Synthesis, FT-IR, 1H, 13C NMR, ESI MS and PM5 studies of a new Mannich base of polyether antibiotic – Lasalocid acid and its complexes with Li+, Na+ and K+ cations

作者: Adam Huczyński , Jacek Rutkowski , Bogumil Brzezinski , Franz Bartl

DOI: 10.1016/J.SAA.2012.11.106

关键词: Carbon-13 NMROrganic chemistryDecarboxylationMannich baseMedicinal chemistryDerivative (chemistry)LasalocidMorpholineChemistryHydrogen bondFormaldehyde

摘要: Abstract The polyether antibiotic Lasalocid acid has been converted to its Mannich base derivative by a chemoselective one-pot reaction with formaldehyde and morpholine through the decarboxylation process. Spectroscopic studies of structure this new have shown that in ortho -phenol O H⋯N intarmolecular hydrogen bond is present. compound forms complexes Li + , Na K cations exclusively 1:1 stoichiometry. structures these studied visualized semi-empirical calculation based on results spectrometric spectroscopic investigation. It demonstrated contrast novel type preferential cation.

参考文章(27)
Norman Holy, Richard Fowler, Ellen Burnett, Robert Lorenz, The mannich reaction-II : Derivatization of aldehydes and ketones using dimethyl(methylene)ammonium salts Tetrahedron. ,vol. 35, pp. 613- 619 ,(1979) , 10.1016/0040-4020(79)87005-2
Adam Huczyński, Małgorzata Ratajczak-Sitarz, Andrzej Katrusiak, Bogumil Brzezinski, X-ray, spectroscopic and semiempirical investigation of the structure of lasalocid 6-bromohexyl ester and its complexes with alkali metal cations Journal of Molecular Structure. ,vol. 998, pp. 206- 215 ,(2011) , 10.1016/J.MOLSTRUC.2011.05.034
Jeffrey J. Hale, Sander G. Mills, Malcolm MacCoss, Conrad P. Dorn, Paul E. Finke, Richard J. Budhu, Robert A. Reamer, Su-Er W. Huskey, Debra Luffer-Atlas, Brian J. Dean, Erin M. McGowan, William P. Feeney, Shuet-Hing Lee Chiu, Margaret A. Cascieri, Gary G. Chicchi, Marc M. Kurtz, Sharon Sadowski, Elzbieta Ber, F. David Tattersall, Nadia M. J. Rupniak, Angela R. Williams, Wayne Rycroft, Richard Hargreaves, Joseph M. Metzger, D. Euan MacIntyre, Phosphorylated morpholine acetal human neurokinin-1 receptor antagonists as water-soluble prodrugs. Journal of Medicinal Chemistry. ,vol. 43, pp. 1234- 1241 ,(2000) , 10.1021/JM990617V
A Koll, S.M Melikova, A Karpfen, P Wolschann, Spectroscopic and structural consequences of intramolecular hydrogen bond formation in ortho-dimethylaminomethylphenol Journal of Molecular Structure. ,vol. 559, pp. 127- 145 ,(2001) , 10.1016/S0022-2860(00)00682-7
Adam Huczyński, Jacek Rutkowski, Joanna Wietrzyk, Joanna Stefańska, Ewa Maj, Małgorzata Ratajczak-Sitarz, Andrzej Katrusiak, Bogumil Brzezinski, Franz Bartl, X-ray crystallographic, FT-IR and NMR studies as well as anticancer and antibacterial activity of the salt formed between ionophore antibiotic Lasalocid acid and amines Journal of Molecular Structure. ,vol. 1032, pp. 69- 77 ,(2013) , 10.1016/J.MOLSTRUC.2012.07.036
Radosław Pankiewicz, Dorota Remlein-Starosta, Grzegorz Schroeder, Bogumił Brzezinski, Biological activity and ESI MS study of oxaalkyl and hydroksyoxaalkyl lasalocid esters Journal of Molecular Structure. ,vol. 783, pp. 136- 144 ,(2006) , 10.1016/J.MOLSTRUC.2005.08.026
Amal Ting, Scott E. Schaus, Organocatalytic Asymmetric Mannich Reactions: New Methodology, Catalyst Design, and Synthetic Applications European Journal of Organic Chemistry. ,vol. 2007, pp. 5797- 5815 ,(2007) , 10.1002/EJOC.200700409
Changfu Cheng, Michael L. Gross, Applications and mechanisms of charge-remote fragmentation Mass Spectrometry Reviews. ,vol. 19, pp. 398- 420 ,(2000) , 10.1002/1098-2787(2000)19:6<398::AID-MAS3>3.0.CO;2-B