An efficient synthesis of the new benzo[c]pyrido[2,3,4-kl]acridine skeleton

被引:18
作者
Chackal, S [1 ]
Houssin, R [1 ]
Hénichart, JP [1 ]
机构
[1] Univ Lille 2, Inst Chim Pharmaceut Albert Lespagnol, EA 2692, F-59006 Lille, France
关键词
D O I
10.1021/jo011057m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of molecules of therapeutic interest, possessing the new skeleton of 1-H-benzo [c] pyrido [2,3,4-kl]-acridine with acyl or aminoacyl and methoxy or aminoalkoxy substituents on the aromatic homocycles were synthesized by means of a Friedlander-type reaction. The requisite 5-aminodihydroquinoline-4-ones 1, whose preparation is described, were reacted with the appropriate alpha-tetralones 2 using an acidic catalyst (PPTS) under azeotropic conditions. Optimized reaction time and yield depend on temperature, which must not be below 90 degreesC.
引用
收藏
页码:3502 / 3505
页数:4
相关论文
共 20 条
[1]  
CHENG CC, 1982, ORG REACTIONS, V28, P37
[2]  
Ding QZ, 1999, CURR MED CHEM, V6, P1
[3]  
ELDELFIELD RC, 1952, CHEM HETEROCYCLIC CO, V4, P45
[4]  
Friedlander P., 1882, BER DTSCH CHEM GES, V15, P272
[5]  
FUJISAWA T, 1995, ENCY REAGENTS ORGANI, V6, P4326
[6]   THE REGIOSPECIFIC SYNTHESIS OF THE A-RING AND B-RING OF PHOMAZARIN [J].
GUAY, V ;
BRASSARD, P .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (06) :1649-1652
[7]  
Jones G., 1977, CHEM HETEROCYCLIC 1, P181
[8]   SYNTHESIS OF WATER-SOLUBLE (AMINOALKYL)CAMPTOTHECIN ANALOGS - INHIBITION OF TOPOISOMERASE-I AND ANTITUMOR-ACTIVITY [J].
KINGSBURY, WD ;
BOEHM, JC ;
JAKAS, DR ;
HOLDEN, KG ;
HECHT, SM ;
GALLAGHER, G ;
CARANFA, MJ ;
MCCABE, FL ;
FAUCETTE, LF ;
JOHNSON, RK ;
HERTZBERG, RP .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :98-107
[9]   THE ANTILEUKEMIC ALKALOID FAGARONINE IS AN INHIBITOR OF DNA TOPOISOMERASE-I AND TOPOISOMERASE-II [J].
LARSEN, AK ;
GRONDARD, L ;
COUPRIE, J ;
DESOIZE, B ;
COMOE, L ;
JARDILLIER, JC ;
RIOU, JF .
BIOCHEMICAL PHARMACOLOGY, 1993, 46 (08) :1403-1412
[10]   Substituted benz[a]acridines and benz[c]acridines as mammalian topoisomerase poisons [J].
Makhey, D ;
Yu, C ;
Liu, A ;
Liu, LF ;
LaVoie, EJ .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (05) :1171-1182