3-Amino- and 5-Aminopyrazoles with Anticonvulsant Activity

Lankau, Hans‐Joachim; Menzer, Manfred; Rostock, A.; Arnold, Thomas; Rundfeldt, Chris; Unverferth, K.

doi:10.1002/(sici)1521-4184(19996)332:6<219::aid-ardp219>3.3.co;2-k

Cited by 3 publications

(4 citation statements)

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“…Besides, pyrazole nucleus comprises an important class in the heterocylic chemistry and it has pronounced pharmacological actions as anxiolytic [14] and anticonvulsant [15][16][17][18] activities. On the other hand much attention has been focused towards pyrazoles as antimicrobial [19 -21], antiviral [22] and anticancer [23] agents of the discovery of the natural pyrazole C-glycoside, pyrazofurin; 4-hydroxy-3-b-D-ribofuranosyl-1H-pyrazole-5-carboxamide.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antinociceptive-antimicrobial activities of some new amide derivatives of 3,5-di/-and 1,3,5-trimethylpyrazoles

Koçyığıt‐Kaymakcioğlu

Toklu

İkiz

et al. 2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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Some N-(3,5-di-/1,3,5-trimethylpyrazole-4-yl)-4-substitutedbenzamide derivatives were prepared as possible antiociceptiveantimicrobial agents. New amide derivatives (3-12) were synthesized by reacting 4-amino-3,5-di and 1,3,5-trimethylpyrazoles with 4-substitutedbenzoyl chlorides. Hotplate and tail-immersion tests were used for the determination of the antinociceptive activity. Morphine, was used as a standard test drug. All compounds were administered at a dose of 100 mg/kg ip and some of them had significant antinociceptive activity in both tests. Compound 10 (N-(1,3,5-trimethylpyrazole-4-yl)-4-bromobenzamide), was the most active one in both tests among the compounds. The antinociceptive activity of the compounds 10, 11 (N-(1,3,5-trimethylpyrazole-4-yl)-4-chlorobenzamide), and 12 (N-(1,3,5-trimethylpyrazole-4-yl)-4-fluorobenzamide), started at 30 minutes and continued up to 150 minutes in the hotplate test. Also compounds were tested for their in vitro antimicrobial activity, but exhibited weak antibacterial activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis and antinociceptive-antimicrobial activities of some new amide derivatives of 3,5-di/-and 1,3,5-trimethylpyrazoles

Koçyığıt‐Kaymakcioğlu

Toklu

İkiz

et al. 2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In these compounds, the strong anticonvulsant effects were displayed via blocking sodium channels. 16 Recent years, numbers of molecules containing pyrazole have been synthesized as potential anticonvulsant agents. [17][18][19][20] As hydrogen bonding forming functional group, pyrazole has become an important pharmacophore for anticonvulsants.…”

Section: -14mentioning

confidence: 99%

Design and Synthesis of Pyrazolyl Thiosemicarbazones as New Anticonvulsants

Deng¹,

Song²

2014

Bulletin of the Korean Chemical Society

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A series of pyrazolyl thiosemicarbazone derivatives were synthesized and evaluated for their anticonvulsant activity using the maximal electroshock (MES) method. Interestingly, all compounds prepared showed long duration of protection effect in the MES screens. Among them, compound 5b was considered as the most promising one with an ED50 value of 47.3 mg/kg, and a PI value of 4.8, which was superior to phenobarbital and valproate in the aspect of safety. Furthermore, compound 5b showed protection against seizures induced by pentylenetetrazole suggesting that compound 5b may exert anticonvulsant activity through GABAmediated mechanisms.

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“…Another novel and potent sodium channel blocker with good anticonvulsant activity and weak activity in ataxia models such as the rotarod is AWD 140-190 ( 47 ), a 3-aminopyrrole derivative. , An extensive SAR study around AWD 140-190 has been undertaken, taking into account the structures of other blockers such as lamotrigine ( 12 ), carbamazepine ( 24 ), and rufinamide ( 48 ), resulting in another series, 3-amino- and 5-aminopyrazoles, being synthesized . In particular, 4-chlorophenyl-3-(morpholin-4-yl)-1 H -pyrazole ( 49 ) was active in the MES model (ED 50 = 47 mg/kg ip) and showed no effect in the rotarod assay at 100 mg/kg.…”

Section: Therapeutic Applicationsmentioning

confidence: 99%

“…121,125 An extensive SAR study around AWD 140-190 has been undertaken, taking into account the structures of other blockers such as lamotrigine (12), carbamazepine (24), and rufinamide (48), resulting in another series, 3-amino-and 5-aminopyrazoles, being synthesized. 122 In particular, 4-chlorophenyl-3-(morpholin-4-yl)-1H-pyrazole (49) was active in the MES model (ED 50 ) 47 mg/kg ip) and showed no effect in the rotarod assay at 100 mg/kg. It will be interesting to follow these potent drug candidates into clinical trials.…”

Section: Therapeutic Applicationsmentioning

confidence: 99%