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Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids
Author(s) -
AzevedoBarbosa Helloana,
Vale Bianca Pereira,
Guidolin Rossi Grazielle,
Santos Siqueira Fallon,
Bordig Guterres Kevim,
Campos Marli Matiko Anraku,
Santos Thiago,
Anthony Hawkes Jamie,
Ferreira Dias Danielle,
Neiva Lavorato Stefânia,
Souza Thiago Belarmino,
Teixeira Carvalho Diogo
Publication year - 2021
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202100066
Subject(s) - dhps , chemistry , sulfonamide , antimicrobial , eugenol , combinatorial chemistry , docking (animal) , substituent , stereochemistry , organic chemistry , biology , medicine , plasmodium falciparum , nursing , malaria , immunology
Using molecular hybridization, specific sulfonamide derivatives of eugenol were synthesized with subtle modifications in the allylic chain of the eugenol subunit (and also in the nature of the substituent group in the sulfonamide aromatic ring) which allowed us to study the influence of structural changes on the antimicrobial potential of the hybrids. Antimicrobial test results showed that most of the synthesized hybrid compounds showed good activity with better results than the parent compounds. Molecular docking studies of the hybrids with the essential bacterial enzyme DHPS showed complexes with low binding energies, suggesting that DHPS could be a possible target for the antibacterial sulfonamide‐eugenol hybrids. Furthermore, most of the final compounds presented similar docking poses to that of the crystallographic ligand sulfamethoxazole. The results obtained allow us to conclude that these are promising compounds for use as new leads in the search for new antibacterial sulfonamides.