8-phenylisothiochroman-1-one | 1382034-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异硫色满
• 英文名称: 8-phenylisothiochroman-1-one
• 英文别名: 8-Phenyl-3,4-dihydroisothiochromen-1-one
• CAS: 1382034-29-8
• 化学式: C₁₅H₁₂OS
• 分子量: 240.326
• InChiKey: MQGCPBHBAPXMQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-phenylisothiochroman-1-one 在 3,3,3-膦三基三丙酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以56%的产率得到3-(2-mercaptoethyl)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
• 作为产物：
  描述：

  2,2-dimethyl-5-vinyl-4H-benzo[d][1,3]dioxin-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 、 caesium carbonate 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 38.5h， 生成 8-phenylisothiochroman-1-one
  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.