Microwave-assisted synthesis of biodegradable and antibacterial thiophene, furan and thiazole derivatives

Abstract

The rise of bacterial resistance to common clinical antibiotics is calling for alternative techniques to synthesize antibacterial drugs with high biodegradability. For instance, microwave-assisted synthesis is a powerful technique that accelerates organic reactions. Here, we report the synthesis of 19 thiophene derivatives, five furan derivatives, and two thiazole derivatives, using Suzuki–Miyaura cross-coupling by microwave irradiation. Compound biodegradability was measured by the closed bottle test. Results show that microwave irradiation conditions have reduced the reaction time and increased the yield, and this method uses less organic solvent compared to conventional heating. Several compounds show broad antibacterial activity. One compound showed significant antibacterial activity against Streptococcus pyogenes with a minimal inhibitory concentration of 0.097 µg/mL and against Salmonella enterica with a minimal inhibitory concentration of 0.78 µg/mL. Two furan derivatives with the best activity against pathogenic bacteria were found biodegradable and non-toxic for environmental bacteria present in wastewater treatment plants.