Synthesis, crystal structures and antibacterial activity studies of aza-derivatives of phytoalexin from cotton plant - gossypol

被引：32

作者：

Przybylski, Piotr ^{[1
]}

Pyta, Krystian ^{[1
]}

Stefanska, Joanna ^{[2
]}

Ratajczak-Sitarz, Malgorzata ^{[1
]}

Katrusiak, Andrzej ^{[1
]}

Huczynski, Adam ^{[1
]}

Brzezinski, Bogumil ^{[1
]}

机构：

[1] Adam Mickiewicz Univ Poznan, Fac Chem, PL-60780 Poznan, Poland

[2] Med Univ, Dept Pharmaceut Microbiol, PL-02007 Warsaw, Poland

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2009年 / 44卷 / 11期

关键词：

Gossypol aza-derivatives; Antibacterial activity; Tautomerism; X-ray; Spectroscopy; PM5 SEMIEMPIRICAL METHODS; INTRAMOLECULAR HYDROGEN-BONDS; PI-ELECTRON DELOCALIZATION; CAMPESTRIS PV MALVACEARUM; C-13; CHEMICAL-SHIFTS; TUMOR-CELL LINES; SCHIFF-BASE; ESI-MS; FT-IR; X-RAY;

D O I：

10.1016/j.ejmech.2009.05.032

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Using Gossypol (GOS) extracted from cotton seeds, a series of its Schiff bases (1-18) and hydrazones (1927) 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. (C) 2009 Elsevier Masson SAS. All rights reserved.

引用

页码：4393 / 4403

页数：11

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