Details

Autor(en) / Beteiligte

• Wu, Xiang-Long
• Liu, Liu
• Li, You-Jia
• Luo, Jie
• Gai, Dong-Wei
• Lu, Ting-Li
• Mei, Qi-Bing

Titel

Synthesis, crystal structure, and antinociceptive effects of some new riluzole derivatives

Ist Teil von

• Medicinal chemistry research, 2018-05, Vol.27 (5), p.1374-1383

Ort / Verlag

New York: Springer US

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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, and 13 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 of 4b , 4c , 4h , 4g , and riluzole had been studied. Compared with the control group (0 mg/kg), the effects of compounds 4b and 4h showed a significant increase (13.78 ± 2.89 s, 12.89 ± 2.94 s, respectively). Compound 4c showed extreme significant increase (18.07 ± 3.08 s) in the time mice spent on the hot plate. The compounds 4b , 4c , and 4h had increased the latency time compared to the blank solvent group. They have potential application in developing new drug candidates with antinociceptive activity.