Abstract
4-(4-Aminophenyl)-1-thia-4-azaspiro[4.5]decan-3-one 1 was prepared and allowed to react with nitrogen nucleophiles to give the corresponding hydrazones 2–4. Further, compound 1 underwent diazotization and afforded the parallel hydrazono derivative 5; moreover, compound 1 refluxed with active methylene derivatives yielded the corresponding aminospirothiazolo pyridine–carbonitrile derivative 6 and spirothiazolopyridinone–carbonitrile derivative 7. Condensation of spirothiazolidine 1 with 4-chlorobenzaldehyde gave the corresponding spiro arylidiene derivative 8, 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-d]thiazol]-6′(1′H)-yl)aniline (9) and 4-(3′-(4-chlorophenyl)-6′H- spiro[cyclohexane-1,5′-thiazolo[5,4-d]isoxazol]-6′-yl)aniline (10). Finally, when spirothiazolo pyridinone–carbonitrile derivative 7 sodium salt generated in situ was reacted with different alkyl halides, it produced the corresponding N-derivatives 12–16. Three compounds, 6, 14, and 16, 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 6 and 9 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).
Highlights
Cancer is a horrible disease, which concerns the medical community all over the world and is likely to become the principal cause of death in most developed countries by 2030 [1,2,3,4,5,6]
Compounds 6 and 9 showed higher therapeutic indices for both of alpha-amylase inhibitor and alpha-glucosidase inhibitor than the other tested compounds compared with the antidiabetic Acarbose
Diabetes mellitus is a metabolic unrest primarily characterized by high blood glucose level [18]
Summary
Cancer is a horrible disease, which concerns the medical community all over the world and is likely to become the principal cause of death in most developed countries by 2030 [1,2,3,4,5,6]. Development of resistance is a key related issue commonly observed in drug therapy [7,8,9,10]. Despite the great efforts in cancer research, resistance is currently insufficient [11,12,13,14,15,16]. Diabetes mellitus was initially counted as a disease of slight significance to world health, but it is considered as an epidemic and one of the major principal threats to human health in the There is a crucial need to logically design novel, molecularly targeted antineoplastic treatments, which are more selective, preferably less toxic, and eventually more effective than conventional therapies [17].
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