Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: as a new class of potent antioxidants and antimicrobials--a novel accost to amend biocompatibility.
In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, (1)H NMR, (13)C NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively.
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, Karnataka, India. rangaswamyteertha@gmail.com
Javarappa
J
Rangaswamy
Honnaiah Vijay
HV
Kumar
Salakatte Thammaiah
ST
Harini
Nagaraja
N
Naik
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D001572:Benzofurans / Q000138:chemical synthesis* / Q000494:pharmacology; D001672:Biocompatible Materials / Q000138:chemical synthesis* / Q000494:pharmacology; D050296:Microbial Viability / Q000187:drug effects; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D000975:Antioxidants; D001572:Benzofurans; D001672:Biocompatible Materials; D011720:Pyrazoles; C031280:pyrazole; C105430:benzofuran