Synthesis, structural determination, and antibacterial studies of Silver(I) and Gold(I) benzimidazolylidene complexes with N-tert-butylacetyl fragments
Por:
Carpio-Granillo, M, Sánchez-Cabrer, G, Zuno-Cruz, FJ, Coronel-Olivares, C, Andrade-López, N, Martínez-Otero, D, Triana-Cruz, L, Rosales-Hoz, MJ
Publicada:
5 mar 2025
Ahead of Print:
1 dic 2024
Resumen:
A standard and reliable methodology was used to synthesize the chloride benzimidazolium symmetric salt 1,3-bis (2-tert-butoxy-2-oxoethyl)-1H-benzimidazol-3-ium chloride, [(AcO-t-Bu)2BzIm]Cl (1) by employing 1H-benzimidazole and tert-butyl 2-chloroacetate as starting materials. Following the silver oxide route, the compound [{Ag(mu-Cl)(NHC)}2] (2) {NHC = (AcO-t-Bu)2BzIm} was obtained as a dimer, and through transmetalation reactions from [AuCl(SMe2)], two benzimidazolylidene N-heterocyclic carbene gold complexes were obtained using different stoichiometric ratios. Complex [AuCl(NHC)] (3) is a monocarbene species, while [Au(NHC)2] [AgCl2] (4) is a biscarbene gold complex having a dichloroargentate anion. All complex structures have been elucidated through multinuclear NMR, FT-IR spectroscopy, HRMS, and single-crystal X-ray crystallography. The antibacterial capacity of the synthesized metallic compounds was evaluated in vitro versus Gram-positives, S. aureus, B. subtilis, and E. faecalis, and Gram-negatives, P. aeruginosa, E. coli, and S. typhi bacteria by Kirby-Bauer and MIC methods. The Kirby-Bauer experiments revealed that all compounds exhibited good antibacterial activity versus all bacterial strains. Silver compound 2 showed higher results against E. faecalis, P. aeruginosa, and S. typhi than the antibiotic. Gold complex 3 showed the highest antibacterial activity versus S. aureus and intermediate activity versus E. faecalis and S. typhi, and compound 4 showed only its best inhibition effect against E. faecalis and S. typhi and a slight upgrade against P. aeruginosa, revealing that no significant differences are having the two kinds of metal atoms. The preliminary results of MIC values for the bacteria tested were 8-13 mu g/ ml for 2 and 9-16 mu g/ml for 3.
Filiaciones:
Carpio-Granillo, M:
Univ Autonoma Estado Hidalgo, Area Academ Quim, Ciudad Unive Carr Pachuca Tulancingo Tulancingo km, Hidalgo 42184, Mexico
Sánchez-Cabrer, G:
Univ Autonoma Estado Hidalgo, Area Academ Quim, Ciudad Unive Carr Pachuca Tulancingo Tulancingo km, Hidalgo 42184, Mexico
Zuno-Cruz, FJ:
Univ Autonoma Estado Hidalgo, Area Academ Quim, Ciudad Unive Carr Pachuca Tulancingo Tulancingo km, Hidalgo 42184, Mexico
Coronel-Olivares, C:
Univ Autonoma Estado Hidalgo, Area Academ Quim, Ciudad Unive Carr Pachuca Tulancingo Tulancingo km, Hidalgo 42184, Mexico
Andrade-López, N:
Univ Autonoma Estado Hidalgo, Area Academ Quim, Ciudad Unive Carr Pachuca Tulancingo Tulancingo km, Hidalgo 42184, Mexico
Martínez-Otero, D:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
UNAM, Ctr Conjunto Invest Quim Sustentable UAEM, Car Toluca Atlacomulco Km 14-5, Toluca 50200, Estado De Mexic, Mexico
Triana-Cruz, L:
Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
UNAM, Ctr Conjunto Invest Quim Sustentable UAEM, Car Toluca Atlacomulco Km 14-5, Toluca 50200, Estado De Mexic, Mexico
Rosales-Hoz, MJ:
Ctr Invest & Estudios Avanzados IPN, Dept Quim, Apdo Postal 14-740, Ciudad De Mexico 07000, Mexico
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