SUPEROXIDE ANION EFFICIENTLY PERFORMS THE OXIDATIVE CLEAVAGE OF C=NOH BONDS OF AMIDOXIMES AND N-HYDROXYGUANIDINES WITH FORMATION OF NITROGEN-OXIDES

被引：37

作者：

SENNEQUIER, N

BOUCHER, JL

BATTIONI, P

MANSUY, D

机构：

[1] Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, associé au CNRS, Université Paris V, 75270 Paris Cedex 06

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 34期

关键词：

D O I：

10.1016/0040-4039(95)01242-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Potassium superoxide stoechiometrically reacts with arylamidoximes with the selective formation of the corresponding benzamide and nitrogen oxides (mainly NO2-) in high yield A similar oxidative cleavage of the C=NOH bond of N-hydroxy-arylguanidines also occurs upon reaction with KO2; the yield of the corresponding urea is lower and large amounts of the corresponding cyanamide are also formed. The significance of this reaction of O-2(.-) with compounds containing a C=NOH bond in the biological formation of nitrogen oxides including NO is discussed.

引用

页码：6059 / 6062

页数：4

共 18 条

[1] FORMATION OF NITRIC-OXIDE BY CYTOCHROME P450-CATALYZED OXIDATION OF AROMATIC AMIDOXIMES [J].

ANDRONIKLION, V ;

BOUCHER, JL ;

DELAFORGE, M ;

HENRY, Y ;

MANSUY, D .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1992, 185 (01) :452-458

[2]

ANDRONIKLION V, 1953, BIOCHEM BIOPH RES CO, V5, P103

[3]

BOUCHER JL, 1993, BIOCHEM BIOPH RES CO, V192, P53

[4]

FELDMAN PL, 1993, CHEM ENG NEWS, V71, P26

[5] CHEMICAL OXIDATION OF N-HYDROXYGUANIDINE COMPOUNDS - RELEASE OF NITRIC-OXIDE, NITROXYL AND POSSIBLE RELATIONSHIP TO THE MECHANISM OF BIOLOGICAL NITRIC-OXIDE GENERATION [J].

FUKUTO, JM ;

WALLACE, GC ;

HSZIEH, R ;

CHAUDHURI, G .

BIOCHEMICAL PHARMACOLOGY, 1992, 43 (03) :607-613

[6] PERACID OXIDATION OF AN N-HYDROXYGUANIDINE COMPOUND - A CHEMICAL-MODEL FOR THE OXIDATION OF N-OMEGA-HYDROXY-L-ARGININE BY NITRIC-OXIDE SYNTHASE [J].

FUKUTO, JM ;

STUEHR, DJ ;

FELDMAN, PL ;

BOVA, MP ;

WONG, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (18) :2666-2670

[7]

FUKUTO JM, 1994, ANNU REP MED CHEM, V29, P83

[8] ANALYSIS OF NITRATE, NITRITE, AND [N-15]-LABELED NITRATE IN BIOLOGICAL-FLUIDS [J].

GREEN, LC ;

WAGNER, DA ;

GLOGOWSKI, J ;

SKIPPER, PL ;

WISHNOK, JS ;

TANNENBAUM, SR .

ANALYTICAL BIOCHEMISTRY, 1982, 126 (01) :131-138

[9] OXIDATION OF NITRIC-OXIDE IN AQUEOUS-SOLUTION TO NITRITE BUT NOT NITRATE - COMPARISON WITH ENZYMATICALLY FORMED NITRIC-OXIDE FROM L-ARGININE [J].

IGNARRO, LJ ;

FUKUTO, JM ;

GRISCAVAGE, JM ;

ROGERS, NE ;

BYRNS, RE .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (17) :8103-8107

[10] FORMATION OF NITROGEN-OXIDES INCLUDING NO FROM OXIDATIVE CLEAVAGE OF C=N(OH) BONDS - A GENERAL CYTOCHROME P450-DEPENDENT REACTION [J].

JOUSSERANDOT, A ;

BOUCHER, JL ;

DESSEAUX, C ;

DELAFORGE, M ;

MANSUY, D .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (05) :423-426

← 1 2 →