SYNTHESIS, REACTIONS, AND PRELIMINARY EVALUATIONS OF ENAMINONE ESTERS

被引:23
作者
EDAFIOGHO, IO [1 ]
MOORE, JA [1 ]
FARRAR, VA [1 ]
NICHOLSON, JM [1 ]
SCOTT, KR [1 ]
机构
[1] HOWARD UNIV,GRAD SCH ARTS & SCI,DEPT CHEM,WASHINGTON,DC 20059
关键词
D O I
10.1002/jps.2600830119
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The objective of this work was to design enaminone esters that would possess potential medicinal properties. The reaction between beta-hydroxyketo esters and primary or secondary amines yielded secondary or tertiary enaminone esters, respectively. The UV spectra of the enaminone esters were determined in acidic, alkaline, and neutral media; the spectra have a hypsochromic shift in acidic media in comparison with neutral media. The enaminone esters provided nucleophilic and electrophilic sites for a variety of reactions. Thus, the enaminone esters were converted into enaminone amides and O-alkylation products exclusively. Although the enaminone esters were generally resistant to reduction by metal hydrides, one unhindered enaminone ester was reduced to an alcohol with sodium borohydride. Another enaminone ester reacted with guanidine to give the corresponding quinazolinone. Due to the variety of nucleophilic and electrophilic sites in the enaminone system, enaminone esters possess a great potential as reaction intermediates and medicinal compounds. Preliminary evaluations of the enaminone esters revealed a histaminergic effect, uterine relaxant properties, and anticonvulsant activity.
引用
收藏
页码:79 / 84
页数:6
相关论文
共 15 条
[1]   REACTIONS OF ENAMINES .6. PROTONATION OF ENAMINO KETONES [J].
ALT, GH ;
SPEZIALE, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (05) :1407-&
[2]   ELECTRONIC-SPECTRA OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS .1. EVALUATION OF INCREMENTS CHARACTERISTIC OF CHANGES IN CONFIGURATION (CIS-TRANS) AND CONFORMATION (S-CIS-S-TRANS) BASED ON DIRECT OBSERVATION OF ISOMERIZATION OF ENAMINO ALDEHYDES AND KETONES [J].
DABROWSKI, J ;
KAMIENSKATRELA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :2826-2834
[3]   USE OF CYCLOHEXANE-1,3-DIONE DERIVATIVES IN PREPARATION OF ENAMINONES [J].
DIXON, K ;
GREENHILL, JV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (20) :2211-2214
[4]   SYNTHESIS AND ANTICONVULSANT ACTIVITY OF ENAMINONES [J].
EDAFIOGHO, IO ;
HINKO, CN ;
CHANG, HJ ;
MOORE, JA ;
MULZAC, D ;
NICHOLSON, JM ;
SCOTT, KR .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (15) :2798-2805
[5]  
EDAFIOGHO IO, 1990, PHARM WORLD J, V7, P20
[6]  
EDAFIOGHO IO, 1989, NIGER J BASIC APPL S, V3, P35
[7]   REACTION OF T-BUTYLAMINE WITH CYCLOHEXANE-1,3-DIONE [J].
GREENHIL.JV .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (08) :1002-&
[8]   AROMATIC ENAMINONES .1. ULTRAVIOLET-ABSORPTION OF N-ARYL ENAMINONES DERIVED FROM DIMEDONE [J].
GREENHILL, JV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (20) :2207-2210
[9]   REACTIONS WITH ALDEHYDES OF ENAMINONES DERIVED FROM DIMEDONE [J].
GREENHILL, JV .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (15) :2699-+
[10]   UNSATURATED AMINES .13. THE SITES OF ALKYLATION AND PROTONATION IN CERTAIN ENAMINOKETONES - SUBSTITUTED TRIMETHINIUM COMPOUNDS FROM O-ALKYLATED ENAMINOKETONES [J].
LEONARD, NJ ;
ADAMCIK, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (03) :595-602