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F Eiden

Publications and source records attributed to F Eiden.

At least 19 recordsLinked to original sources
PubMed1992

[CNS-agents: synthesis and properties of 3-anilino-8-oxatropanes].

Reaction of the 8-oxabicyclooctenone and -octanone derivatives 3 and 4 with aniline and metal hydrides yields the 3 alpha-isomers of the aniline derivatives 7 and 8, preferably. The configuration can be determined by NMR-spectroscopy and by cyclization to the scopoline analogue 9b. Depending on the N-substitution the pyran rings of the alpha-isomers are flattened (7,8) or deformed to give a boat conformation (10,11,13). The conformationally restricted aniline derivative 18 can be obtained from 4 with 2-aminobenzaldehyde and diborane, trans-configuration is preferred in 18. Some substrates reveal CNS-effects in mice.

Analgesics↗
PubMed1992

[Synthesis, reactions, and CNS-actions of 6,7-annealed 8-oxatropane derivatives].

The butadiene derivatives 10a-c react with the oxa-bicyclooctanone 9 to give the cyclohexene annulated oxatropanes 11a-c. The acetoxyderivatives 11b and 11c can be transformed into the cyclohexadiene or benzene derivatives 13 and 12, respectively. 11a reacts with HN3 to afford the tricyclic oxazepanone 14 which can be reduced to give 15a; the oxime-tosylate 16b reacts with Al(CH3)3/DIBALH to yield the oxazepane 15c. Treatment of the oxabicyclooctanes 9 and 19 with benzonitrile oxide or diazomethane affords the isoxazoline or pyrazoline annulated oxatropanes 21, 22, and 20, respectively. 21 was reduced to the amino alcohol 23. 15c and 23 show CNS-activity in the mouse.

Analgesics↗
PubMed1990

[5,6-Dihydro-6-methoxy-2H-pyran-3(4H)-one, a building block for the synthesis of CNS agents].

The phenyl-pyranyl-piperidin derivative 5, prepared from the title compound 2, shows a strong stimulating effect in animals. Reactions of 2 with 2-amino-phenylcarbonyl derivatives or phenylhydrazine can lead to [3,2-b] as well as [3,4-b] annulated pyranes. Regioselective reactions in 2- or 4-position of 2 are successful after conversion to the enamine 14a, the silylenolether 24 and the lithioenamine 29. Cycloadditions, cyclocondensations or electrophilic aldoleractions yield the pyrano-pyranes 16 and 19a, resp., or the hydroxybenzyl- and hydroxybenzylidenpyranes 25 and 30, resp.

Animals↗
PubMed1990

[Synthesis and CNS- activity of cis-pyrano[2,3-b]-[1,4]dioxane derivatives ].

The alcohols 2, the amines 5, 7 and 10, the indole- and quinoline-derivatives 13 and 14, the enamines 3 and 4 and the silylenolethers 17 and 18 were prepared starting with the title compound 1. The 1-(7-phenyl-7-pyranodioxinyl)-piperidines 10-cis and 10-trans show striking CNS-activity. The transisomer is about twice as active as the cis-isomer.

Animals↗
PubMed1989

[Synthesis and bronchodilator action of 4-(methoxycarbonylalkylsulfinyl)-4-pyrrol carboxylic esters].

The dihydro-dimethoxyfuran carboxylic ester 3 reacts with different mercaptoalkyl carboxylates to give the carbomethoxyalkylthio-tetrahydrofuran carboxylic esters 4. Methanol elimination of 4 yields the dihydrofuran derivatives 5. 4 and 5 can be oxidized to afford the sulfoxides 6 and the sulfones 7, respectively. 4 reacts with primary amines to give the title compounds 8. Derivatives of 8 can be cyclized to afford the thienopyrroles 11 and 12 as well as the thienopyranopyrrole 14. The mercaptopyrrole carboxylic ester 10 is obtained from 8f by elimination of propenic acid. 8e shows bronchodilatoric activity in low concentration.

Animals↗