4-(mercaptomethyl)biphenyl-2-carboxylic Acid | 1382034-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(mercaptomethyl)biphenyl-2-carboxylic Acid
• 英文别名: 2-Phenyl-5-(sulfanylmethyl)benzoic acid
• CAS: 1382034-09-4
• 化学式: C₁₄H₁₂O₂S
• 分子量: 244.314
• InChiKey: BITSNFAHNIBYST-UHFFFAOYSA-N

物化性质

• 沸点：
  416.0±40.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-5-甲基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 potassium hydrogencarbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 9.75h， 生成 4-(mercaptomethyl)biphenyl-2-carboxylic 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

文献信息

• Design, Synthesis, and Pharmacological Evaluation of Glutamate Carboxypeptidase II (GCPII) Inhibitors Based on Thioalkylbenzoic Acid Scaffolds
  作者：Doris Stoermer、Dilrukshi Vitharana、Niyada Hin、Greg Delahanty、Bridget Duvall、Dana V. Ferraris、Brian S. Grella、Randall Hoover、Camilo Rojas、Megan K. Shanholtz、Kyle P. Smith、Marigo Stathis、Ying Wu、Krystyna M. Wozniak、Barbara S. Slusher、Takashi Tsukamoto

  DOI：10.1021/jm300488m

  日期：2012.6.28

  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.