N-Phosphorylated Derivatives of 5-Nitroindazole as Antimicrobial and Antioxidant Agents and Docking Study Against DNA Gyrasea

GRAPHICAL ABSTRACT

Abstract

A series of new phosphoramidate derivatives 7a-l were synthesized by reacting 5-nitroindazole with 4-chlorophenyl dichlorophosphate (4), and then further with various bio-potent aromatic/hetero/alkyl amines 6a-l. All the newly synthesized compounds were characterized by spectroscopic data (IR, ¹H, ¹³C, ³¹P NMR and mass) and elemental analysis. The products 7a-l were evaluated for their antioxidant activity (DPPH, H₂O₂ methods and IC₅₀ values) and antimicrobial activity against the growth of Gram bacterial (positive and negative) and fungal pathogens. In the entire bio-screening data, we observed that 7j is the most active compound in terms of its antimicrobial and antioxidant activities. Further to know the binding interactions of title products with DNA GyraseA enzyme (E. coli), molecular docking studies were performed which revealed 7j and 7k exhibited high binding affinities towards the enzyme, DNA GyraseA (GyrA), and are higher than that of the standard antibiotic, streptomycin.

Keywords::

• 5-Nitroindazole
• phosphoramidates
• antimicrobial activity
• antioxidant activity
• molecular docking studies