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

被引：17

作者：

Brito, Vinicius B. M. ^{[1
]}

Santos, Gilmar F. ^{[2
]}

Silva, Thiago D. S. ^{[3
]}

Souza, Julia L. C. ^{[3
]}

Militao, Gardenia C. G. ^{[3
]}

Martins, Felipe T. ^{[5
]}

Silva, Fabio P. L. ^{[2
]}

Oliveira, Boaz G. ^{[4
]}

Araujo, Edigenia C. C. ^{[1
]}

Vasconcellos, Mario L. A. A. ^{[2
]}

Lima-Junior, Claudio G. ^{[2
]}

Alencar-Filho, Edilson B. ^{[1
]}

机构：

[1] Fed Univ San Francisco Valley UNIVASF, Postgrad Program Hlth & Biol Sci, Collegiate Pharmaceut Sci, Postgrad Program Biosci Ex Nat Resources Semiarid, Petrolina, PE, Brazil

[2] Fed Univ Paraiba UFPB, Dept Chem, LASOM PB, Joao Pessoa, Paraiba, Brazil

[3] Fed Univ Pernambuco UFPE, Dept Physiol & Pharmacol, Recife, PE, Brazil

[4] Fed Univ West Bahia UFOB, LQTAIM, Postgrad Program Pure & Appl Chem, Barreiras, BA, Brazil

[5] Fed Univ Goias UFG, Inst Chem, Goiania, Go, Brazil

来源：

MOLECULAR DIVERSITY | 2020年 / 24卷 / 01期

关键词：

Synthesis of Morita-Baylis-Hillman adducts from isatin derivatives; Anti-proliferative activity; H-1 NMR spectroscopy; DFT calculations and QSAR modeling; X-Ray crystallography; QSAR; ANTICANCER; QSPR;

D O I：

10.1007/s11030-019-09950-7

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 H-1 NMR experimental spectra, molecular modeling results and crystallographic data available. [GRAPHICS] .

引用

页码：265 / 281

页数：17

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