1-(Naphthylalkyl)-1H-imidazole derivatives, a new class of anticonvulsant agents

Walker, K.; Wallach, Marshall B.; Hirschfeld, Donald R.

doi:10.1021/jm00133a015

Cited by 76 publications

(38 citation statements)

References 4 publications

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“…Compounds with small alkyl groups such as methyl, ethyl, propyl, allyl were active in l100 mg kg -1 dose levels whereas larger groups such as benzyl and substituted benzyl molecules resulted in a lack of anticonvulsant activity and a decrease in toxicity. Although it has been reported in the literature that the activity of nafimidone and denzimol, as well as the other (arylalkyl)imidazoles, are highly MES specific in mice, most of the active compounds 2-6 exhibited activity against both MES and scMet induced seizures [5,8]. This data is in accordance with our previous studies [9,10].…”

Section: Anticonvulsant Activitysupporting

confidence: 91%

Synthesis of Some Oxime Ether Derivatives of 1‐(2‐Naphthyl)‐2‐(1,2,4‐triazol‐1‐yl)ethanone and Their Anticonvulsant and Antimicrobial Activities

Karakurt

Aytemir

Stables

et al. 2006

Archiv der Pharmazie

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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 exhibited both anticonvulsant and antimicrobial activities, the O-arylalkyl substituted compounds were found to be inactive in both screening paradigms.

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Section: Anticonvulsant Activitysupporting

confidence: 91%

Synthesis of Some Oxime Ether Derivatives of 1‐(2‐Naphthyl)‐2‐(1,2,4‐triazol‐1‐yl)ethanone and Their Anticonvulsant and Antimicrobial Activities

Karakurt

Aytemir

Stables

et al. 2006

Archiv der Pharmazie

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“…Compounds II and III were also active but their activities were less than the anticonvulsant effect of phenobarbital. This result is in consistance with the findings of Niardi et al (10) for N-(p-tolyl) derivatives as well.…”

supporting

confidence: 93%

Preliminary Studies on a New Group of Imidazole Derivatives with Anticonvulsant Activity : Antikonvülzan Aktivite Gösteren İmidazol Türevi Yeni Bir Grup Madde ile Yapılan Ön Çalışmalar

Üstünes¹,

Pabuççuoğlu²,

Berkan³

et al. 1989

Ankara Universitesi Eczacilik Fakultesi Dergisi

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SUMMARYIn a preliminary study, the anticonvulsant profiles of three compounds having the basic structures w-(l H-l-imidazolyl)-N-(p-substituted phenyl) acetamide, propionamide and butiramide with methyl substituents on the para position of benzene ring have been evaluated in mice in comparison with the standart antiepileptic drug, phenobarbital. The anticonvulsant activities of these compounds against maximal electroshock induced seizures were comparable to or less than that of phenobarbital. Further studies on the anticonvulsant activities and the toxicological characteristics of these compounds are now in progress in our department. ÖZETBenzen halkasının para pozisyonunda metil sübstitüentleri taşıyan w-(lH-l-imidazolil)-N-(p-sübstitüefenil) asetamid, propioamid ve bütiramid yapısındaki üç bileşiğin antikonvülzan aktiviteleri standart antiepileptik bir ilaç olarak seçilen fenobarbitalle karşılaştır-malı olarak bir ön çalışma halinde araştırılmıştır. Antikonvülzan aktivitenin araştırılmasında maksimal elektroşok testi kullanılmış ve elektroşokla oluşturulan konvülziyonlara karşı sentezlenen bileşiklerin feRedaksiyona verildiği tarih: 17.6.1988

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“…2-Bromo-1-(naphthalen-2-yl)ethanone (7) was prepared according to the literature method [13]. Melting points were determined on a Kofler hot stage apparatus and are uncorrected.…”

Section: Experimental Chemistrymentioning

confidence: 99%

“…A mixture of compound 8a (0.55 mmol), quinolone 1-3 (0.5 mmol) and NaHCO 3 (0.5 mmol) in DMF (5 ml) was stirred at room temperature for 72 h. After consumption of quinolone, water (20 ml) was added and the precipitate was filtered, washed with water and crystallized from methanolchloroform (9:1) to give compounds 5d-f. 11.08 (s, NOH, E-isomer), 11.58 (s, NOH, Z-isomer), 15.17 (s, 1H, COOH). 13 13 General procedure for the synthesis of 7-[4-[2-(naphthalen-2-yl)-2-methoxyimino ethyl]piperazinylquinolones (5g-i). To a stirred solution of 2-bromo-1-(naphthalen-2-yl)ethanone 7 (498 mg, 2.0 mmol) in methanol (8 ml) at room temperature, was added 25% solution of Omethylhydroxylammonium chloride in diluted HCl (1002 mg, 3.0 mmol).…”

Section: General Procedures For the Synthesis Of 7-[4-[2-(naphthalen-2mentioning

confidence: 99%

Synthesis and antibacterial activity of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones

Shafiee

Emami

Ghodsi

et al. 2009

JICS

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A series of N- [2-(2-naphthyl)ethyl]piperazinyl quinolones containing a carbonyl related functional groups (oxo-or oxyimino-) on the ethyl spacer was synthesized and evaluated for antibacterial activity. The synthesis of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones was achieved through the versatile and efficient synthetic route that involved reaction of piperazinyl quinolones with appropriate Į-bromoketone or Į-bromooxime derivatives. The structures of new compounds were confirmed by elemental analysis, IR and NMR spectra. Antibacterial data indicated that some of the new N-[2-(2-naphthyl)ethyl]piperazinyl quinolones showed good antibacterial activity and modification of the position 8 and N-1 substituent on quinolone ring, and ethyl spacer functionality produced significant changes in activity against Gram-positive and Gram-negative bacteria.

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1-(Naphthylalkyl)-1H-imidazole derivatives, a new class of anticonvulsant agents

Cited by 76 publications

References 4 publications

Synthesis of Some Oxime Ether Derivatives of 1‐(2‐Naphthyl)‐2‐(1,2,4‐triazol‐1‐yl)ethanone and Their Anticonvulsant and Antimicrobial Activities

Synthesis of Some Oxime Ether Derivatives of 1‐(2‐Naphthyl)‐2‐(1,2,4‐triazol‐1‐yl)ethanone and Their Anticonvulsant and Antimicrobial Activities

Preliminary Studies on a New Group of Imidazole Derivatives with Anticonvulsant Activity : Antikonvülzan Aktivite Gösteren İmidazol Türevi Yeni Bir Grup Madde ile Yapılan Ön Çalışmalar

Synthesis and antibacterial activity of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones

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