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Diclofenac‐Based Hydrazones and Spirothiazolidinones: Synthesis, Characterization, and Antimicrobial Properties
Author(s) -
Kocabalkanlı Ayşe,
CihanÜstündağ Gökçe,
Naesens Lieve,
MataracıKara Emel,
Nassozi Mebble,
Çapan Gültaze
Publication year - 2017
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201700010
Subject(s) - diclofenac , antimicrobial , chemistry , antibacterial agent , characterization (materials science) , combinatorial chemistry , stereochemistry , pharmacology , antibiotics , organic chemistry , medicine , nanotechnology , materials science , biochemistry
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 EC 50 values between 6.6 µg/mL and 14.7 μg/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 625 μg/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 µg/mL and 78.12 μg/mL, respectively.