[Synthesis and melanoma inhibiting properties of 4-alkylpyrocatechol-2-O-beta-D-glucopyranosiduronic acids and their esters].
Using two sources of selection, the higher beta-glucuronidase and tyrosinase content of malignant melanomas, new transport forms are synthetized, which are toxified to quinoids, cytotoxic products by the above mentioned enzymes. These transport forms selectively inhibit the growth of melanomas. For instance, 4-methylcatechol-2-O-beta-D-glucopyranosiduronic acid (3) is synthetized by the reaction of 4-methylcatechol with tetra-O-acetyl-beta-D-glucopyranosiduronic acid methyl ester in the presence of p-toluenesulfonic acid following treatment with alkali. 3 inhibits the growth of B16 melanoma of the mouse significantly.
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Zentralinstitut für Krebsforschung der Akademie der Wissenschaften, DDR, Berlin-Buch.
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D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002396:Catechols / Q000138:chemical synthesis* / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis / Q000494:pharmacology; D008546:Melanoma, Experimental / Q000188:drug therapy*; D051379:Mice; D008810:Mice, Inbred C57BL
D000970:Antineoplastic Agents; D002396:Catechols; D006027:Glycosides
Synthese und melanomhemmende Eigenschaften der 4-Alkylbrenzcatechin-2-O-beta-D-glucopyranosiduronsäuren und ihrer Ester.