Citation: Zhou Guan, Liang Guochao, Zhong Yifan, Han Xiaoyan, Chen Guofeng, Song Yali. Ultrasound Promoted Synthesis of Novel Substituted Spirooxindole Compounds Containing Thiochroman Moiety with Antifungal Activity[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 143-150. doi: 10.6023/cjoc201508007 shu

Ultrasound Promoted Synthesis of Novel Substituted Spirooxindole Compounds Containing Thiochroman Moiety with Antifungal Activity

Zhou Guan ^a,b ,
Liang Guochao ^a,b ,
Zhong Yifan ^a,b ,
Han Xiaoyan ^a,b ,
Chen Guofeng ^c ,
Song Yali ^a,b,*,,

a.
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding 071002
b.
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis, Ministry of Education, Hebei University, Baoding 071002
c.
College of Chemistry and Environmental Science, Hebei University, Baoding 071002

Corresponding author: Song Yali, yalisong@hbu.edu.cn
Received Date: 6 August 2015
Revised Date: 23 September 2015

Fund Project: the Open Project Program of Key Laboratory of Pharmaceutical Quality Control of Hebei Province, the National Major Scientific and Technological Special Project for 'Significant New Drugs Development' 2012ZX09103-101-057

Figures(1)

A rapid and efficient ultrasound-promoted one-pot synthesis of 2'-amino-2-oxo-5'H-spiro[indoline-3, 4'-thiochromeno[4, 3-b]pyran]-3'-carbonitrile compounds by one-pot three-component reaction had been developed. Structures of all products were characterized by ¹H NMR, ¹³C NMR and HRMS. The effect of ultrasound on yield and reaction time had been studied to understand the role of ultrasound in the reaction. The antifungal activity was determined by micro dilution method. Compound 4f exhibited inhibitory activity to Cryptococcus neoformans, Epidermophyton floccosum and Mucor racemosus better than the positive control drug fluconazole.
- thiochromanone,
- ultrasound,
- spirooxindole,
- one-pot three-component reaction,
- antifungal activity
1. [1]
  Wickel, S. M.; Citron, C. A.; Dickschat, J. S. Eur. J. Org. Chem. 2013, 2906.
2. [2]
  Patil, S. A.; Wang, J.; Li, X. S.; Chen, J.; Jones, T. S.; Hosni-Ahmed, A.; Patil, R.; Seibel, W. L.; Li, W.; Miller, D. D. Bioorg. Med. Chem. Lett. 2012, 22, 4458. doi: 10.1016/j.bmcl.2012.04.074
3. [3]
  Makawana, J. A.; Patel, M. P.; Patel, R. G. Arch. Pharm. 2012, 345, 314. doi: 10.1002/ardp.v345.4
4. [4]
  Venkatesham, A.; Rao, R. S.; Nagaiah, K.; Yadav, J. S.; RoopaJones, G.; Basha, S. J.; Sridhar, B.; Addlagatta, A. MedChemComm 2012, 3, 652. doi: 10.1039/c2md20023f
5. [5]
  Houlihan, W. J.; Remers, W. A.; Brown, R. K. Indoles: Part I, Wiley, New York, 1992.
6. [6]
  Sundberg, R. J. The Chemistry of Indoles, Academic, New York, 1996.
