By Waldemar Priebe, editor
Unresolved structure-activity relationships in anthracycline analogue improvement / Edward M. Acton --
Non-cross-resistant anthracyclines with diminished 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 --
Synthetic techniques 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 learn of structure-activity relationships of latest 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 by way of 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 --
Signal transduction platforms in doxorubicin hydrochloride mechanism of motion / Paul Vichi, James track, Jean Hess, and Thomas R. Tritton --
Analysis of multidrug transporter in residing cells : software to uptake and liberate of anthracycline derivatives via drug-resistant K562 cells / Arlette Garnier-Suillerot, Frédéric Frézard, Marie-Nicole Borrel, Elene Pereira, Jolanta Tarasiuk, and Marina Fiallo --
Role of reactive-oxygen metabolism in cardiac toxicity of anthracycline antibiotics / James H. Doroshow --
Amelioration of anthracycline-induced cardiotoxicity by way of natural chemical substances / Donald T. Witiak and Eugene H. Herman --
Use of drug companies to ameliorate the healing index of anthracycline antibiotics / Roman Perez-Soler, Steven Sugarman, Yiyu Zou, and Waldemar Priebe
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Additional resources for Anthracycline antibiotics : new analogues, methods of delivery, and mechanisms of action : developed from a symposium sponsored by the Division of Carbohydrate Chemistry at the 205th National Meeting of the American Chemical Society, Denver, Colorado, Mar
3'-Hydroxy Anthracyclines Halogenated at the C-2' Position / 2'-Iodo-3 -deamino Daunorubicins. ; ACS Symposium Series; American Chemical Society: Washington, DC, 1994. 28 A N T H R A C Y C L I N E ANTIBIOTICS that series were 2'-iodo daunorubicins having a-L-talo and a-L-manno configurations (33, 38, 41, 44). In a one-step reaction, daunomycinone was coupled with 3,4-di-O-acetyl-L-fucal (3) in the presence of N-iodosuccinimide (NIS) to give 2'-iodo-3',4'-diacetoxy-a-L-ffl/o-daunorubicin 35. AcO-—ο NIS OAc CH3O 36 CH3O Ο OH OH 9 Ο OH Ο CH3O AcO^o I Ο OH Ο AcO /CH3 AcCT-O AcO 37 (a-L-manno) 38 (fr-L-gluco) HO I 39 (WP8) SCHEME 5 A similar reaction with 3,4-di-O-acetyl-L-rhamnal (36) (Scheme 5) gave two 2'-iodo trans addition products having a-L-manno (37) and β-L-g/wco (38) configurations.
Similarly, the corresponding derivative in the natural (daunorubicin) series was obtained starting from 16b (in the optically active form). The two compounds were therefore chosen as intermediates for the synthesis of 8-(S)-fluoro-anthracyclines 17a and 17b. Compound 16a was synthesized in four steps (Figure 2), at a 52% overall yield, from the readily available l,4-dimethoxy-2,3-bis-(bromomethyl)anthraquinone, following an adaptation of Cava's route to anthracyclinones (25). The introduction of fluorine was then accomplished by means of the Olah's reagent and the desired fluorohydrin (Figure 3) was obtained in 60% yield (26).
32. 33. 34. 35. 36. 37. 38. 39. 40. 41. 42. 43. 44. 45. 46. 47. 48. 49. 50. ET AL. ; Neamati, N . ; Perez-Soler, R. J. Antibiot. 1990, 43, 838. ; Priebe, W. Cancer Chemother. Pharmacol. 1992, 30, 267. ; Pommier, Y. Int. J. Cancer, 1994, 58, 85-94. Chaires, J. ; Graves, D. ; Burke, T. G. J. Am. Chem. Soc. 1993, 115, 5360. Friedman, R. A. ; Manning, G. Biopolymers 1984, 23, 2671. ; Wright, H . ; Sweatman, T. ; Israel, M . Oncol. Res. 1992, 4, 343. ; Sweatman, T. ; Docter, M . ; Israel, M . Cancer Res.
Anthracycline antibiotics : new analogues, methods of delivery, and mechanisms of action : developed from a symposium sponsored by the Division of Carbohydrate Chemistry at the 205th National Meeting of the American Chemical Society, Denver, Colorado, Mar by Waldemar Priebe, editor