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Efficient synthesis of 1,3-naphtoxazine derivatives using reusable magnetic catalyst (GO-Fe3O4–Ti(IV)): anticonvulsant evaluation and computational studies.

Authors :
Khabnadideh, Soghra
solhjoo, Aida
Heidari, Reza
Amiri Zirtol, Leila
Sakhteman, Amirhossein
Rezaei, Zahra
Babaei, Elaheh
Rahimi, Samaneh
Emami, Leila
Source :
BMC Chemistry; 6/10/2022, Vol. 16 Issue 1, p1-18, 18p
Publication Year :
2022

Abstract

A series of 2-aryl/alkyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines (S<subscript>1</subscript>–S<subscript>11</subscript>) were synthesized with an eco-friendly and recoverable nanocatalyst (GO-Fe<subscript>3</subscript>O<subscript>4</subscript>–Ti<superscript>(IV)</superscript>) as an efficient magnetic composite. The new nanocatalyst was characterized by FT-IR, XRD and, EDS analysis. A conformable procedure, easy to work up and having a short reaction time with high yields are some advantages of this method. The new catalyst is also thermal-stable, reusable and, environment-friendly. The chemical structures of the synthesized 1,3-oxazine compounds were confirmed by comparing their melting points with those reported in literature. Then, the anticonvulsant activity of these compounds was assessed by the intraperitoneal pentylenetetrazole test (ipPTZ). Compounds S<subscript>10</subscript> and S<subscript>11</subscript> displayed considerable activity against chemically-induced seizure tests. The molecular simulation was also done to achieve their binding affinities as γ‐aminobutyric acid A (GABA‐A) receptor agonists as an assumptive mechanism of their anticonvulsant action. The result of molecular studies represented strongly matched with biological activity. Molecular docking simulation of the potent compound (S<subscript>10</subscript>) and diazepam as the positive control was performed and some critical residues like Thr262, Asn265, Met286, Phe289, and Val290 were identified. Based on the anticonvulsant results and also in silico ADME predictions, S<subscript>11</subscript> can be to become a potential drug candidate as an anticonvulsant agent. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
2661801X
Volume :
16
Issue :
1
Database :
Complementary Index
Journal :
BMC Chemistry
Publication Type :
Academic Journal
Accession number :
157414889
Full Text :
https://doi.org/10.1186/s13065-022-00836-8