Hybrid 4‐Aminoquinoline‐1,3,5‐triazine Derivatives: Design, Synthesis, Characterization, and Antibacterial Evaluation

Abstract

A series of novel 4‐aminoquinoline 1,3,5‐triazine derivatives were synthesized and characterized by FTIR, 1H‐NMR, 13C‐NMR, MS, and elemental analysis. The antibacterial activities of synthesized compounds were tested against three Gram‐positive bacteria, namely Bacillus subtilis (NCIM‐2063), Bacillus cereus (NCIM‐2156), and Staphylococcus aureus (NCIM‐2079), and four Gram‐negative bacteria, namely Proteus vulgaris (NCIM‐2027), Proteus mirabilis (NCIM‐2241), Escherichia coli (NCIM‐2065), and Pseudomonas aeruginosa (NCIM‐2036), using ciprofloxacin as reference standard drug. Results showed compound 9a and 9e as potent antibacterial agents against all bacterial strains except Bacillus cereus (NCIM‐2156). Copyright © 2014 HeteroCorporation

Quinazoline based 1,3,5‐triazine derivatives as cancer inhibitors by impeding the phosphorylated RET tyrosine kinase pathway: Design, synthesis, docking, and QSAR study

“…Further, the derivative 6‐bromo‐2‐methyl‐4‐oxo‐4 H ‐quinazoline‐3‐carboxylic acid amide ( 4 ) was synthesized by the reaction of derivatives ( 3 ) and urea under reflux. The synthesis of 4,6‐dichloro‐2‐piperazin‐1‐yl‐[1,3,5]triazine ( 6 ) was carried in fourth reaction scheme. In this step cyanuric chloride ( 5 ) and piperazine were reacted between at 0–5°C.…”

“…In this step cyanuric chloride ( 5 ) and piperazine were reacted between at 0–5°C. In the next step (v), the second chlorine atom was substituted from 4,6‐dichloro‐2‐piperazin‐1‐yl‐[1,3,5]triazine ( 6 ) . The reaction was carried out in the presence of various aliphatic and aromatic amines at 40–45°C.…”

“…The reaction was carried out in the presence of various aliphatic and aromatic amines at 40–45°C. As a result, disubstituted 1,3,5‐triazine derivatives ( 7a‐o ) were formed . The sixth and final reaction scheme was nucleophilic substitution reaction and the final product ( 8a‐o ) was synthesized by this method.…”

Novel 4,6-Disubstituted s-Triazin-2-yl Amino Acid Derivatives as Promising Antifungal Agents

“…In medicinal chemistry, the s -triazine ring has proved to be a privileged structure, and, therefore, its derivatives have been extensively studied against a broad number of biological targets. In this respect, s -triazine derivatives have shown antiprotozoal [ 11 ], anti-HIV [ 12 ], anticancer [ 13 , 14 ], antimalarial [ 15 , 16 ], antibacterial [ 17 , 18 , 19 ], antifungal [ 20 , 21 , 22 ], and antileishmanial activity [ 23 ], carbonic anhydrase inhibitors [ 24 , 25 ], and human monoamine oxidase (MAO) inhibitors [ 26 ].…”

Structural and biological survey of 7‐chloro‐4‐(piperazin‐1‐yl)quinoline and its derivatives

“…Pathak et al in 2015 identified the hybrid compound 45 between 1,3,5‐triazine derivative and 7 ‐chloro‐4‐(piperazin‐1‐yl)quinoline with potential activity (MIC in μg/ml) against Bacillus subtilis (3.125), Bacillus cereus (6.25), and Staphylococcus aureus (6.25), and four Gram‐negative bacteria, namely Proteus vulgaris (3.125), Proteus mirabilis (3.125), Escherichia coli (12.5), and Pseudomonas aeruginosa (3.125) (Pathak, Thakur, Bhat, & Singh, 2015). Again in 2016, another hybrid between isatin and 7 ‐chloro‐4‐(piperazin‐1‐yl)quinoline ( 46 ) was synthesized by Bogdanov and coauthors.…”