5-acetyl-4-methyl-2-(m-methylphenylamino)thiazole | 478078-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-acetyl-4-methyl-2-(m-methylphenylamino)thiazole
• 英文别名: 1-{4-Methyl-2-[(3-methylphenyl)amino]-1,3-thiazol-5-yl}ethan-1-one；1-[4-methyl-2-(3-methylanilino)-1,3-thiazol-5-yl]ethanone
• CAS: 478078-66-9
• 化学式: C₁₃H₁₄N₂OS
• 分子量: 246.333
• InChiKey: ITWNYYGBHNCFGS-UHFFFAOYSA-N

物化性质

• 溶解度：
  3 [ug/mL]

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：

  5-acetyl-4-methyl-2-(m-methylphenylamino)thiazole 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 18.0h， 生成 N’-{1-[2-(m-tolylamino)-4-methylthiazol-5-yl]ethylidene}-4-(4-methoxyphenyl)piperazine-1-carbothiohydrazide
  参考文献：
  名称：

  微波辐射下5-乙酰基-2-芳氨基-4-甲基噻唑缩氨基硫脲的合成及其体外抗癌活性

  摘要：

  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。

  DOI：

  10.3184/174751916x14519928918516
• 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 5-acetyl-4-methyl-2-(m-methylphenylamino)thiazole
  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 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.
• Thiazole fused thiosemicarbazones: Microwave-assisted synthesis, biological evaluation and molecular docking study
  作者：Neelam P. Prajapati、Kinjal D. Patel、Rajesh H. Vekariya、Hitesh D. Patel、Dhanaji P. Rajani

  DOI：10.1016/j.molstruc.2018.11.025

  日期：2019.3

  In the present study, series of novel compounds (E)-2-(1-(4-methyl-2-(substituted-phenylamino)thiazol-5-yl)ethylidene)hydrazinecarbothio-amide (5a-j) and (E)-N-cyclohexyl-2-(1-(4-methyl-2-(substituted-phenylamino)thiazol-5-yl)ethylidene)hydrazinecarbothioamide (6a-j) have been synthesized using microwave irradiation method in high yields and characterized by IR, H-1 NMR, C-13 NMR and mass spectral analysis. Synthesized compounds were evaluated for their in-vitro antimicrobial, antimalarial and anti-tuberculosis activity as well as in-silico study. The obtained results indicate that compound 6b and 6g were found to be the most potent against S. aureus bacterial strain. Further, the molecular docking study has been performed for all the new compounds with the immune system of S. aureus (PDB ID: 5D1Q) as a target enzyme, and this study validated the experimental results. (C) 2018 Elsevier B.V. All rights reserved.
• 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。
• Synthesis of Novel Thiazolyl-Pyrimidines and Their Anticancer Activity in Vitro
  作者：Hai-Bo Shi、Hai-Bo Li、Kong-Qin Lu、Xia-Re Zhu、Wei-Xiao Hu、Wen Pei

  DOI：10.1002/ardp.201000238

  日期：2011.10

  A series of novel compounds 7–43 were prepared via the condensation of enaminones 4a–h and the guanidines carbonate 6a–f. The structures of these newly synthesized compounds were confirmed by 1H‐NMR, MS, EA and IR. All the compounds were tested for their cytotoxic activity in vitro against human cancer cell lines including Ishikawa, A549, BEL‐7404, SPC‐A‐01 and SGC‐7901. Most of them showed moderate

  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。