Novel spiroanellated 1,2,4-trioxanes with high in vitro antimalarial activities

被引：65

作者：

Griesbeck, AG

El-Idreesy, TT

Höinck, LO

Lex, J

Brun, R

机构：

[1] Univ Cologne, Inst Chim Organ, D-50939 Cologne, Germany

[2] Swiss Trop Inst, CH-4002 Basel, Switzerland

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 03期

关键词：

peroxides; antimalarial; synthesis;

D O I：

10.1016/j.bmcl.2004.11.043

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A remarkable increase in antimalarial in vitro activity was achieved by integration of spiroadamantane motifs in 6-alkylidene 1,2,4-trioxanes 3a-h via diastereoselective photo oxygenation of allylic alcohols and subsequent BF3-catalyzed peroxyacetalization with adamantanone to give the active compounds 3e-h. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：595 / 597

页数：3

相关论文

共 28 条

[1] Synthesis and antimalarial activity of trioxaquine derivatives [J].

Dechy-Cabaret, O ;

Benoit-Vical, F ;

Loup, C ;

Robert, A ;

Gornitzka, H ;

Bonhoure, A ;

Vial, H ;

Magnaval, JF ;

Séguéla, JP ;

Meunier, B .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (07) :1625-1636

[2] Artemisinins target the SERCA of Plasmodium falciparum [J].

Eckstein-Ludwig, U ;

Webb, RJ ;

van Goethem, IDA ;

East, JM ;

Lee, AG ;

Kimura, M ;

O'Neill, PM ;

Bray, PG ;

Ward, SA ;

Krishna, S .

NATURE, 2003, 424 (6951) :957-961

[3] Antimalarial drug discovery: Efficacy models for compound screening [J].

Fidock, DA ;

Rosenthal, PJ ;

Croft, SL ;

Brun, R ;

Nwaka, S .

NATURE REVIEWS DRUG DISCOVERY, 2004, 3 (06) :509-520

[4] New trends in anti-malarial agents [J].

Frédérich, M ;

Dogné, JM ;

Angenot, L ;

De Mol, P .

CURRENT MEDICINAL CHEMISTRY, 2002, 9 (15) :1435-1456

[5]

Griesbeck A. G., 2003, PHOTOCHEM PHOTOBIOL, V2, P977

[6] Photooxygenation in polystyrene beads with covalently and non-covalently bound tetraarylporphyrin sensitizers [J].

Griesbeck, AG ;

El-Idreesy, TT ;

Bartoschek, A .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :245-251

[7] Synthesis of antimalarial 1,2,4-trioxanes via photooxygenation of a chiral allylic alcohol [J].

Griesbeck, AG ;

El-Idreesy, TT ;

Fiege, M ;

Brun, R .

ORGANIC LETTERS, 2002, 4 (24) :4193-4195

[8]

Haynes R. K., 2004, ANGEW CHEM, V116, P1405, DOI DOI 10.1016/j.tips.2008.07.004

[9] Highly antimalaria-active artemisinin derivatives: Biological activity does not correlate with chemical reactivity [J].

Haynes, RK ;

Ho, WY ;

Chan, HW ;

Fugmann, B ;

Stetter, J ;

Croft, SL ;

Vivas, L ;

Peters, W ;

Robinson, BL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (11) :1381-1385

[10]

Jefford C. W., 1997, ADV DRUG RES, P29