New benzo[d]thiazol-2-yl-aminoacetamides as potential anticonvulsants: synthesis, activity and prediction of molecular properties

Archiv der Pharmazie
Ruhi Ali, Nadeem Siddiqui

Abstract

A series of N-(substituted-2-oxo-4-phenylazetidin-1-yl)-2-((6-substitutedbenzo[d]thiazol-2-yl)amino)acetamide derivatives were synthesized using pharmacophoric features with aromatic hydrophobic aryl ring (A), NH-C=O as hydrogen bonding domain, the nitrogen atom as electron donor (D), and phenyl as distal aryl ring (C). The synthesized molecules were initially screened for anticonvulsant activity using the maximal electroshock seizure (MES) test and the subcutaneous pentylenetetrazole test in albino mice. An acute neurotoxicity study on the synthesized molecules was also carried out using the rotarod test. The results of these tests revealed that two compounds, 5b and 5q, showed promising activity with ED50 values of 15.4 and 18.6 mg/kg and protective indices of 20.7 and 34.9 in the MES test, respectively, which are found to be approximately fourfold higher than those of the standard drugs phenytoin (6.9) and carbamazepine (8.1). These molecules may act as lead of the designed scheme. The pharmacokinetic profiles of all the synthesized compounds were estimated using Molinspiration software. None of the compounds violated Lipinski's "rule of five". The possible structure-activity relationship was discussed. In conclusion, this m...Continue Reading

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Citations

May 5, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Hassan M FaidallahKhalid A Khan
Sep 8, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ümide Demir ÖzkayÖzgür Devrim Can
Nov 30, 2018·Archiv der Pharmazie·Sana TariqMohammad Amir
Jul 10, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Ismail M M OthmanAbd El-Galil E Amr
Nov 8, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Gamze TokgözZafer Asım Kaplancıklı
Oct 18, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Thuraya Al-HarthyRaid Abdel-Jalil
May 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Larisa V ZhilitskayaNina O Yarosh

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