Notes

Synthesis and Biological Activity of Pyrazolo[3,4-d]pyrimidine Derivatives Containing 1,3,4-Thiadiazole

  • Song Xinjian ,
  • Shao Yu ,
  • Duan Zhengcao ,
  • Li Shirong
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  • a Key Laboratory of Biological Resources Protection and Utilization of Hubei Province, Hubei University for Nationalities, Enshi 445000;
    b School of Chemical and Environmental Engineering, Hubei University for Nationalities, Enshi 445000

Received date: 2011-10-08

  Revised date: 2011-11-23

  Online published: 2012-04-24

Supported by

Project supported by the Natural Science Foundation of Hubei Province (No. 2011CDB087) and the Scientific Research Fund of Hubei Provincial Education Department (No. D20111904).

Abstract

Twelve novel pyrazolo[3,4-d]pyrimidine derivatives containing a 1,3,4-thiadiazole group were synthesized through cyclization of 5-amino-4-cyano-1-phenylpyrazole with formic acid, followed by chloridization and SNAr reaction. The structures of all these title compounds were confirmed by IR, 1H NMR, MS techniques and elemental analysis. The preliminary bioassay showed that most of the title compounds exhibit relatively good fungicidal activities against Rhizoctonia cerealis at the concentration of 50 mg/L, especially the inhibitory rates of compounds 5b, 5d and 5j reach above 90%.

Cite this article

Song Xinjian , Shao Yu , Duan Zhengcao , Li Shirong . Synthesis and Biological Activity of Pyrazolo[3,4-d]pyrimidine Derivatives Containing 1,3,4-Thiadiazole[J]. Chinese Journal of Organic Chemistry, 2012 , 32(04) : 755 -759 . DOI: 10.6023/cjoc1110081

References

[1] Manetti, F.; Santucci, A.; Locatelli, G. A.; Maga, G.; Spreafico, A.; Serchi, T.; Orlandini, M.; Bernardini, G.; Caradonna, N. P.; Spallarossa, A.; Brullo, C.; Schenone, S.; Bruno, O.; Ranise, A.; Bondavalli, F.; Hoffmann, O.; Bologna, M.; Angelucci, A.; Botta, M. J. Med. Chem. 2007, 50, 5579.  

[2] Song, X. J.; Shao, Y.; Dong, X. G. Chin. Chem. Lett. 2011, 22, 1036.  

[3] Radi, M.; Dreassi, E.; Brullo, C.; Crespan, E.; Tintori, C.; Bernardo, V.; Valoti, M.; Zamperini, C.; Daigl, H.; Musumeci, F.; Carraro, F.; Naldini, A.; Filippi, I.; Maga, G.; Schenone, S.; Botta, M. J. Med. Chem. 2011, 54, 2610.  

[4] Rashad, A. E.; Hegab, M. I.; Abdel-Megeid, R. E.; Micky, J. A.; Abdel-Megeid, F. M. E. Bioorg. Med. Chem. 2008, 16, 7102.  

[5] Holla, B. S.; Mahalinga, M.; Karthikeyan, M. S.; Akberalib, P. M.; Shetty, N. S. Bioorg. Med. Chem. 2006, 14, 2040.  

[6] Bakavoli, M.; Bagherzadeh, G.; Vaseghifar, M.; Shiri, A.; Pordel, M.; Mashreghi, M.; Pordeli, P.; Araghi, M. Eur. J. Med. Chem. 2010, 45, 647.

[7] Abbas, S. E. S.; Georgey, H. H.; Abdelrahman, S. M.; El-Taliawi, G. M. Bull. Pharm. Sci. 2008, 31, 197.

[8] Vicentini, C. B.; Romagnoli, C.; Andreotti, E.; Mares, D. J. Agric. Food Chem. 2007, 55, 10331.  

[9] Wang, T.; Luo, J.; Zheng, C. H. Chin. J. Org. Chem. 2010, 30, 1749 (in Chinese). (王涛, 罗劲, 郑彩华, 有机化学, 2010, 30, 1749.)

