3-[4-[[4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylamino]phenyl]propanoic acid | 885102-00-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-[4-[[4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylamino]phenyl]propanoic acid
• CAS: 885102-00-1
• 化学式: C₂₁H₁₉F₃N₂O₂S
• 分子量: 420.455
• InChiKey: IJEJUKTZOQSPOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  90.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[4-[[4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylamino]phenyl]propanoic acid 在 氨 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3-[4-[[4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylamino]phenyl]propanamide
  参考文献：
  名称：

  Synthesis and activity of small molecule GPR40 agonists

  摘要：

  The first report on the identification and structure-activity relationships of a novel series of GPR40 agonists based on a 3(4-{[N-alkyl]amino phenyl)propanoic acid template is described. Structural modifications to the original screening hit yielded compounds with a 100-fold increase in potency at the human GPR40 receptor and pEC(50)s in the low nanomolar range. The carboxylic acid moiety is not critical for activity but typically elicits an agonistic response higher than those observed with carboxamide replacements. These compounds may prove useful in unraveling the therapeutic potential of this receptor for the treatment of Type 2 diabetes. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.007
• 作为产物：
  描述：

  4-甲基-2-[4-(三氟甲基)苯基]-1,3-噻唑-5-甲醛 、 3-(4-氨基苯基)丙酸 在 Na(OAc)3H 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 3-[4-[[4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylamino]phenyl]propanoic acid
  参考文献：
  名称：

  Synthesis and activity of small molecule GPR40 agonists

  摘要：

  The first report on the identification and structure-activity relationships of a novel series of GPR40 agonists based on a 3(4-{[N-alkyl]amino phenyl)propanoic acid template is described. Structural modifications to the original screening hit yielded compounds with a 100-fold increase in potency at the human GPR40 receptor and pEC(50)s in the low nanomolar range. The carboxylic acid moiety is not critical for activity but typically elicits an agonistic response higher than those observed with carboxamide replacements. These compounds may prove useful in unraveling the therapeutic potential of this receptor for the treatment of Type 2 diabetes. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.007

文献信息

• Synthesis and activity of small molecule GPR40 agonists
  作者：Dulce M. Garrido、David F. Corbett、Kate A. Dwornik、Aaron S. Goetz、Thomas R. Littleton、Steve C. McKeown、Wendy Y. Mills、Terrence L. Smalley、Celia P. Briscoe、Andrew J. Peat

  DOI：10.1016/j.bmcl.2006.01.007

  日期：2006.4

  The first report on the identification and structure-activity relationships of a novel series of GPR40 agonists based on a 3(4-[N-alkyl]amino phenyl)propanoic acid template is described. Structural modifications to the original screening hit yielded compounds with a 100-fold increase in potency at the human GPR40 receptor and pEC(50)s in the low nanomolar range. The carboxylic acid moiety is not critical for activity but typically elicits an agonistic response higher than those observed with carboxamide replacements. These compounds may prove useful in unraveling the therapeutic potential of this receptor for the treatment of Type 2 diabetes. (C) 2006 Elsevier Ltd. All rights reserved.