Synthesis of New N-Substituted 5-Arylidene-2,4-thiazolidinediones as Anti-Inflammatory and Antimicrobial Agents

• Published in: Archiv der Pharmazie (Weinheim) 2013-06, Vol.346 (6), p.481-490
• Main Authors: Nastasă, Cristina, Tiperciuc, Brînduşa, Pârvu, Alina, Duma, Mihaela, Ionuţ, Ioana, Oniga, Ovidiu
• Format: Article
• Language: English
• Subjects: 2-Phenyl-thiazole; 4-thiazolidinedione; 5-Arylidene-2; 5‐Arylidene‐2,4‐thiazolidinedione; Animals; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Anti-inflammatory activity; Anti-Inflammatory Agents - chemical synthesis; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - pharmacology; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Antimicrobial activity; Antimicrobial agents; Candida albicans - drug effects; Disease Models, Animal; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; Inflammation - drug therapy; Inflammation - pathology; Magnetic Resonance Spectroscopy; Male; Phagocytes - drug effects; Phagocytes - metabolism; Rats; Rats, Wistar; Structure-Activity Relationship; Thiazines - pharmacology; Thiazoles - pharmacology; Thiazolidinediones - chemical synthesis; Thiazolidinediones - chemistry; Thiazolidinediones - pharmacology
• ISSN: 0365-6233; 1521-4184
• DOI: 10.1002/ardp.201300021

A novel series of 5‐arylidene‐2,4‐thiazolidinediones (TZDs) 2a–p was synthesized from the condensation of 3‐((2‐phenylthiazol‐4‐yl)methyl)thiazolidine‐2,4‐dione with different benzaldehyde derivatives. All the structures were confirmed by their spectral (IR, 1H NMR, 13C NMR and mass) and elemental analytical data. The new molecules were evaluated in vivo as anti‐inflammatory agents in an acute experimental inflammation, evaluating the acute phase bone marrow response and phagocyte activity. All compounds, excepting one, reduced the absolute leukocytes count due to the lower neutrophil percentage. Phagocytary index was decreased by the same molecules, while only half of them reduced the phagocytary activity. The effect was superior to meloxicam, the reference anti‐inflammatory drug, for the majority of the TZD derivatives. The new molecules were also investigated for their antimicrobial properties on Gram‐positive and Gram‐negative bacteria and one fungal strain. Two compounds (2e and 2n) manifested growth inhibition capacity on all the tested strains. New 5‐arylidene‐2,4‐thiazolidinediones (TZDs) 2a–p were synthesized and evaluated in vivo as anti‐inflammatory agents. All except one displayed good results. The phagocytic parameters were decreased by the new molecules. The effect was superior to meloxicam, for the majority of the TZD derivatives. The compounds were also investigated for their antimicrobial properties. Two of them (2e and 2n) manifested growth inhibition capacity on all the tested strains.