1-[4-甲基-2-(4-甲基苯胺基)-1,3-噻唑-5-基]乙酮 | 71047-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-[4-甲基-2-(4-甲基苯胺基)-1,3-噻唑-5-基]乙酮
• 英文名称: 5-acetyl-4-methyl-2-(p-methylphenylamino)thiazole
• 英文别名: 1-(4-methyl-2-(p-tolylamino)thiazol-5-yl)ethanone；1-(4-methyl-2-(p-tolylamino)-1,3-thiazol-5-yl)ethan-1-one；1-(4-methyl-2-(p-tolylamino)thiazol-5-yl)ethan-1-one；1-[4-methyl-2-(4-methyl-anilino)-thiazol-5-yl]-ethanone；1-(4-Methyl-2-(4-toluidino)-1,3-thiazol-5-yl)-1-ethanone；1-[4-methyl-2-(4-methylanilino)-1,3-thiazol-5-yl]ethanone
• CAS: 71047-48-8
• 化学式: C₁₃H₁₄N₂OS
• mdl: MFCD00749311
• 分子量: 246.333
• InChiKey: USXHFWPMWDRNAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[4-甲基-2-(4-甲基苯胺基)-1,3-噻唑-5-基]乙酮 在 氢溴酸 、 溴 作用下， 以 1,4-二氧六环 为溶剂， 以50%的产率得到2-bromo-1-(4-methyl-2-(p-tolylamino)thiazol-5-yl)ethanone
  参考文献：
  名称：

  Substituted N-Phenyl-5-(2-(phenylamino)thiazol-4-yl)isoxazole-3-carboxamides Are Valuable Antitubercular Candidates that Evade Innate Efflux Machinery

  摘要：

  Tuberculosis remains one of the deadliest infectious diseases in the world, and the increased number of multidrug-resistant and extremely drug-resistant strains is a significant reason for concern. This makes the discovery of novel antitubercular agents a cogent priority. We have previously addressed this need by reporting a series of substituted 2-aminothiazoles capable to inhibit the growth of actively replicating, nonreplicating persistent, and resistant Mycobacterium tuberculosis strains. Clues from the structureactivity relationships lining up the antitubercular activity were exploited for the rational design of improved analogues. Two compounds, namely N-phenyl-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 7a and N-(pyridin-2-yl)-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 8a, were found to show high inhibitory activity toward susceptible M. tuberculosis strains, with an MIC90 of 0.1250.25 mu g/mL (0.330.66 mu M) and 0.060.125 mu g/mL (0.160.32 mu M), respectively. Moreover, they maintained good activity also toward resistant strains, and they were selective over other bacterial species and eukaryotic cells, metabolically stable, and apparently not susceptible to the action of efflux pumps.

  DOI：

  10.1021/acs.jmedchem.7b00793
• 作为产物：
  描述：

  乙酰丙酮 在 N-氯代丁二酰亚胺 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 5.0h， 生成 1-[4-甲基-2-(4-甲基苯胺基)-1,3-噻唑-5-基]乙酮
  参考文献：
  名称：

  新型噻唑基嘧啶的合成及其体外抗癌活性

  摘要：

  通过烯胺酮 4a-h 和碳酸胍 6a-f 的缩合制备了一系列新型化合物 7-43。这些新合成化合物的结构经 1H-NMR、MS、EA 和 IR 证实。测试了所有化合物对包括 Ishikawa、A549、BEL-7404、SPC-A-01 和 SGC-7901 在内的人类癌细胞系的体外细胞毒活性。它们中的大多数对测试的细胞系显示出中等的细胞毒性。其中，最有效的化合物 9 和 30 对 Ishikawa A549 表现出更有效的活性。

  DOI：

  10.1002/ardp.201000238

文献信息

• Synthesis of 5-acetyl-2-arylamino-4-methylthiazole Thiosemicarbazones under Microwave Irradiation and their in Vitro Anticancer Activity
  作者：Hai-Bo Shi、Wei-Xiao Hu、Wei-Mao Zhang、Yan-Fei Wu

  DOI：10.3184/174751916x14519928918516

  日期：2016.2

  new tri- and tetra-cyclic thiosemicarbazone derivatives were prepared via the condensation of morpholine, piperazine or N-(4-methoxyphenyl)piperazine with seven methyl hydrazine-carbodithioate derivatives of 5-acetyl-2-arylamino-4-methylthiazoles under microwave irradiation. All compounds were tested for their cytotoxic activity in vitro against human gastric, lung and breast cancer cell lines. The results

  通过吗啉、哌嗪或 N-(4-甲氧基苯基)哌嗪与 7 种 5-乙酰基-2-芳氨基-4-甲基噻唑的甲基肼-碳二硫代酯衍生物缩合反应，制备了一系列 21 种新型三环和四环缩氨基硫脲衍生物在微波照射下。测试了所有化合物对人胃癌、肺癌和乳腺癌细胞系的体外细胞毒活性。结果表明，一些化合物显示出中等的抗癌活性。最有效的化合物是吗啉取代的类似物，对人类乳腺癌细胞表现出显着的活性。
• Study on condensation of N-aryl thioureas with 3-bromo-acetylacetone: Synthesis of aminothiazoles and iminodihydrothiazoles, and their in vitro antiproliferative activity on human cervical cancer cells
  作者：Hai-Bo Shi、Shi-Jie Zhang、Yan-Fang Lin、Wei-Xiao Hu、Chao-Ming Cai

