N,N'-bis(3-methyl-3-thiazolidinylidene)succinamide | 65400-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N,N'-bis(3-methyl-3-thiazolidinylidene)succinamide
• 英文别名: N,N'-bis-(3-methyl-thiazolidin-2-ylidene)-succinamide；N,N'-Bis(3-methyl-2-thiazolidinylidene)succinamide；N,N'-bis(3-methyl-1,3-thiazolidin-2-ylidene)butanediamide
• CAS: 65400-75-1
• 化学式: C₁₂H₁₈N₄O₂S₂
• 分子量: 314.433
• InChiKey: GWDKUUJFCRVEMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  478.2±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-carboxy-N-(3-methyl-2-thiazolidinylidene)proionamide 在 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 51.0h， 生成 N,N'-bis(3-methyl-3-thiazolidinylidene)succinamide
  参考文献：
  名称：

  Inhibitors of indoleethylamine N-methyltransferase. Derivatives of 3-methyl-2-thiazolidinimine. In vitro, in vivo, and metabolic studies

  摘要：

  A variety of substituent groups has been attached to the exocyclic imine function of 2-imino-3-methylthiazolidine (1) in a search for metabolic precursors of this potent inhibitor of the enzyme indoleethylamine N-methyltransferase (INMT) which would exhibit superior pharmacodynamic properties in animals. It has been determined that chemically stable derivatives of 1 based on succinic, nicotinic, and N-acylated amino acids, although they lack in vitro efficacy, are potent inhibitors of INMT when administered orally or intravenously to rabbits. Metabolic studies carried out with 14C-labeled N,N'-bix(3-methyl-2-thiazolidinylidene)succinamide (3) have established that conversion of this compound to 1 occurs both in the whole rabbit and in the isolated rabbit liver. 1 itself has been shown to be metabolically inert in rabbits, being excreted primarily in the urine.

  DOI：

  10.1021/jm00181a014

文献信息

• Inhibitors of indoleethylamine N-methyltransferase. Derivatives of 3-methyl-2-thiazolidinimine. In vitro, in vivo, and metabolic studies
  作者：Joshua Rokach、Yves Girard、Pierre Hamel、Grant Reader、C. Stanley Rooney、Lewis R. Mandel、Edward J. Cragoe、Anthony G. Zacchei

  DOI：10.1021/jm00181a014

  日期：1980.7

  A variety of substituent groups has been attached to the exocyclic imine function of 2-imino-3-methylthiazolidine (1) in a search for metabolic precursors of this potent inhibitor of the enzyme indoleethylamine N-methyltransferase (INMT) which would exhibit superior pharmacodynamic properties in animals. It has been determined that chemically stable derivatives of 1 based on succinic, nicotinic, and N-acylated amino acids, although they lack in vitro efficacy, are potent inhibitors of INMT when administered orally or intravenously to rabbits. Metabolic studies carried out with 14C-labeled N,N'-bix(3-methyl-2-thiazolidinylidene)succinamide (3) have established that conversion of this compound to 1 occurs both in the whole rabbit and in the isolated rabbit liver. 1 itself has been shown to be metabolically inert in rabbits, being excreted primarily in the urine.