Synthesis and anticonvulsant activity of some novel 7-(benzylamino) -1H-benzo[b][1,4]diazepine-2,4(3H, 5H)-dione derivatives
A series of novel 7-(benzylamino)-1 H -benzo[b][1,4]diazepine-2,4(3 H , 5 H )-dione derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, subcutaneous pentylenetetrazol (scPTZ) test, and their neurotoxicity was evaluated by the rotarod...
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| Veröffentlicht in: | Medicinal chemistry research 2018-02, Vol.27 (2), p.642-652 |
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| creator | Shao, Yun-Peng Han, Rong-Bi Wu, Hui-Fan Piao, Feng-Yu |
| description | A series of novel 7-(benzylamino)-1
H
-benzo[b][1,4]diazepine-2,4(3
H
, 5
H
)-dione derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, subcutaneous pentylenetetrazol (scPTZ) test, and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The study showed that the compound
8c
(7-(4-fluorobenzylamino)-1,5-dimethyl-1
H
-benzo[b][1,4]diazepine-2,4(3
H
,5
H
)-dione) was the most promising compound, with median effective dose (ED
50
) of 36.5 mg/kg, and protective index (PI) values of 4.5 in the MES test. In the scPTZ test, compound
8c
also exhibited better anticonvulsant activity (ED
50
= 68.2 mg/kg), and the ED
50
values of compounds
8c
were smaller than that of the reference antiepileptic drugs carbamazepine (ED
50
> 100 mg/kg), phenytoin (ED
50
> 300 mg/kg), and sodium valproate (ED
50
= 149 mg/kg). The possible structure activity relationship was discussed. |
| doi_str_mv | 10.1007/s00044-017-2089-1 |
| format | Article |
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H
-benzo[b][1,4]diazepine-2,4(3
H
, 5
H
)-dione derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, subcutaneous pentylenetetrazol (scPTZ) test, and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The study showed that the compound
8c
(7-(4-fluorobenzylamino)-1,5-dimethyl-1
H
-benzo[b][1,4]diazepine-2,4(3
H
,5
H
)-dione) was the most promising compound, with median effective dose (ED
50
) of 36.5 mg/kg, and protective index (PI) values of 4.5 in the MES test. In the scPTZ test, compound
8c
also exhibited better anticonvulsant activity (ED
50
= 68.2 mg/kg), and the ED
50
values of compounds
8c
were smaller than that of the reference antiepileptic drugs carbamazepine (ED
50
> 100 mg/kg), phenytoin (ED
50
> 300 mg/kg), and sodium valproate (ED
50
= 149 mg/kg). The possible structure activity relationship was discussed.</description><identifier>ISSN: 1054-2523</identifier><identifier>EISSN: 1554-8120</identifier><identifier>DOI: 10.1007/s00044-017-2089-1</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Anticonvulsants ; Antiepileptic agents ; Biochemistry ; Biomedical and Life Sciences ; Biomedicine ; Carbamazepine ; Cell Biology ; Convulsions & seizures ; Derivatives ; Diketones ; Neurotoxicity ; Original Research ; Pharmacology/Toxicology ; Phenytoin ; Sodium valproate ; Valproic acid</subject><ispartof>Medicinal chemistry research, 2018-02, Vol.27 (2), p.642-652</ispartof><rights>Springer Science+Business Media, LLC 2017</rights><rights>Copyright Springer Science & Business Media 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-d23e0356f8b83a8dde7bcfe3fb34a803d132a21123a44a99742d948d978a2fb93</citedby><cites>FETCH-LOGICAL-c316t-d23e0356f8b83a8dde7bcfe3fb34a803d132a21123a44a99742d948d978a2fb93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00044-017-2089-1$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00044-017-2089-1$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Shao, Yun-Peng</creatorcontrib><creatorcontrib>Han, Rong-Bi</creatorcontrib><creatorcontrib>Wu, Hui-Fan</creatorcontrib><creatorcontrib>Piao, Feng-Yu</creatorcontrib><title>Synthesis and anticonvulsant activity of some novel 7-(benzylamino) -1H-benzo[b][1,4]diazepine-2,4(3H, 5H)-dione derivatives</title><title>Medicinal chemistry research</title><addtitle>Med Chem Res</addtitle><description>A series of novel 7-(benzylamino)-1
H
-benzo[b][1,4]diazepine-2,4(3
H
, 5
H
)-dione derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, subcutaneous pentylenetetrazol (scPTZ) test, and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The study showed that the compound
8c
(7-(4-fluorobenzylamino)-1,5-dimethyl-1
H
-benzo[b][1,4]diazepine-2,4(3
H
,5
H
)-dione) was the most promising compound, with median effective dose (ED
50
) of 36.5 mg/kg, and protective index (PI) values of 4.5 in the MES test. In the scPTZ test, compound
8c
also exhibited better anticonvulsant activity (ED
50
= 68.2 mg/kg), and the ED
50
values of compounds
8c
were smaller than that of the reference antiepileptic drugs carbamazepine (ED
50
> 100 mg/kg), phenytoin (ED
50
> 300 mg/kg), and sodium valproate (ED
50
