ethyl 4-methyl-2-(3-phenylureido)thiazole-5-carboxylate

• 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-phenylureido)thiazole-5-carboxylate
• 英文别名: 4-methyl-2-[3-phenylureido]thiazole-5-carboxylic acid ethyl ester；Ethyl 4-methyl-2-(phenylcarbamoylamino)thiazole-5-carboxylate；ethyl 4-methyl-2-(phenylcarbamoylamino)-1,3-thiazole-5-carboxylate
• 化学式: C₁₄H₁₅N₃O₃S
• 分子量: 305.357
• InChiKey: AIIUEMKMJFUMMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  109
• 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-phenylureido)thiazole-5-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以41%的产率得到1-(5-(hydrazinecarbonyl)-4-methylthiazol-2-yl)-3-phenylurea
  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 、 异氰酸苯酯 在 吡啶 作用下， 以76%的产率得到ethyl 4-methyl-2-(3-phenylureido)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

• Aryl Urea Derivatives for Treating Obesity
  申请人：Bloxham Jason

  公开号：US20080261952A1

  公开（公告）日：2008-10-23

  A method of treating a condition associated with the CB-1 receptor, in particular obesity, by administering an effective amount of an aryl urea CB-1 receptor modulating compound to a subject in need of such treatment.

  通过向需要此类治疗的受试者施用有效量的芳基脲CB-1受体调节化合物来治疗与CB-1受体相关的疾病，尤其是肥胖症的方法。
• 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.