The autoxidn. of 9-anthrone (I) [90-44-8] in the presence of excess cysteine Et ester [3411-58-3] was investigated. In addn. to the corresponding 9,10-anthraquinone [84-65-1], an ether-insol. adduct was formed which was shown by spectral anal. to be II [93929-10-3]. The possibility that anthralin (III) [1143-38-0] may undergo an analogous reaction to form 1,8-dihydroxy-10-(2-amino-2-carboxethylthio)-9-anthrone (IV) is discussed; synthesis of the IV-HCl salt [93956-73-1] is given. The relation of these results to the antipsoriatic activity of III is discussed.
Interaction of anthralin with cysteine: a new entry into the chemistry of biologically active anthrones
M. D'ISCHIA;
1984
Abstract
The autoxidn. of 9-anthrone (I) [90-44-8] in the presence of excess cysteine Et ester [3411-58-3] was investigated. In addn. to the corresponding 9,10-anthraquinone [84-65-1], an ether-insol. adduct was formed which was shown by spectral anal. to be II [93929-10-3]. The possibility that anthralin (III) [1143-38-0] may undergo an analogous reaction to form 1,8-dihydroxy-10-(2-amino-2-carboxethylthio)-9-anthrone (IV) is discussed; synthesis of the IV-HCl salt [93956-73-1] is given. The relation of these results to the antipsoriatic activity of III is discussed.File in questo prodotto:
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