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

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 <b>2a-2i</b> 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, <b>2a</b>, <b>2b</b>, <b>2d</b>, <b>2e</b>, and <b>2g</b> showed antifungal and antibacterial activities in 70-83% of the strains tested. The adduct <b>2e</b> exhibited significant antifungal activity with a minimum inhibitory concentration value of 128 μg mL<sup>-1</sup> compared to the standard drug fluconazole (minimum inhibitory concentration, 256 μg mL<sup>-1</sup>).

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Publication Details

Journal
ACS Omega
Published
2024-11-07
DOI
https://doi.org/10.1021/acsomega.4c05386
Citations
6
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
1.50

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article

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

Rodrigo Cristiano, SILVANA MARIA MAGALHÃES ANDRADE, José Yure Gomes dos Santos, José Lucas Ferreira Marques Galvão et al.
6 citations
ACS Omega
Multicomponent Synthesis of Heterocycles
1.50
article

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

Rodrigo Cristiano, SILVANA MARIA MAGALHÃES ANDRADE, José Yure Gomes dos Santos, José Lucas Ferreira Marques Galvão, Edeltrudes de Oliveira Lima, Girlyanderson Araújo da Silva, Rodolfo Bezerra da Silva, Rhuan Karlos Santos Mendes, Cláudio Gabriel Lima-Júnior, Emelly Suelen de Freitas Reis Santos, Fausthon Fred da Silva
article en
6 citations

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 <b>2a-2i</b> 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, <b>2a</b>, <b>2b</b>, <b>2d</b>, <b>2e</b>, and <b>2g</b> showed antifungal and antibacterial activities in 70-83% of the strains tested. The adduct <b>2e</b> exhibited significant antifungal activity with a minimum inhibitory concentration value of 128 μg mL<sup>-1</sup> compared to the standard drug fluconazole (minimum inhibitory concentration, 256 μg mL<sup>-1</sup>).

ACS OmegaVol. 9(46)
Universidade Federal da Paraíba (BR)
Conselho Nacional de Desenvolvimento Científico e Tecnológico, Fundação de Apoio à Pesquisa do Estado da Paraíba
Life in Land
Openalex Percentile: Top 19%
Multicomponent Synthesis of Heterocycles
1.50
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