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dc.contributor.author
Elejalde Cadena, Nerith Rocio
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dc.contributor.author
Butassi, Estefanía
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dc.contributor.author
Zacchino, Susana
dc.contributor.author
Macías, Mario A.
dc.contributor.author
Portilla, Jaime
dc.date.available
2021-12-02T16:03:10Z
dc.date.issued
2019-11
dc.identifier.citation
Elejalde Cadena, Nerith Rocio; Butassi, Estefanía; Zacchino, Susana; Macías, Mario A.; Portilla, Jaime; Intermolecular interaction energies and molecular conformations in N -substituted 4-aryl-2-methylimidazoles with promising in vitro antifungal activity; International Union of Crystallography; Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials; 75; 6; 11-2019; 1197-1207
dc.identifier.uri
http://hdl.handle.net/11336/147973
dc.description.abstract
A convenient one-pot synthesis of 4-aryl-2-methyl-N-phenacylimidazoles (4) through a microwave-assisted pseudo-tricomponent reaction of -bromoacetophenones (1) with acetamidine hydrochloride (2) is reported. Ketones (4) were successfully used as substrates for the preparation of the respective N-(2- hydroxyethyl)imidazoles (5) with yields up to 87%. The synthesized compounds were characterized by NMR and high-resolution mass spectrometry analyses, and several structures were confirmed and studied by single-crystal X-ray diffraction. The analysis of the whole-of-molecule interactions shows that, despite the difference in the atom–atom contacts forming the crystals, dispersion energies make the largest contribution to the formation of the solids, giving an isotropic tendency in the topology of the energy framework diagrams for pairs of molecules. In addition, the in vitro antifungal activity of both families of compounds [ketones (4) and alcohols (5)] against Candida albicans and Cryptococcus neoformans was evaluated, where the 2,4-dichlorophenylsubstituted alcohol (5f), an isomer of the drug miconazole, showed the highest activity (IC50 = 7.8 mg ml1 against C. neoformans).
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
International Union of Crystallography
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
4-ARYL-2-METHYL-N-PHENACYLIMIDAZOLES
dc.subject
X-RAY DIFFRACTION
dc.subject
CRYSTALLOGRAPHIC STUDIES
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ANTIFUNGAL ACTIVITY
dc.subject.classification
Otras Ciencias Químicas
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Intermolecular interaction energies and molecular conformations in N -substituted 4-aryl-2-methylimidazoles with promising in vitro antifungal activity
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-11-25T17:28:52Z
dc.identifier.eissn
2052-5206
dc.journal.volume
75
dc.journal.number
6
dc.journal.pagination
1197-1207
dc.journal.pais
Dinamarca
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dc.description.fil
Fil: Elejalde Cadena, Nerith Rocio. Universidad de los Andes; Colombia
dc.description.fil
Fil: Butassi, Estefanía. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.description.fil
Fil: Zacchino, Susana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
dc.description.fil
Fil: Macías, Mario A.. Universidad de los Andes; Colombia
dc.description.fil
Fil: Portilla, Jaime. Universidad de los Andes; Colombia
dc.journal.title
Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S2052520619013271
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1107/S2052520619013271
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