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Antifungal activity of alkyl and heterocyclic aza-derivatives of gossypol as well as their complexes with NaClO4 against Fusarium oxysporum f. sp. lupini.
- Source :
-
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2009 Apr 01; Vol. 19 (7), pp. 1996-2000. Date of Electronic Publication: 2009 Feb 20. - Publication Year :
- 2009
-
Abstract
- Eight alkyl and six heterocyclic aza-derivatives of gossypol (2-15) have been synthesized using gossypol (1) extracted from Gossypium Herbaceum cottonseeds. The ability of gossypol aza-derivatives to form complexes with NaClO(4) has been investigated by electrospray ionisation (ESI) mass spectra recorded in the positive and negative ion detection modes. The gossypol aza-derivatives have been characterized by FT-IR, (1)H and (13)C NMR spectroscopic methods and subsequently tested for their antifungal properties against Fusarium oxysporum. Four alkyl aza-derivatives (2-5), present in the enamine-enamine tautomeric form, have shown activity comparable or higher than that of gossypol against this fungus. To improve the antifungal activity the complexes of the most active compounds 2-5 with NaClO(4) were prepared. Complexes of 2 and 5 with NaClO(4) have shown antifungal activity higher than that of the uncomplexed compounds.
- Subjects :
- Antifungal Agents chemical synthesis
Antifungal Agents chemistry
Aza Compounds chemical synthesis
Aza Compounds chemistry
Gossypium chemistry
Gossypol chemical synthesis
Gossypol isolation & purification
Gossypol pharmacology
Microbial Sensitivity Tests
Spectrometry, Mass, Electrospray Ionization
Antifungal Agents pharmacology
Aza Compounds pharmacology
Fusarium drug effects
Gossypol analogs & derivatives
Gossypol chemistry
Perchlorates chemistry
Sodium Compounds chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3405
- Volume :
- 19
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry letters
- Publication Type :
- Academic Journal
- Accession number :
- 19264482
- Full Text :
- https://doi.org/10.1016/j.bmcl.2009.02.051