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

• Published in: Mini reviews in medicinal chemistry Vol. 20; no. 2; p. 152
• Main Authors: Flefel, Eman M, El-Sofany, Walaa I, Awad, Hanem M, El-Shahat, Mahmoud
• Format: Journal Article
• Language: English
• Published: Netherlands 01.01.2020
• Subjects: HepG2; Azaspiro[4.5]decan-3-one; RPE-1; anticancer activity; antimicrobial activity; arylidene
• ISSN: 1875-5607
• DOI: 10.2174/1389557519666190920114852

Spirothiazolidines are versatile synthetic scaffold possessing wide spectrum of biological interests involving potential anticancer activity. To report the first synthesis of Bis Spiro-thiazolidine as a novel heterocyclic ring system. 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. 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. The novel bis-spirothiazolidine deriviatives have been synthesized for the first time and showed excellent anticancer activities compare with the corresponding spirothiazolidine derivatives.