Microwave-assisted synthesis of N-alkylated benzotriazole derivatives: antimicrobial studies.
Synthesis and characterization of N-alkylated benzotriazole derivatives 2(a-g) bearing pharmaceutically important bioactive substituents and their antimicrobial studies in vitro are described. The syntheses of the compounds were achieved by N-alkylation of the benzotriazole with different bioactive alkyl halides in presence of powdered K2CO3 in DMF solution and by microwave irradiation method with good yield compared to conventional method. The crystal structure analysis shows that compound 4'-benzotriazol-1-yl-methyl-biphenyl-2-carbonitrile 2a crystallizes in the space group P1 with cell parameters a = 8.526 (3) A, b = 12.706 (3) A, c = 7.966 (2) A, alpha = 100.89 (2) degrees , beta = 101.63 (3) degrees , gamma = 102.20(2) degrees, Volume = 801.7(4) A degrees , Z = 2 and the final R factor is 0.0559 for 6130 reflections with 218 parameters and zero restraint. This structure exhibits intermolecular hydrogen bonding. Compounds 2e, 2a showed significant antimicrobial activity.
Nanjunda Swamy
S
S
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, India.
Basappa
Sarala
G
G
Priya
B S
BS
Gaonkar
S L
SL
Shashidhara Prasad
J
J
Rangappa
K S
KS
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology / Q000528:radiation effects; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology / Q000528:radiation effects; D001419:Bacteria / Q000187:drug effects; D003460:Crystallization; D018360:Crystallography, X-Ray; D005658:Fungi / Q000187:drug effects; D006860:Hydrogen Bonding; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D008958:Models, Molecular; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis / Q000494:pharmacology / Q000528:radiation effects
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D014230:Triazoles; C012771:benzotriazole