Studies on spirothiazolidinone derivatives of 4-tert-butylbenzohydrazide

This study describes the synthesis of novel 4-tert-butyl-N-(6,7,8-(non)substituted-2-methyl-3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)benzamide derivatives (2-9) and evaluation of their antimicrobial activity. In the course of the syntheses 4-tert-butylbenzohidrazide, an appropriate cyclohexanone (cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, 4-ethylcyclohexanone, 4-propylcyclohexanone, 4-tert-butylcyclohexanone, 4-phenylcyclohexanone) and 2-mercaptopropionic acid were reacted in one pot . The reaction mechanisms involved in the formation of the end products have been discussed and the structures of the new compounds were confirmed by the data obtained from elemental analysis, UV, IR, 1H-NMR, 13C-NMR (APT), 2D-NMR (HSQC), and ESI-MS spectra. All compounds were tested for antiviral activity against selected DNA and RNA viruses in MDCK, CRFK, Vero, HEL, HeLa and MT-4 cells. Compound 5 (4-tert-butyl-N-(2,8-dimethyl-3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)benzamide) was found to be active against influenza A/H2N3 and compounds 8 (4-tert-butyl-N-(2-methyl-8-tert-butyl-3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)benzamide) and 9 (4-tert-butyl-N-(2-methyl-8-phenyl-3-oxo-1-thia-4-azaspiro[4.5}dec-4-yl)benzamide) were found to be active against Feline corona virus and Feline herpes virus. The compounds were inactive against the tested bacteria and Candida albicans.