Synthesis of Rhodanine Substituted 4(3H)-Quinazolinone Derivatives and their Antimicrobial Evaluation

Heterocyclic scaffold including nitrogen, sulfur and oxygen has been under exploration due to their significant therapeutic and medicinal properties. Among these types of molecules, 4thiazolidinones have displayed various important biological activities. Especially rhodanine (2-thioxothiazolidine-4-ones) derivatives represent privileged scaffolds in drug discovery, due to the presence of >N–C–S linkage [1] and have been found to be important both structurally as well as pharmacologically. Its derivatives have significant antitubercular activity [2] and used in the treatment of diabetic complications [3]. Some of them are under clinical trials as a potential thromimatic, antimicrobial, antiviral, antiischaermeric, cardiovascular, anticancer and thrombolytic drugs [3]. They also displayed a wide range of activities like anti-HIV-1 [4, 5], anticancer and antiangiogenic [6]. Moreover, quinazolinone and its derivatives comprise an important class of heterocyclic molecules. In consideration of extensive range of bioactivities, this class of molecules reside an important role in medicinal and pharmaceutical chemistry. Quinazolinone having a broad spectrum of biological and pharmacological properties, as analgesic [7], antimicrobial and antitubercular [8, 9], antitumor [10], anticancer [11], antiinflammatory [12], anticonvulsant [13], antimalarial and antihistamine [14]. Furthermore, there are many reports regarding synthesis of 4-thiazolidinones derivatives [15-20] but no reports are available in which rhodanine is substituted at 3 position of quinazolinone through hydrazino benzenesulfonamide linkage. Looking to the above mentioned literature and our ongoing research in the field of quinazolinone derivatization [21, 22], we are reporting here synthesis of various rhodanine substituted quinazolinone derivatives linked through hydrazino benzenesulfonamide, while some of these compounds showed excellent antimicrobial activity.