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Design, Synthesis, Fluorescence Properties and Antibacterial Activities of New 8-Chloro-3-Alkyl-3H-Pyrazolo[4,3-a]acridine-11-Carbonitriles

  • Rahmani, Zeynab ;
  • Pordel, Mehdi ;
  • Davoodnia, Abolghasem
  • Received : 2013.08.28
  • Accepted : 2013.11.29
  • Published : 2014.02.20

Abstract

The treatment of alkylated nitro derivatives of indazole with 2-(4-chlorophenyl)acetonitrile under basic conditions gave the new 8-chloro-3-alkyl-3H-pyrazolo[4,3-a]acridine-11-carbonitriles via the nucleophilic substitution of hydrogen which proceeds at room temperature with concomitant cyclisation in fairly good yields. The structures of all newly synthesized compounds were confirmed by IR, $^1H$ NMR, $^{13}C$ NMR and mass spectral data. Fluorescence experimental results of all newly synthesized compounds revealed remarkable photoluminescence properties and strong green fluorescence properties. Also, the new compounds exhibited potent antibacterial activity and their antibacterial activity (MIC) against Gram positive (Staphylococcuse aureus methicillin resistant S. aureus and Bacillus subtilis) and negative bacterial (Pseudomonas aeruginosa and Escherichia coli) species were determined.

Keywords

5-Nitro-1H-indazole;Pyrazolo[4,3-a]acridine;Fluorescence;Antibacterial agents

References

  1. Sun, Y. F.; Song, H. C.; Li, W. M.; Xu, Z. L. Chin. J. Org. Chem. 2003, 23, 1286.
  2. Bellina, F.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 4571. https://doi.org/10.1016/j.tet.2007.02.075
  3. Hu, Z. J.; Yang, J. X.; Tian, Y. P.; Zhou, H. P.; Tao, X. T.; Xu, G. B. et al. J. Mol. Struct. 2007, 839, 50. https://doi.org/10.1016/j.molstruc.2006.10.044
  4. Cui, Y. Z.; Fang, Q.; Huang, Z. L.; Xue, G.; Yu, W. T.; Lei, H. Opt. Mater. 2005, 27, 1571. https://doi.org/10.1016/j.optmat.2004.12.009
  5. Tsai, M. H.; Hong, Y. H.; Chang, C. H.; Su, H. C.; Wu, C. C.; Matoliukstyte, A. et al. Adv. Mater. 2007, 19, 862. https://doi.org/10.1002/adma.200600822
  6. Hunger, K. Industrial Dyes; Wiley-VCH: Weiheim, Germany, 2003; p 569.
  7. Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules; Academic Press: New York, 1971.
  8. (a) Kodiro, K.; Inoue, Y. A. J. Am Chem. Soc. 2003, 125, 421. https://doi.org/10.1021/ja028401x
  9. (b) Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2000, 122, 6793. https://doi.org/10.1021/ja001042q
  10. Harvey, M. D.; Bablekis, V.; Banks, P. R.; Skinner, C. D. J. Chromatogr. B 2001, 754, 345. https://doi.org/10.1016/S0378-4347(00)00627-7
  11. Rahimizadeh, M.; Pordel, M.; Bakavoli, M.; Eshghi, H. Dyes Pigm. 2010, 86, 266. https://doi.org/10.1016/j.dyepig.2010.01.013
  12. Rahimizadeh, M.; Pordel, M.; Ranaei, M.; Bakavoli, M. J. Heterocyclic Chem. 2012, 49, 208. https://doi.org/10.1002/jhet.681
  13. Pordel, M. J. Chem. Res. 2012, 595.
  14. Pakjoo, V.; Roshani, M.; Pordel, M.; Hoseini, T. Arkivoc 2012, 9, 195.
  15. Sahraei, R.; Pordel, M.; Behmadi, H.; Razavi, B. J. Lum. 2013, 136, 334. https://doi.org/10.1016/j.jlumin.2012.12.024
  16. Hoseini-Hesar, T.; Pordel, M.; Roshani, M.; Shams, A. J. Chem. Res. 2013, 438.
  17. Daemi, F.; Allameh, S.; Pordel, M. J. Chem. Res. 2012, 579.
  18. Rahimizadeh, M.; Pordel, M.; Bakavoli, M.; Rezaeian, Sh.; Sadeghian, A. World. J. Microbiol. Biotechnol. 2010, 26, 317. https://doi.org/10.1007/s11274-009-0178-0
  19. Sadeghian, H.; Sadeghian, A.; Pordel, M.; Rahimizadeh, M.; Jahandari, P.; Orafaie, A.; Bakavoli, M. Med. Chem. Res. 2010, 19, 103. https://doi.org/10.1007/s00044-009-9175-y
  20. Sadeghian, A.; Pordel, M.; Safdari, H.; Fahmidekar, M. A.; Sadeghian, H. Med. Chem. Res. 2012, 21, 3897. https://doi.org/10.1007/s00044-011-9933-5
  21. Rahimizadeh, M.; Pordel, M.; Bakavoli, M.; Bakhtiarpoor, Z.; Orafaie, A. Monatsh. Chem. 2009, 140, 633. https://doi.org/10.1007/s00706-009-0109-7
  22. Pordel, M.; Abdollahi, A.; Razavi, B. Russ. J. Bioorg. Chem. 2013, 39, 240.
  23. Bouissane, L.; Kazzouli, S. E.; Leger, J. M.; Jarry, C.; Rakib, E. M.; Khouili, M.; Guillaumet, G. Tetrahedron 2005, 61, 8218. https://doi.org/10.1016/j.tet.2005.06.038
  24. Finegold, S. M.; Garrod, L. Bailey and Scott's Diagnostic Microbiology, 8th ed.; Chap 13. C.V. Mosby: Toronto, 1995; p 171.
  25. M'kosza, M.; Wojciechowski, K. Chem. Rev. 2004, 104, 2631. https://doi.org/10.1021/cr020086+
  26. Davis, R. B.; Pizzini, L. C. J. Org Chem. 1960, 25, 1884. https://doi.org/10.1021/jo01081a015
  27. Umberger, J. Q.; LaMer, V. K. J. Am. Chem. Soc. 1945, 67, 1099. https://doi.org/10.1021/ja01223a023
  28. Sztaricskai, F.; Pinter, G.; Roth, E.; Herczegh, P.; Kardos, S.; Rozgonyi, F.; Boda, Z. J. Antibiot. 2007, 60, 529. https://doi.org/10.1038/ja.2007.68
  29. Joux, F.; Lebaron, P. Microbes Infect. 2000, 2, 1523. https://doi.org/10.1016/S1286-4579(00)01307-1

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