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

Abstract

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.

New Anti‐Seizure (Arylalkyl)azole Derivatives: Synthesis, In Vivo and In Silico Studies

“…In the X‐ray studies on (arylalkyl)azoles we reported previously, the oxime, oxime ether, and oxime ester functions were found in the Z configuration . Moreover, 1 H NMR spectra of the remaining compounds were in accordance with 4d regarding the chemical shifts of the protons sensitive to changes of configuration.…”

“…The alkyl bridge usually includes substitutions often referred to as “tail” . Previously, Karakurt et al designed and prepared several oxime ether derivatives of 1‐(2‐naphthyl)‐2‐(1 H ‐1,2,4‐triazol‐1‐yl)ethanone, carboxylic ester derivatives of nafimidone alcohol , and oxime ester derivatives of nafimidone , some of which were showed to be potent anticonvulsants. Similarly, we reported a set of 1‐(2‐naphthyl)‐2‐(1 H ‐1,2,4‐triazol‐1‐yl)ethanone oxime (NTO) esters with potent anticonvulsant properties, with predicted GABA A R and VGSC affinities derived from molecular docking studies .…”

Synthesis, anticonvulsant screening, and molecular modeling studies of new arylalkylimidazole oxime ether derivatives

“…(Arylalkyl)azoles (AAAs) emerged as a class of antiepileptic compounds with nafimidone and denzimol. Various chemical modifications on AAAs have shown that those containing oxygen groups on the alkyl chain between the naphthalene and the azole rings are the most active (Karakurt, Alagöz, Sayo glu, Calıs, & Dalkara, 2012;Karakurt et al, 2001Karakurt et al, , 2006Karakurt, Özalp, Işık, Stables, & Dalkara, 2010;Ozdemir et al, 2015;Robertson et al, 1986;Sari et al, 2016Sari et al, , 2017.…”

Synthesis and Antimicrobial Activity of 2‐(4‐(Hydroxyalkyl)‐1H‐1,2,3‐triazol‐1‐yl)‐N‐substituted propanamides

“…In this sequence, five membered heterocyclic ring systems like triazole gained appreciable attention due to wide range of biological activities . Triazoles have been reported to exhibit broad biological spectrum as anticancer , anti‐HIV , antitubercular , antioxidant , antitrypanosomal , antimicrobial , anticonvulsant , antimalarial , antihistamines , antitumor , immune potentiators , antiviral , anti‐inflammatory and , agents. In addition to aforementioned medicinal value, several members of the 1,2,3‐triazoles family also show interesting industrial applications in form of corrosion inhibitions , dyes , and optical brightners .…”