Abstract
Background:Furan, quinoline and triazoles are known for their wide spectrum biologically active molecules. A series of novel furan C-2 quinoline and 1, 2, 4-triazole (FQT) coupled hybrids were designed and synthesized to evaluate for their DNA cleavage and cytotoxic studies.Objectives:In this work we describe the synthesis and biological evaluation of furan C-2 quinoline coupled triazoles exposed for cytotoxic and DNA cleavage study.Methods:The electrophoretic DNA cleavage studies on λ-DNA (Eco-RI/Hinda-III double digest) using agarose gelelectrophoresis and the cytotoxic activity were carried out by MTT assay method.Results:The results revealed that, the molecules 7(a-o) did cleave the DNA completely with no trace of fragments at 100 µg concentration, on the other hand, cytotoxic assay was achieved by two different human cancer cell lines (melanoma cell line-A375 and breast cancer cell line MDA-MB 231). Among the synthesized compounds 7a, 7b, 7c and 7k exhibited potent cytotoxic activity with IC50 values ranging from 2.9, 4.0, 7.8 and 5.1 µg/ml against A375 and 6.2, 9.5, 11.3 and 7.3 µg/ml against, MDA-MB 231, respectively.Conclusion:In synthesized compounds 7(a-o) exhibited complete DNA cleavage at 100 µg/ml and the compounds 7a, 7b, 7c and 7k showed very less cytotoxic in nature. The structure activity relationship revealed that, the presence of halogen group/atoms at para position of phenyl ring remarkably enhanced the DNA cleavage and cytotoxic activities among the synthesized compounds.
Highlights
Cancer is the primary cause of human death worldwide [1]
Pt.) of the synthesized compounds were determined with the help of digital Raga digital melting point apparatus, Bengaluru, India and are uncorrected; Infrared data were recorded on a Bruker spectrophotometer using KBr pellets. 1H and 13C NMR spectra were recorded on Bruker AVANCE II 400 and 100 MHz instruments using DMSO-d6/CDCl3 as a solvent and TMS as an internal standard; chemical shifts are expressed as δ values
Formation of products was confirmed by spectroscopic analysis as in case compound 2-(1-furan-2-yl)-4-(5-phenyl-4H-1,2,4-triazol-3-yl) quinoline 7(a-o), the IR spectra indicated the absence of band around 3200 cm-1 due to the absence of -NH2 and observed band at 3405 cm-1 due to the presence of -NH group in triazole ring system
Summary
Cancer is the primary cause of human death worldwide [1]. Among all types of cancer, lung, breast, colorectal, stomach, and prostate cancer are the underlying causes for the majority of cancer death. Literature survey reveals that important chemotherapeutics, such as Vorozole, Letrozole and Anastrozole that consist of substituted 1,2,4-triazole ring, are currently being used for the treatment of breast cancer [15]. In addition to these important biological applications, coupled 1,2,4-triazoles are of great utility in preparative organic chemistry as useful intermediates for the preparation some of the drug molecules. Quinoline and triazoles are known for their wide spectrum biologically active molecules. A series of novel furan C-2 quinoline and 1, 2, 4-triazole (FQT) coupled hybrids were designed and synthesized to evaluate for their DNA cleavage and cytotoxic studies
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