Syntheses and preliminary pharmacological evaluation of the two epimers of the 5-F2t-isoprostane

被引:21
作者
Durand, T
Cracowski, JL
Guy, A
Rossi, JC
机构
[1] Univ Montpellier I, Fac Pharm, CNRS, UMR 5074, F-34060 Montpellier 2, France
[2] Fac Med Grenoble, Pharmacol Lab, F-38706 La Tronche, France
关键词
D O I
10.1016/S0960-894X(01)00473-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The total synthesis of the 5-F-2t-isoprostane I and its 5-epimer 2 from diacetone-D-glucose is described. We report preliminary data on the vascular properties of these compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2495 / 2498
页数:4
相关论文
共 12 条
[1]   Total synthesis of a novel isoprostane IPF2 alpha-I and its identification in biological fluids [J].
Adiyaman, M ;
Lawson, JA ;
Hwang, SW ;
Khanapure, SP ;
FitzGerald, GA ;
Rokach, J .
TETRAHEDRON LETTERS, 1996, 37 (28) :4849-4852
[2]   Vascular biology of the isoprostanes [J].
Cracowski, JL ;
Devillier, P ;
Durand, T ;
Stanke-Labesque, F ;
Bessard, G .
JOURNAL OF VASCULAR RESEARCH, 2001, 38 (02) :93-103
[3]   NEW SYNTHESES OF SOME FUNCTIONALIZED AND ACETYLENIC BETA-KETO PHOSPHONATES [J].
DELAMARCHE, I ;
MOSSET, P .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5453-5457
[4]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[5]  
Durand T, 2001, EUR J ORG CHEM, V2001, P809
[6]   Quantitative high performance liquid chromatography tandem mass spectrometric analysis of the four classes of F2-isoprostanes in human urine [J].
Li, HW ;
Lawson, JA ;
Reilly, M ;
Adiyaman, M ;
Hwang, SW ;
Rokach, J ;
FitzGerald, GA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (23) :13381-13386
[7]   A SERIES OF PROSTAGLANDIN-F2-LIKE COMPOUNDS ARE PRODUCED INVIVO IN HUMANS BY A NONCYCLOOXYGENASE, FREE RADICAL-CATALYZED MECHANISM [J].
MORROW, JD ;
HILL, KE ;
BURK, RF ;
NAMMOUR, TM ;
BADR, KF ;
ROBERTS, LJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (23) :9383-9387
[8]   SELECTIVE SILYLATION OF BETA-D-GALACTOSIDES - A NEW APPROACH TO THE SYNTHESIS OF (1-]6)-BETA-D-GALACTOPYRANOOLIGOSACCHARIDES [J].
NASHED, EM ;
GLAUDEMANS, CPJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) :5255-5260
[9]   ASYMMETRIC-SYNTHESIS VIA AXIALLY DISSYMMETRIC MOLECULES .6. RATIONAL DESIGNING OF EFFICIENT CHIRAL REDUCING AGENTS - HIGHLY ENANTIOSELECTIVE REDUCTION OF AROMATIC KETONES BY BINAPHTHOL-MODIFIED LITHIUM ALUMINUM-HYDRIDE REAGENTS [J].
NOYORI, R ;
TOMINO, I ;
TANIMOTO, Y ;
NISHIZAWA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (22) :6709-6716
[10]   Measurement of F2-isoprostanes as an index of oxidative stress in vivo [J].
Roberts, LJ ;
Morrow, JD .
FREE RADICAL BIOLOGY AND MEDICINE, 2000, 28 (04) :505-513