Synthesis and Biological Activity of 2‐Adamantanone Oxime Carbamate Derivatives

Abstract

The synthesis of a number of new 2-adamantanone oxime carbamate derivatives (7a-h) is described. When tested in the carrageenin-induced rat paw edema assay, some of the compounds exerted moderate anti-inflammatory activity. In addition, the title 2-adamantanone oxime carbamates showed in vitro antifungal activity against yeast and systemic mycoses and dermatophytes. Synthese uad biologisehe AktivitZt von 2-Adamantanonoxim-CarbamatenEs wird die Synthese von einigen neuer Carbamaten des Adamantanon-2 Oxims beschrieben. Bei der Prufung des durch Carrageenin ausgelosten Pfotenodem-Modell der Ratte zeigten einige Derivate mafiige entzundungshemmende Wirkungen. AuJ3erdem wirkten die im Titel genannten Adamantanon-2-oxim-Carbamate pilzhemmend in vitro gegen Hefen, systematische Mykosen und Dermatophyten.Over the years, a number of oxime ether derivatives of acetophenone'-E), (iso)phthalaldehydic I), benzophenonei2, and benzyl methyl ketone'4) have been prepared and studied for biological activity. Most notably, anti-inflammatory1 9,12-14), as well as immunosuppresdve9~ lo), a n a l g e s i~~-~.~-~, !*-I4), antipyreticg), anticonvulsant6, l4) and thymolytici4) activities were found to be associated with the presence of an oxime ether group. Furthermore, a series of phenylcyanomethylene q~inone oxime ether derivatives 1 were synthesized by Seidl and Nesemannl5) and reported to possess antiallergic, analgesic, fungicidal and parasiticidal activities.As reported by van Dijk and Zwagemakerss) a number of new 2-hydroxyethyl and carboxyalkyl ethers of aromatic oximes displayed a potent anti-inflammatory activity in the carrageenin-induced rat paw edema assay. One of their compounds, cloximate 12) was selected to undergo clinical evaluation as anti-inflammatory agent. However, relatively very little has been reported on the synthesis and biological activity of 2-adamantanone oxime analogs. Thus, the O-(2-dimethylaminoethyl)-2-adamantanone oxime (CM 54903) (3) has shown psychotropic activityi6). 1 2 NOCR tI NOCH*CHzN( CH3) 2 3 4 0 0365-6233/87/0505-465 $02.50/0 0 VCH Verlagsgesellschaft mbH, D-6940 Weinheim, 1987Georgiev and coworkers Arch. Pharm.

In Silico and In Vitro Experimental Studies of New Dibenz[b,e]oxepin-11(6H)one O-(arylcarbamoyl)-oximes Designed as Potential Antimicrobial Agents

“…New N-methyl-N-(3-trifluoromethylphenylsulfenyl)-carbonyloxime carbamates display strong insecticidal, acaricidal, nematicidal, fungicidal and bactericidal properties [16]. Tricyclic compounds such as the 2-adamantanone oxime carbamates showed in vitro antifungal activity against yeast and systemic mycoses and dermatophytes [17]. 2-Bromo-6-(4-pyridin-2-yl-piperazin-1-yl)-indeno [2,1-c]quinolin-7-one N,N-dimethylcarbamoyl oxime showed tuberculostatic activity, being active against Mycobacterium tuberculosis H37Rv [18].…”

Unexpected Simple and Catalyst‐Free Condensation Reaction of Spiro Dihydrofurans with 2,4‐Dinitrophenylhydrazine, Thiosemicarbazide, and Hydroxylamine for the Synthesis of Novel Corresponding 4,4,6′,6′‐Tetramethyl‐3′‐aryl‐3′,5′,6′,7′‐tetrahydrospiro[cyclohexane‐1,2′‐indole]‐4′,6(1′H)‐diones: Crystal Structure

“…Some thiosemicarbazone derivatives have exhibited antiviral activity and potent anticancer effect . Besides, oxime derivatives of aldehydes and ketones also are important and have pharmaceutical behavior .…”

Thermodynamic Investigation of Tripeptide Tyr-Aaa-Gly in Gas Phase in Different Solvents

“…antiviral 2 , antibacterial 3 , antifungal 4 , antiinflammatory 5 , central nervous 6 and 11b-HSD1 inhibitory activities 7 are the most important ones. Due to the high lipophilicity of adamantane, the incorporation of the adamantyl moiety into several molecules results in compounds with relatively high lipophilicity, which in turn can modify the biological availability of these molecules.…”