Abstract
The new thiopyrano[2,3-b]pyridines 4-9 could be synthesized from the nicotinonitrile derivative 1. The cytotoxicity activity of the selected compounds 5, 6 and 8 was tested against MCF-7 and HCT-116 cell lines. The compound 5 (TP5) exhibited significant inhibitory activity and displayed the most potent activity, more than 6 and 8. The compound 5 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent. In the light of this result, the labeled 125I-compound 5 (125I-TP5) was prepared and its cytotoxicity against ascites tumor in mice has been evaluated. The results show that compound 5 (TP5) may be potentially used as a radiopharmaceutical for tumor diagnosis when labeled with 125I.
Highlights
Cancer is one of the main leading causes of death in both developing and developed countries.[1]
The key step in this trial to explore an anticancer drug is the synthesis of 5,7-dimethyl-4-oxothiopyrano[3,4-b]pyridine (4) from 2-mercapto-4,6-dimethylnicotinonitrile (1)
The acidic hydrolysis of 3 led to the formation of the cyclic ketone 4 as a target precursor to synthesize the new thiopyranopyridines of pharmaceutical interest
Summary
Cancer is one of the main leading causes of death in both developing and developed countries.[1] Cancer treatment has been a major research and development effort in academia and the pharmaceutical industry for numerous years.[2,3] Despite the fact that there is a large amount of information available dealing with the clinical aspects of cancer chemotherapy, there was a clear requirement for an updated treatment from the point of view of medicinal chemistry and drug design.[4] Another major goal for developing new anticancer agents is to overcome cancer resistance to drug treatment, which has made many of the currently available chemotherapeutic agents ineffective.[5] The pyridine nucleus is an integral part of anti-inflammatory and anticancer agents.[6,7] Some of 4-oxothiopyrano[2,3-b] pyridines were reported as potential antihypertensive agents.[8,9] α,β-Unsaturated compounds have exhibited excellent antitumor, anti-inflammatory, antimalarial and other pharmacological effects.[10,11,12,13] In recent years, the synthesis and antifungal activities of 3-substituted methylene-4-oxothiopyrano[2,3-b]pyridines were published.[14,15] A number of the spiropyrazolo-3,3’-thiopyrano[2,3-b] pyridines and new tetra- and penta-heterocycles, which could be obtained by treating 3-(N,N-dimethylamino) methylene derivatives with nitrilimines and aminoazoles, respectively, showed high antifungal and anti-bacterial activities.[15]
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