OXIDATION OF THE METHYL-GROUPS OF N,N-DIMETHYLBENZAMIDES BY A CYTOCHROME P450 MONO-OXYGENASE MODEL SYSTEM

被引:9
作者
ILEY, J [1 ]
CONSTANTINO, L [1 ]
NORBERTO, F [1 ]
ROSA, E [1 ]
机构
[1] FAC FARM LISBOA,CECF,INST NACL INVEST CIENTIFICA,P-1699 LISBON,PORTUGAL
关键词
D O I
10.1016/S0040-4039(00)97769-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidation of N,N-dimethylbenzamides to the corresponding N-formyl-N-methylbenzamides using tetraphenylporphyrinato-iron(III)-ButOOH is independent of the substituent in the aryl ring of the benzamide group and subject to a kinetic deuterium isotope effect of 5.6. These results are consistent with a mechanism involving direct hydrogen atom abstraction from the substrate. © 1990.
引用
收藏
页码:4921 / 4922
页数:2
相关论文
共 8 条
[1]   DETECTION OF ALKYLPEROXO AND FERRYL, (FEIV=O)2+, INTERMEDIATES DURING THE REACTION OF TERT-BUTYL HYDROPEROXIDE WITH IRON PORPHYRINS IN TOLUENE SOLUTION [J].
ARASASINGHAM, RD ;
CORNMAN, CR ;
BALCH, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :7800-7805
[2]   ELECTROCHEMICAL MODELS FOR CYTOCHROME-P-450 - N-DEMETHYLATION OF TERTIARY AMIDES BY ANODIC-OXIDATION [J].
HALL, LR ;
IWAMOTO, RT ;
HANZLIK, RP .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2446-2451
[3]   HOMOLYTIC AND HETEROLYTIC SCISSION OF ORGANIC HYDROPEROXIDES BY (MESO-TETRAPHENYLPORPHINATO)IRON(III) AND ITS RELATION TO OLEFIN EPOXIDATION [J].
LABEQUE, R ;
MARNETT, LJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6621-6627
[4]  
MIWA GT, 1983, J BIOL CHEM, V258, P4445
[5]  
MROZ J, 1989, TOXICOL APPL PHARM, V98, P507
[6]   REVIEW OF THE BIODISTRIBUTION AND TOXICITY OF THE INSECT REPELLENT N,N-DIETHYL-M-TOLUAMIDE (DEET) [J].
ROBBINS, PJ ;
CHERNIACK, MG .
JOURNAL OF TOXICOLOGY AND ENVIRONMENTAL HEALTH, 1986, 18 (04) :503-525
[7]  
TAYLOR TG, 1990, J AM CHEM SOC, V112, P178
[8]  
TAYLOR WG, 1986, DRUG METAB DISPOS, V14, P532