Synthesis and Antimicrobial of Certain New Thiazolidinone, Thiazoline, and Thiophene Derivatives

Abstract

2-Cyano-N-(9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetamide (1) was utilized as a key intermediate for the synthesis of thiazolidin-4-one 2 and thiocarbamoyl 5 derivatives via reaction with 2-sulfanylacetic acid and phenyl isothiocyanate, respectively. Compound 5 reacted with different α-halo compounds to give thiazolidin-5-one 4, thiazolidine 7a,b, thiazolidin-4-one 8, and thiophene derivatives 10a,b. Thiazoline 6 and tetrahydro-benzothiophene 12 derivatives were obtained via a one-pot reaction of compound 1 with phenyl isothiocyanate/sulfur and cyclohexanone/sulfur, respectively. Representative compounds of the synthesized products were evaluated as antimicrobial agents. Some of these compounds exhibited promising activities.

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Keywords:

• Aminoanthraquinone
• antimicrobial activity
• thiazole
• thiazolidinone
• thiazoline
• thiophene

Acknowledgments

We offer our thanks to Prof. Dr. Yhia A. O. Ellazeik and Dr. Ehab Ali Metwally for carrying out the microbiology screening, Botany Department, Faculty of Science, Mansoura University, Mansoura, Egypt.