Synthesis,Crystal Structure,and Biological Activity of Naphthalen-2-yl4-methyl-1,2,3-thiadiazole-5-carboxylate  

作　　者：王守信 付一峰 范志金 米娜 张海科 宋海斌 Belskaya N.P. Bakulev V.A. 

机构地区：[1]School of Pharmaceutical Science and Technology,Tianjin University [2]State Key Laboratory of Elemento Organic Chemistry,Nankai University [3]The Ural Federal University Named after the First President of Russia B.N.Yeltsin,Yeltsin UrFU 620002,Ekaterinburg,Russia

出　　处：《Chinese Journal of Structural Chemistry》2011年第2期235-239,共5页结构化学（英文）

基　　金：Supported by the National Natural Science Foundation of China (Nos. 20872071 and 20911120069);the Natural Science Foundation of Tianjin (10JCZDJC17500);the National Key Project for Basic Research (2010CB126105);the Key Laboratory of Pesticide Chemistry and Application,Ministry of Agriculture (MOA) (No. MOAPCA200903);the Russian Foundation for Basic Research (grant numbers RFBR 08-03-00376 a and RFBR/NNSF 08-03-92208 a)

摘　　要：The title compound naphthalen-2-yl-4-methyl-1,2,3-thiadiazole-5-carboxylate （C 14 H 10 N 2 O 2 S,M r=270.31） was synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 2-naphthol,and its structure was characterized by IR,1 H NMR,high-resolution mass spectrometry and single-crystal X-ray diffraction.The crystal belongs to orthorhombic,space group Pbcn with a=23.475（5）,b=9.6640（19）,c=10.814（2）,β=90.00°,Z=8,V=2453.2（9） 3,M r=270.30,D c=1.464 g/cm 3,μ=0.262 mm-1,F（000）=1120,R=0.0444 and wR=0.1099.X-ray analysis revealed that the thiadiazole and naphthalene rings were non-planar,while the thiadiazole ring and the ester group were essentially planar,and two intermolecular hydrogen bonds C（6） H（6）···O（1） and C（14） H（14）···O（1） were observed.The preliminary biological test showed that the title compound had antifungal and antivirus activities against tobacco mosaic virus.The title compound naphthalen-2-yl-4-methyl-1,2,3-thiadiazole-5-carboxylate （C 14 H 10 N 2 O 2 S,M r=270.31） was synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 2-naphthol,and its structure was characterized by IR,1 H NMR,high-resolution mass spectrometry and single-crystal X-ray diffraction.The crystal belongs to orthorhombic,space group Pbcn with a=23.475（5）,b=9.6640（19）,c=10.814（2）,β=90.00°,Z=8,V=2453.2（9） 3,M r=270.30,D c=1.464 g/cm 3,μ=0.262 mm-1,F（000）=1120,R=0.0444 and wR=0.1099.X-ray analysis revealed that the thiadiazole and naphthalene rings were non-planar,while the thiadiazole ring and the ester group were essentially planar,and two intermolecular hydrogen bonds C（6） H（6）···O（1） and C（14） H（14）···O（1） were observed.The preliminary biological test showed that the title compound had antifungal and antivirus activities against tobacco mosaic virus.

关 键 词：X-ray diffraction crystal structure SYNTHESIS 1 2 3-thiadiazole 

分 类 号：O621.2[理学—有机化学]