Azepines from the intramolecular Prins cyclization of an aminoderivative of lapachol

被引:17
作者
Camara, CA
Pinto, AC
Vargas, MD
Zukerman-Schpector, J
机构
[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil
[2] Univ Fed Rio de Janeiro, Ctr Tecnol, Inst Quim, BR-21945970 Rio De Janeiro, Brazil
[3] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
azepine; naphthoquinone; lapachol; Prins reaction; ketal hydrolysis;
D O I
10.1016/S0040-4020(02)00581-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular Prins reaction of the 2-(2,2-dimethoxyethylamino)-3-(3-methyl-2-butenyl)-1,4-dihydro-1,4-naphthalene-6,11-dione, an amino derivative of lapachol, under hydrolytic conditions, yielded novel azepines condensed with the naphthoquinone nucleus of lapachol. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6135 / 6140
页数:6
相关论文
共 36 条
[1]   Mechanism of the carbonyl-ene reaction [J].
Achmatowicz, O ;
BialeckaFlorjanczyk, E .
TETRAHEDRON, 1996, 52 (26) :8827-8834
[2]   NEW ANTHRACENEDIONES WITH POTENTIAL ANTICANCER ACTIVITY - SYNTHESIS AND CHARACTERIZATION OF BIS-DIETHYLAMINOPROPIONAMIDO DERIVATIVES [J].
ANTONELLO, C ;
URIARTE, E ;
PALUMBO, M .
ARCHIV DER PHARMAZIE, 1988, 321 (09) :513-515
[3]  
BAKOLACHRISTIANOPOULOU MN, 1986, EUR J MED CHEM, V21, P385
[4]  
Bleeker C, 1999, PHARMAZIE, V54, P645
[5]   Secondary amines and unexpected 1-aza-anthraquinones from 2-methoxylapachol [J].
Camara, CA ;
Pinto, AC ;
Rosa, MA ;
Vargas, MD .
TETRAHEDRON, 2001, 57 (47) :9569-9574
[6]  
CHENNA PH, 2001, J MED CHEM, V44, P2486
[7]   Some applications of electrochemistry in biomedical chemistry. Emphasis on the correlation of electrochemical and bioactive properties [J].
de Abreu, FC ;
Ferraz, PAD ;
Goulart, MOF .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2002, 13 (01) :19-35
[8]  
De Moura KCG, 2001, J BRAZIL CHEM SOC, V12, P325
[9]   ANTIINFLAMMATORY ACTION OF LAPACHOL [J].
DEALMEIDA, ER ;
DASILVA, AA ;
DOSSANTOS, ER ;
LOPES, CAC .
JOURNAL OF ETHNOPHARMACOLOGY, 1990, 29 (02) :239-241
[10]  
dos Santos AF, 2000, INT J PARASITOL, V30, P1199, DOI 10.1016/S0020-7519(00)00114-4