Synthesis, molecular structure, thermal and spectroscopic analysis of a novel bromochalcone derivative with larvicidal activity.
FIRMINO, Pollyana P.; QUEIROZ, Jaqueline E.; DIAS, Lucas Danilo; WENCESLAU, Patricia R. S.; SOUZA, Larissa Marila de; IERMAK, Ievgeniia; VAZ, Wesley F.; CUSTÓDIO, Jean M. F.; OLIVER, Allen G.; AQUINO, Gilberto L. B.; NAPOLITANO, Hamilton B.
FIRMINO, Pollyana P.; QUEIROZ, Jaqueline E.; DIAS, Lucas Danilo; WENCESLAU, Patricia R. S.; SOUZA, Larissa Marila de; IERMAK, Ievgeniia; VAZ, Wesley F.; CUSTÓDIO, Jean M. F.; OLIVER, Allen G.; AQUINO, Gilberto L. B.; NAPOLITANO, Hamilton B.
Abstract: Chalcones belong to the flavonoids family and are natural compounds which show promising larvicidal property against Aedes aegypti larvae. Aiming to obtain a synthetic chalcone derivative with high larvicidal activity, herein, a bromochalcone derivative, namely (E)-3-(4-butylphenyl)-1-(4- bromophenyl)-prop-2-en-1-one (BBP), was designed, synthesized and extensively characterized by 1H- and 13C- nuclear magnetic resonance (NMR), infrared (IR), Raman spectroscopy, mass spectrometry (MS), ultraviolet?visible spectroscopy (UV-Vis), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and X-ray diffraction. Further, the quantum mechanics calculations implemented at the B3LYP/6-311+G(d)* level of the theory indicate that the supramolecular arrangement was stabilized by C-H O and edge-to-face C-H interactions. The EGAP calculated (3.97 eV) indicates a good reactivity value compared with other similar chalcone derivatives. Furthermore, the synthesized bromochalcone derivative shows promising larvicidal activity (mortality up to 80% at 57.6 mg L??1) against Ae. aegypti larvae.
@article={003075085,author = {FIRMINO, Pollyana P.; QUEIROZ, Jaqueline E.; DIAS, Lucas Danilo; WENCESLAU, Patricia R. S.; SOUZA, Larissa Marila de; IERMAK, Ievgeniia; VAZ, Wesley F.; CUSTÓDIO, Jean M. F.; OLIVER, Allen G.; AQUINO, Gilberto L. B.; NAPOLITANO, Hamilton B.},title={Synthesis, molecular structure, thermal and spectroscopic analysis of a novel bromochalcone derivative with larvicidal activity},journal={Crystals},note={v. 12, n. 4, p. 440-1-440-18},year={2022}}