Abstract
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).