合成路线:The condensation of 2-(4-nitrophenyl)ethyl bromide (I) with 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (II) by means of K2CO3 and KI in DMF at 100 C gives 6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline (III),which is reduced with H2 over Pd/C in ethanol to yield the corresponding amine (IV).Finally,this compound is condensed with 5-methoxy-9-oxo-9,10-dihydroacridine-4-carboxylic acid (V) by means of DCC and HOBt in DMF to afford the target carboxamide.The intermediate 5-methoxy-9-oxo-9,10-dihydroacridine-4-carboxylic acid (V) has been obtained as follows: The condensation of 2-amino-3-methoxybenzoic acid (VI) with 2-bromobenzoic acid (VII) by means of K2CO3 and copper dust give the diphenylamine (VIII),which is cyclized to the target acridine (V) by means of POCl3 in refluxing acetonitrile.
参考文献标题:Synthesis of acridine deriv.multidrug-resistant inhibitors
文献作者:Sharp,M.J.; Mader,C.J.; Strachan,C.(GlaxoSmithKline plc)
参考来源:WO 9852923
合成路线:The condensation of 2-(4-nitrophenyl)ethyl bromide (I) with 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (II) by means of K2CO3 and KI in DMF at 100 C gives 6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline (III),which is reduced with H2 over Pd/C in ethanol to yield the corresponding amine (IV).Finally,this compound is condensed with 5-methoxy-9-oxo-9,10-dihydroacridine-4-carboxylic acid (V) by means of DCC and HOBt in DMF to afford the target carboxamide.The intermediate 5-methoxy-9-oxo-9,10-dihydroacridine-4-carboxylic acid (V) has been obtained as follows: The condensation of 2-amino-3-methoxybenzoic acid (VI) with 2-bromobenzoic acid (VII) by means of K2CO3 and copper dust give the diphenylamine (VIII),which is cyclized to the target acridine (V) by means of POCl3 in refluxing acetonitrile.
参考文献标题:Synthesis and activity against multidrug resistance in Chinese hamster ovary cells of new acridone-4-carboxamides
文献作者:Dodic,N.; Dumaitre,B.; Daugan,A.; Pianetti,P.
参考来源:J Med Chem 1995,38(13),2418
产品链接: CAS No. 143664-11-3›› 产品链接: CAS No.143851-98-3››