1. Synthesis, crystal structure, and antinociceptive effects of some new riluzole derivatives.
- Author
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Wu, Xiang-Long, Liu, Liu, Li, You-Jia, Luo, Jie, Gai, Dong-Wei, Lu, Ting-Li, and Mei, Qi-Bing
- Abstract
Nine N-alkylated derivatives of riluzole were synthesized in order to obtain new compounds with potential antinociceptive activity. Riluzole was firstly transformed into (6-trifluoromethoxy-benzothiazol-2-yl)-hydrazine, then it was chlorinated by SOCl
2 to obtain 2-chloro-6-trifluoromethoxy-benzothiazole. This intermediate product was treated with nine alkylamines to give N-alkylated derivatives of riluzole respectively. The structures of compounds were confirmed by means of elemental analysis, IR,1 H NMR, and13 C NMR. The synthetic route was optimized and four novel crystals were obtained by recrystallization. This study investigated the antinociceptive activity of some N-alkylated derivatives of riluzole by hot plate test in mice. The relationship between antinociceptive activity and the doses of4b ,4c ,4h ,4g , and riluzole had been studied. Compared with the control group (0 mg/kg), the effects of compounds4b and4h showed a significant increase (13.78 ± 2.89 s, 12.89 ± 2.94 s, respectively). Compound4c showed extreme significant increase (18.07 ± 3.08 s) in the time mice spent on the hot plate. The compounds4b ,4c , and4h had increased the latency time compared to the blank solvent group. They have potential application in developing new drug candidates with antinociceptive activity. [ABSTRACT FROM AUTHOR]- Published
- 2018
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