Synthesis and antifungal activities of small molecule arylthiazolamine derivatives.

IF 3.9 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2024-10-08 DOI:10.1007/s11030-024-11002-8

Xu Zhong, Jian He, Taigui Ma, Guobin Chen, Yong Zhang, Min Zhang, Lei Tang, Yong Li, Lingling Fan

{"title":"Synthesis and antifungal activities of small molecule arylthiazolamine derivatives.","authors":"Xu Zhong, Jian He, Taigui Ma, Guobin Chen, Yong Zhang, Min Zhang, Lei Tang, Yong Li, Lingling Fan","doi":"10.1007/s11030-024-11002-8","DOIUrl":null,"url":null,"abstract":"<p><p>Developing new fungicides to compensate for the deficiencies of existing fungicides resistance in phytopathogenic fungi is a research hotspot in the field of pesticides. Aiming to discover novel template small molecules with excellent antifungal activity, thirty-eight arylthiazolamine derivatives were synthesized through bromination, cyclization, halogenation, and acylation reactions. The synthesized compounds were screened for antifungal activity against ten typical fungal pathogens, and some halogenated arylthiazolamines and amides exhibited excellent broad-spectrum antifungal activity, especially compounds 4m (3.96-47.76 μg/mL), 5k (0.10-7.70 μg/mL) and 5n (2.08-11.21 μg/mL). Among them, compound 5k provided comparable protection and curative effects to chloroticonil and boscalid against B. dothidea and V. mali infection in apple and apple tree branches, respectively, and it could exert antifungal effects by inhibiting the differentiation of mycelium spores, spore germination, and bud tube growth. This study provides high-efficiency and inexpensive candidate compounds for managing of diseases caused by plant pathogenic fungi.</p>","PeriodicalId":708,"journal":{"name":"Molecular Diversity","volume":" ","pages":""},"PeriodicalIF":3.9000,"publicationDate":"2024-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Molecular Diversity","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s11030-024-11002-8","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}

引用次数: 0

Abstract

Developing new fungicides to compensate for the deficiencies of existing fungicides resistance in phytopathogenic fungi is a research hotspot in the field of pesticides. Aiming to discover novel template small molecules with excellent antifungal activity, thirty-eight arylthiazolamine derivatives were synthesized through bromination, cyclization, halogenation, and acylation reactions. The synthesized compounds were screened for antifungal activity against ten typical fungal pathogens, and some halogenated arylthiazolamines and amides exhibited excellent broad-spectrum antifungal activity, especially compounds 4m (3.96-47.76 μg/mL), 5k (0.10-7.70 μg/mL) and 5n (2.08-11.21 μg/mL). Among them, compound 5k provided comparable protection and curative effects to chloroticonil and boscalid against B. dothidea and V. mali infection in apple and apple tree branches, respectively, and it could exert antifungal effects by inhibiting the differentiation of mycelium spores, spore germination, and bud tube growth. This study provides high-efficiency and inexpensive candidate compounds for managing of diseases caused by plant pathogenic fungi.

查看原文本刊更多论文

小分子芳基噻唑胺衍生物的合成和抗真菌活性。

开发新型杀菌剂以弥补植物病原真菌对现有杀菌剂抗性的不足是农药领域的研究热点。为了发现具有优异抗真菌活性的新型模板小分子，研究人员通过溴化、环化、卤化和酰化反应合成了 38 个芳基噻唑胺衍生物。对合成的化合物进行了抗十种典型真菌病原体的抗真菌活性筛选，一些卤代芳基噻唑胺和酰胺类化合物表现出优异的广谱抗真菌活性，尤其是化合物 4m（3.96-47.76 μg/mL）、5k（0.10-7.70 μg/mL）和 5n（2.08-11.21 μg/mL）。其中，化合物 5k 分别对苹果和苹果树枝条上的多菌灵和苹果蠹蛾感染提供了与氯噻酮和啶虫脒相当的保护和治疗效果，它可以通过抑制菌丝孢子分化、孢子萌发和芽管生长来发挥抗真菌作用。这项研究为防治植物病原真菌引起的病害提供了高效、廉价的候选化合物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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;