Synthesis of thio- and oxo-analogues of isopsoralen

被引:25
作者
Clarke, DJ [1 ]
Robinson, RS [1 ]
机构
[1] Univ KwaZulu Natal, Sch Chem & Phys Sci, Warren Res Lab, ZA-3209 Pietermaritzburg, South Africa
基金
新加坡国家研究基金会;
关键词
benzopyrans; rearrangements; ozonolysis;
D O I
10.1016/S0040-4020(02)00161-8
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
A range of novel 5'-substituted 7-oxo and 7-thioisopsoralens were synthesized via a Claisen rearranged allyl aryl ether followed by reductive ozonolysis in the presence of a suitable solvent. In some cases dimethylthiocarbamoyl chloride was used as a protecting group and to introduce the thiol moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2831 / 2837
页数:7
相关论文
共 21 条
[1]
SEQUENCE SPECIFICITY IN PHOTOREACTION OF VARIOUS PSORALEN DERIVATIVES WITH DNA - ROLE IN BIOLOGICAL-ACTIVITY [J].
BOYER, V ;
MOUSTACCHI, E ;
SAGE, E .
BIOCHEMISTRY, 1988, 27 (08) :3011-3018
[2]
PSORALENS AS PHOTOACTIVE PROBES OF NUCLEIC-ACID STRUCTURE AND FUNCTION - ORGANIC-CHEMISTRY, PHOTOCHEMISTRY, AND BIOCHEMISTRY [J].
CIMINO, GD ;
GAMPER, HB ;
ISAACS, ST ;
HEARST, JE .
ANNUAL REVIEW OF BIOCHEMISTRY, 1985, 54 :1151-1193
[3]
DANNO K, 1993, INT CONGR SER, V1021, P97
[4]
Farrugia L.J., 1998, ORTEP 3 WINDOWS V1 0
[5]
Gasparro F.P., 1994, EXTRACORPOREAL PHOTO
[6]
6-METHYLANGELICINS - A NEW SERIES OF POTENTIAL PHOTOCHEMOTHERAPEUTIC AGENTS FOR THE TREATMENT OF PSORIASIS [J].
GUIOTTO, A ;
RODIGHIERO, P ;
MANZINI, P ;
PASTORINI, G ;
BORDIN, F ;
BACCICHETTI, F ;
CARLASSARE, F ;
VEDALDI, D ;
DALLACQUA, F ;
TAMARO, M ;
RECCHIA, G ;
CRISTOFOLINI, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (08) :959-967
[7]
GUITTO A, 1995, IL FARMACO, V50, P479
[8]
JAKOBS EA, 1994, TETRAHEDRON, V31, P9315
[10]
MCARDLE P, OSCAIL VERSION 8