Chemical modification of the ester group of diketocoriolin B.
5,8-Di-O-tetrahydropyranylcoriolin B (2) was synthesized and its two expoxide groups were found to be resistant to alkaline hydrolysis to give di-O-tetrahydropyranldihydrocoriolin (3). Acylation or alkylation of the free hydroxyl group at C-1 of 3 followed by hydrolysis of the tetrahydropyranylether groups and oxidation of the hydroxyl groups at C-5 and C-8 afforded a numer of 1-O-acyl or alkyl analogs of diketocoriolin B. All of them showed antibacterial and antitumor activities.
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D004352:Drug Resistance, Microbial; D051379:Mice; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000903:Antibiotics, Antineoplastic; D012717:Sesquiterpenes; C001615:diketocoriolin B