3-oxo-N-(3-methyl-2-thiazolidinylidene)butyramide | 65400-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oxo-N-(3-methyl-2-thiazolidinylidene)butyramide
• 英文别名: N-(3-Methylthiazolidin-2-yliden)acetoacetamid；N-(3-methyl-thiazolidin-2-ylidene)-3-oxo-butyramide；2-Acetoacetylimino-3-methylthiazolidine；N-(3-methyl-1,3-thiazolidin-2-ylidene)-3-oxobutanamide
• CAS: 65400-80-8
• 化学式: C₈H₁₂N₂O₂S
• 分子量: 200.261
• InChiKey: AFHXHOBDABGXKL-UHFFFAOYSA-N

物化性质

• 沸点：
  321.3±44.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  双乙烯酮 、 3-甲基-1,3-噻唑烷-2-亚胺 以 乙醇 为溶剂， 以60%的产率得到3-oxo-N-(3-methyl-2-thiazolidinylidene)butyramide
  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

• Derivatives of 2-iminothiazolidines and thiazolines
  申请人：Merck & Co., Inc.

  公开号：US04181661A1

  公开（公告）日：1980-01-01

  2-(Substituted imino)thiazolidines and thiazolines are inhibitors of indoleamine-N-methyl transferase in vivo. They are prepared by alkylation or acylation of the free imino group.

  2-（取代亚胺基）噻唑啉和噻唑烷在体内是色胺-N-甲基转移酶的抑制剂。它们通过自由亚胺基的烷基化或酰化来制备。
• 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.