Methoxylated Quinoline-Chalcones with Potential Pesticidal Activity: From Synthesis to Supramolecular Framework

In this work, the molecular properties of the (E)-3-(4-nitrobenzylidene)-2-(4-methoxyphenyl)-2,3-dihydro-1-(phenylsulfonyl)-quinolin-4(1H)-one were studied, both in a solid and isolated state. The effect of changing the substituent groups –OCH₃ and –Cl in the phenyl portion was verified, where the structural and electronic properties were compared. The density functional theory was employed using the hybrid exchange-correlation functional with long-range correction M06-2X, combined with the polarized and diffuse basis set 6-311++G(d,p), in the gas phase. The electronic structure was also analyzed by frontier molecular orbitals and molecular electrostatic potential maps, where information about its chemical reactivity was obtained. Also, the supramolecular arrangement was analyzed by Hirshfeld surface (HS), 2D fingerprint plots, and quantum theory of atoms in molecules (QTAIM). The natural bond orbitals (NBO) calculations were carried out to analyze the stability and hyperconjugation energy. Finally, molecular docking was carried out to investigate the affinities of the quinoline-chalcone with a bacterial protein (Agrobacterium pathogens) and an ecdysone receptor-potential pesticidal activity. The results encourage further in vitro and in vivo analyses of the two kinds of organisms investigated.

Keywords:
quinoline-chalcones; X-ray diffraction; Hirshfeld surface; density functional theory