2-(4-chlorophenyl)-N-(4-phenylthiazol-2-yl)acetamide | 518993-08-3

• 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-chlorophenyl)-N-(4-phenylthiazol-2-yl)acetamide
• 英文别名: 2-(4-chlorophenyl)-N-(4-phenyl-1,3-thiazol-2-yl)acetamide
• CAS: 518993-08-3
• 化学式: C₁₇H₁₃ClN₂OS
• mdl: MFCD03486940
• 分子量: 328.822
• InChiKey: NUCLDLOABHOOOA-UHFFFAOYSA-N

物化性质

• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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

• 作为产物：
  描述：

  2-氨基-4-苯基噻唑 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 2-(4-chlorophenyl)-N-(4-phenylthiazol-2-yl)acetamide
  参考文献：
  名称：

  Design and discovery of Novel Thiazole acetamide derivatives as anticholinesterase agent for possible role in the management of Alzheimer’s

  摘要：

  A novel series of thiazole acetamides was synthesized in excellent yields and characterized with the aid of various spectroscopic and elemental analysis. These compounds were evaluated for in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities for possible benefit in Alzheimers disease (AD). Among the synthesized compound, 6d was identified as the most potent compound of AChE (IC50 = 3.14 +/- 0.16 mu M) with a selectivity index (SI) of 2.94 against BuChE. These compounds were further tested for inhibition of Ab aggregation and beta-secretase, where it showed potent inhibition which confirmed its multifactorial benefits in AD. The toxicity and docking study were also carried out to exemplify the pharmacological profile of compound 6d as prospective lead molecule against AD. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2016.01.001

文献信息

• Design and synthesis of thiazole derivatives as potent FabH inhibitors with antibacterial activity
  作者：Jing-Ran Li、Dong-Dong Li、Rong-Rong Wang、Jian Sun、Jing-Jun Dong、Qian-Ru Du、Fei Fang、Wei-Ming Zhang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2013.11.020

  日期：2014.3

  bond between aromatic acid and 4-phenylthiazol-2-amine or 4-(4-bromophenyl)thiazol-2-amine. These thiazole derivatives have evaluated as potent FabH inhibitors. Nineteen compounds (4b–4h, 4k, 4l, 5a–5h, 5k, 5l) are reported for the first time. Most of the synthesized compounds exhibited antibacterial activity in the MTT assay. The MIC value of these compounds ranged from 1.56 μg/mL to 100 μg/mL. Moreover

  脂肪酸生物合成途径的组成已被确定为开发新型抗菌剂的有吸引力的目标。A系列（4a - 4g）和B系列（5a - 5g）的化合物是通过在芳族酸和4-苯基噻唑-2-胺或4-（4-溴苯基）噻唑-2-胺之间形成胺键合成的。这些噻唑衍生物已被评估为有效的FabH抑制剂。19种化合物（4b – 4h，4k，4l，5a – 5h，5k，5l）是首次报告。大多数合成的化合物在MTT分析中显示出抗菌活性。这些化合物的MIC值在1.56μg/ mL至100μg/ mL的范围内。此外，测试化合物还显示出FabH抑制能力，IC 50值在5.8μM至48.1μM的范围内。IC 50值接近MIC值。化合物5f具有最佳的抗菌和大肠杆菌FabH抑制活性。进行了对接模拟和QSAR研究，以了解结合模式以及结构与活性之间的关系。
• Design, synthesis and antibacterial activity studies of thiazole derivatives as potent ecKAS III inhibitors
  作者：Kui Cheng、Jia-Yu Xue、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2013.05.006

  日期：2013.7

  compounds with broad-spectrum antibacterial activities were further tested for their ecKAS III inhibitory activity. Last, we have successfully found that compound 4e showed both the promising broad antibacterial activity with MIC of 1.56–6.25 μg/mL against the representative bacterial stains, and also processed the most potent ecKAS III inhibitory activity with IC50 of 5.3 μM. In addition, docking simulation

  合成并开发了两个系列的具有酰胺骨架的噻唑衍生物，作为有效的大肠杆菌β-酮酰基-（酰基载体蛋白）合酶III（ecKAS III）抑制剂。测定了所有24种新合成化合物对革兰氏阴性和革兰氏阳性细菌菌株的抗菌活性，包括大肠杆菌，铜绿假单胞菌，枯草芽孢杆菌和金黄色葡萄球菌。其中，对10种具有广谱抗菌活性的化合物的ecKAS III抑制活性进行了进一步测试。最后，我们成功地发现了化合物4e既显示出有希望的广泛的抗菌作用，其对代表性细菌染色的MIC为1.56-6.25μg/ mL，还处理了最有效的ecKAS III抑制活性，IC 50为5.3μM 。此外，在这项研究中还进行了对接模拟，以给出小分子与ecKAS III（PDB代码：1hnj）蛋白之间的有效预测结合方式。