3-carboxy-N-(3-methyl-2-thiazolidinylidene)proionamide | 65400-82-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-carboxy-N-(3-methyl-2-thiazolidinylidene)proionamide
• 英文别名: 3-Methyl-2-Succinyliminothiazolidin；N-(3-methyl-thiazolidin-2-ylidene)-succinamic acid；3-Carboxy-N-(3-methyl-2-thiazolidinylidene)propionamide；4-[(3-methyl-1,3-thiazolidin-2-ylidene)amino]-4-oxobutanoic acid
• CAS: 65400-82-0
• 化学式: C₈H₁₂N₂O₃S
• 分子量: 216.261
• InChiKey: BJLULHPWVYLSSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3-甲基-1,3-噻唑烷-2-亚胺 、 丁二酸酐 以 二氯甲烷 为溶剂， 反应 3.0h， 以84.2%的产率得到3-carboxy-N-(3-methyl-2-thiazolidinylidene)proionamide
  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.