Synthesis and Anticonvulsant Activity of 1-Substituted-7-Benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Cui, Li; Xie, Zhi Feng; Piao, Hu‐Ri; Li, Gao; Chai, Kyu Yun; Quan, Zhe‐Shan

doi:10.1248/bpb.28.1216

Cited by 30 publications

(16 citation statements)

References 17 publications

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“…Quinoline anticonvulsant compounds. (Table 1), with TD50 values of greater than 300 mg/kg which was better than most of the market drugs [13].…”

Section: The Quinoline Functional Groupmentioning

confidence: 92%

“…Anticonvulsant activity was evaluated in the MES test, sc-Met test, and rotarod neurotoxicity test. The safest compound was 2 (Table 1), with TD 50 values of greater than 300 mg/kg which was better than most of the market drugs [13].…”

Section: The Quinoline Functional Groupmentioning

confidence: 96%

“…Quinoline has been found to possess anti-malarial, antibacterial, antifungal, anthelmintic, cardiotonic, anticonvulsant, anti-inflammatory, and analgesic activity. Our laboratory has studied a lot of quinoline derivatives for antiepileptic activity [12][13][14][15][16][17][18][19][20][21][22][23].…”

Section: The Quinoline Functional Groupmentioning

confidence: 99%

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Current Research on Antiepileptic Compounds

2015

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Epilepsy affects about 1% of the world's population. Due to the fact all antiepileptic drugs (AEDs) have some undesirable side effects and about 30% of epileptic patients are not seizure-free with the existing AEDs, there is still an urgent need for the development of more effective and safer AEDs. Based on our research work on antiepileptic compounds and other references in recent years, this review covers the reported work on antiepileptic compounds which are classified according to their structures. This review summarized 244 significant anticonvulsant compounds which are classified by functional groups according to the animal model data, although there are some limitations in the data. This review highlights the properties of new compounds endowed with promising antiepileptic properties, which may be proven to be more effective and selective, and possibly free of unwanted side effects. The reviewed compounds represent an interesting possibility to overcome refractory seizures and to reduce the percentage of patients with a poor response to drug therapy.

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“…Quinoline anticonvulsant compounds. (Table 1), with TD50 values of greater than 300 mg/kg which was better than most of the market drugs [13].…”

Section: The Quinoline Functional Groupmentioning

confidence: 92%

Section: The Quinoline Functional Groupmentioning

confidence: 96%

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Current Research on Antiepileptic Compounds

2015

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“…8 In the followed studies, we synthesized several [1,2,4]triazolo [4,3-a]quinoline derivatives and tested their anticonvulsant activities. We found that 1-substituted-7-benzyloxy-4,5-dihydro- [1,2,4]triazolo [4,3-a]quinolines, 9 7-alkoxyl-4,5-dihydro- [1,2,4]triazolo [4,3-a]quinolines 10 and 5-alkoxy- [1,2,4] triazolo [4,3-a]quinolines [In press] had significant anticonvulsant activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Studies on Anticonvulsant and Antidepressant Activities of 5-Alkoxy-tetrazolo[1,5-a]quinolines

Deng¹,

Wei²,

Song³

et al. 2010

Bulletin of the Korean Chemical Society

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A series of 5-alkoxy-tetrazolo [1,5-a]quinolines were synthesized to evaluate their anticonvulsant and antidepressant effects. Anticonvulsant effects and neurotoxicity of the compounds when injected intraperitoneally to mice were determined by a maximal electroshock (MES) test and a rotarod test, respectively. Only three of the synthesized compounds (4a, 4b, 4c) displayed anticonvulsant activity at a dose of 300 mg/kg. Most of the compounds significantly reduced immobility times during the forced swimming test (FST) at a dose of 100 mg/kg, indicative of antidepressant activity. Among the compounds, 5-(2-fluorobenzyloxy)tetrazolo[1,5-a]quinoline (4k) reduced immobility time by 66.85% at 30 mg/kg compared with the same dose of Fluoxetine, which reduced immobility time by 52.30%. According to the results of the 5-Hydroxytryptophan induced head-twitch test and yohimbine toxicity potentiation test, the noradrenergic system seems not to be involved in the antidepressant-like effect of compound 4k while the serotonergic system seems a little to be involved.

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“…Compounds 3a -3o were prepared by the reaction of compounds 2a -2o with phosphorous pentasulfide in acetonitrile in the presence of triethylamine [15]. Since compound 2p (6-(2,4-dichlorobenzyloxy)quinoline-2-one) did not dissolve in acetonitrile, dioxane was used as solvent and compound 2p and phosphorous pentasulfide reacted in dioxane with stirring and refluxing for 24 h, which produced 3p (6-(2,4-dichloro-benzyloxy)-quinoline-2-thione) with a moderate yield.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐inflammatory Activity Evaluation of Novel 7‐Alkoxy‐1‐amino‐4,5‐dihydro[1,2,4]triazole[4,3‐a]quinolines

Sun

Wei

Chai

et al. 2008

Archiv der Pharmazie

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In this study, a novel series of 7-alkoxy-1-amino-4,5-dihydro[1,2,4]triazole[4,3-a]quinolines were synthesized by using 6-hydroxy-3,4-dihydro-2(1H)-quinolone as the starting material. These compounds were evaluated for anti-inflammatory activity through monitoring their ability to inhibit xylene-induced ear edema in mice. Some of the tested compounds exhibited significant activity, and the compounds 5f (7-(benzyloxy)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinolin-1-amine) and 5i (7-(p-chlorobenzyloxy)-4,5-dihydro[1,2,4]triazolo[4,3-a]quinolin-1-amine) showed the highest anti-inflammatory activity (52% and 58% inhibition, respectively, at 2 h pre-administration) which were comparable to or even slightly more potent than the reference drug ibuprofen (55%). Furthermore, the structure-activity relationship of these 1,2,4-triazole quinolines was demonstrated.

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Synthesis and Anticonvulsant Activity of 1-Substituted-7-Benzyloxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Abstract: ؊1 and 13, respectively. The PI value of compound 4g was better than that of most marketed drugs. Structure-activity relationships are also described in this paper.

Cited by 30 publications

References 17 publications

Current Research on Antiepileptic Compounds

Current Research on Antiepileptic Compounds

Synthesis and Studies on Anticonvulsant and Antidepressant Activities of 5-Alkoxy-tetrazolo[1,5-a]quinolines

Synthesis and Anti‐inflammatory Activity Evaluation of Novel 7‐Alkoxy‐1‐amino‐4,5‐dihydro[1,2,4]triazole[4,3‐a]quinolines

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