Proficient synthesis of biologically active pregnane derivatives and its glycoside – Experimental and theoretical approach

• Synthesis of a novel pregnane glycoside is described. All the reaction products were synthesized in a single step reaction.
• Structures of synthesized compounds were established on the basis of their physical, chemical and spectral analysis (UV–Vis, 1H NMR, MS and IR).
• Experimental 1H NMR chemical shifts and IR frequencies were compared with the theoretical values.
• Chemical reactivity of the reactants studied with the aid of reactivity descriptors.
• The newly synthesized compounds were screened for anti-dyslipidemic and anti-oxidant activity.

Synthesis of a number of pregnane derivatives including the glycoside has been described in detail. These compounds were synthesized by reaction of 3β-acetoxy-5, 16-pregnadiene-20-one, derived from diosgenin and then treating it with different nucleophilic reagents. The structures of these newly synthesized compounds were established on the basis of their physical, chemical and spectral data. The molecular geometry of compounds were calculated in ground state by density functional theory method (DFT/B3LYP) using 6-31G (d,p) basis set. 1H NMR chemical shifts were also studied using gauge-including atomic orbital (GIAO) approach, which were found in good agreement with the experimental values. The study of electronic properties such as UV–Vis spectral analysis, HOMO and LUMO energy calculations were performed with time dependent DFT (TD-DFT). Global and local reactivity descriptors were calculated to study the reactive sites within the molecules. These compounds were also evaluated for their anti-dyslipidemic (Triton model) and in vitro anti-oxidant activities. Out of these, compound 9 showed potent anti-dyslipidemic and anti-oxidant activity.