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Mini-Reviews in Medicinal Chemistry

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ISSN (Online): 1875-5607

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Research Article

First Synthesis for Bis-Spirothiazolidine Derivatives as a Novel Heterocyclic Framework and Their Biological Activity

Author(s): Eman M. Flefel, Walaa I. El-Sofany*, Hanem M. Awad and Mahmoud El-Shahat

Volume 20, Issue 2, 2020

Page: [152 - 160] Pages: 9

DOI: 10.2174/1389557519666190920114852

Price: $65

Abstract

Background: Spirothiazolidines are versatile synthetic scaffold possessing wide spectrum of biological interests involving potential anticancer activity.

Objective: To report the first synthesis of Bis Spiro-thiazolidine as a novel heterocyclic ring system.

Methods: One-pot three-component reaction including condensation of p-phenyllene diamine; cyclohexanone and thioglycolic acid produced Spiro-thiazolidine 4, which underwent further condensation with cyclohexanone and thioglycolic acid with equimolar ratio to introduce Bis-Spiothiazolidine 5 as the first synthesis. Also, bis spiro-thiazolidine arylidene derivatives 6-13 were synthesized by the reaction of Bis-Spiothiazolidine 5 with different aromatic benzaldehydes.

Results: Four compounds 13, 12, 9 and 11 have shown highly significant anticancer activity compared to Doxorubicin® (positive control) against Human liver carcinoma (HepG2) and Human Normal Retina pigmented epithelium (RPE-1) cell lines.

Conclusion: The novel bis-spirothiazolidine deriviatives have been synthesized for the first time and showed excellent anticancer activities compare with the corresponding spirothiazolidine derivatives.

Keywords: Azaspiro[4.5]decan-3-one, arylidene, antimicrobial activity, anticancer activity, HepG2, RPE-1.

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