1-oxoisothiochroman-8-yl trifluoromethanesulfonate | 1382034-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-oxoisothiochroman-8-yl trifluoromethanesulfonate
• 英文别名: (1-Oxo-3,4-dihydroisothiochromen-8-yl) trifluoromethanesulfonate
• CAS: 1382034-28-7
• 化学式: C₁₀H₇F₃O₄S₂
• 分子量: 312.29
• InChiKey: NXBGZNBIJFVBQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-oxoisothiochroman-8-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 3,3,3-膦三基三丙酸 、 caesium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 生成 3-(2-mercaptoethyl)biphenyl-2,3′-dicarboxylic 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：

  2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one 在 吡啶 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 3,3,3-膦三基三丙酸 、 potassium carbonate 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 41.0h， 生成 1-oxoisothiochroman-8-yl trifluoromethanesulfonate
  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