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

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 sta...

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Published in:Molecular diversity 2020-02, Vol.24 (1), p.265-281
Main Authors: Brito, Vinicius B. M., Santos, Gilmar F., Silva, Thiago D. S., Souza, Júlia L. C., Militão, Gardenia C. G., Martins, Felipe T., Silva, Fábio P. L., Oliveira, Boaz G., Araújo, Edigenia C. C., Vasconcellos, Mário L. A. A., Lima-Júnior, Claudio G., Alencar-Filho, Edilson B.
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Ketones
Life Sciences
Lung cancer
Organic Chemistry
Original Article
Pharmacy
Polymer Sciences
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Summary: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 1 H NMR experimental spectra, molecular modeling results and crystallographic data available. Graphical abstract
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-019-09950-7