2-chloro-N-(4,5-diphenylthiazol-2-yl)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-chloro-N-(4,5-diphenylthiazol-2-yl)acetamide
• 英文别名: 2-chloro-N-(4,5-diphenyl-1,3-thiazol-2-yl)acetamide
• 化学式: C₁₇H₁₃ClN₂OS
• 分子量: 328.822
• InChiKey: HNMOBYQUPAWGDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(4,5-diphenylthiazol-2-yl)acetamide 在 ammonium acetate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 8.0h， 生成 2-((4,5-diphenylthiazol-2-yl)imino)-5-(pyridin-4-ylmethylene)thiazolidin-4-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel diphenylthiazole-based cyclooxygenase inhibitors as potential anticancer agents

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) are among the most widely used medications as analgesics and antipyretics. Currently, there is a growing interest in their antitumor activity and their ability to reduce the risk and mortality of several cancers. While several studies revealed the ability of NSAIDs to induce apoptosis and inhibit angiogenesis in cancer cells, their exact anticancer mechanism is not fully understood. However, both cyclooxygenase (COX)-dependent and -independent pathways were reported to have a role. In an attempt to develop new anticancer agents, a series of diphenylthiazole substituted thiazolidinone derivatives was synthesized and evaluated for their anticancer activity against a panel of cancer cell lines. Additionally, the inhibitory activity of the synthesized derivatives against COX enzymes was investigated as a potential mechanism for the anticancer activity. Cytotoxicity assay results showed that compounds 15b and 16b were the most potent anticancer agents with half maximal inhibitory concentrations (IC50) between 8.88 and 19.25 mu M against five different human cancer cell lines. Interestingly, COX inhibition assay results were in agreement with that of the cytotoxicity assays where the most potent anticancer compounds showed good COX-2 inhibition comparable to that of celecoxib. Further support to our results were gained by the docking studies which suggested the ability of compound 15b to bind into COX-2 enzyme with low energy scores. Collectively, these results demonstrated the promising activity of the newly designed compounds as leads for subsequent development into potential anticancer agents. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.10.001
• 作为产物：
  描述：

  2-氯-2-苯基苯乙酮 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-chloro-N-(4,5-diphenylthiazol-2-yl)acetamide
  参考文献：
  名称：

  新型二苯基噻唑-噻唑烷酮杂化物的设计、合成和抗炎评价

  摘要：

  合成了一系列二苯基噻唑-噻唑烷酮杂化物，并作为抗炎/镇痛剂在体外和体内进行了评估。环加氧酶（COX）的抑制被认为是杂种发挥抗炎作用的分子机制。在这些化合物中，13b、14 和 15b 显示出最有效的 COX 抑制活性，IC50 值介于 2.03 和 12.27 µM 之间，但具有不同的选择性。使用三种动物模型在体内进一步评估了所有化合物的抗炎/镇痛活性。有趣的是，COX 测定的结果与体内测定的结果一致，其中最有效的 COX 抑制剂 13b、14 和 15b 与双氯芬酸相比表现出最高的抗炎/镇痛活性。相反，

  DOI：

  10.1002/ardp.201500104

文献信息

• Synthesis and evaluation of novel diphenylthiazole derivatives as potential anti-inflammatory agents
  作者：Ahmed H. Abdelazeem、Maha Habash、Ibrahim A. Maghrabi、Mutasem O. Taha

  DOI：10.1007/s00044-015-1418-5

  日期：2015.10

  In the presented study, we synthesized a novel series of 18 diphenylthiazole derivatives and tested their anti-inflammatory properties. They showed significant anti-inflammatory properties in inflamed mice paws animal model. Docking-based analysis suggested that they act as COX enzyme inhibitors. The most potent compound 9e is significantly more active in reducing inflamed animal paws compared to diclofenac. Accordingly, we believe these compounds are good leads for further development into potent anti-inflammatory drugs.
• Kulkarni, R. A.; Thaker, S. R., Journal of the Indian Chemical Society, 1988, vol. 65, p. 432 - 434
  作者：Kulkarni, R. A.、Thaker, S. R.

  DOI：——

  日期：——
• KULKARNI, R. A.;THAKER, S. R., J. INDIAN CHEM. SOC., 65,(1988) N 6, C. 432-434
  作者：KULKARNI, R. A.、THAKER, S. R.

  DOI：——

  日期：——
• Design, Synthesis, and Anti-Inflammatory Evaluation of Novel Diphenylthiazole-Thiazolidinone Hybrids
  作者：Ahmed H. Abdelazeem、Samir A. Salama、Ibrahim A. Maghrabi

  DOI：10.1002/ardp.201500104

  日期：2015.7

  A series of diphenylthiazole–thiazolidinone hybrids was synthesized and evaluated in vitro and in vivo as anti‐inflammatory/analgesic agents. The inhibition of cyclooxygenase (COX) enzymes was suggested as a molecular mechanism for the hybrids to exert their anti‐inflammatory action. Of these compounds, 13b, 14, and 15b showed the most potent COX inhibitory activity with IC50 values between 2.03 and

  合成了一系列二苯基噻唑-噻唑烷酮杂化物，并作为抗炎/镇痛剂在体外和体内进行了评估。环加氧酶（COX）的抑制被认为是杂种发挥抗炎作用的分子机制。在这些化合物中，13b、14 和 15b 显示出最有效的 COX 抑制活性，IC50 值介于 2.03 和 12.27 µM 之间，但具有不同的选择性。使用三种动物模型在体内进一步评估了所有化合物的抗炎/镇痛活性。有趣的是，COX 测定的结果与体内测定的结果一致，其中最有效的 COX 抑制剂 13b、14 和 15b 与双氯芬酸相比表现出最高的抗炎/镇痛活性。相反，
• Design, synthesis and biological evaluation of novel diphenylthiazole-based cyclooxygenase inhibitors as potential anticancer agents
  作者：Ahmed H. Abdelazeem、Ahmed M. Gouda、Hany A. Omar、Mai F. Tolba

  DOI：10.1016/j.bioorg.2014.10.001

  日期：2014.12

  Non-steroidal anti-inflammatory drugs (NSAIDs) are among the most widely used medications as analgesics and antipyretics. Currently, there is a growing interest in their antitumor activity and their ability to reduce the risk and mortality of several cancers. While several studies revealed the ability of NSAIDs to induce apoptosis and inhibit angiogenesis in cancer cells, their exact anticancer mechanism is not fully understood. However, both cyclooxygenase (COX)-dependent and -independent pathways were reported to have a role. In an attempt to develop new anticancer agents, a series of diphenylthiazole substituted thiazolidinone derivatives was synthesized and evaluated for their anticancer activity against a panel of cancer cell lines. Additionally, the inhibitory activity of the synthesized derivatives against COX enzymes was investigated as a potential mechanism for the anticancer activity. Cytotoxicity assay results showed that compounds 15b and 16b were the most potent anticancer agents with half maximal inhibitory concentrations (IC50) between 8.88 and 19.25 mu M against five different human cancer cell lines. Interestingly, COX inhibition assay results were in agreement with that of the cytotoxicity assays where the most potent anticancer compounds showed good COX-2 inhibition comparable to that of celecoxib. Further support to our results were gained by the docking studies which suggested the ability of compound 15b to bind into COX-2 enzyme with low energy scores. Collectively, these results demonstrated the promising activity of the newly designed compounds as leads for subsequent development into potential anticancer agents. (C) 2014 Elsevier Inc. All rights reserved.