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Open AccessArticle

Synthesis of New Quinoline-Piperonal Hybrids as Potential Drugs against Alzheimer’s Disease

1
Medicinal Chemistry Group, Department of Chemistry, Military Institute of Engineering, Praça General Tibúrcio 80, 22290-270 Rio de Janeiro, RJ, Brazil
2
Laboratory of Molecular Modeling Applied to the Chemical and Biological Defense (LMCBD), Military Institute of Engineering, Praça General Tibúrcio 80, 22290-270 Rio de Janeiro, Brazil
3
Graduate Program in Adult Health, Federal University of Maranhão, Avenida dos Portugueses, 1966. Vila Bacanga, 65080-805 São Luís, MA, Brazil
4
Department of Chemistry, Faculty of Science, University of Hradec Kralove, Rokitanskeho 62, 50003 Hradec Kralové, Czech Republic
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2019, 20(16), 3944; https://doi.org/10.3390/ijms20163944
Received: 2 June 2019 / Revised: 1 August 2019 / Accepted: 9 August 2019 / Published: 14 August 2019
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Abstract

Six quinoline-piperonal hybrids were synthesized and evaluated as potential drugs against Alzheimer’s disease (AD). Theoretical analysis of the pharmacokinetic and toxicological properties of the compounds suggest that they present good oral bio-availability and are also capable of penetrating the blood–brain barrier, qualifying as leads for new drugs against AD. Evaluation of their inhibitory capacity against acetyl- and butyrilcholinesterases (AChE and BChE) through Ellmann’s test showed that three compounds present promising results with one of them being capable of inhibiting both enzymes. Further docking studies of the six compounds synthesized helped to elucidate the main interactions that may be responsible for the inhibitory activities observed. View Full-Text
Keywords: piperonal; quinolines; guanil-hydrazones; acetylcholinesterase; Alzheimer’s disease piperonal; quinolines; guanil-hydrazones; acetylcholinesterase; Alzheimer’s disease
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de Oliveira C. Brum, J.; Neto, D.C.F.; de Almeida, J.S.F.D.; Lima, J.A.; Kuca, K.; França, T.C.C.; Figueroa-Villar, J.D. Synthesis of New Quinoline-Piperonal Hybrids as Potential Drugs against Alzheimer’s Disease. Int. J. Mol. Sci. 2019, 20, 3944.

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