The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
SYNTHESIS AND CYTOSTATIC PROPERTIES OF DAUNORUBICIN DERIVATIVES, CONTAINING N-PHENYLTHIOUREA OR N-ETHYLTHIOUREA MOIETIES IN THE 3'-POSITION
M. N. PREOBRAZHENSKAYAE. V. BAKINAL. S. POVAROVE. I. LAZHKOL. G. ALEKSANDROVAJ. BALZARINIE. DE CLERCQ
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1991 Volume 44 Issue 2 Pages 192-199

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Abstract

A series of phenylthiourea and ethylthiourea derivatives of daunorubicin and its congeners was prepared by reaction of the 3'-amino group of the antibiotic with phenylisothiocyanate or ethylisothiocyanate. S-Methylation yielded S-methylisothiouronium salts which when reacted with amines resulted in an intramolecular cyclization with the participation of the neighboring 4'-OH group. The structures and predominant conformations of the thiourea derivatives and daunorubicino(3'-N, 4'-O-d)oxazolines were determined by 1H and 13C NMR. Cytostatic activities of the thiourea and oxazoline derivatives were compared with the cytostatic activities of N-methylurea and N-methyl-N-nitrosourea containing daunorubicin and its congeners. Carminomycin derivatives were endowed with the highest cytostatic activity.

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