Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Studies on Anticonvulsant and Antidepressant Activities of 5-Alkoxy-tetrazolo[1,5-a]quinolines

  • Deng, Xian-Qing (College of Pharmacy, Yanbian University) ;
  • Wei, Cheng-Xi (Institute of Neurosurgery, Inner Mongolia University for Nationalities) ;
  • Song, Ming-Xia (College of Pharmacy, Yanbian University) ;
  • Chai, Kyu-Yun (Department of chemistry, Wonkwang University) ;
  • Sun, Zhi-Gang (Institute of Neurosurgery, Inner Mongolia University for Nationalities) ;
  • Quan, Zhe-Shan (College of Pharmacy, Yanbian University)
  • Published : 2010.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

A series of 5-alkoxy-tetrazolo[1,5-a]quinolines were synthesized to evaluate their anticonvulsant and antidepressant effects. Anticonvulsant effects and neurotoxicity of the compounds when injected intraperitoneally to mice were determined by a maximal electroshock (MES) test and a rotarod test, respectively. Only three of the synthesized compounds (4a, 4b, 4c) displayed anticonvulsant activity at a dose of 300 mg/kg. Most of the compounds significantly reduced immobility times during the forced swimming test (FST) at a dose of 100 mg/kg, indicative of antidepressant activity. Among the compounds, 5-(2-fluorobenzyloxy)tetrazolo[1,5-a]quinoline (4k) reduced immobility time by 66.85% at 30 mg/kg compared with the same dose of Fluoxetine, which reduced immobility time by 52.30%. According to the results of the 5-Hydroxytryptophan induced head-twitch test and yohimbine toxicity potentiation test, the noradrenergic system seems not to be involved in the antidepressant-like effect of compound 4k while the serotonergic system seems a little to be involved.

Keywords

References

  1. Joseph, B.; Darro, F.; Behard, A.; Lesur, B.; Collignon, F.; Decaestecker, C.; Frydman, A.; Guillaumet, G.; Kiss, R. J. Med. Chem. 2002, 45, 2543-2555. https://doi.org/10.1021/jm010978m
  2. Xiao, Z.; Waters, N. C.; Woodard, C. L.; Li, Z.; Li, P. K. Bioorg. Med. Chem. Lett. 2001, 11, 2875-2878. https://doi.org/10.1016/S0960-894X(01)00578-9
  3. Nishi, T.; Kimura, Y.; Nakagawa, K. Zasshi. yaqugaku. 2000, 120, 1247-1260.
  4. Oshiro, Y.; Sakurai, Y.; Sato, S.; Kurahashi, N.; Tanaka, T.; Kikuchi, T.; Tottori, K.; Uwahodo, Y.; Miwa, T.; Nishi, T. J. Med. Chem. 2000, 43, 177-189. https://doi.org/10.1021/jm980333v
  5. Otsubo, K.; Morita, Uchida, S. M.; Yamasaki, K.; Kanbe, T.; Shimizu, T. Chem. Pharm. Bull. 1991, 39, 2906-2909. https://doi.org/10.1248/cpb.39.2906
  6. Banno, K.; Fujioka, T.; Kikuchi, T.; Oshiro, Y.; Hiyama, T.; Nakagawa, K. Chem. Pharm. Bull. 1988, 36, 4377-4388. https://doi.org/10.1248/cpb.36.4377
  7. Bell, A. S.; Campbell, S. F.; Roberts, D. A.; Ruddock, K. S. J. Med. Chem. 1989, 32, 2042-2049. https://doi.org/10.1021/jm00129a005
  8. Quan, Z. S.; Wang, J. M.; Rho, J. R.; Kwak, K. C.; Kang, H. C.; Qun, C. S.; Chai, K. Y. Bull. Korean Chem. Soc. 2005, 26, 1757- 1759. https://doi.org/10.5012/bkcs.2005.26.11.1757
  9. Cui, L. J.; Xie, Z. F.; Piao, H. R.; Li, G.; Chai, K. Y.; Quan, Z. S. Biol. Pharm. Bull. 2005, 28, 1216-20. https://doi.org/10.1248/bpb.28.1216
  10. Xie, Z. F.; Chai, K. Y.; Piao, H. R.; Kwak. K. C.; Quan, Z. S. Bioorg. Med. Chem. Lett. 2005, 15, 4803-5. https://doi.org/10.1016/j.bmcl.2005.07.051
  11. Krall, R. L.; Penry, J. K.; White, B. G.; Kupferberg, H. J.; Swinyard, E. A. Epilepsia 1978, 19, 409-412. https://doi.org/10.1111/j.1528-1157.1978.tb04507.x
  12. Porter, R. J.; Cereghino, J. J.; Gladding, G. D.; Hessie, B. J.; Kupferberg, H. J.; Scoville, B.; White, B. G. Cleve Clin Q. 1984, 51, 293-295. https://doi.org/10.3949/ccjm.51.2.293
  13. Porsolt, R. D.; Bertin, A.; Jalfre, M. Arch. Int. Pharmacodyn. Ther. 1977, 229, 327-336.
  14. Elhwuegi, A. S. Prog. Neuropsychopharmacol. Biol. Psychiatry 2004, 28, 435-51. https://doi.org/10.1016/j.pnpbp.2003.11.018
  15. Millan, M. J. Eur. J. Pharmacol. 2004, 500, 371-84. https://doi.org/10.1016/j.ejphar.2004.07.038
  16. Chen, Y. L.; Hung, H. M.; Lu, C. M.; Li, K. C.; Tzeng, C. C. Bioorg. Med. Chem. 2004, 12, 6539-6546. https://doi.org/10.1016/j.bmc.2004.09.025
  17. Bekhit, A. A.; El-Sayed, O. A.; Aboulmagd, E.; Park, J. Y. Eur. J. Med. Chem. 2004, 39, 249-55. https://doi.org/10.1016/j.ejmech.2003.12.005
  18. Voger, H. G.; Voger, W. H. Drug Discovery and Evaluation-Pharmacological Assays; antidepressant activity; Springer-Verlag: Berlin heidelberg, 1997; p 411.
  19. Hanna, M. M. Bioorg. Med. Chem. 2007, 15, 7765-7772. https://doi.org/10.1016/j.bmc.2007.08.055
  20. Willner, P.; Mitchell, P. J. Behav. Pharmacol. 2002, 13, 169-188. https://doi.org/10.1097/00008877-200205000-00001
  21. Lapin, I. P. Psychopharmacology 1980, 70, 179-85. https://doi.org/10.1007/BF00435311