[10] Wang, H. Q.; Liu, Z. J.; Yang, L. M.; Ding, M. W. J. Heterocycl. Chem. 2004, 41, 393.  

[11] Yang, C.; Yang, S.; Song, B.-A.; Hu, D.-Y.; Chen, H.-J., Xue, W.; Jin, L.-H.; Wu, J.; Xu, W.-M.; Bai, S. Chin. J. Org. Chem. 2010, 30, 1327 (in Chinese).(杨超, 杨松, 宋宝安, 胡德禹, 陈红军, 薛伟, 金林红, 吴剑, 徐维明, 柏松, 有机化学, 2010, 30, 1327.)

[12] Song, X.-J.; Tan, X.-H.; Wang, Y.-G. J. Chem. Crystallogr. 2008, 38, 479.  

[13] Han, F.; Wan, R.; Wang, Y; Wang, P.; Wang, J.-T. Chin. J. Org. Chem. 2010, 30, 132 (in Chinese). (韩锋, 万嵘, 王瑶, 王朋, 王锦堂, 有机化学, 2010, 30, 132.)

[14] Bian, W.-D.; Chai, A.; Yu, S.-R.; Xue, S.-J. Chin. J. Org. Chem. 2008, 28, 1475 (in Chinese). (卞王东, 柴安, 吁松瑞, 薛思佳, 有机化学, 2008, 28, 1475.)

[15] Wang, T.-T.; Miao, W.-K.; Wu, S.-S.; Bing, G.-F.; Zhang, X.; Qin, Z.-F.; Yu, H.-B.; Qin, X.; Fang, J.-X. Chin. J. Chem. 2011, 29, 959.

[16] Song, X.-J.; Wang, F.-S.; Li, S.-R.; Hu, W.-B.; Wang, Y.-G. Chin. J. Org. Chem. 2011, 31, 572 (in Chinese). (宋新建, 王发松, 李世荣, 胡卫兵, 汪焱钢, 有机化学, 2011, 31, 572.)

[17] Song, X.-J.; Wang, S.; Tan, X.-H.; Wang, Z.-Y.; Wang, Y.-G. Chin. J. Org. Chem. 2007, 27, 72 (in Chinese). (宋新建, 王胜, 谭小红, 王子云, 汪焱钢, 有机化学, 2007, 27, 72.)

[18] An, Y.; Wei, W.; Mu, P.-P.; Jia, J.-Y.; Lü, J.-Z.; Chen, X. Chin. J. Org. Chem. 2010, 30, 1726 (in Chinese). (安悦, 魏魏, 牟萍萍, 贾金英, 吕建州, 陈欣, 有机化学, 2010, 30, 1726.)

[19] Zhao, P.-L.; Wang, F.; Huang, W.; Chen, Q.; Liu, Z.-M. Chin. J. Org. Chem. 2010, 30, 1567 (in Chinese). (赵培亮, 王福, 黄伟, 陈琼, 刘祖明, 有机化学, 2010, 30, 1567.)

[20] Niswender, C. M.; Lebois, E. P.; Luo, Q.; Kim, K.; Muchalski, H.; Yin, H.; Conn, P. J.; Lindsley, C. W. Bioorg. Med. Chem. Lett. 2008, 18, 5626.  

[21] Wang, Y.-G.; Cao, L.; Yang, J.; Ye, W.-F.; Lu, B.-X. Chem. J. Chin. Univ. 1999, 20, 1903 (in Chinese). (汪焱钢, 曹蕾, 杨军, 叶文法, 卢冰熙, 高等学校化学学报, 1999, 20, 1903.)

[22] Foroumadi, A.; Firoozpour, L.; Emami, S.; Mansouri, S.; Ebrahimabadi, A. H.; Asadipour, A.; Amini, M.; Saeid-Adeli, N.; Shafiee A. Arch. Pharm. Res. 2007, 30, 138.  

[23] Zhang, W.-H.; Jiang, M.-G. Chin. J. Org. Chem. 2010, 30, 254 (in Chinese). (章维华, 蒋木庚, 有机化学, 2010, 30, 254.)
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