Synthesis and Antibacterial Evaluation of N-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties

Abstract

A series of new N-phenylacetamide derivatives containing 4-arylthiazole moieties was designed and synthesized by introducing the thiazole moiety into the amide scaffold. The structures of the target compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. Their in vitro antibacterial activities were evaluated against three kinds of bacteria—Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac) and X.oryzae pv. oryzicola (Xoc)—showing promising results. The minimum 50% effective concentration (EC50) value of N-(4-((4-(4-fluoro-phenyl)thiazol-2-yl)amino)phenyl)acetamide (A1) is 156.7 µM, which is superior to bismerthiazol (230.5 µM) and thiodiazole copper (545.2 µM). A scanning electron microscopy (SEM) investigation has confirmed that compound A1 could cause cell membrane rupture of Xoo. In addition, the nematicidal activity of the compounds against Meloidogyne incognita (M. incognita) was also tested, and compound A23 displayed excellent nematicidal activity, with mortality of 100% and 53.2% at 500 μg/mL and 100 μg/mL after 24 h of treatment, respectively. The preliminary structure-activity relationship (SAR) studies of these compounds are also briefly described. These results demonstrated that phenylacetamide derivatives may be considered as potential leads in the design of antibacterial agents.

Design, Synthesis, and Biological Activity of Novel Ferulic Amide Ac5c Derivatives

“…Using different substituted halogen compounds as starting materials, the synthesis of target compounds 4a – 4q went through three steps, − including substitution, hydrolysis, and acylation (Figure ). Then, the target compounds 5a – 5q were prepared via hydrolysis of compounds 4a – 4q (Scheme S1).…”

Magnesium Powder-Catalyzed, Highly Efficient, Solvent-Free Synthesis of Amides through N-Acetylation of Amines and their Antibacterial Activity

“…Acetamide derivatives are reported to possess several bioactivities such as antimicrobial [1][2][3][4][5], antitubercular [6,7], antimalarial [8], antiparasitic [9], antidiabetic [10,11], antipsychotic [12], antioxidant activities [13], etc. Acetamides are used also as chemotherapeutic agents for inflammation and inflammation-associated cancers [14,15].…”

Synthesis, Molecular Docking and Biological Evaluation of 2‐Aryloxy‐N‐Phenylacetamide and N′‐(2‐Aryloxyoxyacetyl) Benzohydrazide Derivatives as Potential Antibacterial Agents

“…reported the synthesis of substituted phenylacetamides and benzamide derivatives as potential antimicrobials. Additionally, Lu et al [23] . described the efficacy of N‐ phenylacetamides containing 4‐arylthiazole scaffold as effective antibacterial agents.…”