Synthesis, characterization, and antimicrobial evaluation of a small library of ferrocene-containing acetoacetates and phenyl analogs: the discovery of a potent anticandidal agent
Nema prikaza
Autori
Radulović, Niko S.Mladenovic, Marko Z.
Stojanovic-Radic, Zorica
Bogdanović, Goran A.
Stevanović, Dragana D.
Vukićević, Rastko D.
Članak u časopisu
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
A library of 16 2-substituted methyl acetoacetates containing ferrocenyl or phenyl units was designed to disclose differences in the antimicrobial activity of ferrocene-containing compounds and their phenyl analogs. Two methyl acetoacetates, whose structures do not contain an aromatic nucleus, were also included in order to probe the inherent activity of the scaffold itself. The acetoacetates were synthesized (low-to-good yields) and fully characterized by spectral (MS, IR, UV-Vis, 1D and 2D NMR) and electrochemical (cyclic voltammetry) techniques. Single-crystal X-ray analysis has been performed for methyl 2-acetyl-2-(ferrocenylmethyl)-5-methylhex-4-enoate. All compounds have demonstrated in vitro antimicrobial activity against six bacterial (three Gram-positive and three Gram-negative) and two fungal strains with minimal inhibitory concentration values of 0.0050-20.6 . The most active compound was 2-acetyl-2-(ferrocenylmethyl)-4-methylpent-4-enoate whose activity was comparable to th...at of nystatin against the yeast Candida albicans. Agglomerative hierarchical clustering statistical analysis of the antimicrobial assay data demonstrated that ferrocene-containing compounds have statistically different and greater antimicrobial activity when compared to their phenyl analogs.
Ključne reči:
Anticandidal activity / Antimicrobial screening / Methyl benzylacetoacetate / Methyl (ferrocenylmethyl) acetoacetate / X-ray crystallographyIzvor:
Molecular Diversity, 2014, 18, 3, 497-510Finansiranje / projekti:
- Kombinatorne biblioteke heterogenih katalizatora, prirodnih proizvoda, modifikovanih prirodnih proizvoda i njihovih analoga: put ka novim biološki aktivnim agensima (RS-MESTD-Basic Research (BR or ON)-172061)
DOI: 10.1007/s11030-014-9511-0
ISSN: 1381-1991; 1573-501X
PubMed: 24623385
WoS: 000338641700003
Scopus: 2-s2.0-84903818508
Kolekcije
Institucija/grupa
VinčaTY - JOUR AU - Radulović, Niko S. AU - Mladenovic, Marko Z. AU - Stojanovic-Radic, Zorica AU - Bogdanović, Goran A. AU - Stevanović, Dragana D. AU - Vukićević, Rastko D. PY - 2014 UR - https://vinar.vin.bg.ac.rs/handle/123456789/6064 AB - A library of 16 2-substituted methyl acetoacetates containing ferrocenyl or phenyl units was designed to disclose differences in the antimicrobial activity of ferrocene-containing compounds and their phenyl analogs. Two methyl acetoacetates, whose structures do not contain an aromatic nucleus, were also included in order to probe the inherent activity of the scaffold itself. The acetoacetates were synthesized (low-to-good yields) and fully characterized by spectral (MS, IR, UV-Vis, 1D and 2D NMR) and electrochemical (cyclic voltammetry) techniques. Single-crystal X-ray analysis has been performed for methyl 2-acetyl-2-(ferrocenylmethyl)-5-methylhex-4-enoate. All compounds have demonstrated in vitro antimicrobial activity against six bacterial (three Gram-positive and three Gram-negative) and two fungal strains with minimal inhibitory concentration values of 0.0050-20.6 . The most active compound was 2-acetyl-2-(ferrocenylmethyl)-4-methylpent-4-enoate whose activity was comparable to that of nystatin against the yeast Candida albicans. Agglomerative hierarchical clustering statistical analysis of the antimicrobial assay data demonstrated that ferrocene-containing compounds have statistically different and greater antimicrobial activity when compared to their phenyl analogs. T2 - Molecular Diversity T1 - Synthesis, characterization, and antimicrobial evaluation of a small library of ferrocene-containing acetoacetates and phenyl analogs: the discovery of a potent anticandidal agent VL - 18 IS - 3 SP - 497 EP - 510 DO - 10.1007/s11030-014-9511-0 ER -
@article{ author = "Radulović, Niko S. and Mladenovic, Marko Z. and Stojanovic-Radic, Zorica and Bogdanović, Goran A. and Stevanović, Dragana D. and Vukićević, Rastko D.", year = "2014", abstract = "A library of 16 2-substituted methyl acetoacetates containing ferrocenyl or phenyl units was designed to disclose differences in the antimicrobial activity of ferrocene-containing compounds and their phenyl analogs. Two methyl acetoacetates, whose structures do not contain an aromatic nucleus, were also included in order to probe the inherent activity of the scaffold itself. The acetoacetates were synthesized (low-to-good yields) and fully characterized by spectral (MS, IR, UV-Vis, 1D and 2D NMR) and electrochemical (cyclic voltammetry) techniques. Single-crystal X-ray analysis has been performed for methyl 2-acetyl-2-(ferrocenylmethyl)-5-methylhex-4-enoate. All compounds have demonstrated in vitro antimicrobial activity against six bacterial (three Gram-positive and three Gram-negative) and two fungal strains with minimal inhibitory concentration values of 0.0050-20.6 . The most active compound was 2-acetyl-2-(ferrocenylmethyl)-4-methylpent-4-enoate whose activity was comparable to that of nystatin against the yeast Candida albicans. Agglomerative hierarchical clustering statistical analysis of the antimicrobial assay data demonstrated that ferrocene-containing compounds have statistically different and greater antimicrobial activity when compared to their phenyl analogs.", journal = "Molecular Diversity", title = "Synthesis, characterization, and antimicrobial evaluation of a small library of ferrocene-containing acetoacetates and phenyl analogs: the discovery of a potent anticandidal agent", volume = "18", number = "3", pages = "497-510", doi = "10.1007/s11030-014-9511-0" }
Radulović, N. S., Mladenovic, M. Z., Stojanovic-Radic, Z., Bogdanović, G. A., Stevanović, D. D.,& Vukićević, R. D.. (2014). Synthesis, characterization, and antimicrobial evaluation of a small library of ferrocene-containing acetoacetates and phenyl analogs: the discovery of a potent anticandidal agent. in Molecular Diversity, 18(3), 497-510. https://doi.org/10.1007/s11030-014-9511-0
Radulović NS, Mladenovic MZ, Stojanovic-Radic Z, Bogdanović GA, Stevanović DD, Vukićević RD. Synthesis, characterization, and antimicrobial evaluation of a small library of ferrocene-containing acetoacetates and phenyl analogs: the discovery of a potent anticandidal agent. in Molecular Diversity. 2014;18(3):497-510. doi:10.1007/s11030-014-9511-0 .
Radulović, Niko S., Mladenovic, Marko Z., Stojanovic-Radic, Zorica, Bogdanović, Goran A., Stevanović, Dragana D., Vukićević, Rastko D., "Synthesis, characterization, and antimicrobial evaluation of a small library of ferrocene-containing acetoacetates and phenyl analogs: the discovery of a potent anticandidal agent" in Molecular Diversity, 18, no. 3 (2014):497-510, https://doi.org/10.1007/s11030-014-9511-0 . .