Preparation of glucosidic derivatives of steganol.
Glucoside derivatives of steganol analogous to the semisynthetic podophyllotoxin derivative, VP 16-213, were prepared. Glucosidation of steganol with 2, 3, 4, 6-tetra-O-benzylglucopyranose gave the alpha-anomer of the glucoside as the major product. Subsequent removal of the benzyl groups and reaction with acetaldehyde dimethyl acetal gave the ethylidene derivative 10. The beta-anomer of the glucoside was similarly converted to 12. All derivatives prepared were screened for activity in the DNA breakage assay.
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology; D004260:DNA Repair / Q000187:drug effects; D005047:Etoposide / Q000031:analogs & derivatives; D006027:Glycosides / Q000138:chemical synthesis; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000032:analysis; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D006027:Glycosides; D005047:Etoposide