Synthesis, spectroscopic analysis (FT-IR, UV and NMR) and DFT analysis of novel prodrugs of pregnane, their apoptotic activity in cervical cancer cell lines

Abstract

We report the synthesis and characterization of novel nitrogen containing pregnane-prodrugs 2, 3 and 4. The synthesized compounds were characterized with the help of modern spectroscopic techniques like 1H, 13C NMR, FT-IR, UV–visible spectroscopy and mass spectrometry. The molecular geometry of synthesized compound was calculated in ground state by Density functional theory (DFT/B3LYP) using two different basis set 6-31G(d, p) and 6-311G (d, p). Conformational analysis of 2 was carried out to determine the most stable conformation. Intramolecular interactions were analyzed by AIM (Atom in molecule) approach. The electronic properties such as HOMO and LUMO energies were calculated using time dependent Density Functional Theory (TD-DFT). The vibrational wavenumbers were calculated using DFT method. First hyperpolarizability value has been calculated to describe the nonlinear optical (NLO) property of the synthesized pregnane-prodrugs. Molecular electrostatic potential (MEP) for synthesized compounds have also been determined to check their electrophilic or nucleophilic reactivity. All these compounds have been tested against cervical cancer cell line HeLa in vitro. All the compounds showed cytotoxic activity, however 3 exhibited the highest apoptotic activity.