  DOI：10.1002/jhet.602

  日期：2011.9

  The condensation of N‐aryl thioureas with 3‐bromo‐acetylacetone in neutral solvent acetone not only led to 5‐acetyl‐4‐methyl‐2‐(substituted anilino) thiazoles 3 but also 2‐imino‐3‐(substituted phenyl)‐4‐methyl‐5‐acetyl‐2,3‐dihydrothiazoles 4. Further study found that different reaction solvents displayed an important role toward the ratio of aminothiazoles 3 and iminodihydrothiazoles 4, and the reaction

  的缩合ñ -芳基与3-溴乙酰丙酮硫脲在中性溶剂丙酮不仅导致5-乙酰基-4-甲基-2-（取代的苯胺基）噻唑类3也2-亚氨基-3-（取代苯基） - 4-甲基-5-乙酰基-2,3-二氢噻唑4。进一步的研究发现，不同的反应溶剂对氨基噻唑3和亚氨基二氢噻唑4的比例具有重要作用，并且扩大了反应范围。提出了一种可能的机制，其中涉及溶剂效应和原位氢溴酸催化。一些选定的异构体在体外表现出中等水平对人类宫颈癌细胞系的抗增殖活性（Hela，Siha）。J.杂环化​​学。（2011）。
• Mechanochemical synthesis of 5‐acetylthiazole: A step toward green and sustainable chemistry
  作者：Abdullah S. Al‐Bogami、Tamer S. Saleh、Adel H. Al‐Shareef

  DOI：10.1002/jhet.4079

  日期：2020.10

  Mechanochemical synthesis of 5‐acetylthiazole derivatives by one‐pot three‐component procedure over Silica Sulfuric acid under solvent‐free conditions, has been developed. The durability of the catalyst was tested. The environmentally benign protocol introduced herein characterized by no hazardous organic solvent used, recyclability of the catalyst up to five runs without loss of its catalytic activity

  已经开发了在无溶剂条件下在二氧化硅硫酸上通过一锅三组分程序进行机械化学合成5-乙酰基噻唑衍生物的方法。测试了催化剂的耐久性。本文介绍的对环境有益的方案，其特征在于不使用危险的有机溶剂，催化剂可循环使用多达五次，而不会损失其催化活性，并且产品收率高，这证实了在所述方案中利用了某些绿色化学原理。
• Iodine‐Mediated Three‐Component Strategy to Synthesize 2‐Aminothiazoles from β‐Diketones/β‐ketoesters, Arylamines and Ammonium Thiocyanate
  作者：Abigail Philips、Ajithkumar Arumugam、Yuvaprabhu Eswaramoorthy、Siva Senthil Kumar Boominathan、Gopal Chandru Senadi

  DOI：10.1002/ejoc.202201233

  日期：2022.12.12

  A one-pot, three-component protocol for the synthesis of 2-aminothiazoles promoted by iodine from readily available starting materials such as b-diketones/b-ketoesters, arylamines, and NH4SCN has been developed. A wide range of arylamines was tolerated well to produce the expected polysubstituted 2-aminothiazoles in moderate to good yields. The characteristic features of this methodology include operational

  已经开发了一种一锅三组分方案，用于从容易获得的起始材料（如 b-二酮/b-酮酯、芳基胺和 NH4SCN）合成 2-氨基噻唑。广泛的芳胺耐受性良好，以中等至良好的产率生产预期的多取代 2-氨基噻唑。该方法的特点包括操作简便、无金属反应条件、克级可扩展性、官能团耐受性和反应时间短。
• Synthesis and anticancer evaluation of thiazolyl–chalcones
  作者：Hai-Bo Shi、Shi-Jie Zhang、Qiu-Fu Ge、Dian-Wu Guo、Chao-Ming Cai、Wei-Xiao Hu

  DOI：10.1016/j.bmcl.2010.09.041

  日期：2010.11

  Thirty-seven (E)-1-(4-methyl-2-arylaminothiazol-5-yl)-3-arylprop-2-en-1-ones were synthesized via Claisen-Schmidt condensation of 1-(4-methyl-2-(arylamino)thiazol-5-yl) ethanone with the corresponding arylaldehydes. All these thiazolyl-chalcones were characterized and evaluated by MTT assay on human cancer cell lines BGC-823, PC-3, NCI-H460, BEL-7402 in vitro. Compounds 5, 8, 26, 37 and 41 are effective against cancer cell lines with IC(50)s below 10 mu M. The antitumor activity in ICR mice bearing sarcoma 180 tumors indicates compounds 10 and 41 have moderate in vivo activity with 22-25% tumor-weight inhibition. (C) 2010 Elsevier Ltd. All rights reserved.