Chemistry Department, Faculty of Science, Ain Shams University, Cairo 11566, Egypt.
Entomology Department, Faculty of Science, Ain Shams University, Cairo 11566, Egypt.
Bioorg Chem. 2024 Sep;150:107591. doi: 10.1016/j.bioorg.2024.107591. Epub 2024 Jun 24.
Some heterocycles bearing a benzo[h]quinoline moiety were synthesized through treating a 3-((2-chlorobenzo[h]quinolin-3-yl)methylene)-5-(p-tolyl)furan-2(3H)-one with four nitrogen nucleophiles comprising ammonium acetate, benzylamine, dodecan-1-amine, and 1,2-diaminoethane. Also, thiation reactions of furanone and pyrrolinone derivatives were investigated. The insecticidal activity of these compounds against mosquito larvae (Culex pipiens L.) was evaluated. All tested compounds exhibited significant larvicidal activity, surpassing that of the conventional insecticide chlorpyrifos. In silico docking analysis revealed that these compounds may act as acetyl cholinesterase (AChE) inhibitors, potentially explaining their larvicidal effect. Additionally, interactions with other neuroreceptors, such as nicotinic acetylcholine receptor and sodium channel voltage-gated alpha subunit were also predicted. The results obtained from this study reflected the potential of benzo[h]quinoline derivatives as promising candidates for developing more effective and sustainable mosquito control strategies. The ADME (absorption, distribution, metabolism, and excretion) analyses displayed their desirable drug-likeness and oral bioavailability properties.
一些含有苯并[h]喹啉部分的杂环化合物是通过用四种氮亲核试剂（包括醋酸铵、苄胺、十二烷-1-胺和 1,2-二氨基乙烷）处理 3-((2-氯苯并[h]喹啉-3-基)亚甲基)-5-(对甲苯基)呋喃-2(3H)-酮合成的。此外，还研究了呋喃酮和吡咯啉酮衍生物的硫代反应。评估了这些化合物对蚊子幼虫（库蚊）的杀虫活性。所有测试的化合物都表现出显著的杀幼虫活性，超过了常规杀虫剂毒死蜱。基于计算机的对接分析表明，这些化合物可能作为乙酰胆碱酯酶（AChE）抑制剂发挥作用，这可能解释了它们的杀幼虫作用。此外，还预测了与其他神经受体（如烟碱型乙酰胆碱受体和钠通道电压门控α亚单位）的相互作用。这项研究的结果反映了苯并[h]喹啉衍生物作为开发更有效和可持续的蚊子控制策略的有前途的候选物的潜力。ADME（吸收、分布、代谢和排泄）分析显示了它们理想的药物样特性和口服生物利用度。
