Synthesis of novel phthalide bearing thiazole, 1,3,4-oxadiazole, and oxime ether groups as potential antifungal agents.

IF 3.8 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2025-09-12 DOI:10.1007/s11030-025-11348-7

Yong Li, Taotao Wu, Guobin Chen, Jian He, Yong Zhang, Qin Zhang, Pengfei Zhou, Wenzhang Chen, Lingling Fan

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Abstract

Twenty-eight novel phthalide derivatives incorporating thiazole, 1,3,4-oxadiazole, and oxime ether moieties were designed and synthesized using a pharmacophore hybridization strategy. Bioactivity assays demonstrated that compounds 1b, 1c, 4a, 4b and 4c exhibited moderate to excellent inhibitory activity against several specific fungi. Notably, compound 1b displayed superior antifungal efficacy against F. solani, F. oxysporum, B. dothidea, and V. mali compared to the commercial fungicides hymexazol and boscalid, with EC₅₀ values of 15.0 μg/mL, 10.0 μg/mL, 6.1 μg/mL, and 11.4 μg/mL, respectively. Additionally, compound 1b provided superior protective efficacy against B. dothidea-infected apples compared to boscalid. Preliminary mechanistic studies revealed that compound 1b could exert its antifungal activity by compromising the integrity of the hyphal cell membrane. This study highlights the potential of phthalide derivatives bearing dihalocarbonyl and oxime moieties as effective antifungal agents for controlling plant pathogenic fungi, warranting further investigation in the future.

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含噻唑、1,3,4-恶二唑和肟醚基团的新型邻苯酞的合成。

采用药效团杂交策略，设计合成了28个含有噻唑、1,3,4-恶二唑和肟醚基团的新型邻苯酞衍生物。生物活性实验表明，化合物1b、1c、4a、4b和4c对几种特定真菌具有中等至优异的抑制活性。值得注意的是，化合物1b对番茄枯萎菌、尖孢镰刀菌、dothidea白僵菌和马里弧菌的抑菌效果优于市售杀菌剂百螨唑和boscalid， EC50值分别为15.0、10.0、6.1和11.4 μg/mL。此外，化合物1b对苹果白僵菌的防治效果优于氯胺酮。初步的机制研究表明，化合物1b可能通过破坏菌丝细胞膜的完整性来发挥其抗真菌活性。本研究强调了含有二卤羰基和肟基的邻苯酞衍生物作为控制植物病原真菌的有效抗真菌剂的潜力，值得在未来进一步研究。

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;