99907-84-3Relevant academic research and scientific papers
Stereospecific Total Synthesis of 9-Aminoanthracyclines: (+)-9-Amino-9-deoxydaunomycin and Related Compounds
Ishizumi, Kikuo,Ohashi, Naohito,Tanno, Norihiko
, p. 4477 - 4485 (2007/10/02)
9-amino-9-deoxydaunomycin and related compounds, in which the hydroxyl group at the 9-position of daunomycin is replaced by an amino group, have been synthesized.Asymmetry was introduced into the synthetic sequence for the AB synthon by resolution of the intermediate amino ester or acetamido acid to afford (R)-(-)-2-acetyl-2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, which was converted to the tetracyclic amido ketones by Friedel-Crafts acylation with phthalic anhydride or its 3-methoxy derivative.The resulting regioisomers 4- and 1-methoxy compounds were separed, after methylation and selective demethylation, by crystallization and preparative TLC.The required introduction of the C7-hydroxyl function proceeded stereosepcifically via a three-step reaction sequence involving formation of an oxazine compound.The silver trifluoromethane assisted glycosidation of the resulting aglycons with 2-deoxy-3,4-di-O-acetyl-D-erythro-pentopyranosyl bromide or N,O-bis(trifluoroacetyl)daunosaminyl chloride, followed by alkaline hydrolysis afforded the target glycosides.The work reported herein comprises an efficient, practical synthesis of 9-amino-9-deoxydaunomycin and its analogues with the same stereochemistry as in the naturally occurring anthracyclines.
Aminonaphthacene derivatives and their use
-
, (2008/06/13)
Aminonaphthacene derivatives of the formula: STR1 wherein A is either one of the following groups: STR2 wherein R1 is a hydrogen atom or a group of the formula: --COR7, R2 and R3 are each a lower alkoxy group or, when taken together, represent an ethylenedioxy group or an oxo group, R4 and R5 are both hydrogen atoms or either one of them is a hydrogen atom and the other is a group of the formula: --COR7, R6 is a hydrogen atom, a hydroxyl group or a group of the formula: --OCOR7 and R7 is a lower alkyl group, a halo(lower)alkyl group, a phenyl group or a halophenyl group, which are useful as anti-microbial and/or anti-tumor agents, or as intermediates in their production.
