N-(4-(2-amino-5-((3-chlorophenyl)diazenyl)thiazol-4-yl)phenyl)benzamide | 1415398-59-2

• 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: N-(4-(2-amino-5-((3-chlorophenyl)diazenyl)thiazol-4-yl)phenyl)benzamide
• 英文别名: N-[4-[2-amino-5-[(3-chlorophenyl)diazenyl]-1,3-thiazol-4-yl]phenyl]benzamide
• CAS: 1415398-59-2
• 化学式: C₂₂H₁₆ClN₅OS
• 分子量: 433.921
• InChiKey: YBRBZAYJLNOMEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(4-乙酰基苯基)苯甲酰胺 在 盐酸 、 碘 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 10.33h， 生成 N-(4-(2-amino-5-((3-chlorophenyl)diazenyl)thiazol-4-yl)phenyl)benzamide
  参考文献：
  名称：

  Design, synthesis and in vitro antimicrobial activity of novel phenylbenzamido-aminothiazole-based azasterol mimics

  摘要：

  Phenylbenzamide framework as a mimic of the azasterol structure was investigated by synthesizing 4-phenylbenzamido-2-aminothiazole 4, and evaluating its MIC against Escherichia coli, Enterobacter cloacae, Bacillus licheniformis and Mycobacterium tuberculosis (MTB) H(37)Rv as well as antifungal activity against three test phytopathogenic fungi. Further, the bioisosterism strategy was implemented to synthesize a series of azo-derivatives of 4 (6a-6j). All the azo-compounds were screened for their antibacterial and antifungal activity. The electronic (UV-vis) absorption characteristics of the final compounds were examined. Resazurin-mediated microtitre plate-antibacterial assay was implemented for first time on these azo-derivatives. Compounds 4 and 6b had significant antibacterial activity. For the compound 4, MIC against Escherichia coli is 7.8 x 10(-3) mg/mL and MIC against Mycobacterium tuberculosis (MTB) H(37)Rv is 16 mu g/mL were identified. Compounds 4, 6d, 6g and 6h showed excellent antifungal activity, when compared to the standard nistatin, against three test phytopathogenic fungi.

  DOI：

  10.1007/s00044-012-0314-5

文献信息

• Design, synthesis and in vitro antimicrobial activity of novel phenylbenzamido-aminothiazole-based azasterol mimics
  作者：Rama Krishna Yadlapalli、O. P. Chourasia、Madhu Prakash Jogi、Appa Rao Podile、Ramu Sridhar Perali

  DOI：10.1007/s00044-012-0314-5

  日期：2013.6

  Phenylbenzamide framework as a mimic of the azasterol structure was investigated by synthesizing 4-phenylbenzamido-2-aminothiazole 4, and evaluating its MIC against Escherichia coli, Enterobacter cloacae, Bacillus licheniformis and Mycobacterium tuberculosis (MTB) H(37)Rv as well as antifungal activity against three test phytopathogenic fungi. Further, the bioisosterism strategy was implemented to synthesize a series of azo-derivatives of 4 (6a-6j). All the azo-compounds were screened for their antibacterial and antifungal activity. The electronic (UV-vis) absorption characteristics of the final compounds were examined. Resazurin-mediated microtitre plate-antibacterial assay was implemented for first time on these azo-derivatives. Compounds 4 and 6b had significant antibacterial activity. For the compound 4, MIC against Escherichia coli is 7.8 x 10(-3) mg/mL and MIC against Mycobacterium tuberculosis (MTB) H(37)Rv is 16 mu g/mL were identified. Compounds 4, 6d, 6g and 6h showed excellent antifungal activity, when compared to the standard nistatin, against three test phytopathogenic fungi.