7-chloro-5-phenyl-1,2,3,5-tetrahydro-4,1-benzothiazepin-2-one | 13540-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: 7-chloro-5-phenyl-1,2,3,5-tetrahydro-4,1-benzothiazepin-2-one
• 英文别名: 7-chloro-5-phenyl-1,5-dihydro-benzo[e][1,4]thiazepin-2-one；5-Phenyl-7-chlor-3,5-dihydro-4,1-benzothiazepin-2(1H)-on；7-Chlor-5-phenyl-3,5-dihydro-1H-4,1-benzothiazepinon-(2)；7-chloro-5-phenyl-1,5-dihydro-4,1-benzothiazepin-2(3H)-one；7-chloro-5-phenyl-1,5-dihydro-4,1-benzothiazepin-2-one
• CAS: 13540-43-7
• 化学式: C₁₅H₁₂ClNOS
• 分子量: 289.785
• InChiKey: DCRFKOGBPXGTPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chloro-5-phenyl-1,2,3,5-tetrahydro-4,1-benzothiazepin-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 7-chloro-1-(3-morpholin-4-yl-propyl)-5-phenyl-1,2,3,5-tetrahydro-benzo[e][1,4]thiazepine
  参考文献：
  名称：

  5-苯基-4,1-苯并噻嗪衍生物的合成

  摘要：

  5-苯基-7-氯-3,5-二氢-4,1-苯并噻嗪-2(1H)-one和5-苯基-7-氯-1,2,3,5-四氢-4的合成，描述了 1-苯并硫氮杂和这些化合物的衍生物。

  DOI：

  10.1002/ardp.19673000403
• 作为产物：
  描述：

  (2-amino-5-chlorophenyl)(phenyl)methanol 在 4-二甲氨基吡啶 、 sodium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 7-chloro-5-phenyl-1,2,3,5-tetrahydro-4,1-benzothiazepin-2-one
  参考文献：
  名称：

  Efficient Syntheses of Benzothiazepines as Antagonists for the Mitochondrial Sodium−Calcium Exchanger:  Potential Therapeutics for Type II Diabetes

  摘要：

  Type II diabetes mellitus is a chronic metabolic disorder that can lead to serious cardiovascular, renal, neurologic, and retinal complications. While several drugs are currently prescribed to treat type II diabetes, their efficacy is limited by mechanism-related side effects (weight gain, hypoglycemia, gastrointestinal distress), inadequate efficacy for use as monotherapy, and the development of tolerance to the agents. Consequently, combination therapies are frequently employed to effectively regulate blood glucose levels. We have focused on the mitochondrial sodium-calcium exchanger (mNCE) as a novel target for diabetes drug discovery. We have proposed that inhibition of the mNCE can be used to regulate calcium flux across the mitochondrial membrane, thereby enhancing mitochondrial oxidative metabolism, which in turn enhances glucose-stimulated insulin secretion (GSIS) in the pancreatic beta-cell. In this paper, we report the facile synthesis of benzothiazepines and derivatives by S-alkylation using 2-aminobenzhydrols. The syntheses of other bicyclic analogues based on benzothiazepine, benzothiazecine, benzodiazecine, and benzodiazepine templates are also described. These compounds have been evaluated for their inhibition of mNCE activity, and the results from the structure-activity relationship (SAR) studies are discussed.

  DOI：

  10.1021/jo020446t