NMR of the Enaminones

作者: Patrice L. Jackson-Ayotunde , Ivan O. Edafiogho , Mariano S. Alexander , Kenneth R. Scott

DOI: 10.1016/B978-1-68108-063-5.50005-9

关键词:

摘要: Abstract: Nuclear Magnetic Resonance (NMR) spectroscopy has advanced as an important tool in support of several studies pharmacological interest. In this chapter, the following sections are discussed: history NMR spectroscopy, enaminone derivatives and their NMR, use molecular modeling techniques adjunct to analysis, a newer class compounds, sulfonamide enaminones intermolecular forces determined via X-ray crystallography. The details field its origin, utilization area structure identification. section on gives detailed look into analyzing various analogs, including our library anticonvulsant enaminones. Examples include work Zhou noting correlation between 17O (which natural abundance) chemical shifts carbonyl atom 1H shifts. Our analogs was complemented by with examples how reactions were analyses. aspects explains Gaussian 03 performs suitable functions determining final reason why some compounds series more potent than others. illustrates sulfonamido now being researched potential agents profile (having 6 Hz ‘psychomotor’ activity) differs from previously investigated derivatives.

参考文章(67)
Rieko Ishima, Dennis A. Torchia, Protein dynamics from NMR Nature Structural & Molecular Biology. ,vol. 7, pp. 740- 743 ,(2000) , 10.1038/78963
Marcel J. J. Blommers, Andre Strauss, Martin Geiser, Paul Ramage, Helmut Sparrer, Wolfgang Jahnke, NMR-Based Strategies to Elucidate Bioactive Conformations of Weakly Binding Ligands. Topics in Current Chemistry. ,vol. 273, pp. 1- 14 ,(2008) , 10.1007/128_2007_16
Giampaolo Barone, Dario Duca, Arturo Silvestri, Luigi Gomez-Paloma, Raffaele Riccio, Giuseppe Bifulco, Determination of the relative stereochemistry of flexible organic compounds by Ab initio methods: conformational analysis and Boltzmann-averaged GIAO 13C NMR chemical shifts. Chemistry: A European Journal. ,vol. 8, pp. 3240- 3245 ,(2002) , 10.1002/1521-3765(20020715)8:14<3240::AID-CHEM3240>3.0.CO;2-G
Giampaolo Barone, Luigi Gomez-Paloma, Dario Duca, Arturo Silvestri, Raffaele Riccio, Giuseppe Bifulco, Structure validation of natural products by quantum-mechanical GIAO calculations of 13C NMR chemical shifts. Chemistry: A European Journal. ,vol. 8, pp. 3233- 3239 ,(2002) , 10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO;2-0
Andria L. Skinner, Jennifer S. Laurence, High-Field Solution NMR Spectroscopy as a Tool for Assessing Protein Interactions with Small Molecule Ligands Journal of Pharmaceutical Sciences. ,vol. 97, pp. 4670- 4695 ,(2008) , 10.1002/JPS.21378
James E. Foster, Jesse M. Nicholson, Raymond Butcher, James P. Stables, Ivan O. Edafiogho, Angela M. Goodwin, Michael C. Henson, Carlynn A. Smith, K.R. Scott, Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants. Bioorganic & Medicinal Chemistry. ,vol. 7, pp. 2415- 2425 ,(1999) , 10.1016/S0968-0896(99)00185-6
John V. Greenhill, Hossein Loghmani-Khouzani, Derek J. Maitland, Tautomerism in ketomethyl quinolines. Part 3. 4-~etometh~lquinolines~ Canadian Journal of Chemistry. ,vol. 69, pp. 696- 701 ,(1991) , 10.1139/V91-104