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>).
Authors
- Rodrigo Cristiano (ORCID: https://orcid.org/0000-0002-5044-377X)
- SILVANA MARIA MAGALHÃES ANDRADE (ORCID: https://orcid.org/0009-0004-7568-0677)
- José Yure Gomes dos Santos (ORCID: https://orcid.org/0000-0001-9840-8132)
- José Lucas Ferreira Marques Galvão (ORCID: https://orcid.org/0009-0000-1640-688X)
- Edeltrudes de Oliveira Lima (ORCID: https://orcid.org/0000-0002-9547-0886)
- Girlyanderson Araújo da Silva
- Rodolfo Bezerra da Silva
- Rhuan Karlos Santos Mendes
- Cláudio Gabriel Lima-Júnior (ORCID: https://orcid.org/0000-0001-6570-8999)
- Emelly Suelen de Freitas Reis Santos
- Fausthon Fred da Silva (ORCID: https://orcid.org/0000-0002-6095-512X)
Institutions
- Universidade Federal da Paraíba (BR)
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
Funders
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação de Apoio à Pesquisa do Estado da Paraíba