Synthesis, X-Ray Crystal Structure, Hirshfeld Combined with DFT and Anticancer Efficacy of (Z)-N Aldonitrones

Abstract

( Z )- N -methyl- C -aryl aldonitrones - O + N (Me) =C(H)R ( 1 R = 2-naphthyl, 2 R = 2-hydroxy-1-naphthyl, 3 R = 1naphthyl, 4 R = 2-hydroxyphenyl) were synthesised and fully characterised by several methods. The supramolecular structure aspects of 1 and 2 were analysed utilizing Hirshfeld topology analysis. In 1 , the most common contacts are the H ... H (45.1 %), C ... H (39.1 %) and O ... H (13.0 %) interactions while the corresponding values in case of 2 are 47.7, 24.0 and 18.8 %, respectively. The C ... H and O ... H interactions have the characteristic features of short important contacts in 1 while only the O ... H interaction is the most significant in case of 2 . Based on DFT calculations, the HOMO, LUMO, natural charges, polarity as well as chemical reactivity descriptors were predicted and compared for both compounds. On the other hand, compounds 1 - 4 reduced the growth of MCF-7 and T47D. Compound 3 , which has the lowest IC 50 values against the MCF-7 and T47D cell lines, is thought to be the most promising applicant as an anticancer drug.