[Studies on the resolution of racemic gossypol. III. Study on the chemical and physical properties of the amino condensates of gossypol].

Fifteen condensates of chiral amines and racemic gossypol were prepared. Their 1HNMR spectra indicated that all the amine condensates tested had the same keto-enamine structures and shifts of protons on C11, C11 of various condensates were analyzed for their structural relationship. The Rf and delta Rf values (difference between (+) and (-)gossypol condensates) on TLC of these derivatives and stability of eight condensates of (-)gossypol were examined. All these properties were discussed in light of the configuration of gossypol. These studies not only provided rational basis of selecting resolving agent, but also gave indications of their relative absorbability and stereochemistry of the condensates which might be useful in postulating their in vivo behaviors and designing derivatives with better pharmacological actions.