Idarubicin hydrochloride, NSC-256439, IMI-30, DMDR, Idamycin, Zavedos

合成路线:The condensation of chiral tetraline (I) with phthalic anhydride (II) by means of AlCl3 at 180 C gives the naphthacenedione (III),which is ketalized at the acetyl group with ethylene glycol and p-toluenesulfonic acid yielding the dioxolane (IV).The hydroxylation of (IV) with Br2 and AIBN in CCl4/CHCl3 affords the 4-demethoxy-7-epidaunomycinone (V),which is isomerized with TFA yielding 4-demethoxydaunomycinone (VI) .The condensation of (VI) with the acylated hexopyranosyl chloride (VII) by means of CF3SO3Ag of Br2Hg affords the trifluoroacetylated 4-demethoxydaunomycin (VIII),which is finally treated with NaOH in order to eliminate the trifluoroacetyl groups

参考文献标题:Daunomycin analogues,their preparation and use
文献作者:Bernardi,L.; Arcamone,F.; Patelli,B.; Di Marco,A.(Pharmacia Corp.)
参考来源:DE 2525633; US 4046878


合成路线:The reaction of daunomycinone (IX) with AlCl3 in dichloromethane gives 4-demethyldaunomycinone (X),which is ketalized with ethylene glycol as before yielding the dioxolane (XI).The selective sulfonation of (XI) with TsCl,DIEA and DMAP in pyridine affords the 4-tosyloxy derivative (XII),which is treated with 4-methoxybenzylamine (XIII) in pyridine providing the secondary benzylamine (XIV).Elimination of the benzyl protecting group of (XIV) with TFA gives 4-amino-4-demethoxydaunomycinone ethylene ketal (XV),which is deaminated by reaction with TFA,NaNO2 and H3PO2 to give 4-demethoxydaunomycinone (XVI).Finally,this compound is submitted to fermentation with Streptomyces peucetius corneus,S.Peucetius caesius,S.Caeruleus,S.Peucetius,S.Coeruleorubidus,and other chemical or radio-induced mutants thereof.

参考文献标题:Process for the preparation of 4-demethoxydaunomycinone,the aglycone of 4-demethoxy-daunorubicin
文献作者:Francalanci,F.; Martinengo,T.; de Bernardinis,S.; Cabri,W.(Pharmacia Corp.)
参考来源:EP 0328399


合成路线:The condensation of chiral tetraline (I) with phthalic anhydride (II) by means of AlCl3 at 180 C gives the naphthacenedione (III),which is ketalized at the acetyl group with ethylene glycol and p-toluenesulfonic acid yielding the dioxolane (IV).The hydroxylation of (IV) with Br2 and AIBN in CCl4/CHCl3 affords the 4-demethoxy-7-epidaunomycinone (V),which is isomerized with TFA yielding 4-demethoxydaunomycinone (VI) .The condensation of (VI) with the acylated hexopyranosyl chloride (VII) by means of CF3SO3Ag of Br2Hg affords the trifluoroacetylated 4-demethoxydaunomycin (VIII),which is finally treated with NaOH in order to eliminate the trifluoroacetyl groups
参考文献标题:Synthesis and antitumour activity of new daunorubicin and adriamycin analogues
文献作者:Arcamone,F.; Bernardi,L.; Patelli,B.; Giardino,P.; Di Marco,A.; Casazza,A.M.; Soranzo,C.; Pratesi,G.
参考来源:Experientia 1978,341255


产品链接: CAS No. 58957-92-9››