Novel fused 1,2,3-triazolo-benzodiazepine derivatives as potent anticonvulsant agents: design, synthesis, in vivo, and in silico evaluations View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2019-03-20

AUTHORS

Arefeh Shafie, Maryam Mohammadi-Khanaposhtani, Mehdi Asadi, Nastaran Rahimi, Parviz Rashidi Ranjbar, Jahan B. Ghasemi, Bagher Larijani, Mohammad Mahdavi, Hamed Shafaroodi, Ahmad Reza Dehpour

ABSTRACT

A novel series of 1,2,3-triazolo-benzodiazepine derivatives 6a-o has been synthesized and evaluated in vivo for their anticonvulsant activities using by pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. The synthetic approach started with diazotizing 2-aminobenzoic acids 1 to produce 2-azidobenzoic acids 2. Next, reaction of the latter compounds with propargylamine 3, benzaldehyde 4, and isocyanides 5 led to the formation of the title compounds 6a-o, in good yields. All the synthesized compounds exhibited high anticonvulsant activity in the PTZ test, comparable to or better than the standard drug diazepam. Among the tested compounds, N-(tert-butyl)-2-(9-chloro-6-oxo-4H-[1,2,3]triazolo[1,5-a][1,4]benzodiazepin-5(6H)-yl)-2-(3-bromophenyl)acetamide 6h was the most potent compound in this assay. Moreover, compounds 6i and 6k showed excellent activity in MES test. Loss of the anticonvulsant effect of compound 6h in the presence of flumazenil in the PTZ test and appropriate interaction of this compound in the active site of benzodiazepine (BZD)-binding site of GABAA receptor confirm involvement of BZD receptors in the anticonvulsant activity of compound 6h. A novel series of 1,2,3-triazolo-benzodiazepine derivatives 6a-o have been synthesized and evaluated in vivo for their anticonvulsant activities using by pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. All the synthesized compounds exhibited high anticonvulsant activity, comparable to or better than the standard drug diazepam in the PTZ test and compounds 6i and 6k showed excellent activity in MES test. Flumazenil test and in silico docking study confirm involvement of benzodiazepine receptors in the anticonvulsant activity of these compounds. More... »

PAGES

1-11

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11030-019-09940-9

DOI

http://dx.doi.org/10.1007/s11030-019-09940-9

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1112900119

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/30895449


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