ethyl 4-methyl-2-(3-(p-tolyl)thioureido)thiazole-5-carboxylate | 1585956-66-6

• 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: ethyl 4-methyl-2-(3-(p-tolyl)thioureido)thiazole-5-carboxylate
• 英文别名: Ethyl 4-methyl-2-[(4-methylphenyl)carbamothioylamino]-1,3-thiazole-5-carboxylate；ethyl 4-methyl-2-[(4-methylphenyl)carbamothioylamino]-1,3-thiazole-5-carboxylate
• CAS: 1585956-66-6
• 化学式: C₁₅H₁₇N₃O₂S₂
• 分子量: 335.451
• InChiKey: PCXBWXMXTSSZEN-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C(Solvent: Ethanol)
• 沸点：
  464.4±47.0 °C(predicted)
• 密度：
  1.355±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-methyl-2-(3-(p-tolyl)thioureido)thiazole-5-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以28%的产率得到1-(5-(hydrazinecarbonyl)-4-methylthiazol-2-yl)-3-(p-tolyl)thiourea
  参考文献：
  名称：

  Bifunctional ethyl 2-amino-4-methylthiazole-5-carboxylate derivatives: Synthesis and in vitro biological evaluation as antimicrobial and anticancer agents

  摘要：

  Thirty thiazole compounds bearing chemotherapeutically-active pharmacophores were synthesized and evaluated for their preliminary in vitro antimicrobial and anticancer activities. Nineteen compounds displayed obvious antibacterial potential, with special bactericidal activity against Gram positive bacteria, whereas, nine analogs showed moderate to weak antifungal activity against Candida albicans. The analog 12f proved to be the most active antimicrobial member identified in this study being comparable to ampicillin and gentamicin sulfate against Staphylococcus aureus and Bacillus subtilis, together with a moderate antifungal activity. Additionally, nine derivatives were tested for their preliminary in vitro anticancer activity according to the current one-dose protocol of the NCI. Compound 9b revealed a broad spectrum of anticancer activity against 29 out of the tested 60 subpanel tumor cell lines. Collectively, compounds 4, 9b, 10b and 12f could be considered as promising dual anticancer antibiotics. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.027
• 作为产物：
  描述：

  2-氨基-4-甲基噻唑-5-甲酸乙酯 、 对甲苯异硫氰酸酯 在 吡啶 作用下， 以80%的产率得到ethyl 4-methyl-2-(3-(p-tolyl)thioureido)thiazole-5-carboxylate
  参考文献：
  名称：

  Bifunctional ethyl 2-amino-4-methylthiazole-5-carboxylate derivatives: Synthesis and in vitro biological evaluation as antimicrobial and anticancer agents

  摘要：

  Thirty thiazole compounds bearing chemotherapeutically-active pharmacophores were synthesized and evaluated for their preliminary in vitro antimicrobial and anticancer activities. Nineteen compounds displayed obvious antibacterial potential, with special bactericidal activity against Gram positive bacteria, whereas, nine analogs showed moderate to weak antifungal activity against Candida albicans. The analog 12f proved to be the most active antimicrobial member identified in this study being comparable to ampicillin and gentamicin sulfate against Staphylococcus aureus and Bacillus subtilis, together with a moderate antifungal activity. Additionally, nine derivatives were tested for their preliminary in vitro anticancer activity according to the current one-dose protocol of the NCI. Compound 9b revealed a broad spectrum of anticancer activity against 29 out of the tested 60 subpanel tumor cell lines. Collectively, compounds 4, 9b, 10b and 12f could be considered as promising dual anticancer antibiotics. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.027

文献信息

• Bifunctional ethyl 2-amino-4-methylthiazole-5-carboxylate derivatives: Synthesis and in vitro biological evaluation as antimicrobial and anticancer agents
  作者：Sherif A.F. Rostom、Hassan M. Faidallah、Mohammed F. Radwan、Mona H. Badr

  DOI：10.1016/j.ejmech.2014.02.027

  日期：2014.4

  Thirty thiazole compounds bearing chemotherapeutically-active pharmacophores were synthesized and evaluated for their preliminary in vitro antimicrobial and anticancer activities. Nineteen compounds displayed obvious antibacterial potential, with special bactericidal activity against Gram positive bacteria, whereas, nine analogs showed moderate to weak antifungal activity against Candida albicans. The analog 12f proved to be the most active antimicrobial member identified in this study being comparable to ampicillin and gentamicin sulfate against Staphylococcus aureus and Bacillus subtilis, together with a moderate antifungal activity. Additionally, nine derivatives were tested for their preliminary in vitro anticancer activity according to the current one-dose protocol of the NCI. Compound 9b revealed a broad spectrum of anticancer activity against 29 out of the tested 60 subpanel tumor cell lines. Collectively, compounds 4, 9b, 10b and 12f could be considered as promising dual anticancer antibiotics. (C) 2014 Elsevier Masson SAS. All rights reserved.