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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine
Autor:Horton, D.; Priebe1, W.; Sznaidmanc, M.L.; Varela, O.
Filiación:Department of Chemistry, Ohio State University, Columbus, Ohio 43210, United States
University of Texas System Cancer Center, M. D. Anderson Hospital Tumor Institute, 1515 Halcombe Blvd, Houston, TX 77030, United States
Department of Organic Chemistry, Burroughs Wellcome Co., Inc, 3030 Cornwallis Road, Research Triangle Park, NC 27709, United States
Universidad de Buenos Aires, Facultad de Ciencias Exact as y Naturales, Departamen to de Quimica Organica, Buenos, Aires, Argentina
Palabras clave:anthracycline derivative; daunosamine; antineoplastic activity; article; chemical structure; drug synthesis; human; human cell; priority journal
Año:1993
Volumen:46
Número:11
Página de inicio:1720
Página de fin:1730
DOI: http://dx.doi.org/10.7164/antibiotics.46.1720
Título revista:Journal of Antibiotics
Título revista abreviado:J. Antibiot.
ISSN:00218820
CAS:daunosamine, 26548-47-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00218820_v46_n11_p1720_Horton

Referencias:

  • El Khadem, H.S., (1982) Anthracycline Antibiotics, , (Ed): Academic Press
  • Arcamone, F., Cassinelli, G., Penco, S., Tognoli, L., (Societa Farmaceutici Italia S.p.A.): Antibiotic from Streptomyces fermentations. Ger. Offen (1970), 1 (923), p. 885. , Jan. 29; Penco, S., Franchi, G., Arcamone, F., (Societa Farmaceutici Italia S.p.A.): Anthracycline disaccharide derivatives (1978) Ger. Offen, 2751, p. 395. , May 18
  • Fuchs, E.F., Horton, D., Weckerle, W., Winter-Mihaly, E., Synthesis and antitumor activity of sugar-ring hydroxyl analogues of daunorubicin (1979) J. Med. Chem, 22, pp. 406-411
  • Horton, D., Priebe, W., Varela, O., 3'-Deamino-4'-epi-3'-hydroxy-daunorubicin and doxorubicin. Synthesis and antitumor activity (1984) J. Antibiotics, 37, pp. 1635-1641
  • Horton, D., Priebe, W., Sznaidman, M., A new approach to 2-deoxyglycosides permitting access to anthracycline glycosides specifically labeled at the 2'-position (1989) Carbohydr. Res, 187, pp. 149-153
  • Thiem, J., Karl, H., Schwentner, J., Synthese a-verknüpfter 2'-deoxy-2'-iododisaccharide (1978) Synthesis, 1978, pp. 696-698
  • Thiem, J., Gerken, M., Synthesis of the E-D-C trisaccharide unit of aureolic acid cytostatics (1985) J. Org. Chem, 50, pp. 954-958
  • Thiem, J., Klaffke, W., Facile stereospecific synthesis of deoxyfucosyl disaccharide units of anthracyclines (1989) J. Org. Chem, 54, pp. 2006-2009
  • Horton, D., Priebe, W., Oxyhalogenation of glycals for the synthesis of antitumor-active 2'-halo daunorubicin analogs (1985) Carbohydr. Res, 136, pp. 391-396
  • Berkowitz, D.B., Danishefsky, S.J., Schulte, G.K., A route to artificial glycoconjugates and oligosaccharides via enzymatically resolved glycals: dramatic effects of the handedness of the sugar domain upon the properties of an anthracycline drug (1992) J. Am. Chem. Soc, 114, pp. 4518-4529
  • Tatsuta, K., Fujimoto, K., Kinoshita, M., Umezawa, S., A novel synthesis of 2-deoxy-α-glycosides (1977) Carbohydr. Res, 54, pp. 85-104
  • Horton, D., Priebe, W., Sznaidman, M., Steric and conformational effects in the dehalogenation of 2-halo sugar derivatives with tributylstannane (1993) J. Org. Chem, 58, pp. 1821-1826
  • Horton, D., Priebe, W., Sznaidman, M., Preparation of 4-O-acetyl-1, 5-anhydro-2, 3, 6-trideoxy-3-trifluoroacetamido-L-lyxo-hex-1-enitol, a key intermediate in synthesis of daunosamine glycosides (1989) Carbohydr. Res, 187, pp. 145-148
  • Horton, D., Priebe, W., Varela, O., Selective acylation of6-deoxyglycals (1985) Carbohydr. Res, 144, pp. 317-324
  • Horton, D., Priebe, W., Sznaidman, M., Iodoalkoxylation of 1, 5-anhydro-2-deoxy-hex-1-enitols (glycals) (1990) Carbohydr. Res, 205, pp. 71-86
  • Horton, D., Priebe, W., Varela, O., Halogenation of 1, 5-anhydroex-1-enitols (glycals). Influence of the C-6 substituent (1986) J. Org. Chem, 51, pp. 3479-3485
  • Boivin, J., Monneret, C., Pais, M., Approche de la synthese d'anthracyclines oligosaccharidiques. Hemisynthese de la 4'-O-(2-desoxy-L-fucosyl) daunorubicine (1981) Tetrahedron, 1981, pp. 4219-4228
  • Berge, J.M., Roberts, S.M., Recommended work-up procedure for reductions employing tri-butyltin hydride (1979) Synthesis, 1979, pp. 471-472

Citas:

---------- APA ----------
Horton, D., Priebe1, W., Sznaidmanc, M.L. & Varela, O. (1993) . Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine. Journal of Antibiotics, 46(11), 1720-1730.
http://dx.doi.org/10.7164/antibiotics.46.1720
---------- CHICAGO ----------
Horton, D., Priebe1, W., Sznaidmanc, M.L., Varela, O. "Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine" . Journal of Antibiotics 46, no. 11 (1993) : 1720-1730.
http://dx.doi.org/10.7164/antibiotics.46.1720
---------- MLA ----------
Horton, D., Priebe1, W., Sznaidmanc, M.L., Varela, O. "Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine" . Journal of Antibiotics, vol. 46, no. 11, 1993, pp. 1720-1730.
http://dx.doi.org/10.7164/antibiotics.46.1720
---------- VANCOUVER ----------
Horton, D., Priebe1, W., Sznaidmanc, M.L., Varela, O. Synthesis and antitumor activity of anthracycline disaccharide glycosides containing daunosamine. J. Antibiot. 1993;46(11):1720-1730.
http://dx.doi.org/10.7164/antibiotics.46.1720