The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
NEW DAUNORUBICIN ANALOGS
3-AMINO-2.3, 6-TRIDEOXY-α- AND β-D-ARABINO- AND 3, 6-DIAMINO-2, 3, 6-TRIDEOXY- β-D-RIBO-HEXOPYRANOSIDES OF DAUNOMYCINONE
ERNST-F. FUCHSDEREK HORTONWOLFGANG WECKERLEBÉAT WINTER
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1979 Volume 32 Issue 3 Pages 223-238

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Abstract

Glycosidation of 2, 3, 6-trideoxy-3-trifluoroacclamido-4-O-tritluoroacetyl-α-D-arabino-hexopyranosyl chloride (19) (or the corresponding 4-p-nitrobenzoate, 20) with daunomycinone under KOENIGS-KNORR conditions afforded, after separation of the anomers and removal of the protecting groups, the individual target glycosides 8 (α anomer; major product) and 9 (β; minor) in acceptable yields. In contrast, the title diamino sugar, suitably protected with N-trifluoroacetyl and O-acetyl (or O-p-nitrobenzoyl) groups, underwent stereospecific coupling to the anthracycline aglycon by the glycal procedure to give, after deprotection, the α glycoside 12. All three analogs were assayed in vivo against P388 lymphocytic leukemia. They showed little (T/C 125 for 8; T/C 115 for 9) or no (compound 12) activity, but were essentially devoid of toxicity at the dose-levels tested.

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© Japan Antibiotics Research Association
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