Cited by

  1. ]pyrimidine Derivatives and Their Antimicrobial Activity vol.51, pp.4, 2014, https://doi.org/10.1002/jhet.2108
  2. Design and evaluation of new hybrid pharmacophore quinazolino-tetrazoles as anticonvulsant strategy vol.23, pp.1, 2014, https://doi.org/10.1007/s00044-013-0630-4
  3. Synthesis and evaluation of anticonvulsant and antidepressant activities of 7-alkyl-7H-tetrazolo[1,5-g]purine derivatives vol.23, pp.10, 2014, https://doi.org/10.1007/s00044-014-1030-0
  4. )-one derivatives for anticancer activity vol.172, pp.5, 2015, https://doi.org/10.1111/bph.12992
  5. ChemInform Abstract: Synthesis and Studies on Anticonvulsant and Antidepressant Activities of 5-Alkoxy-tetrazolo[1,5-a]quinolines. vol.41, pp.30, 2010, https://doi.org/10.1002/chin.201030158
  6. Use of Nanocrystalline ZnO as an Efficient and Reusable Catalyst for a One-Pot, Three-Component Synthesis of 6-Chloro- and 5,7-Dichloro-4-Hydroxy-3-[Aryl (Piperidin-1-yl)Methyl]Quinolin-2(1H)-Ones in vol.42, pp.2, 2010, https://doi.org/10.3184/174751918x15192990175864
  7. Synthesis and Evaluation of Antidepressant Activities of 5-Aryl-4,5-dihydrotetrazolo [1,5-a]thieno[2,3-e]pyridine Derivatives vol.24, pp.10, 2019, https://doi.org/10.3390/molecules24101857
  8. Aryl and heteroaryl azo dyes derived from 6, 8‐dichloro‐4‐hydroxyquinolin‐2 (1 H )‐one: synthesis, characterisation, solvatochromism and spectroscopic properties vol.135, pp.5, 2019, https://doi.org/10.1111/cote.12426
  9. Tetrazoloquinolines: Synthesis, Reactions, and Applications vol.24, pp.None, 2010, https://doi.org/10.2174/1385272824666200217095341