Solvent-free microwave-assisted synthesis of novel pyrazolo[40 ,30 :5,6]pyrido[2,3-d]pyrimidines with potential antifungal activity
Novel fused pyrazolo[40 ,30 :5,6]pyrido[2,3-d]pyrimidines 5 were prepared by a solvent-free microwave assisted reaction of heterocyclic o-aminonitriles 3 and cyanopyridines 4 in the presence of tBuOK as catalyst. This protocol provides a versatile procedure for the synthesis of the title compou...
| Autores principales: | , , , , , , |
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| Formato: | article artículo publishedVersion |
| Lenguaje: | Inglés |
| Publicado: |
Elsevier
2020
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| Materias: | |
| Acceso en línea: | http://hdl.handle.net/2133/19493 http://hdl.handle.net/2133/19493 |
| Aporte de: |
| id |
I15-R121-2133-19493 |
|---|---|
| record_format |
dspace |
| institution |
Universidad Nacional de Rosario |
| institution_str |
I-15 |
| repository_str |
R-121 |
| collection |
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) |
| language |
Inglés |
| orig_language_str_mv |
eng |
| topic |
Pyrazolo-Pyrido-Pyrimidine o-Aminonitriles Cyanopyridines Microwave Irradiation Antifungal Activity |
| spellingShingle |
Pyrazolo-Pyrido-Pyrimidine o-Aminonitriles Cyanopyridines Microwave Irradiation Antifungal Activity Acosta, Paola Insuasty, Braulio Ortiz, Alejandro Abonia, Rodrigo Sortino, Maximiliano Zacchino, Susana Quiroga, Jairo Solvent-free microwave-assisted synthesis of novel pyrazolo[40 ,30 :5,6]pyrido[2,3-d]pyrimidines with potential antifungal activity |
| topic_facet |
Pyrazolo-Pyrido-Pyrimidine o-Aminonitriles Cyanopyridines Microwave Irradiation Antifungal Activity |
| description |
Novel fused pyrazolo[40
,30
:5,6]pyrido[2,3-d]pyrimidines 5 were prepared by a solvent-free
microwave assisted reaction of heterocyclic o-aminonitriles 3 and cyanopyridines 4 in the presence
of tBuOK as catalyst. This protocol provides a versatile procedure for the synthesis of the title
compounds with the advantages of easy work-up, mild reaction conditions and good yields. All
compounds were also tested for antifungal properties against two clinically important fungi;
Candida albicans and Cryptococcus neoformans. Several compounds showed moderate activity
against both fungi, being 5a the most active compound. Analysis of the antifungal behavior of
properly grouped compounds allowed to determine that the position of the N in the pyrimidyl
moiety per se does not play a role in the activity. In turn, the type of 4-R substituent appears to
influence the activity. In addition to the above considerations, the lipophilicity of compounds measured as logP showed to be not related to the activity and regarding the dipole moment (D), no net
correlation was observed, although it is the most active compounds (% inhibition >50%) that have
a D P 7.5, mainly against C. albicans. |
| format |
article artículo publishedVersion |
| author |
Acosta, Paola Insuasty, Braulio Ortiz, Alejandro Abonia, Rodrigo Sortino, Maximiliano Zacchino, Susana Quiroga, Jairo |
| author_facet |
Acosta, Paola Insuasty, Braulio Ortiz, Alejandro Abonia, Rodrigo Sortino, Maximiliano Zacchino, Susana Quiroga, Jairo |
| author_sort |
Acosta, Paola |
| title |
Solvent-free microwave-assisted synthesis of novel pyrazolo[40 ,30 :5,6]pyrido[2,3-d]pyrimidines with potential antifungal activity |
| title_short |
Solvent-free microwave-assisted synthesis of novel pyrazolo[40 ,30 :5,6]pyrido[2,3-d]pyrimidines with potential antifungal activity |
| title_full |
Solvent-free microwave-assisted synthesis of novel pyrazolo[40 ,30 :5,6]pyrido[2,3-d]pyrimidines with potential antifungal activity |
| title_fullStr |
Solvent-free microwave-assisted synthesis of novel pyrazolo[40 ,30 :5,6]pyrido[2,3-d]pyrimidines with potential antifungal activity |
| title_full_unstemmed |
Solvent-free microwave-assisted synthesis of novel pyrazolo[40 ,30 :5,6]pyrido[2,3-d]pyrimidines with potential antifungal activity |
| title_sort |
solvent-free microwave-assisted synthesis of novel pyrazolo[40 ,30 :5,6]pyrido[2,3-d]pyrimidines with potential antifungal activity |
| publisher |
Elsevier |
| publishDate |
2020 |
| url |
http://hdl.handle.net/2133/19493 http://hdl.handle.net/2133/19493 |
| work_keys_str_mv |
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