Molecular sieves promoted, ultrasound-mediated synthesis, biological evaluation and docking study of 3-(5-substituted-1,3,4-thiadiazol-2-ylimino)indolin-2-ones as a potential anticonvulsant agents

Abstract

In this work, the combined use of ultrasonic energy and molecular sieves was investigated for synthesis of 3-(5-substituted-1,3,4-thiadiazol-2-ylimino)indolin-2-one derivatives 5(a–j). The equimolar quantities of 5-substituted-1,3,4-thiadiazol-2-amine and isatin were sonicated in the presence of activated molecular sieves 3 Å at a temperature of 50 °C and at a frequency 20 kHz, and higher yields (73–92 %) and faster reaction times (43–75 min) were obtained when ultrasonic irradiation was used in comparison with conventional methods. The synthesized compounds were evaluated for anticonvulsant (MES and sc-PTZ model) and behavioral activity (actophotometer) in mice. The compounds 5b, 5i and 5j have shown protection against MES model at 0.5- and 4-h period at dose level of 100 mg/kg, while the compound 5c showed protection against sc-PTZ model at the same dose level. To exploit the mode of action of the synthesized compounds, docking study against sodium channel receptor was performed and the results revealed good binding interactions with the receptor. ADME properties of synthesized compounds were also analyzed and showed potential to develop as good oral drug candidates.

DOI: 10.1007/s00044-015-1458-x

Extracted Key Phrases

7 Figures and Tables

Cite this paper

@article{Nikalje2015MolecularSP, title={Molecular sieves promoted, ultrasound-mediated synthesis, biological evaluation and docking study of 3-(5-substituted-1,3,4-thiadiazol-2-ylimino)indolin-2-ones as a potential anticonvulsant agents}, author={Anna Pratima G. Nikalje and Sameer I. Shaikh and Firoz A. Kalam Khan and Shoaib Shaikh and Jaiprakash N. Sangshetti}, journal={Medicinal Chemistry Research}, year={2015}, volume={24}, pages={4058-4069} }