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1.
Molecules ; 25(22)2020 Nov 11.
Artigo em Inglês | MEDLINE | ID: mdl-33187075

RESUMO

A novel strategy via the triple process (multicomponent reactions (MCR)-domino)/tandem was developed for the synthesis of restricted and constrained bis-1,2,3-triazole-linked pyrrolo[3,4-b]pyridine peptidomimetics dimers in overall yields of 20-55%. This strategy allows the construction of six heterocycles in two stages of the reaction.


Assuntos
Química Click/métodos , Reação de Cicloadição/métodos , Dimerização , Peptidomiméticos/síntese química , Cromatografia em Camada Fina , Cianetos/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Piridinas , Espectrometria de Massas por Ionização por Electrospray , Especificidade por Substrato , Triazóis
2.
Front Chem ; 7: 546, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31448260

RESUMO

6-Triazolylmethyl-pyrrolo[3,4-b]pyridin-5-one tris-heterocycles were synthesized in 43-57% overall yields. The two-stage synthesis involved a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) followed by a copper-assisted alkyne-azide [3+2] cycloaddition (CuAAC). This efficient and convergent strategy proceeded via complex terminal alkynes functionalized with a fused bis-heterocycle at the α-position. The final products are ideal candidates for SAR studies as they possess two privileged scaffolds in medicinal chemistry: 4-substituted or 1,4-substituted 1H-1,2,3-triazoles and pyrrolo[3,4-b]pyridin-5-ones.

3.
Org Biomol Chem ; 15(11): 2363-2369, 2017 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-28066847

RESUMO

A rapid and efficient synthesis of a series of (±)-nuevamine, (±)-lennoxamine and magallanesine aza analogues is described. The synthetic strategy involves Ugi-3CR and two further condensation processes, aza-Diels-Alder cycloaddition and the Pomeranz-Fritsch reaction. The variation of the chain-size in aldehyde moieties provided structural diversity in only two operational reaction steps.


Assuntos
Dioxanos/síntese química , Alcaloides Indólicos/síntese química , Dioxanos/química , Alcaloides Indólicos/química , Estrutura Molecular , Estereoisomerismo
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