In silico study of CYP450 inhibitor activity of (E)-1-(3-((4-chlorophenyl) diazenyl)-4-hydroxyphenyl)ethanone

Abstract

Molecular docking and single crystal study of azo dye (E)-1-(3-((4-chlorophenyl)diazenyl)-4-hydroxyphenyl)ethanone (3) is reported here. It has been synthesized by diazotization of 4-chloroaniline followed by coupling with 4-hydroxyacetophenone. Molecule is almost planar with acetyl as well as azo groups only slightly deviating from the plane of C3–C8 phenyl ring as evident by C1–C2–C3–C8 and N2–N1–C7–C6 torsion angles of –3.6(3)° and –3.9(3)°, respectively. Torsion angle N1–N2–C9–C14 between azo group and chlorophenyl ring is somewhat larger being –13.1(3)° leading to torsion angle between phenyl C3–C8 and chlorophenyl C9–C14 ring of 17.26(11)°. Intramolecular O2–H2ꞏꞏꞏN2 hydrogen-bonding is observed here. Pillars along b-axis are formed due to π∙∙∙π stacking interactions of parallel molecules in head-to-head fashion with centroid-to-centroid distance of 3.8829(14) Å and ring slippage of 1.416 Å. Title compound shows good binding affinity towards six enzymes of CYP450 family. Both nitrogens of the azo bond show significant involvement in bonding interactions with proteins in case of all the six enzymes.