= 149 mg/kg). The possible structure activity relationship was discussed.</description><subject>Anticonvulsants</subject><subject>Antiepileptic agents</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Carbamazepine</subject><subject>Cell Biology</subject><subject>Convulsions & seizures</subject><subject>Derivatives</subject><subject>Diketones</subject><subject>Neurotoxicity</subject><subject>Original Research</subject><subject>Pharmacology/Toxicology</subject><subject>Phenytoin</subject><subject>Sodium valproate</subject><subject>Valproic acid</subject><issn>1054-2523</issn><issn>1554-8120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kE9Lw0AQxYMoWKsfwNuClxa6OvsnTXKUokYoeFBPpSyb7Ea3pLs1mwZS_PBuieDJwzCP4b038IuiawK3BCC58wDAOQaSYApphslJNCJxzHFKKJwGDUHTmLLz6ML7DQBLgMej6Pu1t-2n9sYjaVWY1pTOdvvaB4lk2ZrOtD1yFfJuq5F1na5RgieFtoe-lltj3RRhkuPjwa2K9YrM-FoZedA7YzWmMz5h-QzF-RQr46xGSjemk6FX-8vorJK111e_exy9Pz68LXK8fHl6XtwvccnIvMWKMg0snldpkTKZKqWToqw0qwrGZQpMEUYlJYQyybnMsoRTlfFUZUkqaVVkbBzdDL27xn3ttW_Fxu0bG14KGrgx4GweBxcZXGXjvG90JXaN2cqmFwTEEbIYIIsAWRwhCxIydMj44LUfuvlr_j_0A77_fhs</recordid><startdate>20180201</startdate><enddate>20180201</enddate><creator>Shao, Yun-Peng</creator><creator>Han, Rong-Bi</creator><creator>Wu, Hui-Fan</creator><creator>Piao, Feng-Yu</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>FR3</scope><scope>M7Z</scope><scope>P64</scope></search><sort><creationdate>20180201</creationdate><title>Synthesis and anticonvulsant activity of some novel 7-(benzylamino) -1H-benzo[b][1,4]diazepine-2,4(3H, 5H)-dione derivatives</title><author>Shao, Yun-Peng ; Han, Rong-Bi ; Wu, Hui-Fan ; Piao, Feng-Yu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-d23e0356f8b83a8dde7bcfe3fb34a803d132a21123a44a99742d948d978a2fb93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Anticonvulsants</topic><topic>Antiepileptic agents</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Carbamazepine</topic><topic>Cell Biology</topic><topic>Convulsions & seizures</topic><topic>Derivatives</topic><topic>Diketones</topic><topic>Neurotoxicity</topic><topic>Original Research</topic><topic>Pharmacology/Toxicology</topic><topic>Phenytoin</topic><topic>Sodium valproate</topic><topic>Valproic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shao, Yun-Peng</creatorcontrib><creatorcontrib>Han, Rong-Bi</creatorcontrib><creatorcontrib>Wu, Hui-Fan</creatorcontrib><creatorcontrib>Piao, Feng-Yu</creatorcontrib><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 1</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Medicinal chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shao, Yun-Peng</au><au>Han, Rong-Bi</au><au>Wu, Hui-Fan</au><au>Piao, Feng-Yu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and anticonvulsant activity of some novel 7-(benzylamino) -1H-benzo[b][1,4]diazepine-2,4(3H, 5H)-dione derivatives</atitle><jtitle>Medicinal chemistry research</jtitle><stitle>Med Chem Res</stitle><date>2018-02-01</date><risdate>2018</risdate><volume>27</volume><issue>2</issue><spage>642</spage><epage>652</epage><pages>642-652</pages><issn>1054-2523</issn><eissn>1554-8120</eissn><abstract>A series of novel 7-(benzylamino)-1
H
-benzo[b][1,4]diazepine-2,4(3
H
, 5
H
)-dione derivatives were synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, subcutaneous pentylenetetrazol (scPTZ) test, and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). The study showed that the compound
8c
(7-(4-fluorobenzylamino)-1,5-dimethyl-1
H
-benzo[b][1,4]diazepine-2,4(3
H
,5
H
)-dione) was the most promising compound, with median effective dose (ED
50
) of 36.5 mg/kg, and protective index (PI) values of 4.5 in the MES test. In the scPTZ test, compound
8c
also exhibited better anticonvulsant activity (ED
50
= 68.2 mg/kg), and the ED
50
values of compounds
8c
were smaller than that of the reference antiepileptic drugs carbamazepine (ED
50
> 100 mg/kg), phenytoin (ED
50
> 300 mg/kg), and sodium valproate (ED
50
= 149 mg/kg). The possible structure activity relationship was discussed.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s00044-017-2089-1</doi><tpages>11</tpages></addata></record> |
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| ispartof | Medicinal chemistry research, 2018-02, Vol.27 (2), p.642-652 |
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| language | eng |
| recordid | cdi_proquest_journals_2000304365 |
| source | SpringerLink Journals - AutoHoldings |
| subjects | Anticonvulsants Antiepileptic agents Biochemistry Biomedical and Life Sciences Biomedicine Carbamazepine Cell Biology Convulsions & seizures Derivatives Diketones Neurotoxicity Original Research Pharmacology/Toxicology Phenytoin Sodium valproate Valproic acid |
| title | Synthesis and anticonvulsant activity of some novel 7-(benzylamino) -1H-benzo[b][1,4]diazepine-2,4(3H, 5H)-dione derivatives |
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