cas 79867-79-1, 6,8,11-trihydroxy-8-(1-hydroxyethyl)-10-[(4S,5S,6S)-5-hydroxy-6-methyl -4-morpholin-4-yl-oxan-2-yl]oxy-1-methoxy-9,10-dihydro-7H-tetracene-5, 12-dione

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Intensely potent morpholinyl anthracyclines
3'-Deamino-3'-(3-cyano-4-morpholinyl)doxorubicin is a new analogue that is 100 to 1000 times more potent than doxorubicin against tumors in cell culture or in mice, that is active by intraperitoneal, intravenous, or oral dosing, and that does not produce chronic myocardial lesions in mice. This analogue was encountered in studies on the reductive alkylation of doxorubicin and daunorubicin with 2,2'-oxybis[acetaldehyde], which constructs a morpholino ring incorporating the amino N. The morpholinyl nitrile byproducts are separated by virtue of their nonbasicity from the expected morpholino derivatives. The 13-dihydro and 5-imino derivatives are also described in this important new class of anthracyclines.
Acton,Tong,Mosher,Wolgemuth
p. 638 - 645
(2007/10/02)

Enhanced Antitumor Properties of 3'-(4-Morpholinyl) and 3'-(4-Methoxy-1-piperidinyl) Dervatives of 3'-Deaminodaunorubicin
Reductive N,N-dialkylation of daunorubicin with 2,2'-oxydiacetaldehyde and NaBH3CN occurred in two steps without interruption and with cyclization to form 3'-(4-morpholinyl)-3'-deaminodaunorubicin.This derivative retained the antitumor efficacy of doxorubicin against mouse leukemia P388 but at one-fortieth the dose; hence, it is the most potent anthracycline analogue synthesized so far.The 4-methoxy-1-piperidinyl derivative, similarly prepared with 3-methoxyglutaraldehyde, showed improved efficacy against P388, though at normal doses.Results with a series of analogues indicate that incorporation of the N in the new ring and the presence of an ether O at the 4-position are critical for enhanced activity.
Mosher, Carol W.,Wu, Helen Y.,Fujiwara, Allan N.,Acton, Edward M.
p. 18 - 24
(2007/10/02)