Development of a Novel Series of Anticancer and Antidiabetic: Spirothiazolidines Analogs.

4-(4-Aminophenyl)-1-thia-4-azaspiro[4.5]decan-3-one was prepared and allowed to react with nitrogen nucleophiles to give the corresponding hydrazones -. Further, compound underwent diazotization and afforded the parallel hydrazono derivative ; moreover, compound refluxed with active methylene derivatives yielded the corresponding aminospirothiazolo pyridine-carbonitrile derivative and spirothiazolopyridinone-carbonitrile derivative . Condensation of spirothiazolidine with 4-chlorobenzaldehyde gave the corresponding spiro arylidiene derivative , which was utilized as a component of Micheal addition to react with excess of nitrogen nucleophiles to yield novel ring frameworks 4-(3-(4-chlorophenyl)-spiro [cyclohexane-1,5-pyrazolo[3,4-]thiazol]-6()-yl)aniline ( and 4-(3-(4-chlorophenyl)-- spiro[cyclohexane-1,5-thiazolo[5,4-]isoxazol]-6-yl)aniline . Finally, when spirothiazolo pyridinone-carbonitrile derivative sodium salt generated in situ was reacted with different alkyl halides, it produced the corresponding -derivatives -. Three compounds, , , and , showed high significantly anticancer activities compared with Doxorubicin® (positive control) against human breast carcinoma (MCF-7) and human liver carcinoma (HepG-2) cell lines. On the other hand, compounds and showed higher therapeutic indices for both of alpha-amylase inhibitor and alpha-glucosidase inhibitor than the other tested compounds compared with the antidiabetic Acarbose (positive control).