Diclofenac-Based Hydrazones and Spirothiazolidinones: Synthesis, Characterization, and Antimicrobial Properties

Kocabalkanli A., Cihan-Ustundag G., NAESENS L., Mataraci-Kara E., Nassozi M., Capan G.

ARCHIV DER PHARMAZIE, vol.350, no.5, 2017 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 350 Issue: 5
  • Publication Date: 2017
  • Doi Number: 10.1002/ardp.201700010
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Keywords: Antimicrobial activity, Cytotoxic activity, Rational drug design, Structure elucidation, Synthesis, NONSTEROIDAL ANTIINFLAMMATORY DRUGS, IN-VITRO, DERIVATIVES, INHIBITORS, VIVO, CYCLOOXYGENASE-2, REPLICATION, DESIGN
  • Istanbul University Affiliated: Yes


We report here the synthesis, structural characterization, and biological evaluation of novel diclofenac-based hydrazone (4a-f) and spirothiazolidinone (5a-f, 6a-f) derivatives designed as potential antimicrobial agents. The compounds were evaluated in vitro for their antiviral activity against a wide spectrum of DNA and RNA viruses. They were further screened in vitro against different strains of bacteria and fungi. The hydrazone derivatives, 4a and 4c-f, were found to be active against herpesviruses (HSV-1, HSV-2, and HSV-1 TK-), vaccinia virus, and Coxsackie B4 virus, with EC50 values between 6.6 mu g/mL and 14.7g/mL, and the selectivity index values were greater than 10 for 4a and 4f. The newly synthesized compounds (4-6) were inactive against the bacterial and the fungal strains tested, at levels below 2500, 1250, or 625g/mL. Interestingly, the key intermediate 3 with a free hydrazide moiety displayed antifungal properties against Candida albicans and C. parapsilosis at MIC values of 4.88 mu g/mL and 78.12g/mL, respectively.