Antibacterial properties of 5-substituted derivatives of rhodanine-3-carboxyalkyl acids. Part II

• Main Authors: Waldemar Tejchman, Izabela Korona-Glowniak, Ludomir Kwietniewski, Ewa Żesławska, Wojciech Nitek, Piotr Suder, Marek Żylewski, Anna Malm
• Format: Article
• Language: English
• Published: Elsevier 2020-04-01
• Series: Saudi Pharmaceutical Journal
• Online Access: http://www.sciencedirect.com/science/article/pii/S1319016420300335

Two series of rhodanine-3-acetic and rhodanine-3-propionic acids derivatives having benzylidene and cinnamylidene substituents with additional electron donating and withdrawing groups at the C-5 position, were synthesised. The structures of the obtained derivatives were confirmed by spectroscopic methods and their lipophilicity was screened. The crystal structures were determined for selected compounds. The antibacterial activity of the derivatives was depended on the type of carboxyalkyl group in the N-3 position and on the type of the substituent in the C-5 position. The derivatives of rhodanine-3-propionic acid demonstrated the highest activity against Gram-positive bacteria. However, none of tested derivatives showed activity against Gram-negative bacteria and yeast. We believe that the presence of the N,N-diethylamine group in the aromatic system and the number of carbon atoms in the carboxyalkyl group is more significant for the biological activity than the fact that the benzylidene or cinnamylidene substituent was present at the C-5 position. Keywords: Rhodanine, Rhodanine-3-carboxyalkyl acids, Antibacterial activity, Antimicrobial activity, Thiazolidine-4-one