoselective synthesis and preliminary evaluation of (+)- and (–)-3-methyl-5-carboxy-thien-2-yl-glycine (3-MATIDA): identification of (+)-3-MATIDA as a novel mGluR1 competitive antagonist

  摘要：

  The synthesis of the (+)- and (-)-isomers of 3-methyl-5-carboxy-thyen-2-yl-glycine (3-MATIDA), heterocyle isosters of carboxyphenylglycines (CPGs), a known class of competitive metabotropic glutamate receptors, was accomplished by a stereoselective Ugi condensation. The two isomers were tested as potential rat mGluR1 ligand and the (+) isomer was found to be a moderately potent antagonist, while the (-) one was inactive.

  DOI：

  10.1016/j.farmac.2003.11.008
• 作为产物：
  描述：

  5-(1,3-Dimethyl-imidazolidin-2-yl)-4-methyl-thiophene-2-carboxylic acid 在 盐酸 、 硫酸 作用下， 反应 36.0h， 生成 甲基5-甲酰基-4-甲基-2-噻吩羧酸酯
  参考文献：
  名称：

  Stereoselective synthesis and preliminary evaluation of (+)- and (–)-3-methyl-5-carboxy-thien-2-yl-glycine (3-MATIDA): identification of (+)-3-MATIDA as a novel mGluR1 competitive antagonist

  摘要：

  The synthesis of the (+)- and (-)-isomers of 3-methyl-5-carboxy-thyen-2-yl-glycine (3-MATIDA), heterocyle isosters of carboxyphenylglycines (CPGs), a known class of competitive metabotropic glutamate receptors, was accomplished by a stereoselective Ugi condensation. The two isomers were tested as potential rat mGluR1 ligand and the (+) isomer was found to be a moderately potent antagonist, while the (-) one was inactive.

  DOI：

  10.1016/j.farmac.2003.11.008

文献信息

• [EN] 2-THENOIC ACID (THIOPHENE) DERIVATIVES HAVING GLUTAMATE RECEPTOR ANTAGONISTIC ACTIVITY<br/>[FR] DERIVES D'ACIDE 2-THENOIQUE (THIOPHENE) PRESENTANT UNE ACTIVITE D'ANTAGONISTE DE RECEPTEURS DE GLUTAMATE
  申请人：GLAXOSMITHKLINE SPA

  公开号：WO2002008220A1

  公开（公告）日：2002-01-31

  Derivatives of 2-thenoic acid of formula (I) with antagonist activity on the glutamate receptors, are described.
• Stereoselective synthesis and preliminary evaluation of (+)- and (–)-3-methyl-5-carboxy-thien-2-yl-glycine (3-MATIDA): identification of (+)-3-MATIDA as a novel mGluR1 competitive antagonist
  作者：Gabriele Costantino、Maura Marinozzi、Emidio Camaioni、Benedetto Natalini、Iran Sarichelou、Fabrizio Micheli、Paolo Cavanni、Stefania Faedo、Christian Noe、Flavio Moroni、Roberto Pellicciari

  DOI：10.1016/j.farmac.2003.11.008

  日期：2004.2

  The synthesis of the (+)- and (-)-isomers of 3-methyl-5-carboxy-thyen-2-yl-glycine (3-MATIDA), heterocyle isosters of carboxyphenylglycines (CPGs), a known class of competitive metabotropic glutamate receptors, was accomplished by a stereoselective Ugi condensation. The two isomers were tested as potential rat mGluR1 ligand and the (+) isomer was found to be a moderately potent antagonist, while the (-) one was inactive.