Abstract

Synthesizing new chemical compounds and studying their biological applications have been important issues in scientific research. In this investigation, we synthesized and characterized ten new N-acetyl phosphoramidate compounds and explored the crystal structure of three others. Furthermore, not only were some kinetic inhibition parameters measured, like IC₅₀, K_i, k_p, K_D for 7 compounds on human acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), but also their hydrophobic parameter was determined by shake-flask technique. All compounds (number 1–10) were investigated for anti-bacterial activity against three Gram-positive and three Gram-negative bacteria, while chloramphenicol was used as a standard antibiotic. In order to find new insecticide, toxicities of 13 acephate (Ace)-derived compounds (number 20–32) were bioassayed on third larval instar of elm leaf beetle and Xanthogaleruca luteola. Additionally, screening in vivo tests revealed that two compounds had had the greatest insecticidal potential in comparison with others. It means these ones inhibited AChE (with mixed mechanisms) and general esterase more than the rest. According to ChE-QSAR models, the inhibitory potency for enzyme and bacteria is directly influenced by the electronic parameters versus structural descriptors. AChE-QSPR model of fluorescence assay indicated that the inhibitory power of AChE is primarily influenced by a set of electronic factors with the priority of: E_HB > PL > δ(³¹P) versus structural descriptor (SA and Mv).

Graphic abstract

Synthesizing new chemical compounds and studying their biological applications have been important issues in scientific research. Toxicities of 13 acephate (Ace)-derived compounds (number 20–32) were bioassayed on third larval instar of elm leaf beetle and Xanthogaleruca luteola. Insect-QSAR equations of these compounds, based on MLR and PCA, showed that non-descriptor net charge nitrogen atom (which was affected by the polarization of N–H group) had the greatest effect on insecticidal potential.

中文翻译：

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单磷酰胺衍生物：合成和晶体结构，其生物学效应的理论和实验研究

摘要

合成新的化合物并研究其生物学应用一直是科学研究的重要课题。在这项研究中，我们合成并表征了十种新的 N-乙酰氨基磷酸酯化合物，并探索了另外三种的晶体结构。此外，不仅测量了一些动力学抑制参数，如7种化合物对人乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的IC ₅₀、K _i、k _p、K _D ，而且还通过摇瓶技术确定了它们的疏水参数。 . 所有化合物（编号1 – 10) 研究了对三种革兰氏阳性菌和三种革兰氏阴性菌的抗菌活性，而氯霉素被用作标准抗生素。为了寻找新的杀虫剂，对 13 种乙酰甲胺磷 (Ace) 衍生化合物（编号20 – 32 ）的毒性对榆叶甲虫和Xanthogaleruca luteola的三龄幼虫进行了生物测定. 此外，体内筛选试验表明，与其他化合物相比，两种化合物具有最大的杀虫潜力。这意味着这些药物比其他药物更能抑制 AChE（具有混合机制）和一般酯酶。根据 ChE-QSAR 模型，酶和细菌的抑制效力直接受电子参数与结构描述符的影响。荧光分析的AChE-QSPR模型表明，AChE的抑制能力主要受一组电子因素的影响，其优先级为：E _HB  > PL > δ( ³¹ P) 与结构描述符(SA和Mv)。

图形摘要

合成新的化合物并研究其生物学应用一直是科学研究的重要课题。对 13 种乙酰甲胺磷 (Ace) 衍生化合物（编号 20-32）的毒性在榆叶甲虫和Xanthogaleruca luteola的三龄幼虫进行了生物测定。基于 MLR 和 PCA 的这些化合物的 Insect-QSAR 方程表明，非描述性净电荷氮原子（受 N-H 基团极化的影响）对杀虫潜力的影响最大。