1,2,4‐Triazole and benzimidazole fused dihydropyrimidine derivatives: Design, green synthesis, antibacterial, antitubercular, and antimalarial activities

This study reports the design and synthesis of novel 1,2,4‐triazolo/benzimidazolo‐pyrimidine linked 1‐benzyl‐4‐[(p‐tolyloxy)methyl]‐1,2,3‐triazole derivatives as potent antimicrobial agents according to their in vitro antibacterial, antifungal, antitubercular as well as antimalarial activities. An e...

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Bibliographic Details
Published in:Archiv der Pharmazie (Weinheim) 2023-04, Vol.356 (4), p.e2200545-n/a
Main Authors: Mokariya, Jaydeep A., Rajani, Dhanji P., Patel, Manish P.
Format: Article
Language:English
Subjects:
1,2,3‐triazole
Anti-Bacterial Agents - pharmacology
Anti-Infective Agents - pharmacology
antimalarial
Antimalarials - pharmacology
antimicrobial
Antimicrobial agents
antitubercular
Antitubercular Agents - pharmacology
benzimidazo[1,2‐a]pyrimidine
Benzimidazoles - pharmacology
Escherichia coli
Malaria
Microbial Sensitivity Tests
Pyrimidines - pharmacology
Structure-Activity Relationship
Triazoles - pharmacology
triazolo[1,5‐a]pyrimidine
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Summary:This study reports the design and synthesis of novel 1,2,4‐triazolo/benzimidazolo‐pyrimidine linked 1‐benzyl‐4‐[(p‐tolyloxy)methyl]‐1,2,3‐triazole derivatives as potent antimicrobial agents according to their in vitro antibacterial, antifungal, antitubercular as well as antimalarial activities. An efficient, ecologically benign, and facile multicomponent synthesis was employed to synthesize these derivatives. The synthesis is accelerated with the mild and eco‐friendly organocatalyst tetrabutylammonium bromide, providing a yield of 82%–96% within the short reaction time of 0.5–1.5 h. Compared with the MIC values of ciprofloxacin and ampicillin on the respective strains, compound d2 showed better activity against Escherichia coli and Streptococcus pyogenes and compound d8 showed better MIC against Staphylococcus aureus. Additionally, compounds d3, d4, and d5 showed potent MIC values against Pseudomonas aeruginosa. All triazolo‐pyrimidine derivatives d1–d8 showed potent inhibitory action against Gram‐positive strains. Compound e3 showed good potency against Mycobacterium tuberculosis H37Rv. The IC50 values of d3 and e2 indicated better activity against Plasmodium falciparum. Collectively, these derivatives depict potent multifaceted activity and provide promising access for further antimicrobial and antimalarial investigations. 1,2,4‐Triazolo/benzimidazolo‐pyrimidine‐linked 1‐benzyl‐4‐[(p‐tolyloxy)methyl]‐1,2,3‐triazole derivatives were synthesized via facile tetrabutylammonium bromide‐catalyzed green multicomponent synthesis. The resulting compounds showed potent antibacterial, antitubercular, and antimalarial activities. The multifaceted biological potential of these dihydropyrimidine derivatives represents their importance in medicinal chemistry.
ISSN:0365-6233
1521-4184
DOI:10.1002/ardp.202200545