摘要
Carbohydrates, with broad-spectrum structures and biological functions, are key organic compounds in nature, along with nucleic acids and proteins. As part of our ongoing efforts to develop a new class of pesticides with novel mechanism of action, a series of novel N-glycosyl-l-pyridyl-lH-pyrazole-5-carboxamide was designed and synthesized via the reactions of glycosyl methanamides and pyridyl-pyrazole acid. The compounds were characte- rized by IH NMR and 13C NMR. The bioassay results indicate that some of these compounds exhibit moderate insec- ticidal activities and assessed as potential inhibitors of calcium channels. The modulation of voltage-gated calcium channels by compounds 4a and 5a in the central neurons isolated from the third instar larvae of Spodoptera exigua was studied by whole-cell patch-clamp technique. In addition, compound 5a inhibits the recorded calcium currents reversible on washout. Experimental results also indicate that compound 5a did not release stored calcium from the Endoplasmic Reticulum. The present work demonstrates that N-glycosyl-l-pyridyl-lH-pyrazole-5-carboxamides cannot be used as possible inhibitors of calcium channels for developing novel pesticides.
Carbohydrates, with broad-spectrum structures and biological functions, are key organic compounds in nature, along with nucleic acids and proteins. As part of our ongoing efforts to develop a new class of pesticides with novel mechanism of action, a series of novel N-glycosyl-l-pyridyl-lH-pyrazole-5-carboxamide was designed and synthesized via the reactions of glycosyl methanamides and pyridyl-pyrazole acid. The compounds were characte- rized by IH NMR and 13C NMR. The bioassay results indicate that some of these compounds exhibit moderate insec- ticidal activities and assessed as potential inhibitors of calcium channels. The modulation of voltage-gated calcium channels by compounds 4a and 5a in the central neurons isolated from the third instar larvae of Spodoptera exigua was studied by whole-cell patch-clamp technique. In addition, compound 5a inhibits the recorded calcium currents reversible on washout. Experimental results also indicate that compound 5a did not release stored calcium from the Endoplasmic Reticulum. The present work demonstrates that N-glycosyl-l-pyridyl-lH-pyrazole-5-carboxamides cannot be used as possible inhibitors of calcium channels for developing novel pesticides.
基金
Supported by the National Basic Research Program of China（No.2010CB126106）, the National Natural Science Foundation of China（No.31000861）, the Tianj in Natural Science Foundation, China（No. 11JCYBJC08600） and the National Key Technologies R＆D Program of China（No.2011BAE06B05）.
