In Silico and In Vitro Assessment of Antimicrobial and Antibiofilm Activity of Some 1,3-Oxazole-Based Compounds and Their Isosteric Analogues

Abstract

In this paper, we report on the antimicrobial activity assessment of 49 compounds previously synthesized as derivatives of alanine or phenylalanine that incorporate a 4-(4-X-phenylsulfonyl)phenyl fragment (X = H, Cl, or Br), namely 21 acyclic compounds (6 × N-acyl-α-amino acids, 1 × N-acyl-α-amino acid ester, and 14 × N-acyl-α-amino ketones) and 28 pentatomic heterocycles from the oxazole-based compound class (6 × 4H-1,3-oxazol-5-ones, 16 × 5-aryl-1,3-oxazoles, and 6 × ethyl 1,3-oxazol-5-yl carbonates). Both in silico and in vitro qualitative and quantitative assays were used to investigate the antimicrobial potential of these derivatives against planktonic and biofilm-embedded microbial strains. Some of the tested compounds showed promising antimicrobial and antibiofilm activity depending on their chemical scaffold and lipophilic character.

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“…The tested essential oils were achieved from commercial producers, according to Table 2. In order to determine the effect of the tested suspensions on the adhesion capacity to the inert substrate, we have used the crystal (purple) violet assay [8][9][10]. For this purpose, serial two-fold microdilutions were performed in 96 well plates in tryptic soy broth (TSB) liquid medium, starting from 1% oil in the first well, in a final volume of 150 μl liquid medium.…”

Lewis Acid-Promoted Three-Component Cyclization for the Construction of Functionalized Oxazoles

“…Substituted oxazoles exhibit extremely valuable properties, and they are found as important structural units that occur ubiquitously in natural products and pharmaceuticals with unique biological properties . In addition, oxazole derivatives occupy irreplaceable roles as essential intermediates and metal-catalyzed ligands in organic synthesis .…”

Special Issue on Synthesis of Novel Heterocyclic Compounds and Evaluation of Their Antimicrobial Activity

“…The presented Special Issue collects seven papers (including five experimental works, a conceptual work and a review) concerning various types of heterocyclic compounds and their highly diversified antimicrobial activity. Apostol et al [1] describe the antimicrobial activity of 28 compounds from 1,3-oxazole and 1,3-oxazol-5-one groups, as well as 21 of their acyclic precursors. All these products have been tested both in silico and in vitro with the use of qualitative and quantitative assays to investigate their antimicrobial potential against planktonic and biofilm-embedded microbial strains.…”

“…In the next paper, Potapov et al [3] report the synthesis of a group of new and highly soluble compounds as a product of annulation reactions of 8-quinolinesulfenyl halides with natural origin alkenes. Using this method, a series of [1,4] thiazino [2,3,4-ij]quinolin-4-ium was obtained with almost quantitative yields. Reactions with styrene derivatives and other terminal alkenes proceeded in a regioselective manner but with the opposite regiochemistry.…”