Antifungal activity of alkyl and heterocyclic aza-derivatives of gossypol as well as their complexes with NaClO4 against Fusarium oxysporum f. sp. lupini
作者： Piotr Przybylski , Krystian Pyta , Dorota Remlein-Starosta , Grzegorz Schroeder , Bogumil Brzezinski
DOI: 10.1016/J.BMCL.2009.02.051
关键词: Chemical synthesis 、 Hydrazone 、 Alkyl 、 Schiff base 、 Gossypol 、 Chemistry 、 Gossypium herbaceum 、 Fusarium oxysporum 、 Stereochemistry 、 Biological activity 、 Organic chemistry 、 Clinical biochemistry 、 Molecular medicine 、 Biochemistry 、 Molecular biology 、 Drug discovery 、 Pharmaceutical Science
摘要: Eight alkyl and six heterocyclic aza-derivatives of gossypol (2-15) have been synthesized using (1) extracted from Gossypium Herbaceum cottonseeds. The ability to form complexes with NaClO(4) has investigated by electrospray ionisation (ESI) mass spectra recorded in the positive negative ion detection modes. characterized FT-IR, (1)H (13)C NMR spectroscopic methods subsequently tested for their antifungal properties against Fusarium oxysporum. Four (2-5), present enamine-enamine tautomeric form, shown activity comparable or higher than that this fungus. To improve most active compounds 2-5 were prepared. Complexes 2 5 uncomplexed compounds.
cabdirect.org
elsevier.com
sci-hub.se 参考文章(36)
E. Turco, C. Vizzuso, S. Franceschini, A. Ragazzi, F.M. Stefanini, The in vitro effect of gossypol and its interaction with salts on conidial germination and viability of Fusarium oxysporum sp. vasinfectum isolates Journal of Applied Microbiology. ,vol. 103, pp. 2370- 2381 ,(2007) , 10.1111/J.1365-2672.2007.03503.X
P E Nelson, M C Dignani, E J Anaissie, Taxonomy, biology, and clinical aspects of Fusarium species. Clinical Microbiology Reviews. ,vol. 7, pp. 479- 504 ,(1994) , 10.1128/CMR.7.4.479
I. I. Tukfatullina, K. Z. Tilyabaev, A. Mamadrakhimov, B. A. Salakhutdinov, F. G. Kamaev, A. M. Yuldashev, M. K. Dowd, S. A. Talipov, B. T. Ibragimov, T. F. Aripov, Membrane-active properties and antiradical activity of gossypol and its derivatives Chemistry of Natural Compounds. ,vol. 44, pp. 440- 445 ,(2008) , 10.1007/S10600-008-9087-Y
Piotr Przybylski, Krystian Pyta, Małgorzata Ratajczak-Sitarz, Andrzej Katrusiak, Bogumił Brzezinski, X-ray, FT-IR, ESI MS and PM5 studies of Schiff base of gossypol with allylamine and its complexes with alkali metal cations and perchlorate anion Structural Chemistry. ,vol. 19, pp. 983- 995 ,(2008) , 10.1007/S11224-008-9385-9
Xi Wang, Thomas H. Beckham, James C. Morris, Feng Chen, J. David Gangemi, Bioactivities of gossypol, 6-methoxygossypol, and 6,6'-dimethoxygossypol. Journal of Agricultural and Food Chemistry. ,vol. 56, pp. 4393- 4398 ,(2008) , 10.1021/JF073297U
Piotr Przybylski, Grzegorz Bejcar, Adam Huczyński, Grzegorz Schroeder, Bogumił Brzezinski, Franz Bartl, 1H- and 13C-NMR, FTIR, UV-VIS, ESI-MS, and PM5 studies as well as emission properties of a new Schiff base of gossypol with 5-methoxytryptamine and a new hydrazone of gossypol with dansylhydrazine. Biopolymers. ,vol. 82, pp. 521- 535 ,(2006) , 10.1002/BIP.20505
Quang Ton That, Kim Phi Phung Nguyen, Poul Erik Hansen, Schiff bases of gossypol: an NMR and DFT study Magnetic Resonance in Chemistry. ,vol. 43, pp. 302- 308 ,(2005) , 10.1002/MRC.1532
Priti Ojha, Janak Dulari Dhar, Anil Kumar Dwivedi, Ram Lakhan Singh, Gopal Gupta, Effect of antispermatogenic agents on cell marker enzymes of rat Sertoli cells in vitro Contraception. ,vol. 73, pp. 102- 106 ,(2006) , 10.1016/J.CONTRACEPTION.2005.06.069
Chaker Ben Salem, Raoudha Slim, Bouraoui Elouni, Houssem Hmouda, Kamel Bouraoui, Drug-Induced Endocrine and Metabolic Disorders Drug Safety. ,vol. 30, pp. 215- 245 ,(2007) , 10.2165/00002018-200730080-00009
Piotr Przybylski, Krystian Pyta, Barbara Wicher, Maria Gdaniec, Bogumił Brzezinski, Structure of a new Schiff base of gossypol with 1-(3-aminopropyl)-2-pyrrolidinone studied by the X-ray, FT-IR, NMR, ESI-MS and PM5 methods Journal of Molecular Structure. ,vol. 889, pp. 332- 343 ,(2008) , 10.1016/J.MOLSTRUC.2008.02.028