Synthesis, spectroscopic and evaluation of anticancer activity of new hydrazone-containing dipyrromethane using experimental and theoretical approaches

Abstract

The purpose of this work is to study in-vitro anticancer activity, chemical reactivity and non-linear optical properties of newly synthesized and characterized hydrazide-hydrazone linkage containing dipyrromethane derivatives. The appearance of singlet at 5.9, 6.9, 5.0, 5.8 and 3.7 ppm of meso–proton designates formation of products (3a-3e). All synthesized compounds have been well characterized by modern spectroscopic (1H and 13C NMR, UV–Visible, FT–IR) techniques. TD–DFT has been used to calculate oscillatory strength (f) and wavelength absorption maxima (λmax), electronic excitations and their molecular orbital coefficients and molecular plots analysis assigns nature of both electronic excitations as π →π* and n →π*. The computed first hyperpolarizability (β0 =14.38, 17.34, 15.47. 19.21, 22.21 × 10–30esu) evaluate the molecules (3a-3e) to be suitable for non–linear optical (NLO) response. The p–Nitroaniline(p–NA), is used a reference molecule having β0 = 11.54 × 10–30 esu). Compounds 3a, 3b, 3c, 3d and 3e exhibited moderate to very high anti-cancer activity against HL-60 and HCT-116, with percentage inhibition of 65.02%, 76.54%, 80.47%, 68.76%, 53.04% and 66.87%, 79.31%, 79.58%, 63.66%, 53.66, respectively; the reference 5-fluorouracil had aninhibitory percentage of 86.53% and 70.54%.