Structure-activity relationships of raphanusanins and their analogues
1993
Sakoda, M. | Usui, K. | Ishizuka, K. | Harada, N. | Ono, H. | Uda, H. | Hasegawa, K.
The structure-activity relationship of raphanusanins A and B [(3R ,6R)-and (3R ,6S)-3-[methoxy (methylthio)methyl]-2-pyrrolidinethione, respectively] and their analogues has been studied for the inhibition of the growth of lettuce hypocotyls and Amaranthus roots. Pyrrolidinethione compounds showed higher activity than pyrrolidinones. The presence of a methoxy(methylthio)methyl group or of a methylthiomethylene moiety at C-3 of pyrrolidinethione was a dominant factor for higher activity. The bis(methylthio)methyl derivative also gave a similar inhibitory activity. It was established that the active sites in the chemical structure of the raphanusanins and their analogues were the thioamide moiety at C-2 of the skeleton and a methoxy(methylthio)methyl, bis(methylthio)methyl, or methylthiomethylene group in the C-3 position of the side chain.
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