Abstract
A series of new glucocorticoid oxadiazines (4–6) were synthesized by reacting glucocorticoids (1–3) with thiosemicarbazide and its derivatives. The structural assignment of products is confirmed on the basis of IR, 1H NMR, 13C NMR, MS and analytical data. The synthesized compounds (4–6) obeyed the Lipinski’s “Rule of Five” analysis based on a computational prediction of molecular and pharmacokinetic properties. The interaction studies of compounds (4–6) with DNA were carried out by employing single-cell gel electrophoresis (comet assay), UV-vis and fluorescence spectroscopy. Compounds (4–6) were found capable of cellular DNA degradation breakage in isolated normal human lymphocytes. Viscometric and steady-state measurements further correlated with the comet assay studies. Hence, it could be suggested that the glucocorticoid compounds bearing a core oxadiazine scaffold would be a potent biological agent. Molecular docking studies further characterize the interaction of the synthesized compounds with DNA.
Highlights
Steroidal compounds have shown tremendous potential as putative curative agents for cancers and other diseases
We report an expedient path for the synthesis of new derivatives (4–6) from a mixture of glucocorticoids (1–3) and thiosemicarbazide/4-phenylthiosemicarbazide/4-methyl-3-thiosemicarbazide/4-ethyl-3-thiosemicarbazide, (Table 1) in EtOH using few of drops conc
The synthesized compounds were subjected to DNA binding studies, and the results show that compounds 4–6 were found to be of order 6 > 5 > 4
Summary
Steroidal compounds have shown tremendous potential as putative curative agents for cancers and other diseases It has been shown in recent studies that incorporation of heteroatoms (N/O/S) enhances the biological activities of steroid molecules [1,2,3,4,5]. It was proved by various in vivo and in vitro assays which show significant antimicrobial, anti-inflammatory, hypotensive, hypocholesterolemic and diuretic activities [6,7,8,9,10,11,12,13,14,15]. In spite of significant advances in the field of the biological chemistry
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