Structural, spectroscopic and microbiological characterization of the chalcone 2E-1-(2 '-hydroxy-3 ',4 ',6 '-trimethoxyphenyl)-3-(phenyl)-prop-2-en-1-one derived from the natural product 2-hydroxy-3,4,6-trimethoxyacetophenone

摘要

Chalcones are important intermediates in the biosynthesis of biologically active compounds such as flavonoids and their derivatives. In this paper, a new chalcone 2E-1-(2'-Hydroxy-3',4',6'-trimethoxyphenyl)-3-(phenyl)-prop-2-en-1-one (HYTPHENYL) was synthesized by the condensation reaction of Claisen-Schmidt in basic medium between the 2-hydroxy-3,4,6-trimethoxyacetophenone (HTMCX) and benzaldehyde. The molecular structure of this chalcone was determined by Nuclear Magnetic Resonance, and characterized by infrared and Raman spectroscopy, at room temperature. Its electrochemical behavior was also evaluated. Vibrational wavenumber and wavevector have been predicted using the Density Functional Theory (DFT) calculations and their normal modes were analyzed in terms of the potential energy distribution (PED). Furthermore, DFT calculations were carried out to obtain the molecular orbitals and the electrostatic surface map. Electronic absorption spectrum of HYTPHENYL was measured and compared with that obtained for the HTMCX compound. Additionally, analysis of the antimicrobial activity and antibiotic resistance modulation was carried out to evaluate the antibacterial potential of the HYTPHENYL chalcone. (C) 2018 Elsevier B.V. All rights reserved.