Design and synthesis of fluorescent symmetric bis-triazolylated-1,4-dihydropyridines as potent antibreast cancer agents |
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Authors: | Rakesh Kumar Parveen Gahlyan Abhishek Verma Ruchi Jain Sharmistha Das Rituraj Konwar |
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Institution: | 1. Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, India;2. Division of Endocrinology, CSIR-Central Drug Research Institute, Lucknow, India |
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Abstract: | Herein, we report the synthesis of fluorescent 1,4-dihydropyridine-linked bis-triazoles (2a–2n) through Hantzsch synthesis by the condensation of o/m-chloro-substituted benzaldehyde, ethyl 3-oxo-4(prop-2-yn-1-yloxy)butanoate, and ammonium acetate in the presence of Ba(NO3)2 as a catalyst followed by the click reaction of resultant Hantzsch product (1) with various aromatic as well as aliphatic azides. All the synthesized compounds were well characterized by 1H-NMR, 13C-NMR, FTIR, and HRMS spectral techniques. Antibreast cancer evaluation of all the synthesized derivatives revealed that the compounds 2f (IC50?=?7?±?0.02?µM) and 2g (IC50?=?5?±?0.03?µM) showed better anticancer activity (lower IC50) than the standard drug tamoxifen (IC50?=?11.2?±?0.01?µM) against breast carcinoma (MDA-MB-231) cell line. The synthesized compounds were also screened against normal human embryonic kidney (HEK-293) cell line and found to be nontoxic. The fluorescent nature and cytotoxicity assay of these newly synthesized hybrids recommend their utility in tumor cell imaging. |
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Keywords: | 1 4-Dihydropyridine anticancer agents bis-triazoles fluorescent |
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