Design and synthesis of fluorescent symmetric bis-triazolylated-1,4-dihydropyridines as potent antibreast cancer agents

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.

GRAPHICAL ABSTRACT

KEYWORDS:

• 1,4-Dihydropyridine
• anticancer agents
• bis-triazoles
• fluorescent

Acknowledgments

P. G. is thankful to UGC for fellowship and USIC at this university for instrument facilities. R. J. thanks to SERB, DST for Start-up Grant (File no. SB/FT/CS-129/2014).

Additional information

Funding

The authors acknowledge University of Delhi for financial support under R&D grant (File No. RC/2015/9677).