Antifungal activity of alkyl and heterocyclic aza-derivatives of gossypol as well as their complexes with NaClO4 against Fusarium oxysporum f. sp. lupini

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 7, 2009, Pages 1996-2000

  Przybylski, Piotr ^a   Pyta, Krystian ^a   Remlein Starosta, Dorota ^b   Schroeder, Grzegorz ^a   Brzezinski, Bogumil ^a   Bartl, Franz ^c  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b INSTITUTE OF PLANT PROTECTION NATIONAL RESEARCH INSTITUTE   (Poland)

^c CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

Antifungal activity; ESI+ and ESI MS; Fusarium oxysporum; Gossypol aza derivatives; Spectroscopy

Indexed keywords

ALKYL GROUP; ENAMINE; GOSSYPOL DERIVATIVE; HETEROCYCLIC COMPOUND; HYPOCHLORITE SODIUM;

ANTIFUNGAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; FUSARIUM OXYSPORUM; INFRARED SPECTROSCOPY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANTIFUNGAL AGENTS; AZA COMPOUNDS; FUSARIUM; GOSSYPIUM; GOSSYPOL; MICROBIAL SENSITIVITY TESTS; PERCHLORIC ACID; SODIUM COMPOUNDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

FUNGI; FUSARIUM OXYSPORUM; GOSSYPIUM HERBACEUM;

EID: 61849111686     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.02.051     Document Type: Article

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33. + m/z = 519.
34. General procedure for the synthesis of gossypol Schiff bases (2-5) and gossypol hydrazones (6-9): To a solution of (1) (500 mg, 0.96 mmol) in dichloromethane (30 mL) the respective amines or hydrazines in dichloromethane (40 mL) were added (1.92 mmol). The mixture was first stirred at 35° C for 5 h and then solvent was evaporated to the 40 mL of total volume. Next the mixture was cooled to the room temperature and subsequently the 10 mL of methanol was added. The products were precipitated, filtered off and dried under reduced pressure. Crude precipitates were recrystallised from 1:1 dichloromethane-ethanol mixture. Gossypol aza-derivatives were obtained as orange or orange-brown solids (Yield from 82% to 91%).
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