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

Javarappa Rangaswamy, Honnaiah Vijay Kumar, Salakatte Thammaiah Harini, Nagaraja Naik

Research output: Contribution to journalArticlepeer-review

60 Scopus citations

Abstract

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, 1H NMR, 13C 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.

Original languageEnglish (US)
Pages (from-to)4773-4777
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number14
DOIs
StatePublished - Jul 15 2012

Keywords

  • Antimicrobial activity
  • Antioxidant activity
  • Benzofuran based 1,3,5-substituted pyrazole analogues
  • Substituted anilines

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