Anthracycline Antibiotics. New Analogues, Methods of by Waldemar Priebe

By Waldemar Priebe

content material: Unresolved structure-activity relationships in anthracycline analogue improvement / Edward M. Acton --
Non-cross-resistant anthracyclines with lowered basicity and elevated balance of the glycosidic bond / Waldemar Priebe, Piotr Skibicki, Oscar Varela, Nouri Neamati, Marcos Sznaidman, Krzysztof Dziewiszek, Grzegorz Grynkiewicz, Derek Horton, Yiyu Zou, Yi-He Ling, and Roman Perez-Soler --
Fluorinated anthracyclinones and their glycosylated items / Antonio Guidi, Franca Canfarini, Alessandro Giolitti, Franco Pasqui, Vittorio Pestellini, and Federico Arcamone --
Semisynthetic rhodomycins and anthracycline prodrugs / Cenek Kolar, Klaus Bosslet, Jörg Czech, Manfred Gerken, Peter Hermentin, Dieter Hoffmann, and Hans-Harold Sedlacek --
artificial innovations for reversal of anthracycline resistance and cardiotoxicity / Claude Monneret, Jean-Claude Florent, Jean-Pierre Gesson, Jean-Claude Jacquesy, François Tillequin, and Michel Koch --
Synthesis and organic actions of fluorinated daunorubicin and doxorubicin analogues / Tsutomu Tsuchiya and Yasushi Takagi --
Redox chemistry of anthracyclines and use of oxomorpholinyl radicals / Tad H. Koch and Giorgio Gaudiano --
Synthesis of anthraquinone analogues of associated anthracycline / Ping Ge and Richard A. Russell --
Synthesis and research of structure-activity relationships of recent periods of anthracyclines / Antonino Suarato, Francesco Angelucci, Alberto Bargiotti, Michele Caruso, Daniela Faiardi, Laura Capolongo, Cristina Geroni, Marina Ripamonti, and Maria Grandi --
Molecular acceptance of DNA through daunorubicin / Jonathan B. Chaires --
Adducts of DNA and anthracycline antibiotics : buildings, interactions, and actions / Jasmine Y.-T. Wang, Mark Chao, and Andrew H.-J. Wang --
DNA topoisomerases and their inhibition through anthracyclines / Yves Pommier --
Anthracycline antihelicase motion : new mechanism with implications for guanosine-cytidine intercalation specificity / Nicholas R. Bachur, Robin Johnson, Fang Yu, Robert Hickey, and Linda Malkas --
Membrane biophysical parameters influencing anthracycline motion / Ratna Mehta and Thomas G. Burke --
sign transduction structures in doxorubicin hydrochloride mechanism of motion / Paul Vichi, James tune, Jean Hess, and Thomas R. Tritton --
research of multidrug transporter in dwelling cells : software to uptake and unencumber of anthracycline derivatives via drug-resistant K562 cells / Arlette Garnier-Suillerot, Frédéric Frézard, Marie-Nicole Borrel, Elene Pereira, Jolanta Tarasiuk, and Marina Fiallo --
position of reactive-oxygen metabolism in cardiac toxicity of anthracycline antibiotics / James H. Doroshow --
Amelioration of anthracycline-induced cardiotoxicity via natural chemical compounds / Donald T. Witiak and Eugene H. Herman --
Use of drug vendors to ameliorate the healing index of anthracycline antibiotics / Roman Perez-Soler, Steven Sugarman, Yiyu Zou, and Waldemar Priebe.

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C. J. Med. Chem. 1977, 20, 957. ; Weckerle, W. Carbohydr. Res. 1977, 57, C36. El Khadem, H . ; Swartz, D. L. Carbohydr. Res. 1978, 65, C1. El Khadem, H . ; Swartz, D. Med. Chem. 1981, 24, 112. ; Winter-Mihaly, E. J. Med. Chem. 1979, 22, 406. ; Turner, W. R. Carbohydr. Res. 1981, 94, 11. ; Varela, O. J. Antibiot. 1984, 37, 853. ; Varela, O. J. Antibiot. 1984, 37, 1635. ; Neamati, N. Abstr. Pap. XIV IUPAC Internat. Carbohydr. Symp. B-64, Stockholm, 1988. ; ACS Symposium Series; American Chemical Society: Washington, DC, 1994.

Again, the 2'-chlorodaunorubicin (48) in L-manno configuration showed good antitumor activity in vivo against P388 leukemia (T/C 248 at 25 mg/kg), whereas both L-gluco (50) and L-galacto (43) 2'-chloro analogues showed no activity against P388 leukemia at doses up to 50 mg/kg. 2'-Iodo-3'-deamino Daunorubicins Modified at C-5'. Very promising results of biological evaluation of 2'-halo-3'-oxy-daunorubicins and a unique observed SAR prompted synthesis of analogues modified at C-5'. AcO I 52 - R = Η (a-L-lyxo) 54 - R = CH OAc (a-L-manno) 2 AcO—Ο 53 - R = Η (β-L-Jcy/o) 55 - R = CH OAc (^-L-gluco) 2 Two modifications were considered: (a) a 6'-methyl group replaced with hydrogen and (b) a 6'-methyl group replaced with hydroxymethyl (CH2OH).

The distance between 0-9 and N-3 of the guanine at the intercalation site indicates a strong hydrogen bond, while an additional hydrogen bond is deduced for the amino group at N-2 in the said guanine and the 0-9. On the other side of the aglycone ring, the C-9 side chain carbonyl oxygen is bound to a water molecule bridging through another hydrogen bond towards the 0-2 on the cytosine above the intercalator. ; ACS Symposium Series; American Chemical Society: Washington, DC, 1994. 3. GUIDI ET AL.

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