The Significance of the Imidazole Ring in Anticonvulsant Activity of (Arylalkyl)imidazoles

Abstract

The imidazole ring in nafimidone I 1 -(2-naphthyl)-2-( 1 -imidazolyl)ethan-one1 was substituted with various grouos to investigate the significance Die Rolle des Imidazolrings in antikonvulsiv wirksamen (Arylalky1)imidazolen -.--Der Imidazolring von NafimidonI 1 -(2-naphthyl)-2-( 1 -imidazolyl)ethanonl wurde durch verschiedene Gruppen substituiert und die Rolle des Imidazolrings auf die antikonvulsive Wirkung untersucht. Dazu wurden einige 2-Acetylnaphthaline und ihre reduzierten Derivate synthetisiert. Als Reduktionsmittel wurde NaBH, verwendet. Die antikonvulsiven Eigenschaften dieser Verbindungen wurden mit Phase I Tests eines Pro-of the imidazole ring in anticonvulsant activity. For this purpose, some 2acetylnaphthalene derivatives and their reduction products were synthesized. Several N-alkylation methods were used to prepare 2-acetylnaphthalenes. NaBH, was used to synthesize their reduction products. Anticonvulsant activities of these compounds were determined by phase I tests of Antiepileptic Drug Development Programme.gramms zur Entwicklung antikonvulsiver Arzneistoffe bestimmt.Although there are a number of antiepileptic drugs available in the market, the development of more efficient compounds with less toxicity is still Arch. Pharm. (Weinheim) 321,841-846 (1988) 0 VCH Verlagsgesellschaft mbH, 0-6940 Weinheim. 1988 0365-6233/88/1212-0841$02.5OfO

Evaluation of Flavonoid and Resveratrol Chemical Libraries Reveals Abyssinone II as a Promising Antibacterial Lead

“…1‐(Naphthalen‐2‐yl)‐2‐(1,2,4‐1 H ‐triazol‐1‐yl)ethanone hydrochloride (61⋅HCl): Recrystallization of the residue from 2‐propanol afforded the free base 61 as a yellow solid, which was converted by treatment with 37 % aqueous HCl in acetone into the hydrochloride, which was obtained as a white solid (236 mg, 17 %); mp: 203–205 °C (EtOH) (lit 56. mp: 196–197 °C); 1 H NMR (400 MHz, [D 6 ]DMSO): δ =6.22 (s, 2 H), 7.64–7.76 (m, 2 H), 7.99–8.07 (m, 2 H), 8.10 (d, J =8.8 Hz, 1 H), 8.16 (d, J =8.0 Hz, 1 H), 8.34 (s, 1 H), 8.85 (s, 1 H), 8.96 ppm (s, 1 H); 13 C NMR (100 MHz, [D 6 ]DMSO): δ =55.8, 123.3, 127.3, 127.9, 128.7, 129.2, 129.7, 130.6, 131.3, 132.1, 135.5, 145.2, 149.6, 192.1 ppm HRMS‐ESI m / z [ M −Cl] + calcd for C 14 H 12 N 3 O: 238.0980, found: 238.0985.…”

Conventional and Microwave Assisted Synthesis of New Triazole Derivatives and Evaluation of Their Antimicrobial Activities

“…The reaction mixture was stirred for two hours in an ice bath, then overnight at room temperature. The reaction medium was poured into ice water, and the resulting precipitate was filtered and purified by crystallization from ethyl acetate/ethanol [21].…”

Synthesis and Anticonvulsant Activity of Some New Dioxolane Derivatives

“…The benzene solution was dried (azeotroped), filtered and treated with gas HC1. The precipitated salt was crystallized from methanol [9].…”

“…The mixture was heated for 6 h under reflux; methanol was evaporated. The crude product was crystallized from benzene [9].…”

“…According to the previous structure-activity relationship studies, the most desirable anticonvulsant activity appeared with a lipophilic aryl group and oxygen containing small substituent in the alkylene bridge and imidazole ring [4][5][6]. These and our previous studies [9,11] on these imidazole containing anticonvulsant drugs have prompted us to study some arylalkylimidazoles having dioxolane group as the alkylene bridge between aryl group and azole ring.…”