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Synthesis of 2-amino-3-cyano-4H-pyran derivatives using GO-Fc@Fe3O4 nanohybrid as a novel recyclable heterogeneous nanocatalyst and preparation of tacrine-naphthopyran hybrids as AChE inhibitors

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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.

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Abbreviations

AD:

Alzheimer’s disease

ACh:

Acetylcholine

AChE:

Acetylcholinesterase

BuChE:

Butyrylcholinesterase

ChEI:

Cholinesterase inhibitor

PAS:

Peripheral anionic site

CAS:

Catalytic active site

GO:

Graphene oxide

mCPBA:

meta-Chloroperoxybenzoic acid

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Acknowledgements

The authors would like to acknowledge the financial support from Iran National Science Foundation (INSF) (To Project Number: 97015588), Health Ministry of Islamic Republic of Iran, Tabriz University of medical sciences and the University of Tabriz.

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Authors and Affiliations

  1. Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, 51664, Iran

    Sakineh Mozaffarnia & Reza Teimuri-Mofrad

  2. Research Center for Pharmaceutical Nanotechnology, Tabriz University of Medical Sciences, Tabriz, Iran

    Sakineh Mozaffarnia & Mohammad-Reza Rashidi

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Mozaffarnia, S., Teimuri-Mofrad, R. & Rashidi, MR. Synthesis of 2-amino-3-cyano-4H-pyran derivatives using GO-Fc@Fe3O4 nanohybrid as a novel recyclable heterogeneous nanocatalyst and preparation of tacrine-naphthopyran hybrids as AChE inhibitors. J IRAN CHEM SOC 18, 1455–1470 (2021). https://doi.org/10.1007/s13738-020-02125-4

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