Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine

Daunosamine, as its 4-O-acetyl-3-N-trinfluoroacetyl glycosyl chloride derivative (1b), has been coupled α-L-glycosidically to the 3- and 4-mono-O-acetyl derivatives of L-rhamnal to afford disaccharide glycal derivatives, whose conversion into the corresponding 2-deoxyglycosides by sequential alkoxyi...

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Autores principales: Horton, D., Priebe1, W., Sznaidmanc, M.L., Varela, O.
Formato: JOUR
Materias:
anthracycline derivative
daunosamine
antineoplastic activity
article
chemical structure
drug synthesis
human
human cell
priority journal
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00218820_v46_n11_p1720_Horton
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00218820_v46_n11_p1720_Horton
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spelling todo:paper_00218820_v46_n11_p1720_Horton2023-10-03T14:21:49Z Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine Horton, D. Priebe1, W. Sznaidmanc, M.L. Varela, O. anthracycline derivative daunosamine antineoplastic activity article chemical structure drug synthesis human human cell priority journal Daunosamine, as its 4-O-acetyl-3-N-trinfluoroacetyl glycosyl chloride derivative (1b), has been coupled α-L-glycosidically to the 3- and 4-mono-O-acetyl derivatives of L-rhamnal to afford disaccharide glycal derivatives, whose conversion into the corresponding 2-deoxyglycosides by sequential alkoxyiodination-tributylstannane reduction has been evaluated. The sequence sucssfully demonstrated with the methyl glycosides was successfully extended with daunomycinone as the aglycon, providing a preparative route to 7-O-[3-O-(3-amino-2, 3, 6-trideoxy-α-L-lyxohexopyranosyl)-2, 6-dideoxy-α-L-arabino-hexopyranosyl]daunomycinone hydrochloride (15), an analogue of natural anthracycline antibiotics containing daunosamine and a 2, 6-dideoxy-L-hexose. © 1993, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00218820_v46_n11_p1720_Horton
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic anthracycline derivative
daunosamine
antineoplastic activity
article
chemical structure
drug synthesis
human
human cell
priority journal
spellingShingle anthracycline derivative
daunosamine
antineoplastic activity
article
chemical structure
drug synthesis
human
human cell
priority journal
Horton, D.
Priebe1, W.
Sznaidmanc, M.L.
Varela, O.
Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine
topic_facet anthracycline derivative
daunosamine
antineoplastic activity
article
chemical structure
drug synthesis
human
human cell
priority journal
description Daunosamine, as its 4-O-acetyl-3-N-trinfluoroacetyl glycosyl chloride derivative (1b), has been coupled α-L-glycosidically to the 3- and 4-mono-O-acetyl derivatives of L-rhamnal to afford disaccharide glycal derivatives, whose conversion into the corresponding 2-deoxyglycosides by sequential alkoxyiodination-tributylstannane reduction has been evaluated. The sequence sucssfully demonstrated with the methyl glycosides was successfully extended with daunomycinone as the aglycon, providing a preparative route to 7-O-[3-O-(3-amino-2, 3, 6-trideoxy-α-L-lyxohexopyranosyl)-2, 6-dideoxy-α-L-arabino-hexopyranosyl]daunomycinone hydrochloride (15), an analogue of natural anthracycline antibiotics containing daunosamine and a 2, 6-dideoxy-L-hexose. © 1993, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.
format JOUR
author Horton, D.
Priebe1, W.
Sznaidmanc, M.L.
Varela, O.
author_facet Horton, D.
Priebe1, W.
Sznaidmanc, M.L.
Varela, O.
author_sort Horton, D.
title Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine
title_short Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine
title_full Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine
title_fullStr Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine
title_full_unstemmed Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine
title_sort synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine
url http://hdl.handle.net/20.500.12110/paper_00218820_v46_n11_p1720_Horton
work_keys_str_mv AT hortond synthesisandantitumoractivityofanthracyclinedisaccharideglycosidescontainingdaunosamine
AT priebe1w synthesisandantitumoractivityofanthracyclinedisaccharideglycosidescontainingdaunosamine
AT sznaidmancml synthesisandantitumoractivityofanthracyclinedisaccharideglycosidescontainingdaunosamine
AT varelao synthesisandantitumoractivityofanthracyclinedisaccharideglycosidescontainingdaunosamine
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