Synthesis and Anticonvulsant Activity of Some New Dioxolane Derivatives

Abstract

Summary In this study, ten 2-acetylnaphthalene derivatives with a dioxolane structure were synthesized and screened for their anticonvulsant activities. Dioxolane derivatives were prepared by the reaction with appropriate ethanone, glycol and p-toluensulphonic acid. The structures of the compounds were elucidated by IR, 1H-NMR and elemental analysis. Anticonvulsant activities of the compounds were determined by maximal electroshock seizure (MES) test and subcutaneous metrazol (ScMet.) test. The rotarod toxicity test was used for the assessment of neurological deficits. According to the activity studies compound 6 was found neurotoxic, compounds, 1, 4, 5, 7?9 were found protective against MES and 7?10 were found protective against ScMet. Compounds 2 and 3 were found inactive.

Crystal structure of 5′′-(4-chlorobenzylidene)-4′-(4-chlorophenyl)-1′-methyltrispiro[acenapthylene-1,2′-pyrrolidine-3′,1′′-cyclohexane-3′′,2′′′-[1,3]dioxane]-2(1H),6′′-dione

“…For the pharmacological properties of spiro compounds, see: Cravotto et al (2001); Raj et al (2003); Stylianakis et al (2003). For the activities of acenaphthylene derivatives, see: Selvanayagam et al Aepkers & Wü nsch (2005); Ozkanlı et al (2003); Liang et al (2006) Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek,2009); software used to prepare material for publication: publCIF (Westrip, 2010). Dioxalane compounds exihibit anti-HIV (Narayanasamy et al, 2007), antibacterial and antifungal (Kucuk et al, 2011),…”

“…antineoplastic (Shirai et al, 1998), antiviral (Bera et al, 2003), anaesthetic (Aepkers & Wünsch, 2005) and anticonvulsant activities (Ozkanlı et al, 2003). Dioxalane moieties play also a significant role in stabilizing the binding between the mutant HIV-1 RT and nucleoside triphosphate and act as nucleoside reverse transcriptase inhibitors (NRTIs) (Liang et al, 2006).…”

Spectroscopic Aspects, Structural Elucidation, Vibrational and Electronic Investigations of 2-Methoxy-1,3-Dioxolane: An Interpretation Based on DFT and QTAIM Approach

“…Aryl, alkyl, imidazole, triazole, pyrazole, benzimidazole, benzotriazole, oxypurine, pyrimidinyl and naphtyl groups are linked to 1,3-dioxolane ring at different positions like 2, 4 or 5. Depending on the position of the substituents, these compounds exhibit a broad spectrum of biological activities such as antifungal [4], antibacterial [5,6], antineoplastic [7], antiviral [8,9], anesthetic [10,11] and anticonvulstant ones [12]. According to the literature survey, several 1,3-dioxolanes are used co-monomer for manufacture of polyacetals and other polymers, solvent for chemical reactions (including inorganic salts), stabilizer for halogenated organic solvents and as a starting material or reagent for organic synthesis [13].…”

Synthesis and Biological Activity of New 1,3-Dioxolanes as Potential Antibacterial and Antifungal Compounds

“…Aryl, alkyl, imidazole, triazole, pyrazole, benzimidazole, benzotriazole, oxypurine, pyrimidinyl and naphtyl groups are linked to 1,3-dioxolane ring at different positions (2,4 or 5). Depending on the structure of the substituents, these compounds exhibit a broad spectrum of biological activities such as antifungal [4], antibacterial [5,6], antineoplastic [7], antiviral [8,9], anesthetic [10,11] and anticonvulstant ones [12]. …”