Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole

Abstract

The infection of Xanthomonas oryzae pv. Oryzae (Xoo), Ralstonia solanacearum (Rs), and Xanthomonas axonopodis pv. Citri (Xac) has become a major problem in agricultural production. In this study, a series of novel chalcone derivatives containing thioether triazoles were designed and synthesized. The structures of the novel compounds were systematically characterized via 1H‐NMR, 13C‐NMR, and HRMS. Moreover, the antibacterial activity results showed that E10, E11, E15, and E16 have adequate antibacterial activities against Xoo, Rs, and Xac. Among the different compounds, E15 exhibited remarkable inhibitory effect against Xac with an EC50 of 9.1 μg.mL‐1, which was better than that of commercial agent bismerthiazol (54.9 μg.mL‐1). In addition, the possible antibacterial mechanism of the target compound E15 against Xac was studied via scanning electron microscopy (SEM).

Chalcones As Broad‐Spectrum Antimicrobial Agents: A Comprehensive Review And Analysis Of Their Antimicrobial Activities

“…investigated pesticides activity 27 (Figure 15) have sufficient antibacterial activity against Xoo, Rs and Xac . Compound 27b at EC 50 of 9.1 μg/ml displayed a significant inhibitory effect against Xac , higher than standered bismertiazole (54.9 μg/ml) [98] …”

“…Compound 27b at EC 50 of 9.1 μg/ml displayed a significant inhibitory effect against Xac, higher than standered bismertiazole (54.9 μg/ml). [98] Solankee et al, have synthesized novel s-triazine based chalcones and their acetylpyrazoline, aminopyrimidines and cyanopyridines derivatives and evaluate for antibacterial activity. The synthesized compounds have shown significant activity against bacteria.…”

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

“…In 2020, Chen et al [79] synthesized a series of novel chalcone derivatives containing thioether triazoles. Among the tested compounds, compound 74 (Figure 17) exhibited remarkable inhibitory effect against Xac, with an EC 50 value of 9.1 μg/mL, which was better than that of Bismerthiazol.…”

Design, Synthesis, and Antifungal Activity of Novel Chalcone Derivatives Containing a Piperazine Fragment

“…We used chalcone as the lead compound and introduced other active groups (Figure S1 of the Supporting Information), such as triazine, 17 quinoxaline, 18 thiophene sulfonate, 19 and thioether triazole. 20 It is worth noting that their biological activities did improve. We used active groups from clinical medicine to be introduced into chalcone to improve its activities against plant pathogenic fungi.…”

“…Many chalcone derivatives have biological activities, such as anticancer, anti-inflammatory, antiviral, insecticidal, antibacterial, and antileishmanial activities. We used chalcone as the lead compound and introduced other active groups (Figure S1 of the Supporting Information), such as triazine, quinoxaline, thiophene sulfonate, and thioether triazole . It is worth noting that their biological activities did improve.…”