Synthesis and assessment of antibacterial and antifungal properties of rhodanine-3-acetic and 3-propionic acid derivatives

V. Pelakauskas Master's Thesis/ Scientific supervisor: prof. habil. dr. Eduardas Tarasevičius, consultant – prof. dr. Alvydas Pavilonis; Lithuanian University of Health Sciences, Faculty of Pharmacy, Department of Drug Chemistry. Kaunas – 2013. The aim of research – synthesis of rhodanine-3-acetic and 3-propionic acid derivatives, antimicrobial evaluation of synthesized compounds and assessment of the structure-activity relationships. Tasks of research: 1.Synthesis of rhodanine-3-acetic and 3-propionic acids and their derivatives, bearing furan ring moiety in 5th position of rhodanine ring. 2.Evaluation of antimicrobial activity of compounds in silico (using PASS) and in vitro (using a serial dilution in agar technique). 3.Assessment of structure-activity relationship of compounds according experimental results. Methods. Compounds were synthesized using conventional methods. Antimicrobial activity of compounds was tested using a PASS software and by a serial dilution in agar technique. Results. Ten rhodanine-3-carboxylic acid derivatives were synthesized bearing furan moiety in the 5th position of thiazolidinone ring. Four compounds have nitrofuran moiety and six – 5-phenylfuran moiety. PASS prognozed higher antifungal activity. PASS prognozed higher antibacterial activity to nitrofuran moiety bearing derivatives. Antimicrobial activity in vitro was seen on five compounds - all nitrofurans, and one 5-phenylfuran. One compound bearing nitrofuran moiety has antifungal activity. Conclusions. According to results it can be concluded that activity of compounds were granted by nitrofuran moiety. Activity of compounds is greater when propionic acid moiety is present in rhodanine ring. Identifying structural patterns of PV-8 compound is complicated since other five similar derivatives have no antibacterial activity