Synthesis and bioactivity of tetrahydrothiopyran derivatives as potential acaricides against Psoroptes cuniculi.

IF 3.9 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2025-06-25 DOI:10.1007/s11030-025-11256-w

Dongdong Chen, Yan Wang, Yujun Wu, Xinying Sun, Yaxuan Wang, Qi Li, Wennuo Zhou, Wen Wu, Jie Long

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Abstract

Thirty-two tetrahydrothiopyran derivatives were synthesized, and their acaricidal activities against Psoroptes cuniculi were evaluated in vitro. The results showed that eight compounds exhibited higher acaricidal activity than ivermectin when evaluated by mass concentration, while six compounds showed superior activity when assessed by molar concentration. Compound b10 showed the lowest LC₅₀ value [62.3 µg/mL (0.12 mM)] and LT₅₀ value (2.2 h at 4.5 mM), far lower than ivermectin [LC₅₀ = 223.3 µg/mL (0.26 mM), LT₅₀ = 8.7 h]. Structure-activity relationship (SAR) analysis showed that the presence of the sulfone structure is crucial for activity, while the types and positions of substituents on the benzene rings are two main factors affecting the activity. Molecular docking results demonstrated that compounds a10, b9, b10 and b11 exhibited good affinity with the AChE protein, along with potential binding modes, suggesting AChE as a promising acaricidal drug target. Overall, these results suggest that tetrahydrothiopyran derivatives, particularly their sulfone derivatives have great potential for the development of novel acaricides.

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四氢硫吡喃类潜在杀螨剂的合成及生物活性研究。

合成了32个四氢硫吡喃衍生物，并对其体外杀螨活性进行了评价。结果表明，以质量浓度评价8个化合物的杀螨活性优于伊维菌素，以摩尔浓度评价6个化合物的杀螨活性优于伊维菌素。化合物b10 LC50值最低[62.3µg/mL (0.12 mM)]， LT50值最低（4.5 mM处2.2 h），远低于伊维菌素[LC50 = 223.3µg/mL (0.26 mM), LT50 = 8.7 h]。构效关系（SAR）分析表明，砜结构的存在是影响活性的关键因素，而苯环上取代基的类型和位置是影响活性的两个主要因素。分子对接结果表明，化合物a10、b9、b10和b11与乙酰胆碱酯酶蛋白具有良好的亲和力，并具有潜在的结合模式，提示乙酰胆碱酯酶是一个很有前景的杀螨药物靶点。总之，这些结果表明，四氢硫吡喃衍生物，特别是其砜衍生物在新型杀螨剂的开发方面具有很大的潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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;