2-(4-nitrophenyl)-N-thiazol-2-ylacetamide | 186371-21-1

• 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: 2-(4-nitrophenyl)-N-thiazol-2-ylacetamide
• 英文别名: 2-(4-nitrophenyl)-N-(1,3-thiazol-2-yl)acetamide
• CAS: 186371-21-1
• 化学式: C₁₁H₉N₃O₃S
• 分子量: 263.277
• InChiKey: ZJHNYEVHAYKTAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)-N-thiazol-2-ylacetamide 在 10percent Pd/C 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以90%的产率得到2-(4-aminophenyl)-N-thiazol-2-ylacetamide
  参考文献：
  名称：

  Synthesis and Evaluation of Potent and Selective β₃ Adrenergic Receptor Agonists Containing Acylsulfonamide, Sulfonylsulfonamide, and Sulfonylurea Carboxylic Acid Isosteres

  摘要：

  Starting from phenethanolamine aniline leads 3a and 3b, we have identified a series of functionally potent and selective beta(3) adrenergic receptor (AR) agonists containing acylsulfonamide, sulfonylsulfonamide, or sulfonylurea groups within the aniline phenethanolamine series. In beta(3) beta(2), and beta(1) AR cAMP functional assays, 3a and other right-hand side (RHS) carboxylate analogues were found to be full agonists that were modestly selective against beta(1) or beta(2) ARs, while analogues lacking RHS acid functionality were active at beta(3) AR but not selective. Replacement of the carboxylate with acylthiazole and acylmethylsulfone gave potent, but only modestly selective, compounds. Increasing the size of the RHS sulfonamide substituent with phenyl or p-toluene afforded compounds with good potency and functional selectivity (beta(3) AR pEC(50) greater than 8; beta(1) and beta(2) AR selectivity greater than 40- and 500-fold, respectively). Our SAR studies suggest that the potency and selectivity profile of the best analogues reported here is a result of both the steric bulk and acidity of the RHS sulfonamide NH group. Although all of the analogues had a pharmacokinetic half-life of less than 2 h, acylsulfonamides 43 and 44 did show moderately low clearance in dogs. These two compounds were further evaluated by thermographic imaging in mice and were found to produce a robust thermogenic response via oral administration.

  DOI：

  10.1021/jm0101500

文献信息

• PHOSPHATASE INHIBITORS
  申请人：Sugen, Inc.

  公开号：EP0831795A2

  公开（公告）日：1998-04-01
• [EN] PHOSPHATASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PHOSPHATASE
  申请人：——

  公开号：WO1996040113A2

  公开（公告）日：1996-12-19

  [EN] The present invention relates to organic molecules capable of inhibiting protein tyrosine phosphatase activity. The invention further relates to the use of such molecules to modulate or regulate signal transduction by inhibiting protein tyrosine phosphatase activity. Finally, the invention relates to the use of such molecules to treat various disease states including diabetes mellitus.
  [FR] L'invention porte sur des molécules organiques capables d'inhiber l'activité de la tyrosine phosphatase, sur leur utilisation pour moduler et réguler la transduction de signaux par inhibition de l'activité de la tyrosine phosphatase, et sur leur utilisation pour le traitement de différents états morbides dont le diabète sucré.