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氯化胆碱-尿素低共熔溶剂/铜-锰亚氨基二乙酸配位聚合物作为合成具有抗菌活性的森田-贝利斯-希尔曼加合物的高效催化体系

Choline Chloride-Urea Deep Eutectic Solvent/Cu-Mn Iminodiacetate Coordination Polymer as an Efficient Catalytic System for Synthesis of Morita-Baylis-Hillman Adducts with Antimicrobial Activity.

作者信息

Mendes Rhuan Karlos Santos, Santos Emelly Suelen de Freitas Reis, de Andrade Sandro Dutra, da Silva Girlyanderson Araújo, Galvão José Lucas Ferreira Marques, Dos Santos José Roberto Dantas de Andrade, Lima Edeltrudes de Oliveira, da Silva Rodolfo B, Cristiano Rodrigo, da Silva Fausthon Fred, Lima-Junior Claudio Gabriel

机构信息

Department of Chemistry, Federal University of Paraíba, Campus I, João Pessoa, Paraíba 58051-900, Brazil.

Department of Pharmaceutical Science, Federal University of Paraíba, Campus I, João Pessoa, Paraíba 58051-900, Brazil.

出版信息

ACS Omega. 2024 Nov 7;9(46):45911-45919. doi: 10.1021/acsomega.4c05386. eCollection 2024 Nov 19.

DOI:10.1021/acsomega.4c05386
PMID:39583655
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11579785/
Abstract

This work shows the synthesis of a series of Morita-Baylis-Hillman adducts from isatin derivatives via an efficient green approach involving the use of a new catalyst system, a mixture of copper-manganese iminodiacetate 1D coordination polymer (Cu/Mn-IDA) and choline chloride-urea deep eutectic solvent (ChCl/urea 1:2). The adducts were obtained in good to excellent yields (59-97%) with shorter reaction times. The results demonstrate for the first time the synergistic catalytic effect of the combination of deep eutectic solvent and coordination polymer on the Morita-Baylis-Hillman reactions. The catalyst recyclability was investigated, and it was found that Cu/Mn-IDA maintains consistent performance for at least four catalytic cycles. The synthesized compounds were evaluated for their in vitro antimicrobial activity against four bacteria and eight fungi species. Among all, , , , , and showed antifungal and antibacterial activities in 70-83% of the strains tested. The adduct exhibited significant antifungal activity with a minimum inhibitory concentration value of 128 μg mL compared to the standard drug fluconazole (minimum inhibitory concentration, 256 μg mL).

摘要

这项工作展示了通过一种高效的绿色方法,从异吲哚酮衍生物合成一系列森田-贝利斯-希尔曼加合物,该方法涉及使用一种新型催化剂体系,即铜-锰亚氨基二乙酸一维配位聚合物(Cu/Mn-IDA)和氯化胆碱-尿素低共熔溶剂(ChCl/urea 1:2)的混合物。加合物的产率良好至优异(59-97%),反应时间更短。结果首次证明了低共熔溶剂和配位聚合物的组合对森田-贝利斯-希尔曼反应具有协同催化作用。研究了催化剂的可回收性,发现Cu/Mn-IDA在至少四个催化循环中保持一致的性能。对合成的化合物进行了针对四种细菌和八种真菌的体外抗菌活性评估。其中, 、 、 、 、 和 在70-83%的测试菌株中表现出抗真菌和抗菌活性。与标准药物氟康唑(最低抑菌浓度,256 μg/mL)相比,加合物 表现出显著的抗真菌活性,最低抑菌浓度值为128 μg/mL。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/7124bbd6e59a/ao4c05386_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/29983e4677a3/ao4c05386_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/1e235727c481/ao4c05386_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/8b33081211df/ao4c05386_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/6d89a7363747/ao4c05386_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/7124bbd6e59a/ao4c05386_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/29983e4677a3/ao4c05386_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/1e235727c481/ao4c05386_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/8b33081211df/ao4c05386_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/6d89a7363747/ao4c05386_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/db19/11579785/7124bbd6e59a/ao4c05386_0004.jpg

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