Abstract

GO-Fc@Fe₃O₄ nanohybrid as a powerful and reusable nanocatalyst was synthesized. The graphene oxide (GO) sheets with meta-chloroperoxybenzoic acid (mCPBA) were treatment, afterward were chemically modified with 4-Fc derivative through the ring-opening reaction between GO nanosheets and 4-ferrocenylbutylamine. Then, the final nanocatalyst was obtained by synthesizing of Fe₃O₄ nanoparticles onto the modified GO surface. The structure and morphology of GO-Fc@Fe₃O₄ nanohybrid were characterized using different analysis, such as FT-IR, XRD, FE-SEM, EDX, and VSM techniques. Then, 2-amino-3-cyano-4H-pyran derivatives (4a–l) as a synthetic precursor were synthesized via multi-component reaction in the presence of GO-Fc@Fe₃O₄ nanohybrid as a novel heterogeneous nanocatalyst. Finally, according to the importance of finding a solution to treat Alzheimer’s disease, 14-aryl-10,11,12,14-tetrahydro-9H-benzo[5,6]chromeno[2,3-b]-quinolin-13-amines (5a–l) as new tacrine-naphthopyran hybrid analogs were designed and prepared as acetylcholinesterase inhibitors. These compounds were synthesized via Friedländer reaction of 2-amino-3-cyano-4H-pyran derivatives (4a–l) with cyclohexanone. HAChE inhibition assay was carried out in vitro on the synthesized compounds 5a–l. Among them, compound 5f exhibited potent hAChE inhibitors with IC₅₀ values of 0.16 µM. Also, the molecular docking and kinetic studies performed for a better understanding of compound 5f as a representative compound.

Graphic abstract

中文翻译：

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以GO-Fc @ Fe 3 O 4纳米杂化物为新型可循环异质纳米催化剂合成2-氨基-3-氰基-4 H-吡喃衍生物，并制备他克林-萘并吡喃杂化物作为AChE抑制剂

摘要

合成了功能强大且可重复使用的GO-Fc @ Fe ₃ O ₄纳米杂化体。用间氯过氧苯甲酸（mCPBA）处理氧化石墨烯（GO）片，然后通过GO纳米片与4-二茂铁基丁基胺之间的开环反应，用4-Fc衍生物进行化学修饰。然后，通过将Fe ₃ O ₄纳米颗粒合成到改性的GO表面获得最终的纳米催化剂。使用不同的分析方法，如FT-IR，XRD，FE-SEM，EDX和VSM技术对GO-Fc @ Fe ₃ O ₄纳米杂化物的结构和形态进行了表征。然后，2-氨基-3-氰基-4 H-吡喃衍生物（4a – l作为新型多相纳米催化剂，在GO-Fc @ Fe ₃ O ₄纳米杂化物的存在下，通过多组分反应合成了作为合成前体的三聚氰胺。最后，根据寻找解决阿尔茨海默氏病的方法的重要性，选择14-芳基-10,11,12,14-四氢-9 H-苯并[5,6] chromeno [2,3-b]-喹啉-13作为新的他克林-萘并吡喃杂化物类似物-胺（5a - 1）被设计并制备为乙酰胆碱酯酶抑制剂。这些化合物是通过2-氨基-3-氰基-4 H-吡喃衍生物（4a - l）与环己酮的Friedländer反应合成的。在合成的化合物上进行了HAChE抑制试验5a – l。其中，化合物5f表现出有效的hAChE抑制剂，IC ₅₀值为0.16 µM。同样，进行了分子对接和动力学研究，以更好地理解化合物5f作为代表化合物。

图形摘要