Santos Sabrina Neves, Alves de Souza Gabriela, Pereira Thiago Moreira, Franco Daiana Portella, de Nigris Del Cistia Catarina, Sant'Anna Carlos Mauricio R, Lacerda Renata Barbosa, Kümmerle Arthur Eugen
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 239897-000 Brazil
Programa de Pós-Gradução em Química (PPGQ), Universidade Federal Rural do Rio de Janeiro Seropédica Rio de Janeiro 239897-000 Brazil.
RSC Adv. 2019 Jul 1;9(35):20356-20369. doi: 10.1039/c9ra04105b. eCollection 2019 Jun 25.
Herein we describe the development of an efficient one-pot regioselective synthesis protocol to obtain -protected or -deprotected 1,5-diaryl-3-amino-1,2,4-triazoles from -acyl--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 IC 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.
在此，我们描述了一种高效的一锅法区域选择性合成方案的开发，该方案可从α-酰基-β-叔丁氧羰基氨基硫代甲酸酯获得N-保护或N-脱保护的1,5-二芳基-3-氨基-1,2,4-三唑。这种使用微波辐射和较短反应时间（最长1小时）的改进方案，以50%至84%的产率提供了所需化合物。这种化学方法适用于具有多种电子取代基的各种芳族基团。氨基的设计和正确衍生导致化合物能够抑制胆碱酯酶，其良好的IC50高达1 μM。此外，通过动力学和分子建模评估描述了该系列化合物的作用模式（混合型）和构效关系分析，表明这类化合物作为这种生物活性的新支架具有潜力。
