An experimental and computational exploration on synthesis, structural elucidation, weaker interaction and anticancer activity analysis of novel progesterone oxadiazole derivative

Progesterone oxadiazole (PRODAZ) derivative was synthesized by substituting the α-hydrogen of acetyl progesterone with iodine and reacting with DMSO and isoniazid. Modern spectroscopy techniques (FT-IR, ¹H NMR, ¹³CNMR, UV–vis and mass spectrometry) and elemental analysis were used to characterize the compound. Quantum chemical calculations were carried at DFT-B3LYP / 6–311G(d,p) basis set. A thorough interpretation of the FT-IR spectrum was performed utilising normal coordinate analysis. Vibrational analysis shows absorptions at 1520 and 1505 cm^-1 in experimental FT-IR spectrum indicating corresponding to 1539 and 1513 cm^-1 theoretical value which verifies the formation of an oxadiazole ring. In ¹H NMR spectrum two methyl group peaks observed at 0.67 and 1.84 ppm, as well as absence of acetyl methyl peak at 2.40 ppm, indicate the involvement of acetyl methyl group in the oxadizole ring formation which corresponds to the ¹³C NMR peak observed at 167 and 171 ppm. In most circumstances, experimental values have a minor percentage deviation compared to theoretical outcomes. The calculated nature of electronic transitions within the molecule found to be π→π* and n→π*. In most circumstances, experimental values have a minor percentage inaccuracy when compared to theoretical outcomes. The rotational barrier between conformer I and II of PRODAZ is 3.6474 Kcal/mol in the gas phase. PRODAZ has a static hyperpolarizability (β₀) of 6.46 × 10^–30 esu, making it suitable for non-linear optical (NLO) applications. The toxicity parameters of ADME were estimated for the investigated chemical. The MDA-MB-231, MCF-7 and DU145 cell lines have been used to test anticancer activity. PRODAZ, includes cytotoxicity, apoptosis-inducing properties, and effect on cell cycle progression. All of the results give critical information for future clinical trials.