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Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society

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Volume 59, Issue 3 (Sep 2009)


Synthesis of some novel triazole derivatives as anti-nociceptive and anti-inflammatory agents

Aiyalu Rajasekaran
  • KMCH College of Pharmacy, Coimbatore, Tamilnadu, India
/ Kalasalingam Rajagopal
  • AK College of Pharmacy, Krishnankoil, Tamilnadu, India
Published Online: 2009-10-09 | DOI: https://doi.org/10.2478/v10007-009-0026-7

Synthesis of some novel triazole derivatives as anti-nociceptive and anti-inflammatory agents

Eight novel 1-[2-(1H-tetrazol-5-yl)ethyl]-1H-benzo[d][1,2,3]triazoles (3a-h) have been synthesized in order to obtain new compounds with potential anti-nociceptive and anti-inflammatory activity. The titled compounds were synthesized by the condensation of 1-[2-(1H-tetrazol-5-yl) ethyl]-1H-benzotriazole (2) and appropriate acid chlorides. Compound 2 was synthesized by reacting 3-(1H-benzo[d][1,2,3]triazol-1-yl)propanonitrile (1) with sodium azide and ammonium chloride in the presence of dimethylformamide. The synthesized compounds were characterized by spectroscopic methods (IR, 1H NMR, mass spectroscopy) and elemental analysis. The titled compounds were evaluated for anti-nociceptive activity by the hot plate method and the writhing response method, and anti-inflammatory activity was evaluated by the carragenean induced paw edema method. 5-(2-(1H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(4-aminophenyl)methanone (3d) and 5-(2-(1H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(2-hydroxyphenyl)methanone (3g) exhibited significant anti-nociceptive activity. 1-(2-(1-Tosyl-1H-tetrazol-5-yl)ethyl)-1H-benzo[d][1,2,3]triazole (3c) and 4,5-(2-(1H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl sulfonyl)benzenamine (3f) elicited superior anti-inflammatory activity compared to other synthesized compounds. Further investigations are needed to discern the mechanism of action.

Sinteza novih derivata triazola kao anti-nociceptivnih i protuuaplnih agenasa

Sintetizirano je osam novih 1-[2-(1H-tetrazol-5-il)etil]-1H-benzo[d][1,2,3]triazola (3a-h) s potencijalnim anti-nociceptivnim i protuupalnim djelovanjem. Navedeni spojevi pripravljeni su kondenzacijom 1-[2-(1H-tetrazol-5-il)etil]-1H-benzotriazola (2) i odgovarajućih kiselinskih klorida. Spoj 2 dobiven je reakcijom 3-(1H-benzo[d][1,2,3]triazol-1-il)propanonitrila (1) s natrijevim azidom i amonijevim kloridom u prisutnosti dimetilformamida. Sintetizirani spojevi su karakterizirani spektroskopskim metodama (IR, 1H NMR, spektroskopijom masa) i elementarnom analizom. Anti-nociceptivno djelovanje ispitivano je metodom vruće ploče i praćenjem odgovora na bolne podražaje, dok je protuupalno djelovanje evaluirano testom s karageninom. 5-(2-(1H-benzo[d][1,2,3]triazo-1-il)etil)-1H-tetrazol-1-il)(4-aminofenil)metanon (3d) i 5-(2-(1H-benzo[d][1,2,3]triazo-1-il)etil)-1H-tetrazol-1-il) (2-hidroksifenil)metanon (3g) pokazali su značajno anti-nociceptivno djelovanje. 1-(2-(1-Tosil-1H-tetrazol-5-il)etil)-1H-benzo[d][1,2,3]triazol (3c) i 4-5-(2-(1H-benzo[d][1,2,3]triazo-1-il)etil)-1H-tetrazol-1-il sulfonil)benzenamin (3f) pokazali su superiorno protuupalno djelovanje u odnosu na druge sintetizirane spojeve. Daljnja istraživanja su nužna kako bi se razjasnio mehanizam djelovanja.

Keywords: synthesis; 1-[2-(1H-tetrazol-5-yl)ethyl]-1H-benzo[d][1,2,3]triazoles; anti-nociception; anti-inflammation

Keywords: sinteza; 1-[2-(1H-tetrazol-5-il)etil]-1H-benzo[d][1,2,3]triazol; nocicepcija; upala

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About the article

Published Online: 2009-10-09

Published in Print: 2009-09-01

Citation Information: Acta Pharmaceutica, ISSN (Online) 1846-9558, ISSN (Print) 1330-0075, DOI: https://doi.org/10.2478/v10007-009-0026-7.

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