Cyclic amidines derived from benz[c,d]indole and 4,5-dihydro-3H-1-benzazepine including some related compounds: Synthesis and pharmacological screening

Author:

Protiva Miroslav,Šedivý Zdeněk,Holubek Jiří,Svátek Emil,Němec Jiří

Abstract

Reactions of naphthostyril (I) with primary and secondary amines and titanium tetrachloride afforded cyclic amidines III-IX. Hydrogenation of I on Pd-C resulted in the 6,7,8,8a-tetrahydro derivative X which gave by treatment with sodium amide and 3-dimethylaminopropyl chloride the N-(aminoalkyl) compound XI. Reduction of I and its N-methyl derivative II with sodium amalgam in aqueous sodium hydroxide gave the 2a,3,4,5-tetrahydro derivatives XII and XIII. Reaction of XIII with sodium amide and 3-dimethylaminopropyl chloride afforded the 2a-(aminoalkyl) compound XIV. 1,3,4,5-Tetrahydro-1-benzazepin-2-one (XV) treated with primary amines and titanium tetrachloride gave the amidines XVI-XVIII. 3-Methyl-7,8,9,9a-tetrahydro-1H-benz[d,e]isoquinoline (XIX) was reduced with sodium borohydride to compound XX which was alkylated with propargyl bromide to 1-methyl-2-propargyl-2,3,3a,4,5,6-hexahydro-1H-benz[d,e]isoquinoline (XXI). An attempt to prepare the 2-(2-phenylethyl) analogue by treatment of compound XX with phenylacetyl chloride and by the following reduction with lithium aluminium hydride resulted in the open-chain amine XXII. The lactams I, II, X, and XIII showed some discoordinating, hypothermic, peripheral vasodilating, hyperglycaemic, diuretic and antiinflammatory effects. The amidines III-IX and XVI-XVIII had local anaesthetic, slight hypotensive, antiarrhythmic, peripheral myorelaxant, papaverine-like spasmolytic and thiopental potentiating effects.

Publisher

Institute of Organic Chemistry & Biochemistry

Subject

General Chemistry

Cited by 5 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. 1,8-Naphtholactam 130-00-7;Sax's Dangerous Properties of Industrial Materials;2004-10-15

2. B;Dictionary of Analytical Reagents;1993

3. Fifty years in chemical drug research;Collection of Czechoslovak Chemical Communications;1991

4. 3 Medicinal Chemistry of 1-Benzazepines;Progress in Medicinal Chemistry;1990

5. ChemInform Abstract: CYCLIC AMIDINES DERIVED FROM BENZ(C,D)INDOLE AND 4,5-DIHYDRO-3H-1-BENZAZEPINE INCLUDING SOME RELATED COMPOUNDS: SYNTHESIS AND PHARMACOLOGICAL SCREENING;Chemischer Informationsdienst;1985-12-24

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