(4-phenyl-2-(phenylamino)thiazol-5-yl)(p-toluyl)methanone | 1224937-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-phenyl-2-(phenylamino)thiazol-5-yl)(p-toluyl)methanone
• 英文别名: (2-anilino-4-phenyl-1,3-thiazol-5-yl)-(4-methylphenyl)methanone
• CAS: 1224937-96-5
• 化学式: C₂₃H₁₈N₂OS
• 分子量: 370.475
• InChiKey: FJMIUNJCELHTHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  噻吩-2-甲醛二甲基腙 、 2-溴-4'-甲基苯乙酮 以 乙腈 为溶剂， 反应 5.0h， 生成 (4-phenyl-2-(phenylamino)thiazol-5-yl)(p-toluyl)methanone
  参考文献：
  名称：

  2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists

  摘要：

  A series of 2-amino-5-benzoyl-4-phenylthiazole derivatives was investigated in radioligand binding studies at adenosine receptor (AdoR) subtypes with the goal to obtain potent and A(1)-selective antagonists. Acylation of the 2-amino group was found to be crucial for high A(1) affinity. The best compound of the present series was 2-benzoylamino-5-p-methylbenzoyl-4-phenylthiazole (16m) showing a K-i value of 4.83 nM at rat and 57.4 nM at human A(1) receptors combined with high selectivity versus the other AdoR subtypes. The compound behaved as an antagonist in GTP shift assays at A(1) receptors. Compound 16m may serve as a new lead structure for the development of second-generation non-xanthine-derived A(1) antagonists which have potential as novel drugs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.072

文献信息

• 2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists
  作者：Anja B. Scheiff、Swapnil G. Yerande、Ali El-Tayeb、Wenjin Li、Gajanan S. Inamdar、Kamala K. Vasu、Vasudevan Sudarsanam、Christa E. Müller

  DOI：10.1016/j.bmc.2010.01.072

  日期：2010.3

  A series of 2-amino-5-benzoyl-4-phenylthiazole derivatives was investigated in radioligand binding studies at adenosine receptor (AdoR) subtypes with the goal to obtain potent and A(1)-selective antagonists. Acylation of the 2-amino group was found to be crucial for high A(1) affinity. The best compound of the present series was 2-benzoylamino-5-p-methylbenzoyl-4-phenylthiazole (16m) showing a K-i value of 4.83 nM at rat and 57.4 nM at human A(1) receptors combined with high selectivity versus the other AdoR subtypes. The compound behaved as an antagonist in GTP shift assays at A(1) receptors. Compound 16m may serve as a new lead structure for the development of second-generation non-xanthine-derived A(1) antagonists which have potential as novel drugs. (C) 2010 Elsevier Ltd. All rights reserved.