Synthesis, anti-proliferative activity, theoretical and 1H NMR experimental studies of Morita-Baylis-Hillman adducts from isatin derivatives. View Full Text


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Article Info

DATE

2019-04-06

AUTHORS

Vinicius B M Brito, Gilmar F Santos, Thiago D S Silva, Júlia L C Souza, Gardenia C G Militão, Felipe T Martins, Fábio P L Silva, Boaz G Oliveira, Edigenia C C Araújo, Mário L A A Vasconcellos, Claudio G Lima-Júnior, Edilson B Alencar-Filho

ABSTRACT

Quaternary or spirocyclic 3-substituted-3-hydroxy-2-oxindole is considered a privileged scaffold. In other words, it is a molecular core present on several compounds with a wide spectrum of biological activities. Among its precursors, activated ketones (isatin nucleus) can be used as interesting starting points to Morita-Baylis-Hillman adducts derivatives, a class of compounds with good cytotoxic potential. In this paper, we present the synthesis, anti-proliferative activity against lung cancer cell line and a theoretical conformational study of 21 of Morita-Baylis-Hillman adducts from isatin derivatives, by DFT quantum chemical calculations, followed by a SAR and QSAR analysis. Besides, an efficient synthetic protocol and good biological activity profile were highlighted interesting observations about 1H NMR experimental spectra, molecular modeling results and crystallographic data available. More... »

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11030-019-09950-7

DOI

http://dx.doi.org/10.1007/s11030-019-09950-7

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1113283537

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30955150


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40 schema:description Quaternary or spirocyclic 3-substituted-3-hydroxy-2-oxindole is considered a privileged scaffold. In other words, it is a molecular core present on several compounds with a wide spectrum of biological activities. Among its precursors, activated ketones (isatin nucleus) can be used as interesting starting points to Morita-Baylis-Hillman adducts derivatives, a class of compounds with good cytotoxic potential. In this paper, we present the synthesis, anti-proliferative activity against lung cancer cell line and a theoretical conformational study of 21 of Morita-Baylis-Hillman adducts from isatin derivatives, by DFT quantum chemical calculations, followed by a SAR and QSAR analysis. Besides, an efficient synthetic protocol and good biological activity profile were highlighted interesting observations about <sup>1</sup>H NMR experimental spectra, molecular modeling results and crystallographic data available.
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