Synthesis, Molecular Structure, Thermal and Spectroscopic Analysis of a Novel Bromochalcone Derivative with Larvicidal Activity

Author(s):Show less -

Firmino, Pollyana P. ; Queiroz, Jaqueline E. ; Dias, Lucas D. ; Wenceslau, Patricia R. S. ; de Souza, Larissa M. ; Iermak, Ievgeniia ; Vaz, Wesley F. ; Custodio, Jean M. F. ; Oliver, Allen G. ; de Aquino, Gilberto L. B. ; Napolitano, Hamilton B.

• Document type: Journal article
• Source: CRYSTALS; v. 12, n. 4, p. 18-pg., 2022-04-01.

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 H-1- and C-13- 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-HMIDLINE HORIZONTAL ELLIPSISO and edge-to-face C-HMIDLINE HORIZONTAL ELLIPSIS pi 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 center dot L-1) against Ae. aegypti larvae. (AU)

• FAPESP's process: 13/07276-1 - CEPOF - Optics and Photonic Research Center
• Grantee: Vanderlei Salvador Bagnato
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 14/50857-8 - National Institute in Basic Optics and Applied to Life Sciences
• Grantee: Vanderlei Salvador Bagnato
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 19/13569-8 - Study of the Mechanisms of Action in Photodynamic Therapy: From Photosensitizer to Practical Application
• Grantee: Lucas Danilo Dias
• Support Opportunities: Scholarships in Brazil - Post-Doctoral