DIHYDROPYRROLIZINE DERIVATIVES FROM UNSATURATED PYRROLIZIDINE ALKALOIDS

被引:150
作者
MATTOCKS, AR
机构
[1] Toxicology Research Unit, Medical Research Council Laboratories, Carshalton, Surrey
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 08期
关键词
D O I
10.1039/j39690001155
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Methods are described for converting alkaloids having the dehydropyrrolizidine ring, and their N-oxides, to dihydropyrrolizine derivatives, which are also formed as metabolites when the alkaloids are administered to animals. Some properties of these products are described. They behave as pyrrole derivatives, and those which are esters are highly reactive alkylating agents, which are probably responsible for toxic effects of the alkaloids.
引用
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页码:1155 / &
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共 33 条
[1]
Adams R, 1939, J AM CHEM SOC, V61, P2815
[3]
HYDROGEN TRANSFER .4. THE USE OF QUINONES OF HIGH POTENTIAL AS DEHYDROGENATION REAGENTS [J].
BRAUDE, EA ;
BROOK, AG ;
LINSTEAD, RP .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (OCT) :3569-3574
[4]
HYDROGEN TRANSFER .2. THE DEHYDROGENATION OF 1-4-DIHYDRONAPHTHALENE BY QUINONES - KINETICS AND MECHANISM [J].
BRAUDE, EA ;
JACKMAN, LM ;
LINSTEAD, RP .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (OCT) :3548-3563
[5]
HYDROGEN TRANSFER .5. DEHYDROGENATION REACTIONS WITH DIPHENYLPICRYLHYDRAZYL [J].
BRAUDE, EA ;
BROOK, AG ;
LINSTEAD, RP .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (OCT) :3574-3578
[6]
THE SENECIO ALKALOIDS .3. THE STRUCTURE OF RETRORSINE AND ISATIDINE, AND THE ISOMERISM OF RETRONECIC ACID AND ISATINECIC ACID [J].
CHRISTIE, SMH ;
KROPMAN, M ;
LEISEGANG, EC ;
WARREN, FL .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (JUL) :1700-1702
[7]
REACTION OF 4-PICOLINE N-OXIDE WITH ACETIC ANHYDRIDE . TRAPPING OF CATIONIC INTERMEDIATE [J].
COHEN, T ;
DEETS, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (15) :3939-&
[8]
USE OF GAMMA-(4-NITROBENZYL)PYRIDINE AS ANALYTICAL REAGENT FOR ETHYLENIMINES AND ALKYLATING AGENTS [J].
EPSTEIN, J ;
ROSENTHAL, RW ;
ESS, RJ .
ANALYTICAL CHEMISTRY, 1955, 27 (09) :1435-1439
[9]
DETOXICATION MECHANISMS .2. IRON-CATALYZED DEALKYLATION OF TRIMETHYLAMINE OXIDE [J].
FERRIS, JP ;
GERWE, RD ;
GAPSKI, GR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) :5270-&
[10]
GOTTLIEB D, 1967, ANTIBIOTICS ED, V1, P211