4-(4-chlorophenyl)-2-phenylamino-thiazole-5-acetic acid | 49779-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-chlorophenyl)-2-phenylamino-thiazole-5-acetic acid
• 英文别名: (2-phenylamino-4-p-chlorophenyl-thiazol-5-yl)-acetic acid；(2-Phenylamino-4-p-chlorophenyl-thiazol-5-yl)-essigsaeure；5-Thiazoleacetic acid, 4-(4-chlorophenyl)-2-(phenylamino)-；2-[2-anilino-4-(4-chlorophenyl)-1,3-thiazol-5-yl]acetic acid
• CAS: 49779-95-5
• 化学式: C₁₇H₁₃ClN₂O₂S
• 分子量: 344.821
• InChiKey: WFGFPCQTDIRWHS-UHFFFAOYSA-N

物化性质

• 沸点：
  568.8±60.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2-N-Phenylamino-4-p-chlorophenyl-thiazol-5-yl)essigsaeureethylester 在 sodium hydroxide 作用下， 生成 4-(4-chlorophenyl)-2-phenylamino-thiazole-5-acetic acid
  参考文献：
  名称：

  5-Substituted 2-amino-4-arylthiazoles

  摘要：

  5-取代的2-氨基-4-芳基噻唑具有抗炎、退热、镇痛、抗菌、CNS抑制剂、抗溃疡和止咳剂等有趣的性质。

  公开号：

  US03933838A1

文献信息

• New Thiazole Acetic Acid Derivatives: A Study to Screen Cardiovascular Activity Using Isolated Rat Hearts and Blood Vessels
  作者：P. Raghunatha、Mohammed Naseeruddin Inamdar、Syed Mohammed Basheeruddin Asdaq、Mansour Almuqbil、Abdullah R. Alzahrani、Saleh I. Alaqel、Mehnaz Kamal、Firas Hamdan Alsubaie、Walaa F. Alsanie、Abdulhakeem S. Alamri、Syed Imam Rabbani、Mahesh Attimarad、S. Mohan、Majid Alhomrani

  DOI：10.3390/molecules27196138

  日期：——

  present research, new synthetic derivatives of thiazole were studied using isolated hearts and blood vessels of rats. The heart and thoracic aorta were tested with six new synthesized thiazole acetic acid derivatives (SMVA-10, SMVA-35, SMVA-40, SMVA-41, SMVA-42 and SMVA-60), and the data obtained were statistically analyzed and compared. Isolated rat hearts were used to record the changes in developed

  心血管疾病是全世界死亡的主要原因之一。在目前的研究中，使用大鼠离体心脏和血管研究了新的噻唑合成衍生物。用六种新合成的噻唑乙酸衍生物（SMVA-10、SMVA-35、SMVA-40、SMVA-41、SMVA-42和SMVA-60）对心脏和胸主动脉进行了测试，并对所得数据进行了统计分析和比较. 离体大鼠心脏用于记录发展张力和心率的变化，而胸主动脉用于测量治疗前后的收缩反应。结果分析表明显着 ( p< 0.01) 通过添加 SMVA-35、SMVA-40、SMVA-41 和 SMVA-42 增加发展的张力，这在肾上腺素存在的情况下得到增强而不影响心率。另一方面，乙酰胆碱显着降低了产生的张力，在化合物（SMVA-35 和 SMVA-60）存在的情况下显着逆转 ( p < 0.01)。然而，在 SMVA-35 和 SMVA-40 存在的情况下，乙酰胆碱诱发的心动过缓显着（p< 0.01) 减少。此外，只有
• Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 1
  作者：Øystein Rist、Marie Grimstrup、Jean-Marie Receveur、Thomas M. Frimurer、Trond Ulven、Evi Kostenis、Thomas Högberg

  DOI：10.1016/j.bmcl.2009.12.008

  日期：2010.2

  Structure-activity relationships of three related series of 4-phenylthiazol-5-ylacetic acids, derived from two hits emanating from a focused library obtained by in silico screening, have been explored as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Several compounds with double digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained in all subclasses. The most potent compound was [2-(4-chloro-benzyl)-4-(4-phenoxy-phenyl)-thiazol-5-yl] acetic acid having an binding affinity of 3.7 nM and functional antagonistic effect of 66 nM in a BRET and 12 nM in a cAMP assay with no functional activity for the other PGD2 DP receptor (27 mu M in cAMP). (C) 2009 Elsevier Ltd. All rights reserved.
• Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 2
  作者：Marie Grimstrup、Øystein Rist、Jean-Marie Receveur、Thomas M. Frimurer、Trond Ulven、Jesper M. Mathiesen、Evi Kostenis、Thomas Högberg

  DOI：10.1016/j.bmcl.2009.12.015

  日期：2010.2

  Structure-activity relationships have been established by exploring the eastern and western side of 5-thiazolyleacetic acids as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Benzhydryl motifs in the 2-position of the thiazole was found to be most advantageous. The 4-thiazole position should either carry 3- or 4-fluorophenyl rings or a 4-pyridyl suitably substituted in the flanking 2-position. Several compounds with single digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained. The compound series display a good PK profile and selectivity over a large number of other targets. (C) 2009 Elsevier Ltd. All rights reserved.
• US3933838A
  申请人：——

  公开号：US3933838A

  公开（公告）日：1976-01-20