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Dergiler / Turkish Journal of Chemistry / 2017 / Cilt: 41 - Sayı: 5

Synthesis and antinociceptive activities of some novel benzimidazole-piperidine derivatives

Özgür Devrim CAN
Ümide DEMİR ÖZKAY
Nazlı TURAN
Betül KAYA ÇAVUŞOĞLU
Sayfa
672–684
Yayın Tarihi
2022-11-03
DOI
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⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

Predictions obtained by theoretical calculations of ADME (absorption, distribution, metabolism, excretion) properties supported the antinociceptive potential of the tested benzimidazole-piperidine derivatives.

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Amaç & Hipotez:In this study, a series of benzimidazole-piperidine derivatives were synthesized with the objective of developing potent antinociceptive agents.
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Temel Bulgular & Veri:Some 2-(4-substituted-phenyl)-1-[2-(piperidin-1-yl)ethyl]-1 H -benzimidazole derivatives were obtained by microwave-supported reaction of an appropriate 2-(4-substituted-phenyl)-1 H -benzimidazole with 2- (piperidine-1-yl)ethyl chloride.
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Sonuç & Katkı:Predictions obtained by theoretical calculations of ADME (absorption, distribution, metabolism, excretion) properties supported the antinociceptive potential of the tested benzimidazole-piperidine derivatives.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Alan Parametreleri

Abstract

In this study, a series of benzimidazole-piperidine derivatives were synthesized with the objective of developing potent antinociceptive agents. Some 2-(4-substituted-phenyl)-1-[2-(piperidin-1-yl)ethyl]-1 H -benzimidazole derivatives were obtained by microwave-supported reaction of an appropriate 2-(4-substituted-phenyl)-1 H -benzimidazole with 2- (piperidine-1-yl)ethyl chloride. The chemical structures of the compounds were elucidated by FT-IR, 1 H NMR, 13 C NMR, and HRMS spectral data. Antinociceptive activity was assessed by conducting hot-plate, paw-pressure, and formalin tests. Morphine (5 mg/kg, i.p) was used as a reference drug. Among the tested compounds 2a 2d and 2f 2h (10 mg/kg) increased the maximum possible effect (MPE)% values calculated for the hot-plate and paw-pressure tests and decreased the paw licking time of rats in the early phase of the formalin test, indicating centrally mediated antinociceptive activities of these derivatives. In the late-phase 2g and 2h were the only compounds reducing the paw licking duration. These data show additional peripherally mediated antinociceptive activities for these two derivatives. Falling latencies of animals in the rotarod test did not change upon the administration of test compounds; thus, the observed antinociceptive effects were specific. Predictions obtained by theoretical calculations of ADME (absorption, distribution, metabolism, excretion) properties supported the antinociceptive potential of the tested benzimidazole-piperidine derivatives.

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Bu Makaleye Atıf Yap

CAN, Ö. D., ÖZKAY, Ü. D., TURAN, N., ÇAVUŞOĞLU, B. K. (2022). Synthesis and antinociceptive activities of some novel benzimidazole-piperidine derivatives. Turkish Journal of Chemistry, Cilt: 41 - Sayı: 5, 672–684. https://ajindex.com/articles/601875

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Kaynakça (23)

  1. Elavarasan, T.; Bhakiaraj, D. P.; Gopalakrishnan, M. ISRN Org. Chem. 2014, 2014, 120173
  2. Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257-10274
  3. Miles, T. J.; Axten, J. M.; Barfoot, C.; Brooks, G.; Brown, P.; Chen, D.; Dabbs, S.; Davies, D. T.; Downie, D. L.; Eyrisch, S. et al. Bioorg. Med. Chem. Lett. 2011, 21, 7489-7495
  4. Maruthavanan, T.; Venkatesan, P. Nat. Prod. Res. 2013, 27, 238-245
  5. Jiang, Z.; Gu, J.; Wang, C.; Wang, S.; Liu, N.; Jiang, Y.; Dong, G.; Wang, Y.; Liu, Y.; Yao, J. et al. Eur. J. Med. Chem. 2014, 82, 490-497
  6. Kang, D.; Fang, Z.; Li, Z.; Huang, B.; Zhang, H.; Lu, X.; Xu, H.; Zhou, Z.; Ding, X.; Daelemans, D. J. Med. Chem. 2016, 59, 7991-8007
  7. Fernandes, ´I. A.; de Almeida, L.; Ferreira, P. E.; Marques, M. J.; Rocha, R. P.; Coelho; L. F.; Carvalho, D. T.; Viegas, C. Jr. Bioorg. Med. Chem. Lett. 2015, 25, 3346-3349
  8. Wang, P.; Cai, J.; Chen, J.; Ji, M. Eur. J. Med. Chem. 2015, 93, 1-8
  9. Bogen, S. L.; Pan, W.; Gibeau, C. R.; Lahue, B. R.; Ma, Y.; Nair, L. G.; Seigel, E.; Shipps, G. W. Jr; Tian, Y.; Wang, Y. et al. ACS Med. Chem. Lett. 2016, 7, 324-329
  10. Imaeda, Y.; Tawada, M.; Suzuki, S.; Tomimoto, M.; Kondo, M.; Tarui, N.; Sanada, T.; Kanagawa, R.; Snell, G.; Behnke, C. A. et al. Bioorg. Med. Chem. 2016, 24, 5771-5780
  11. Terry, B.; Hirsch, G.; Hook, J. B. Eur. J. Pharmacol. 1968, 4, 289-297
  12. Grimmett, M. R. Imidazole and Benzimidazole Synthesis; Academic Press: London, UK, 1997
  13. Fei, F.; Zhou, Z. Expert. Opin. Ther. Pat. 2013, 23, 1157-1179
  14. Ozkay, Y.; Tunalı, Y.; Karaca, H.; I¸sıkda˘g, I. Arch. Pharm. (Weinheim) 2011, 344, 264-271
  15. Lyakhova, E. A.; Gusyeva, Y. A.; Nekhoroshkova, J. V.; Shafran, L. M.; Lyakhov, S. A. Eur. J. Med. Chem. 2009, 44, 3305-3312
  16. Lim, C. J.; Kim, N.; Lee, E. K.; Lee, B. H.; Oh, K. S.; Yoo, S. E.; Yi, K. Y. Bioorg. Med. Chem. Lett. 2011, 21, 2309-2312
  17. Langtry, H. D.; Wilde, M. I. Drugs 1998, 56, 447-486
  18. Singh, G.; Bansal, Y.; Bansal, G.; Goel, R. K. Med. Chem. 2014, 10, 418-425
  19. Kennis, L. E. J.; Vandenberk, J.; Boey, J. M.; Mertens, J. C.; Van Heertum, A. H. M.; Janssen, M.; Awouters, F. Drug Dev. Res. 1986, 8, 133-140
  20. Lipunova, G. N.; Nosova, E. V.; Charushin, V. N. Chem. Het. Comp. 2014, 50, 764-790
  21. Schwartz, J. C. Br. J. Pharmacol. 2011, 163, 713-721
  22. Sadek, B.; Khan, N.; Darras, F. H.; Pockes, S.; Decker, M. Physiol. Behav. 2016, 165, 383-391
  23. Zhou, D.; Zhou, W.; Song, J. K.; Feng, Z. Y.; Yang, R. Y.; Wu,