Synthesis, crystal structures and antibacterial activity studies of aza-derivatives of phytoalexin from cotton plant--gossypol.
Using Gossypol (GOS) extracted from cotton seeds, a series of its Schiff bases (1-18) and hydrazones (19-27) have been synthesized and evaluated for their antimicrobial activities against Gram-positive bacteria, Gram-negative bacteria and yeast-like organisms. Of the 27 aza-derivatives of gossypol, 11 have been found active against the microorganisms tested, similar to gossypol. Crystal structures of the new Schiff base (compound 7) and hydrazone (compound 25) of gossypol reveal the presence of two different tautomers within two types of the aza-derivatives studied. The newly synthesized aza-derivatives of gossypol are characterized by the FT-IR, NMR and MS methods.
Przybylski
Piotr
P
Faculty of Chemistry, A. Mickiewicz University, 60-780 Poznan, Poland. piotrp@amu.edu.pl
Pyta
Krystian
K
Stefańska
Joanna
J
Ratajczak-Sitarz
Małgorzata
M
Katrusiak
Andrzej
A
Huczyński
Adam
A
Brzezinski
Bogumil
B
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D003368:Gossypium / Q000737:chemistry*; D006072:Gossypol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D017550:Spectroscopy, Fourier Transform Infrared; D015003:Yeasts / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D006835:Hydrazones; D012545:Schiff Bases; D006072:Gossypol