2-methylthiobenzothiazole hydroiodide | 117883-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-methylthiobenzothiazole hydroiodide
• 英文别名: 2-methylsulfanyl-benzothiazole; hydriodide；2-Methylmercapto-benzothiazol; Hydrojodid；(Methylsulfanyl)benzo thiazolium iodide；2-methylsulfanyl-1,3-benzothiazol-3-ium;iodide
• CAS: 117883-09-7
• 化学式: C₈H₇NS₂*HI
• 分子量: 309.195
• InChiKey: SWXJHTTZXWLBSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methylthiobenzothiazole hydroiodide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以72.4%的产率得到2-(甲磺酰基)苯并噻唑
  参考文献：
  名称：

  Synthesis of 2-Piperazinylbenzothiazole and 2-Piperazinylbenzoxazole Derivatives with 5-HT3 Antagonist and 5-HT4 Agonist Properties

  摘要：

  New 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives were prepared and tested as 5-HT3 receptor antagonists. Some of the new compounds antagonized the effect of 5-HT at the longitudinal muscle myenteric plexus (LMMP) preparation of the guinea pig ileum, and two benzothiazole derivatives, compounds 2e and 2f, were more potent than ondansetron in this regard. However, these two compounds were much weaker than the typical 5-HT3 receptor antagonist as displacers of [H-3]BRL-43694 binding to rat cerebral cortex homogenates or as antagonists of the bradycardia response to 5-HT in the anaesthetized rat. Like the prokinetic agent cisapride, some of the new compounds enhanced gastric emptying in rats. Compound 2f not only markedly enhanced gastric emptying but was also a potent agonist at the isolated rat oesophageal tunics muscularis mucosae, a preparation sensitive to 5-HT4 receptor stimulation, and enhanced the twitch response in the LMMP preparation. The latter effect was blocked by a high concentration of tropisetron or by previous desensitization with 6-methoxytryptamine Compound 2f appears to show a promising pharmacological profile as a potential gastrokinetic agent.

  DOI：

  10.1021/jm00035a012
• 作为产物：
  描述：

  2-巯基苯并噻唑 、 碘甲烷 以 丙酮 为溶剂， 反应 0.75h， 以48.7%的产率得到2-methylthiobenzothiazole hydroiodide
  参考文献：
  名称：

  Synthesis of 2-Piperazinylbenzothiazole and 2-Piperazinylbenzoxazole Derivatives with 5-HT3 Antagonist and 5-HT4 Agonist Properties

  摘要：

  New 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives were prepared and tested as 5-HT3 receptor antagonists. Some of the new compounds antagonized the effect of 5-HT at the longitudinal muscle myenteric plexus (LMMP) preparation of the guinea pig ileum, and two benzothiazole derivatives, compounds 2e and 2f, were more potent than ondansetron in this regard. However, these two compounds were much weaker than the typical 5-HT3 receptor antagonist as displacers of [H-3]BRL-43694 binding to rat cerebral cortex homogenates or as antagonists of the bradycardia response to 5-HT in the anaesthetized rat. Like the prokinetic agent cisapride, some of the new compounds enhanced gastric emptying in rats. Compound 2f not only markedly enhanced gastric emptying but was also a potent agonist at the isolated rat oesophageal tunics muscularis mucosae, a preparation sensitive to 5-HT4 receptor stimulation, and enhanced the twitch response in the LMMP preparation. The latter effect was blocked by a high concentration of tropisetron or by previous desensitization with 6-methoxytryptamine Compound 2f appears to show a promising pharmacological profile as a potential gastrokinetic agent.

  DOI：

  10.1021/jm00035a012

文献信息

• Synthesis of 2-Piperazinylbenzothiazole and 2-Piperazinylbenzoxazole Derivatives with 5-HT3 Antagonist and 5-HT4 Agonist Properties
  作者：Antonio Monge、Maria del Carmen Pena、Juan Antonio Palop、Jose Maria Caldero、Juan Roca、Elisa Garcia、Gonzalo Romero、Joaquin del Rio、Berta Lasheras

  DOI：10.1021/jm00035a012

  日期：1994.4

  New 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives were prepared and tested as 5-HT3 receptor antagonists. Some of the new compounds antagonized the effect of 5-HT at the longitudinal muscle myenteric plexus (LMMP) preparation of the guinea pig ileum, and two benzothiazole derivatives, compounds 2e and 2f, were more potent than ondansetron in this regard. However, these two compounds were much weaker than the typical 5-HT3 receptor antagonist as displacers of [H-3]BRL-43694 binding to rat cerebral cortex homogenates or as antagonists of the bradycardia response to 5-HT in the anaesthetized rat. Like the prokinetic agent cisapride, some of the new compounds enhanced gastric emptying in rats. Compound 2f not only markedly enhanced gastric emptying but was also a potent agonist at the isolated rat oesophageal tunics muscularis mucosae, a preparation sensitive to 5-HT4 receptor stimulation, and enhanced the twitch response in the LMMP preparation. The latter effect was blocked by a high concentration of tropisetron or by previous desensitization with 6-methoxytryptamine Compound 2f appears to show a promising pharmacological profile as a potential gastrokinetic agent.