benzothiazol-2-yl-bis-{[1-(naphthalen-1-yl)-1H-[1,2,3]triazol-4-yl]methyl}amine | 1443032-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzothiazol-2-yl-bis-{[1-(naphthalen-1-yl)-1H-[1,2,3]triazol-4-yl]methyl}amine
• 英文别名: N,N-bis[(1-naphthalen-1-yltriazol-4-yl)methyl]-1,3-benzothiazol-2-amine
• CAS: 1443032-62-9
• 化学式: C₃₃H₂₄N₈S
• 分子量: 564.673
• InChiKey: QKAHSPAETPFRDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氨基苯并噻唑 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 、 potassium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 18.0h， 生成 benzothiazol-2-yl-bis-{[1-(naphthalen-1-yl)-1H-[1,2,3]triazol-4-yl]methyl}amine
  参考文献：
  名称：

  Design, synthesis and antimicrobial activity of novel benzothiazole analogs

  摘要：

  In an attempt to design and synthesize a new class of antimicrobials, dialkyne substituted 2-aminobenzothiazole was reacted with various substituted aryl azides to generate a small library of 20 compounds (3a-t) by click chemistry. Structures of the newly synthesized compounds were established on the basis of spectral data. These compounds were screened for their antibacterial activity against Gram+ bacteria (Staphylococcus aureus and Enterococcus faecalis), Gram- bacteria (Salmonella typhi, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Shigella boydii) and antifungal activity against Candida tropicalis, Candida albicans, Candida krusei, Cryptococcus neoformans) as well as molds (Aspergillus niger, Aspergillus fumigatus). The compound 3e showed maximum potency against all Gram+/gram- bacterial strains with MIC value 3.12 mu g/ml, which is two fold more active as compared to standard drug ciprofloxacin (MIC 6.25 mu g/ml). However, all compounds were found ineffective against S. boydii (clinical isolate). Further, only one compound 3n was found to be the most active against all fungal strains with MIC value in the range of 1.56 mu g/ml-12.5 mu g/ml while the remaining compounds showed moderate to weak antifungal activity. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.027

文献信息

• Design, synthesis and antimicrobial activity of novel benzothiazole analogs
  作者：Manavendra K. Singh、Ragini Tilak、Gopal Nath、Satish K. Awasthi、Alka Agarwal

  DOI：10.1016/j.ejmech.2013.02.027

  日期：2013.5

  In an attempt to design and synthesize a new class of antimicrobials, dialkyne substituted 2-aminobenzothiazole was reacted with various substituted aryl azides to generate a small library of 20 compounds (3a-t) by click chemistry. Structures of the newly synthesized compounds were established on the basis of spectral data. These compounds were screened for their antibacterial activity against Gram+ bacteria (Staphylococcus aureus and Enterococcus faecalis), Gram- bacteria (Salmonella typhi, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Shigella boydii) and antifungal activity against Candida tropicalis, Candida albicans, Candida krusei, Cryptococcus neoformans) as well as molds (Aspergillus niger, Aspergillus fumigatus). The compound 3e showed maximum potency against all Gram+/gram- bacterial strains with MIC value 3.12 mu g/ml, which is two fold more active as compared to standard drug ciprofloxacin (MIC 6.25 mu g/ml). However, all compounds were found ineffective against S. boydii (clinical isolate). Further, only one compound 3n was found to be the most active against all fungal strains with MIC value in the range of 1.56 mu g/ml-12.5 mu g/ml while the remaining compounds showed moderate to weak antifungal activity. (c) 2013 Elsevier Masson SAS. All rights reserved.