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

1
Department of Photochemistry, Chemical Industries Research Division, National Research Centre, 33 EL-Bohouth St., Dokki 12622, Giza, Egypt
2
Department of Chemistry, College of Science, Taibah University, Al-Madinah Al-Monawarah 1343, Saudi Arabia
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(13), 2511; https://doi.org/10.3390/molecules24132511
Received: 13 June 2019 / Revised: 3 July 2019 / Accepted: 3 July 2019 / Published: 9 July 2019
(This article belongs to the Section Medicinal Chemistry)
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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 24. 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 1216. 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). View Full-Text
Keywords: azaspiro[4.5]decan-3-one; spirothiazolopyridines; MCF-7; HepG-2; alpha-amylase inhibitor; alpha-glucoidase inhibitor azaspiro[4.5]decan-3-one; spirothiazolopyridines; MCF-7; HepG-2; alpha-amylase inhibitor; alpha-glucoidase inhibitor
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Flefel, E.M.; El-Sofany, W.I.; Al-Harbi, R.A.; El-Shahat, M. Development of a Novel Series of Anticancer and Antidiabetic: Spirothiazolidines Analogs. Molecules 2019, 24, 2511.

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