Design, synthesis, crystal structure, and in vitro antibacterial activities of sulfonamide derivatives bearing the 4-aminoquinazoline moiety

Wan, Suran; Wu, Nan; Ye, Yan; Yang, Yehui; Tian, Guangmin; An, Lian; Bao, Xiaoping

doi:10.1007/s11030-022-10484-8

Cited by 3 publications

(1 citation statement)

References 34 publications

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“…As far as the 2-aminothiazole backbone is concerned, its unique electron-rich character and strong polarity enable it to easily interact with relevant targets in organisms through different noncovalent interactions such as hydrogen bonds, coordination bonds, and π-π stacking interactions. 25 In addition, 4-aminoquinazoline derivatives demonstrate a range of biological activities, including antibacterial, 26,27 antiviral, 28 anti-tumor, 29 and anti-mutagenic 30 efficacies. As a privileged structure, 4-aminoquinzoline is present in many approved drugs such as the anticancer drugs erlotinib/ lapatinib, anti-importin ⊎ agent importazole, anti-hypertensive drug prazosin, and alfuzosin, a drug for the treatment of benign prostatic hyperplasia.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and antimicrobial evaluation of 2‐aminothiazole derivatives bearing the 4‐aminoquinazoline moiety against plant pathogenic bacteria and fungi

Wan,

Yang,

Tian

et al. 2023

Pest Management Science

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BACKGROUNDTo find more effective agricultural antibiotics, a class of new 2‐aminothiazole derivatives containing the 4‐aminoquinazoline moiety were synthesized and evaluated for their antimicrobial properties against phytopathogenic bacteria and fungi of agricultural importance.RESULTSAll the target compounds were fully characterized by 1H NMR, 13C NMR, and high‐resolution mass spectrometry. The bioassay results showed that compound F29 with a 2‐pyridinyl substituent exhibited an outstanding antibacterial effect against Xanthomonas oryzae pv. oryzicola (Xoc) in vitro, having an half‐maximal effective concentration (EC50) value as low as 2.0 μg/mL (over 30‐fold more effective than the commercialized agrobactericide bismerthiazol, with an EC50 value of 64.3 μg/mL). In addition, compound F8 with a 2‐fluorophenyl group demonstrated a good inhibitory activity toward the bacterium Xanthomonas axonopodis pv. citri (Xac), around twofold more active than bismerthiazol in terms of their EC50 values (22.8 versus 71.5 μg/mL). Interestingly, this compound also demonstrated a notable fungicidal effect against Phytophthora parasitica var. nicotianae, with an EC50 value largely comparable with that of the commercialized fungicide carbendazim. Finally, mechanistic studies revealed that compound F29 exerted its antibacterial effects by increasing the permeability of bacterial membranes, reducing the release of extracellular polysaccharides, and triggering morphological changes of bacterial cells.CONCLUSIONCompound F29 has promising potential as a lead compound for developing more efficient bactericides to fight against Xoc. © 2023 Society of Chemical Industry.

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