7. [7]
  Abdel-Rahman, A. H.; Keshk, E. M.; Hanna, M. A.; El-Bady, S. M. Bioorg. Med. Chem. 2004, 12, 2483. doi: 10.1016/j.bmc.2003.10.063
8. [8]
  Li, Y.; Chen, H.; Shi, C.; Shi, D.; Ji, S. J. Comb. Chem. 2012, 12, 231.
9. [9]
  Jadidi, K.; Ghahremanzadeh, R.; Bazgir, A. J. Comb. Chem. 2009, 11, 341.
  (b) Guo, R. Y.; An, Z. M.; Mo, L. P.; Wang, R. Z.; Liu, H. X.; Wang, S. X.; Zhang, Z. H. ACS Comb. Sci. 2013, 15, 557.
  (c) Zou, Y.; Hu, Y.; Liu, H.; Shi, D. ACS Comb. Sci. 2012, 14, 38.
  (d) Baharfar, R.; Azimi, R. Synth. Commun. 2014, 44, 868.
10. [10]
  Li, H. Y.; Hu, C. Chin. Pharm. J. 2005, 40, 41.
  (b) Zheng, W.; Sun, G.; Sun, B. J.; Zhi, H.; Hu, C. Fine Chem. Intermed. 2009, 39, 30 (in Chinese).
  (郑伟, 孙光, 孙宝佳, 郅慧, 胡春, 精细化工中间体, 2009, 39, 30.)
11. [11]
  Siddaiah, V.; Maheswara, M.; Venkata Rao, C.; Venkateswarlu, S.; Subbaraju, G. V. Bioorg. Med. Chem. Lett. 2007, 17, 1288. doi: 10.1016/j.bmcl.2006.12.008
12. [12]
  Mahapatra, T.; Jana, N.; Nanda, S. Tetrahedron: Asymmetry 2008, 19, 1224. doi: 10.1016/j.tetasy.2008.04.024
13. [13]
  Meng, L. G.; Liu, H. F.; Wei, J. L.; Gong, S. N.; Song, X. Tetrahedron Lett. 2010, 51, 1748. doi: 10.1016/j.tetlet.2010.01.093
14. [14]
  Song, Y. L.; Dong, Y. F.; Yang, T.; Zhang, C. C.; Su, L. M.; Huang, X.; Zhang, D. N.; Yang, G. L.; Liu, Y. X. Bioorg. Med. Chem. 2013, 21, 7624. doi: 10.1016/j.bmc.2013.10.034
15. [15]
  Luche, J. L. Synthetic Organic Sonochemistry, Plenum Press, New York, 1998.
  (b) Li, J. T.; Wang, S. X.; Chen, G. F.; Li, T. S. Curr. Org. Synth. 2005, 2, 415.
  (c) Mehrabi, H. Ultrason. Sonochem. 2012, 19, 125.
  (d)Fu, Z. Y.; Shao, H. W. Ultrason. Sonochem. 2011, 18, 520.
16. [16]
  Li, J. T.; Zhai, X. L.; Chen, G. F. Ultrason. Sonochem. 2010, 17, 356.
  (b) Wang, L. J.; Keyume, A.; Feng, J. Ultrason. Sonochem. 2015, 22, 113.
  (c) Ghahremanzadeh, R.; Rashid, Z.; Zarnani, A.-H.; Naeimi, H. Ultrason. Sonochem. 2014, 21, 1451.
  (d) Song, Y. L.; Dong, Y. F.; Wu, F.; Yang, T.; Yang, G. L. Ultrason. Sonochem. 2015, 22, 119.
  (e) Chen, B. H.; Li, J. T.; Lan, R. J.; Chen, G. F. Chin. J. Org. Chem. 2013, 33, 1965 (in Chinese).
  (陈宝华, 李记太, 兰瑞家, 陈国锋, 有机化学, 2013, 33, 1965.)
17. [17]
  Li, Y. L.; Chen, H.; Shi, C. L.; Shi, D. Q.; Ji, S. J. J. Comb. Chem. 2010, 12, 231.
  (b) Zhao, L. Q.; Zhou, B.; Li, Y. Q. Heteroatom Chem. 2011, 22, 673.
18. [18]
  Liu, X. M.; Yang, G. L.; Song, Y. L.; Liu, J. J.; Wang, Y.; Zhang, D. N. Lett. Org. Chem. 2013, 10, 228. doi: 10.2174/1570178611310030016
19. [19]
  Da, Silva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001, 12, 273. doi: 10.1590/S0103-50532001000300002
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