Synthesis and trichomonacidal activity of perketals and hydroperoxides

被引:2
作者
Cointeaux, L
Berrien, JF [1 ]
Camuzat-Dedenis, B
Peyrou, V
Provot, O
Bories, C
Loiseau, PM
Mayrargue, J
机构
[1] Fac Pharm Chatenay Malabry, Chim Organ Lab, UPRESA Biocis 8076, F-92296 Chatenay Malabry, France
[2] Fac Pharm Chatenay Malabry, Parasitol Lab, EA 398, F-92296 Chatenay Malabry, France
来源
FARMACO | 2002年 / 57卷 / 06期
关键词
perketals; peroxides; hydroperoxides; Trichomonas vaginalis;
D O I
10.1016/S0014-827X(02)01238-7
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Some perketals were synthesized by the Dussault procedure using simple bromides and 2-methoxyprop-2-yl hydroperoxide. Treatment with acetic acid gave the corresponding hydroperoxides. Both perketals and hydroperoxides were tested in vitro as trichomonacidal agents. Most of them exhibited very good activities. Them most powerful compound was 2-methoxyprop-2-yl hexadec-1-yl peroxide which exhibited an IC50 value of 0.51 muM being 10 times more effective than the reference compound Metronidazole. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
引用
收藏
页码:457 / 462
页数:6
相关论文
共 11 条
[1]   Trichomonas vaginalis epidemiology:: parameterising and analysing a model of treatment interventions [J].
Bowden, FJ ;
Garnett, GP .
SEXUALLY TRANSMITTED INFECTIONS, 2000, 76 (04) :248-256
[2]   THE ALLYLIC REARRANGEMENT OF HYDROPEROXIDES - THE ALLYLPEROXYL RADICAL [J].
BRILL, WF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (04) :621-627
[3]   Synthesis and in vitro Trichomonacidal activities of some new dialkylperoxides and 1,2,4-trioxanes [J].
Camuzat-Dedenis, B ;
Provot, O ;
Cointeaux, L ;
Perroux, V ;
Berrien, JF ;
Bories, C ;
Loiseau, PM ;
Mayrargue, JL .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (10) :837-842
[4]   Hydrogen peroxide is a product of oxygen consumption by Trichomonas vaginalis [J].
Chapman, A ;
Linstead, DJ ;
Lloyd, D .
JOURNAL OF BIOSCIENCES, 1999, 24 (03) :339-344
[5]   2-METHOXYPROP-2-YL HYDROPEROXIDE - A CONVENIENT REAGENT FOR THE SYNTHESIS OF HYDROPEROXIDES AND PERACIDS [J].
DUSSAULT, P ;
SAHLI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :1009-1012
[6]   ANTIOXIDANT DEFENSES IN THE MICROAEROPHILIC PROTOZOAN TRICHOMONAS-VAGINALIS - COMPARISON OF METRONIDAZOLE-RESISTANT AND SENSITIVE STRAINS [J].
ELLIS, JE ;
YARLETT, N ;
COLE, D ;
HUMPHREYS, MJ ;
LLOYD, D .
MICROBIOLOGY-SGM, 1994, 140 :2489-2494
[7]   Chemoselective oxidation of organozinc reagents with oxygen [J].
Klement, I ;
Lutjens, H ;
Knochel, P .
TETRAHEDRON, 1997, 53 (27) :9135-9144
[8]   ASYMMETRIC REDUCTIONS OF PROCHIRAL KETONES WITH LITHIUM [2-[2-(BENZYLOXY)ETHYL]-6,6-DIMETHYLBICYCLO[3.1.1]-3-NONYL]-9-BORATABICYCLO-[3.3.1]NONANE(LITHIUM NB-ENANTRIDE) AND ITS DERIVATIVES [J].
MIDLAND, MM ;
KAZUBSKI, A ;
WOODLING, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1068-1074
[9]   Metronidazole-resistant vaginal trichomoniasis - An emerging problem [J].
Sobel, JD ;
Nagappan, V ;
Nyirjesy, P .
NEW ENGLAND JOURNAL OF MEDICINE, 1999, 341 (04) :292-293
[10]  
TERAO J, 1989, MEMBRANE LIPID OXYDA, V1, P417