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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, 1 H NMR, 13 C 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.

Background: Corticosteroids are important group of polycyclic compounds having a wide range of pharmacological and physiological properties. Thiopyran derivatives are important building blocks of many biologically active compounds. Objective: Keeping in mind the wide range of application of corticosteroid and thiopyran, herein we intend to develop a simple and efficient strategy to synthesize steroidal thiopyran derivatives starting with different commercially available corticosteroid and study their biological property. Materials and Methods: To achieve our aim, we employed a one-pot multicomponent synthesis of steroidal thiopyran derivatives by the reaction of corticosteriods, malononitrile and carbon disulphide in presence of triethyl amine as a catalyst. Results and Discussion : An array of novel thiopyran compounds were obtained with the highest product yield using Et3N. Scanning electron microscopy analysis manifested agglomeration pertaining to brick - shaped crystals of corticosteroid thiopyran. Synthesized compound were also found to be active as antibacterial agents. Conclusion: We describe a facile one-pot multicomponent synthesis of corticosteroid thiopyran derivatives which are found to possess antibacterial activity. Excellent yields of the products, simple work-up, easily available starting materials and non-chromatographic purification are some main advantages of this protocol.

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