[[[[(4-chloro-2-methylphenyl)amino]thioxomethyl]methylamino]oxy]acetic acid | 409132-43-0

• 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: [[[[(4-chloro-2-methylphenyl)amino]thioxomethyl]methylamino]oxy]acetic acid
• 英文别名: 2-[(4-chloro-2-methylphenyl)carbamothioyl-methylamino]oxyacetic acid
• CAS: 409132-43-0
• 化学式: C₁₁H₁₃ClN₂O₃S
• 分子量: 288.755
• InChiKey: WBNCXFGIOIMOKS-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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [[[[(4-chloro-2-methylphenyl)amino]thioxomethyl]methylamino]oxy]acetic acid 在 五氯化磷 作用下， 以 苯 为溶剂， 反应 0.5h， 以12.8 g的产率得到4-(4-Chloro-2-methylphenyl)-2-methyl-3-thioxo-1,2,4-oxadiazin-5-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：

  4-氯-2-甲基苯基异硫氰酸酯 、 N-methyl aminooxy acetic acid hydrochloride 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以69%的产率得到[[[[(4-chloro-2-methylphenyl)amino]thioxomethyl]methylamino]oxy]acetic 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

• 3-thioxo-[1,2,4]-oxadiazinan-5-one derivatives
  申请人：American Home Products Corporation

  公开号：US20020061883A1

  公开（公告）日：2002-05-23

  1 wherein R is alkyl, alkenyl, or alkynyl; R 1 and R 2 are each independently hydrogen alkyl, or aryl; and Ar is phenyl, indanyl, benzhydryl, or phenyl, substituted with one or more groups selected from the group consisting of halogen, alkyl, perfluoroalkyl, lower alkoxy, perfluoroalkylalkoxy, dialkylamino, and aroyloxy.

  其中R为烷基、烯基或炔基；R1和R2各自独立地为氢、烷基或芳基；Ar为苯基、茚基、苄基或苯基，其上取代一个或多个来自卤素、烷基、全氟烷基、低烷氧基、全氟烷氧基、二烷基胺基和芳酰氧基的基团。
• 3-thioxo-[1,2,4]-oxadiazinan-5-one derivatives
  申请人：Wyeth

  公开号：US06562814B2

  公开（公告）日：2003-05-13

  wherein R is alkyl, alkenyl, or alkynyl; R1 and R2 are each independently hydrogen alkyl, or aryl; and Ar is phenyl, indanyl, benzhydryl, or phenyl, substituted with one or more groups selected from the group consisting of halogen, alkyl, perfluoroalkyl, lower alkoxy, perfluoroalkylalkoxy, dialkylamino, and aroyloxy.

  其中R是烷基，烯基或炔基; R1和R2各自独立地是氢，烷基或芳基; 而Ar是苯基，茚基，苯甲基或苯基，其上取代有一个或多个来自卤素，烷基，全氟烷基，低级烷氧基，全氟烷氧基，二烷基氨基和芳香氧基的基团。
• US6472430B2
  申请人：——

  公开号：US6472430B2

  公开（公告）日：2002-10-29
• US6562814B2
  申请人：——

  公开号：US6562814B2

  公开（公告）日：2003-05-13
• [EN] 3-THIOXO-[1,2,4]-OXADIAZINAN-5-ONE AND THEIR USE AS ANTI-ANTHEROSCLEROTIC AGENTS<br/>[FR] 3-THIOXO-[1,2,4]-OXADIAZINAN-5-ONES ET LEUR UTILISATION COMME AGENTS ANTIATHEROSCLEREUX
  申请人：AMERICAN HOME PROD

  公开号：WO2002028845A1

  公开（公告）日：2002-04-11

  This invention relates to 3/thioxo/[1,2,4]-oxadiazinan-5-one derivatives of formula: (I), wherein R is alkyl, alkenyl, or alkynyl; R1 and R2 are each independently hydrogen, alkyl, or aryl; and Ar is phenyl, indanyl, benzhydryl, or phenyl, substituted with one or more groups selected from the group consisting of halogen, alkyl, perfluoroalkyl, lower alkoxy, perfluoroalkoxy, dialkylamino, and aroyloxy; that elevate HDL cholesterol concentration, and which may be useful for the treatment of atherosclerotic conditions such as coronary heart disease.