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dc.contributor.author
Ramírez, Juan
dc.contributor.author
Svetaz, Laura Andrea
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dc.contributor.author
Quiroga, Jairo
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Abonia, Rodrigo
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Raimondi, Marcela
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Zacchino, Susana
dc.contributor.author
Insuasty, Braulio
dc.date.available
2017-02-24T14:24:00Z
dc.date.issued
2015-03
dc.identifier.citation
Ramírez, Juan; Svetaz, Laura Andrea; Quiroga, Jairo; Abonia, Rodrigo; Raimondi, Marcela; et al.; Synthesis of novel thiazole-based 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as potential antitumor and antifungal agents; Elsevier Masson; European Journal Of Medical Chemistry; 92; 3-2015; 866–875
dc.identifier.issn
0223-5234
dc.identifier.uri
http://hdl.handle.net/11336/13358
dc.description.abstract
A new series of novel thiazole-based 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines 6a–g and 7a–g were obtained with high regioselectivity from the reaction of triamino- or tetraaminopyrimidines 4 and 5 with α,β-unsaturated carbonyl compounds 3a–g based on 2,4-dichlorothiazol-5-carbaldehyde 1. Twelve of the synthesized compounds were selected and tested by US National Cancer Institute (NCI) for their antitumor activity against 60 different human tumor cell lines. Compounds 7d and 7g showed important GI50 ranges of 1.28–2.98 μM and 0.35–2.78 μM respectively under in vitro assays. In addition, 6a–g and 7a–g were tested for antifungal properties against the clinical important fungi Candida albicans and Cryptococcus neoformans. Although these compounds showed moderate activities against C. albicans, the 2-amino derivatives 7a–g and mainly 7a and 7b, showed high activity against standardized and clinical isolates of C. neoformans with MIC50 = 7.8–31.2 μg/mL, MIC80 = 15.6–31.2 μg/mL and MIC100 = 15.6–62.5 μg/mL. In addition, since both compounds were fungicide rather than fungistatic these thiazole-based 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines appear as good candidates for further development not only as antifungal but also as antitumor drugs.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Masson
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Thiazole
dc.subject
Regioselectivity
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Pyrimido[4,5-B][1,4]Diazepines
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Antitumor Activity
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Antifungal Activity
dc.subject.classification
Química Orgánica
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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
Synthesis of novel thiazole-based 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as potential antitumor and antifungal agents
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2017-02-23T13:56:21Z
dc.journal.volume
92
dc.journal.pagination
866–875
dc.journal.pais
Francia
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dc.journal.ciudad
Paris
dc.description.fil
Fil: Ramírez, Juan. Universidad del Valle. Departamento de Química; Colombia
dc.description.fil
Fil: Svetaz, Laura Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Cientifico Tecnológico Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Area Farmacognosia; Argentina
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Fil: Quiroga, Jairo. Universidad del Valle. Departamento de Química; Colombia
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Fil: Abonia, Rodrigo. Universidad del Valle. Departamento de Química; Colombia
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Fil: Raimondi, Marcela. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Area Farmacognosia; Argentina
dc.description.fil
Fil: Zacchino, Susana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Area Farmacognosia; Argentina
dc.description.fil
Fil: Insuasty, Braulio. Universidad del Valle. Departamento de Química; Colombia
dc.journal.title
European Journal Of Medical Chemistry
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.ejmech.2015.01.053
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0223523415000732
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