Single crystal structure of 3-(2-(3-acetylphenyl)hydrazono)pentane-2,4-dione and molecular docking study with CYP450 members for anticancer molecular screening

Abstract

Coupling of acetyl acetone with diazotized 3-aminoacetophenone was carried out to give the compound 3. The compound was characterized by IR, 1HNMR, MS and elemental analysis. The X-ray analysis of 3 revels its planar nature with torsion angles between phenyl ring and acetyl group C2–C3–C7–O1 and C2–C3–C7–C8 of 177.8(3)° and −0.9(4)°, respectively. Small deviations from planarity are evident also by torsion angles N1–N2–C9–C10 and N2–C9–C12–O3 of 176.6(2)° and 2.9(4)°, while the N2–C9–C10–O2 torsion angle with the value of −165.2(3)° deviates from planarity. Hydrogen-bonded chain formed through C5–H5⋯O2 is connected with the adjacent antiparallel chain through C11–H11B···π interaction between the methyl group of the acetyl substituent and phenyl ring forming a double-layered chain. N1–N2 shows presence of single bond, showing it to be a hydrazone. Molecular docking study of the title compound with six members from CYP450 family shows encouraging activity.