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Abstract

Synthesis, Docking Studies and Acetylcholinesterase Inhibition of Open-Chain Carbohydrate Amides †

by
Maria Isabel Ismael
1,2,*,
Rita Gonçalves-Pereira
1,2,3,
Susana D. Lucas
4,
José Albertino Figueiredo
2,
Maria Isabel García-Moreno
3,
Carmen Mellet
3 and
Amélia Pilar Rauter
1
1
Centro de Química Estrutural, Institute of Molecular Sciences, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal
2
Departamento de Química, Unidade I&D FibEnTech, Universidade da Beira Interior, Av. Marquês d’Ávila e Bolama, 6201-001 Covilhã, Portugal
3
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, C/Prof. García González 1, 41012 Sevilla, Spain
4
Department of Medicinal Chemistry, Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal
*
Author to whom correspondence should be addressed.
†
Presented at the 8th International Electronic Conference on Medicinal Chemistry, 1–30 November 2022; Available online: https://ecmc2022.sciforum.net/.
Med. Sci. Forum 2022, 14(1), 52; https://doi.org/10.3390/ECMC2022-13483
Published: 1 November 2022
(This article belongs to the Proceedings of The 8th International Electronic Conference on Medicinal Chemistry)
Versions Notes

Abstract

:
Alzheimer’s disease (AD) is the most common age-related cause of dementia among elderly people. AD is a severe neurodegenerative disorder characterized by progressive memory and cognition loss that leads to disability and inevitably to death and is considered as an urgent public health problem. It is the third leading cause of death after cancer and heart disease. According to an update in 2020 of the estimates given in the World Alzheimer Report 2015, there are over 50 million people worldwide living with dementia in 2020. This number will almost double every 20 years, reaching 152 million in 2050. AChE inhibitors are the mainstay drugs for early disease stages. In this work we report on the development of a synthetic route to yield open chain sugar amides from commercially available carbohydrates. The synthetic pathway starts with diacetone glucose (DAG), which is converted into perbenzyl d-glucono-1,4-lactone in six steps. Reaction with aromatic or aliphatic amines in dichloromethane under reflux (0.5 h to 2 h) afforded the corresponding amides in high yield (80–95%). Bis(amidation) of a diamine was also accessed by this procedure in 3 h but the reaction product was isolated in a very low yield (13%). Docking studies and evaluation of acetylcholinesterase inhibition were carried out and the results will be disclosed.

Supplementary Materials

The following are available online at https://www.mdpi.com/article/10.3390/ECMC2022-13483/s1.

Author Contributions

Conceptualization, A.P.R., M.I.I., C.M.; methodology, R.G.-P.; software, S.D.L.; validation, A.P.R., M.I.I., C.M., formal analysis, J.A.F.; A.P.R., M.I.I., C.M.; investigation, R.G.-P., A.P.R., M.I.I., J.A.F., M.I.G.-M., C.M.; resources, A.P.R., M.I.I., C.M.; data curation, A.P.R., M.I.I., C.M.; writing—original draft preparation; A.P.R., M.I.I., R.G.-P.; writing—review and editing, A.P.R., M.I.I., C.M.; visualization A.P.R., M.I.I., C.M.; supervision, A.P.R., M.I.I., C.M.; project administration, A.P.R., M.I.I., C.M.; funding acquisition, A.P.R., M.I.I., C.M. All authors have read and agreed to the published version of the manuscript.

Funding

The Spanish Ministerio de Economía y Competitividad (MINECO, contract number SAF2013-44021-R) is acknowledged. Cofinancing from the European Regional Development Funds (FEDER and FSE) is also thanked. Financial support of Fundação para a Ciência e a Tecnologia is gratefully acknowledged for the support of Centro de Química Estrutural (projects UIDB/00100/2020 and UIDP/00100/2020), and Institute of Molecular Sciences, an Associate Laboratory funded through project LA/P/0056/2020, by A. P. Rauter and by S.D. Lucas (IF/00472/2014; Pest-OE/SAL/UI4013/2014).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Share and Cite

MDPI and ACS Style

Ismael, M.I.; Gonçalves-Pereira, R.; Lucas, S.D.; Figueiredo, J.A.; García-Moreno, M.I.; Mellet, C.; Rauter, A.P. Synthesis, Docking Studies and Acetylcholinesterase Inhibition of Open-Chain Carbohydrate Amides. Med. Sci. Forum 2022, 14, 52. https://doi.org/10.3390/ECMC2022-13483

AMA Style

Ismael MI, Gonçalves-Pereira R, Lucas SD, Figueiredo JA, García-Moreno MI, Mellet C, Rauter AP. Synthesis, Docking Studies and Acetylcholinesterase Inhibition of Open-Chain Carbohydrate Amides. Medical Sciences Forum. 2022; 14(1):52. https://doi.org/10.3390/ECMC2022-13483

Chicago/Turabian Style

Ismael, Maria Isabel, Rita Gonçalves-Pereira, Susana D. Lucas, José Albertino Figueiredo, Maria Isabel García-Moreno, Carmen Mellet, and Amélia Pilar Rauter. 2022. "Synthesis, Docking Studies and Acetylcholinesterase Inhibition of Open-Chain Carbohydrate Amides" Medical Sciences Forum 14, no. 1: 52. https://doi.org/10.3390/ECMC2022-13483

APA Style

Ismael, M. I., Gonçalves-Pereira, R., Lucas, S. D., Figueiredo, J. A., García-Moreno, M. I., Mellet, C., & Rauter, A. P. (2022). Synthesis, Docking Studies and Acetylcholinesterase Inhibition of Open-Chain Carbohydrate Amides. Medical Sciences Forum, 14(1), 52. https://doi.org/10.3390/ECMC2022-13483

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