methyl 2-(3-(methoxycarbonyl)benzyloxy)-5-(tritylthiomethyl)benzoate | 1382034-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 2-(3-(methoxycarbonyl)benzyloxy)-5-(tritylthiomethyl)benzoate
• CAS: 1382034-16-3
• 化学式: C₃₇H₃₂O₅S
• 分子量: 588.724
• InChiKey: CIZQVYUGDJIJLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.06
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-(methoxycarbonyl)benzyloxy)-5-(tritylthiomethyl)benzoate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以88%的产率得到2-(3-carboxybenzyloxy)-5-(tritylthiomethyl)benzoic acid
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Glutamate Carboxypeptidase II (GCPII) Inhibitors Based on Thioalkylbenzoic Acid Scaffolds

  摘要：

  A series of thiol-based glutamate carboxypeptidase II (GCPII) inhibitors have been synthesized with either a 3-(mercaptomethyl)benzoic acid or 2-(2-mercaptoethyl)benzoic acid scaffold. Potent inhibitors were identified from each of the two scaffolds with IC50 values in the single-digit nanomolar range, including 2-(3-carboxybenzyloxy)-5-(mercaptomethyl)benzoic acid 27c and 3-(2-mercaptoethyl)-biphenyl-2,3'-dicarboxylic acid 35c. Compound 35c was found to be metabolically stable and selective over a number of targets related to glutamate-mediated neurotransmission. Furthermore, compound 35c was found to be orally available in rats and exhibited efficacy in an animal model of neuropathic pain following oral administration.

  DOI：

  10.1021/jm300488m
• 作为产物：
  描述：

  5-甲基水杨酸甲酯 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 丙酮 为溶剂， 反应 90.0h， 生成 methyl 2-(3-(methoxycarbonyl)benzyloxy)-5-(tritylthiomethyl)benzoate
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Glutamate Carboxypeptidase II (GCPII) Inhibitors Based on Thioalkylbenzoic Acid Scaffolds

  摘要：

  A series of thiol-based glutamate carboxypeptidase II (GCPII) inhibitors have been synthesized with either a 3-(mercaptomethyl)benzoic acid or 2-(2-mercaptoethyl)benzoic acid scaffold. Potent inhibitors were identified from each of the two scaffolds with IC50 values in the single-digit nanomolar range, including 2-(3-carboxybenzyloxy)-5-(mercaptomethyl)benzoic acid 27c and 3-(2-mercaptoethyl)-biphenyl-2,3'-dicarboxylic acid 35c. Compound 35c was found to be metabolically stable and selective over a number of targets related to glutamate-mediated neurotransmission. Furthermore, compound 35c was found to be orally available in rats and exhibited efficacy in an animal model of neuropathic pain following oral administration.

  DOI：

  10.1021/jm300488m