3-(2,6-dimethylphenyl)-1-(prop-2-ynyl)-2-thioxo-imidazolidin-4-one

• 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: 3-(2,6-dimethylphenyl)-1-(prop-2-ynyl)-2-thioxo-imidazolidin-4-one
• 英文别名: 3-(2,6-dimethylphenyl)-1-prop-2-ynyl-2-sulfanylideneimidazolidin-4-one
• 化学式: C₁₄H₁₄N₂OS
• 分子量: 258.344
• InChiKey: ADXXTCBRIQADAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-炔丙基甘氨酸乙酯 、 2,6-二甲基异硫氰酸苯酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-(2,6-dimethylphenyl)-1-(prop-2-ynyl)-2-thioxo-imidazolidin-4-one
  参考文献：
  名称：

  2-thioxo-imidazolidin-4-one derivatives

  摘要：

  式I的化合物##STR1##中，其中R为炔基；X和Y分别为烷基、卤素、全氟烷基、全氟烷氧基，或者X和Y一起为邻位取代的三亚甲基或四亚甲基，在增加血清高密度脂蛋白水平方面具有用处。

  公开号：

  US05663363A1

文献信息

• Use of 2-thioxo-imidazolin-4-one derivatives in the treatment of
  申请人：American Home Products Corporation

  公开号：US05554607A1

  公开（公告）日：1996-09-10

  A method for increasing the HDL cholesterol concentration in the blood of a mammal in need of increased HDL cholesterol blood concentration, which comprises administering to said mammal, orally or parenterally, a compound of formula I: ##STR1## wherein R is alkyl; a substituted or unsubstituted aromatic N, O or S heterocycle; substituted or unsubstituted aryl, arylalkyl, benzhydryl or indanyl, in which the substituents are one to three members independently selected from the group consisting of alkyl, alkoxy, alkylthio, alkenyl, alkynyl, halo, perfluoroalkyl, perfluoroalkyl or hydroxy; and R.sup.1 is aryl, alkyl, alkenyl, alkynyl or substituted aryl where the substituents are one to three members independently selected from the group consisting of alkyl, alkoxy, alkylthio, alkenyl, alkynyl, halo, perfluoroalkyl, perfluoroalkoxy or hydroxy.

  一种用于增加需要增加高密度脂蛋白胆固醇血浓度的哺乳动物血液中HDL胆固醇浓度的方法，包括向所述哺乳动物口服或静脉注射化合物I的步骤：##STR1##其中R为烷基；取代或未取代的芳香族N、O或S杂环；取代或未取代的芳基、芳基烷基、苯基甲基或茚基，在其中取代基是从烷基、烷氧基、烷硫基、烯基、炔基、卤素、全氟烷基、全氟烷基或羟基组成的群中独立选择的一到三个成员；以及R.sup.1为芳基、烷基、烯基、炔基或取代芳基，其中取代基是从烷基、烷氧基、烷硫基、烯基、炔基、卤素、全氟烷基、全氟烷氧基或羟基组成的群中独立选择的一到三个成员。
• 2-thioxo-imidazolidin-4-one derivatives
  申请人：American Home Products Corporation

  公开号：US05663363A1

  公开（公告）日：1997-09-02

  The compound of formula I ##STR1## in which R is alkynyl; and X and Y are, independently, alkyl, halo, perfluoralkyl, perfluoralkoxy, or, taken together, X and Y are ortho substituted trimethylene or tetramethylene are useful for increasing blood serum HDL levels.

  式I的化合物##STR1##中，其中R为炔基；X和Y分别为烷基、卤素、全氟烷基、全氟烷氧基，或者X和Y一起为邻位取代的三亚甲基或四亚甲基，在增加血清高密度脂蛋白水平方面具有用处。
• US5554607A
  申请人：——

  公开号：US5554607A

  公开（公告）日：1996-09-10
• US5663363A
  申请人：——

  公开号：US5663363A

  公开（公告）日：1997-09-02
• Design, Synthesis, and Biological Evaluation of Thio-Containing Compounds with Serum HDL-Cholesterol-Elevating Properties
  作者：Hassan Elokdah、Theodore S. Sulkowski、Magid Abou-Gharbia、John A. Butera、Sie-Yearl Chai、Geraldine R. McFarlane、Mar-Lee McKean、John L. Babiak、Steven J. Adelman、Elaine M. Quinet

  DOI：10.1021/jm030219z

  日期：2004.1.1

  A novel series of substituted sulfanyldihydroimidazolones (1) that modulates high-density lipoprotein cholesterol (HDL-C) has been reported to have HDL-elevating properties in several animal models. Concerns about the chemical and metabolic stability of I directed us to explore the structure-activity relationship (SAR) of a related series of substituted thiohydantoins (2). Expansion of the scope of the thiohydantoin series led to exploration of compounds in related thio-containing ring systems 3-7 and the N-cyanoguanidine derivative 8. Compounds were tested sequentially in three animal models to assess their HDL-C elevating efficacy and safety profiles. Further evaluation of selected compounds in a dose-response paradigm culminated in the identification of compound 2.39 as a candidate compound for advanced preclinical. studies.