Issue 35, 2019, Issue in Progress
From the journal:

RSC Advances

Regioselective microwave synthesis and derivatization of 1,5-diaryl-3-amino-1,2,4-triazoles and a study of their cholinesterase inhibition properties†

Sabrina Neves Santos,ab   Gabriela Alves de Souza,ab   Thiago Moreira Pereira,ab   Daiana Portella Franco,ab   Catarina de Nigris Del Cistia,b   Carlos Mauricio R. Sant'Anna,b   Renata Barbosa Lacerdaab  and  Arthur Eugen Kümmerle ORCID logo *ab  

* Corresponding authors

a Laboratório de Diversidade Molecular e Química Medicinal (LaDMol-QM, Molecular Diversity and Medicinal Chemistry Laboratory), Chemistry Institute, Universidade Federal Rural do Rio de Janeiro, Seropédica, Rio de Janeiro, Brazil
E-mail: akummerle@hotmail.com

b Programa de Pós-Gradução em Química (PPGQ), Universidade Federal Rural do Rio de Janeiro, Seropédica, Rio de Janeiro, Brazil

Abstract

Herein we describe the development of an efficient one-pot regioselective synthesis protocol to obtain N-protected or N-deprotected 1,5-diaryl-3-amino-1,2,4-triazoles from N-acyl-N-Boc-carbamidothioates. This improved protocol using microwave irradiation and low reaction times (up to 1 h) furnished desired compounds in yields ranging from 50 to 84%. This chemistry is useful for a variety of aromatic groups with electronically diverse substituents. The design and correct derivation of the amino group led to compounds able to inhibit cholinesterases with good IC50 of up to 1 μM. Also, the mode of action (mixed-type) and SAR analysis for this series of compounds was described by means of kinetic and molecular modelling evaluations, showing potential for this class of compounds as new scaffolds for this biological activity.

Graphical abstract: Regioselective microwave synthesis and derivatization of 1,5-diaryl-3-amino-1,2,4-triazoles and a study of their cholinesterase inhibition properties

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Article information

DOI
https://doi.org/10.1039/C9RA04105B
Article type
Paper
Submitted
30 May 2019
Accepted
22 Jun 2019
First published
01 Jul 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 20356-20369

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Regioselective microwave synthesis and derivatization of 1,5-diaryl-3-amino-1,2,4-triazoles and a study of their cholinesterase inhibition properties

S. N. Santos, G. Alves de Souza, T. M. Pereira, D. P. Franco, C. de Nigris Del Cistia, C. M. R. Sant'Anna, R. B. Lacerda and A. E. Kümmerle, RSC Adv., 2019, 9, 20356 DOI: 10.1039/C9RA04105B

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