Synthesis and three-dimensional quantitative structure-activity relationship study of quinazoline derivatives containing a 1,3,4-oxadiazole moiety as efficient inhibitors against Xanthomonas axonopodis pv. citri

Abstract

A series of quinazoline derivatives containing a 1,3,4-oxadiazole moiety were synthesized and evaluated for their antibacterial activities against Xanthomonas axonopodis pv. citri (Xac) and Ralstonia solanacearum (Rs). Antibacterial bioassays indicated that most of target compounds exhibited significant antibacterial activities against Xac and Rs in vitro. Strikingly, compounds 6d-6i, 6m-6r and 6u-6x showed antibacterial activity against Xac, with [Formula: see text] values ranging from 14.42 to 38.91 [Formula: see text]g/mL, which are better than that of bismerthiazol (39.86 [Formula: see text]g/mL). Based on the antibacterial activity against Xac, comparative molecular filed analysis and comparative molecular similarity index analysis models were generated to investigate the structure-activity relationship of title compounds against Xac. The analytical results indicated that the above models exhibited good predictive accuracy and could be used as practical tools for guiding the design and synthesis of more potent quinazoline derivatives containing a 1,3,4-oxadiazole moiety.

1,3,4‐oxadiazole derivatives as potential antimicrobial agents

“…The CoMSIA model showed the involvement of hydrophobic (0.482), electrostatic (0.291) and steric (0.203) interactions in antibacterial activity, which signifies the major contribution of hydrophobic interactions in bioactivity. The analysis of results depicted that 1,3,4‐oxadiazole with p ‐chlorobenzyl group ( 312 , Figure 11) has superior anti‐ Xac activity than other derivatives with phenyl and phenoxy groups (Wang et al, 2018).…”

Recent achievements on the agricultural applications of thioether derivatives: A 2010–2020 decade in review

“…Meanwhile, greenhouse trials indicated that compound 60 was effective in reducing rice bacterial leaf blight relative to Thiodiazole copper and Bismerthiazol. Wang et al [72] synthesized a series of thioether derivatives containing a 1,3,4-oxadiazole moiety and evaluated for their in vitro antibacterial activities against Xac and R. solanacearum. Antibacterial bioassays indicated that compound 61 (Figure 15) exhibited significant antibacterial activity (EC 50 = 14.42 μg/mL) against Xac, which was even better than that of Bismerthiazol.…”

Xanthomonas citri subsp. citri: host interaction and control strategies

“…On the other hand, sulfone derivatives containing 1,3,4oxadiazole were tested in vitro and in field conditions to control X. citri growth (Li et al 2015;Wang et al 2018). After exposing navel oranges to three rounds of spray with 1,3,4oxadiazole, a 60-64% reduction in citrus canker was observed, compared to a 50-56% reduction obtained with copper-based compounds (Li et al 2015).…”