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Synthesis of Some Oxime Ether Derivatives of 1‐(2‐Naphthyl)‐2‐(1,2,4‐triazol‐1‐yl)ethanone and Their Anticonvulsant and Antimicrobial Activities
Author(s) -
Karakurt Arzu,
Aytemir Mutlu D.,
Stables James P.,
Özalp Meral,
Betül Kaynak F.,
Özbey Süheyla,
Dalkara Sevim
Publication year - 2006
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200500248
Subject(s) - chemistry , oxime , anticonvulsant , antimicrobial , organic chemistry , medicinal chemistry , stereochemistry , medicine , psychiatry , epilepsy
In this study, oxime and oxime ether derivatives of [1‐(2‐naphthyl)‐2‐(1,2,4‐triazol‐1‐yl)ethanone] were prepared as potential anticonvulsant and antimicrobial compounds. The oxime was synthesized by the reaction of ketone and hydroxylamine hydrochloride. O ‐Alkylation of the oxime by various alkyl halides gave the oxime ether derivatives. Anticonvulsant activity of the compounds was determined by maximal electroshock and subcutaneous metrazole tests in mice and rats according to procedures of the Anticonvulsant Screening Program of National Institutes of Health. Neurotoxicity was determined by the rotorod test in mice and the positional sense test, gait and stance test in rats. In addition to anticonvulsant tests, all compounds were also evaluated against the following microorganisms: S. aureus , E. coli , P. aeruginosa , E. faecalis , C. albicans , C. parapsilosis, and C. krusei using microdilution broth method for possible antibacterial and antifungal activities. Although most of the O ‐alkyl substituted oxime ethers 2 ‐ 6 exhibited both anticonvulsant and antimicrobial activities, the O ‐arylalkyl substituted compounds 7–10 were found to be inactive in both screening paradigms.