Abstract
In a one pot procedure a series of (R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-3-phenylthiazolidin-4-ones 9a-g and 2-((2R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-4-oxo-3-phenylthiazolidin-5-yl)acetic acids 10a-g was prepared by condensation of (2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-carbaldehyde with mercapto acids and primary amines in the presence of ZnCl2 under both microwave irradiation and conventional heating conditions. Characterization of new compounds has been done by means of IR, NMR, MS and elemental analysis. The cytotoxicity was assessed against a panel of four different human tumor cell lines: A549 derived from human alveolar adenocarcinoma epithelial cells (ATCC No. CCL-185), Hela derived from human cervical cancer cells (ATCC No. CCL-2), MDA-MB-231 derived from human breast adenocarcinoma cells (ATCC No. HTB22) and HEK 293 (normal human embryonic kidney cell line) using the MTT assays. Among the tested compounds 9e and 10e showed the most potent activity against MCF-7 breast cancer cell line with IC50 values of 1.91 and 1.95 µM whereas 9b, 10b, 9g and 10g showed promising activity against MDA-MB-231 and Hela cell lines with IC50 values of 5.84, 5.74, 7.89 and 7.65 µM respectively.
Highlights
Carbohydrates, besides being the most abundant class of bio-molecules, a vital source of energy and structural components, have an important role in biological processes, organic synthesis and chemical industries.[1]
The stability, polar nature and possible hydrogen bonding ability of a triazole ring combined with the biocompatibility and presence of stereogenic centers of Srinivas et al.: Microwave-Assisted Synthesis and Anticancer Activity
Following the successful introduction, inspired by the biological profile of triazoles, thiazolidinones, and in the continuation of our work on biologically active heterocycles[37,38,39,40,41,42,43,44,45,46] we have developed a series of novel triazolyl thiazolidine derivatives of pyrene, and evaluated their anticancer activity
Summary
Carbohydrates, besides being the most abundant class of bio-molecules, a vital source of energy and structural components, have an important role in biological processes, organic synthesis and chemical industries.[1]. The introduction of a carbohydrate moiety into a system often imparts interesting properties, such as hydrophilicity, lowered toxicity and enhanced bioactivities.[4] Organic chemists have linked carbohydrates to various biologically potent compounds to enhance their biological applications, such as steroids, aminoacids and other therapeutic agents.[5] One of the methods used to link a carbohydrate moiety with a potential compound is via a triazole ring using the well known click-chemistry reactions.[6] The versatility of the alkyne- azide cyclisation reaction and the introduction of a triazole ring makes this process an efficient method to obtain cyclized products with biological potential.[7] The strategy of linking a carbohydrate moiety with another species via a triazole ring is gaining importance in organic synthesis, natural products chemistry and biochemistry.[8] The stability, polar nature and possible hydrogen bonding ability of a triazole ring combined with the biocompatibility and presence of stereogenic centers of Srinivas et al.: Microwave-Assisted Synthesis and Anticancer Activity. Following the successful introduction, inspired by the biological profile of triazoles, thiazolidinones, and in the continuation of our work on biologically active heterocycles[37,38,39,40,41,42,43,44,45,46] we have developed a series of novel triazolyl thiazolidine derivatives of pyrene, and evaluated their anticancer activity
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