New Thiazoline-Tetralin Derivatives and Biological Activity Evaluation

Gülhan Turan-Zitouni,Aouatef Tabbi,Halide Temel,Leyla Yurttaş,Gülşen Akalın Çiftçi,Zafer Kaplancıklı

doi:10.3390/molecules23010135

Gülhan Turan-Zitouni, Aouatef Tabbi + Show 4 more

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https://doi.org/10.3390/molecules23010135

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Abstract

In this study, novel N′-(3-cyclohexyl/phenyl-4-(substituted phenyl)thiazole-2(3H)-ylidene)-2-[(5,6,7,8-tetrahydronaphthalen-2-yl)oxy]acetohydrazide (4a–4k) derivatives were synthesized and their anticancer potency were evaluated on human breast adenocarcinoma cell line (MCF-7), human lung carcinoma cell line (A549) and mouse embryoblast cell line (NIH/3T3) using the MTT method, DNA synthesis inhibition and flow cytometric analysis. Compound 4e bearing 4-methoxyphenyl moiety exhibited the highest antitumor efficiency against MCF-7 cell line with higher DNA synthesis inhibition and apoptotic cell percentages (ealy+late apoptotic cell). On the other hand, compounds 4f, 4g, and 4h bearing 4-bromo, 4-chloro and 4-florophenyl moieties, respectively caused excellent apoptosis levels against A549 cell line when treated with lower concentration even than cisplatin. Anticholinesterase activity of the compounds were also tested, compound 4h showed 49.92% inhibition of acetylcholinesterase (AChE).

Highlights

Thiazole ring is an important pharmacologically active heterocylic ring whose mono, di, three-substituted, condensed derivatives and reduced analogs have been widely studied in medicinal chemistry [1,2,3,4,5,6]
Various thiazoline derivatives were reported with a broad spectrum of activity attributed to this property [8,9]
When considering molecular aspects and biological diversity, a wide variety of thiazoline derivatives were encountered with anticancer activity

Summary

Introduction

Thiazole ring is an important pharmacologically active heterocylic ring whose mono-, di-, three-substituted, condensed derivatives and reduced analogs (thiazoline, thiazolidine) have been widely studied in medicinal chemistry [1,2,3,4,5,6]. Among these molecules with common origin, thiazoline derivatives have attracted attention due to existing in many biochemical reactions in organisms [7]. Bacterial isolates ulbactin F, G, aerugine and pyochelin, which possess tandemly connected thiazoline and thiazolidine ring systems, were declared with tumor cell migration inhibitory activity (Figure 1) [12]. Apoptosis inducing [23] and cell division inhibiting [24] abilities were reported as anticancer activity mechanism

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Discussion

Conclusion