Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation.
Org Biomol Chem
; 11(34): 5621-33, 2013 Sep 14.
Article
em En
| MEDLINE
| ID: mdl-23863885
ABSTRACT
Diverse reactivity by coupling of substituted anilines with ethyl trifluoropyruvate was developed under microwave irradiation without catalysts to generate 3-trifluoromethyl-3-hydroxy oxindoles, aromatic hydroxy trifluoromethyl esters, and 1,2-dicarbonyl compounds in a fast and efficient manner. The plausible mechanism for obtaining different products was proposed. Furthermore, the anti-HIV activity of aromatic hydroxy trifluoromethyl esters was first reported. The best inhibitory activity against wild-type HIV-1 IIIB was exemplified by trifluoromethyloxindole 3q with an IC50 = 5.8 µM, which also displayed potential activity against Y181C mutant virus with an IC50 = 7.5 µM. More significantly, the activities of oxindoles 3q and 3r to inhibit K103N/Y181C double mutant HIV-1 reverse transcriptase (RT) are probably similar to that of the second-generation nonnucleoside inhibitor HBY 097 by docking calculation.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
HIV-1
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Inibidores da Transcriptase Reversa
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Ácido Pirúvico
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Fármacos Anti-HIV
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Transcriptase Reversa do HIV
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Compostos de Anilina
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Micro-Ondas
Idioma:
En
Revista:
Org Biomol Chem
Ano de publicação:
2013
Tipo de documento:
Article