Derivatives of saquayamycins A and B. Regio- and diastereoselective addition of alcohols to the L-aculose moiety.
In continuation of our structure-activity investigations on angucycline antibiotics we prepared derivatives of saquayamycins A (1) and B (4) by regio- and diastereoselective nucleophilic addition of different alcohols to the L-aculose moiety. Reversible protection of the 4'-hydroxy group in 1 by silylation allowed a derivatization at both L-aculose moieties without cyclization towards cinerulose B. The in vitro cytotoxic activity remained almost unchanged after variation at the L-aculose moieties whereas a change in the aglycone structure led to a total loss of the biological activity.
Henkel
T
T
Institut für Organische Chemie, Universität Göttingen, FRG.
Zeeck
A
A
D000438:Alcohols; D000818:Animals; D000880:Anthraquinones / Q000494:pharmacology / Q000633:toxicity; D000903:Antibiotics, Antineoplastic / Q000494:pharmacology / Q000633:toxicity; D005026:Ethylene Glycols; D007939:Leukemia L1210; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects; D000095602:Angucyclines and Angucyclinones
D000438:Alcohols; D000880:Anthraquinones; D000903:Antibiotics, Antineoplastic; D005026:Ethylene Glycols; D000432:Methanol; C100443:saquayamycin B; D000095602:Angucyclines and Angucyclinones