3-[3-(5-chloro-2-methylphenyl)-1-ethylthioureido]propionic acid | 196794-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[3-(5-chloro-2-methylphenyl)-1-ethylthioureido]propionic acid
• 英文别名: 3-[(5-Chloro-2-methylphenyl)carbamothioyl-ethylamino]propanoic acid
• CAS: 196794-85-1
• 化学式: C₁₃H₁₇ClN₂O₂S
• 分子量: 300.809
• InChiKey: YSBRQXFIXZSXOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[3-(5-chloro-2-methylphenyl)-1-ethylthioureido]propionic acid 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 3-(5-Chloro-2-methyl-phenyl)-1-ethyl-2-thioxo-tetrahydro-pyrimidin-4-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Thio-Containing Compounds with Serum HDL-Cholesterol-Elevating Properties

  摘要：

  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.

  DOI：

  10.1021/jm030219z
• 作为产物：
  描述：

  5-氯-2-甲基异硫氰酸苯酯 、 3-(乙胺基)丙酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-[3-(5-chloro-2-methylphenyl)-1-ethylthioureido]propionic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Thio-Containing Compounds with Serum HDL-Cholesterol-Elevating Properties

  摘要：

  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.

  DOI：

  10.1021/jm030219z

文献信息

• 2-thioxo-tetrahydropyrimidin-4-one derivatives
  申请人：American Home Products Corporation

  公开号：US05807864A1

  公开（公告）日：1998-09-15

  This invention relates to the use of 2-thioxotetrahydropyrimidin-4-one derivatives to increase HDL cholesterol concentration and as therapeutic compositions for treating atherosclerotic conditions such as dyslipoproteinemias and coronary heart disease. The compounds of this invention are represented by the formula: ##STR1## wherein: R is C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.2 -C.sub.6 alkynyl; and R.sup.1, R.sup.2, and R.sup.3 are independently hydrogen, halogen or lower alkyl.

  本发明涉及使用2-硫代四氢嘧啶-4-酮衍生物来增加高密度脂蛋白胆固醇浓度，并作为治疗动脉粥样硬化疾病（如脂蛋白异常和冠心病）的治疗组合物。本发明的化合物由以下公式表示：##STR1## 其中：R为C.sub.1 -C.sub.6烷基，C.sub.2 -C.sub.6烯基或C.sub.2 -C.sub.6炔基；R.sup.1，R.sup.2和R.sup.3独立地为氢、卤素或较低烷基。
• US5807864A
  申请人：——

  公开号：US5807864A

  公开（公告）日：1998-09-15
• 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.