Spectroscopic study of stepwise gossypol sulfonylation with tosyl chloride in the presence of 4-methoxypyridine N-oxide and triethylamine

Intramolecular hydrogen bonds of gossypol imine derivatives

“…Gossypol is a yellow-colored polyphenol and natural toxin found in different parts of the cotton plant [1][2][3][4][5][6][7][8] and exhibits a wide range of biological activities. [4][5][6][7][8][9][10][11][12][13][14][15] The toxicity of gossypol at high concentrations, related to the presence of two aldehyde groups, limits its use in pharmacy.…”

“…Gossypol is a yellow-colored polyphenol and natural toxin found in different parts of the cotton plant [1][2][3][4][5][6][7][8] and exhibits a wide range of biological activities. [4][5][6][7][8][9][10][11][12][13][14][15] The toxicity of gossypol at high concentrations, related to the presence of two aldehyde groups, limits its use in pharmacy. [5][6][7][8][9][16][17][18] Condensation with primary amines and hydrazines results in gossypol imine derivatives, and is an effective way to reduce the toxicity of gossypol.…”

“…[4][5][6][7][8][9][10][11][12][13][14][15] The toxicity of gossypol at high concentrations, related to the presence of two aldehyde groups, limits its use in pharmacy. [5][6][7][8][9][16][17][18] Condensation with primary amines and hydrazines results in gossypol imine derivatives, and is an effective way to reduce the toxicity of gossypol. [7][8][9][10][11][12][13][14][15][19][20][21][22][23][24][25] This simple method of gossypol modification minimizes its toxicity and preserves the therapeutic effect of the original polyphenol.…”