Synthesis and antifungal activity of novel (1-aryl-2-heterocyclyl)ethylideneaminooxymethyl-substituted dioxolanes

Baji, H; Flammang, M.; Kimny, Tan; Gasquez, F.; Compagnon, PL; Delcourt, A.

doi:10.1016/0223-5234(96)88277-8

Cited by 34 publications

(19 citation statements)

References 22 publications

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“…The oxime (c) was synthesized by the reaction of the ketone and hydroxylamine hydrochloride [15]. O-Alkylation of the oxime with appropriate alkyl halides gave the oxime ether derivatives (d) (Scheme 1) [11].…”

Section: Resultsmentioning

confidence: 99%

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: Resultsmentioning

confidence: 99%

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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“…Nafi midone ( 2 ) was obtained by bromination of 1-(2-naphthyl)ethanone ( 3 ) in presence of acetic acid according to Immediata method [ 15 ] , to aff ord 1-(2-naphthyl)-2-bromoethanone ( 4 ) and then subsequent treatment with imidazole in presence of dimethylformamide. The starting compound 1-(2-naphthyl)-2-(imidazol-1-yl)ethanone oxime ( 5 ) was synthesized by treating 2 with hydroxylamine hydrochloride as reported earlier [ 18 ] . The compound has been assigned Z confi guration on the basis of earlier reports, which state that methylene protons present between oxime group and imidazole ring resonates as a singlet at δ 5.3 in case of Z isomer in comparison to E isomer, where an upfi eld shift at 5.0 ppm was observed for methylene protons due to shielding eff ects [ 14 , 18 ] .…”

Section: ▼ Chemistrymentioning

confidence: 99%

Synthesis and Anticonvulsant Activity of O-alkylated Derivatives of 1-(2-naphthyl)-2-(imidazol-1-yl)ethanone Oxime

Bansal

Chauhan

Sharma

2012

Arzneimittelforschung

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In this study, O-alkylated derivatives of nafimidone oxime chemically, 1-(2-naphthyl)-2-(imidazol-1-yl)ethanone oxime have been synthesized as potential anticonvulsant compounds. O-alkylation of the oxime using hydrochlorides of various dialkylaminoethyl chlorides, methyl chloroacetate and alkyl dihalides gave the O-alkylated derivatives. Anticonvulsant activity of the compounds was determined against pentylenetetrazole induced convulsions in mice. The newly synthesized compounds exhibited moderate to significant activity compared to diazepam.

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“…The stereochemical assignment of the oxime derivatives 5d-l was elucidated by 1 H and 13 C NMR spectroscopy. It is known from the literature that the assignment of geometry in Į-substituted ethanone oximes is possible on the basis of the chemical shifts of the methylene attached to the imino-group [15][16][17][18]. The selected 1 H and 13 C NMR spectroscopic data of Z and E-isomers are presented in Table 1.…”

Section: Chemistrymentioning

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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Synthesis and antifungal activity of novel (1-aryl-2-heterocyclyl)ethylideneaminooxymethyl-substituted dioxolanes

Cited by 34 publications

References 22 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

Synthesis and Anticonvulsant Activity of O-alkylated Derivatives of 1-(2-naphthyl)-2-(imidazol-1-yl)ethanone Oxime

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

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