Synthesis, photo-physical, computational and invitro cytotoxic studies of 4-((E)-2-benzylidenehydrazinyl)benzonitrile derivatives

Abstract

Hydrazones of type 4-((E)-2- benzylidenehydrazinyl)benzonitriles were obtained by the condensation of 4-cyanophenylhydrazine hydrochloride separately with 4-diethylaminosalicylaldehyde(M1), 5-nitrosalicylaldehyde(M2), 5-chlorosalicylaldehyde(M3), 2-hydroxylnaphthylaldehyde(M4), 2-acetylpyridine(M5) 2,6-diacetylpyridine(M6) and 2-methoxynaphthylaldehyde(M7) in methanol (Scheme 1). They were characterized using physico- chemical techniques and x-ray crystallography. Their absorption, emission spectra and fluorescence life time measured in solution as well as in the solid state, display the effect of substituents on their properties. All compounds except M2 and M3, display strong emission. The compounds, M1 and M6 exhibit in vitro cytotoxicity against MDA MB435 s (melanoma) with IC 50 values as 12 × 10 -5 , 1.3 × 10 -5 respectively. The compound, M1 also displays activity against C6 (glioma) with IC 50 value of 5.9 × 10 -5 M. © 2019