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Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society


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1846-9558
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Synthesis of some novel triazole derivatives as anti-nociceptive and anti-inflammatory agents

Aiyalu Rajasekaran1 / Kalasalingam Rajagopal1

KMCH College of Pharmacy, Coimbatore, Tamilnadu, India1

AK College of Pharmacy, Krishnankoil, Tamilnadu, India2

This content is open access.

Citation Information: Acta Pharmaceutica. Volume 59, Issue 3, Pages 355–364, ISSN (Online) 1846-9558, ISSN (Print) 1330-0075, DOI: 10.2478/v10007-009-0026-7, October 2009

Publication History

Published Online:
2009-10-09

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

  • A. Rajasekaran and P. P. Thampi, Synthesis and anti-nociceptive activity of some substituted-{5-[2-1,2,3,4-tetrahydrocarbazol-9-yl)ethyl]tetrazol-1-yl}alkanones, Eur. J. Med. Chem. 40 (2005) 1359-1364; DOI: 10.1002/chin.200617137. [CrossRef]

  • A. Rajasekaran and P. P. Thampi, Synthesis and anti-inflammatory activity of some 10-[(1-acyl-1H-tetrazol-5-yl)ethyl]-10h-phenothiazines, Acta Pharm. Turc. 45 (2003) 235-240.

  • A. O. De Souza, M. T. Pedrosa, J. B. Alderete, A. F. Cruz, M. A. Prado, R. B. Alves and C. L. Silva, Cytotoxicity, antitumoral and antimycobacterial activity of tetrazole and oxadiazole derivatives, Pharmazie 60 (2005) 396-397. [PubMed]

  • A. Rajasekaran and P. P. Thampi, Synthesis and analgesic evaluation of some 5-[beta-(10-phenothiazinyl) ethyl]-1-(acyl)-1,2,3,4-tetrazoles, Eur. J. Med. Chem. 39 (2004) 273-279; DOI: 10.1002/chin.200433179. [CrossRef]

  • A. Rajasekaran, S. Murugesan and K. Anandarajagopal, Antibacterial, antifungal and anticonvulsant evaluation of newly synthesized 1-1-[2-(1H-tetrazol-5-yl)ethyl]-1H-benzo[d][1,2,3]triazoles, Arch. Pharm. Res. 29 (2006) 535-540. [PubMed] [CrossRef]

  • U. S. Göksen, N. G. Kelekçi, O. Göktas, Y. Köysal, E. Kiliç, S. Isik, G. Aktay and M. Ozalp, 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities, Bioorg. Med. Chem. 15 (2007) 5738-5751; DOI: 10.1086/586711. [Web of Science] [CrossRef]

  • R. M. Claramunt, D. S. María, E. Pinilla, M. R. Torres and J. Elguero, Structural studies of two Tinuvin P analogs: 2-(2,4-dimethylphenyl)-2H-benzotriazole and 2-phenyl-2H-benzotriazole, Molecules 21 (2007) 2201-2214; DOI: 10.3390/12092201. [CrossRef] [Web of Science] [PubMed]

  • A. Rajasekaran, V. Rajamanickam, P. T. Kumaresan, S. Murugesan and V. Sivakumar, Analgesic and anti-epileptic activity of N-Mannich bases of some substituted benztriazole, Int. J. Chem. Sci. 2 (2004) 445-449.

  • T. Yoshikawa, Y. Mine, K. Morikage and N. Yoshida, Pharmacological profile of AS-9705, a novel benzotriazole carboxamide derivative, as a gastroprokinetic agent with potent anti-emetic activity, Arzneimittelforsch. 53 (2003) 98-106; DOI: 10.1088/0953-8984. [CrossRef]

  • A. B. Najda, M. Lebska M, A. Orzeszko, K. Kopañska, E. Krzywiñska, G. Muszyñska and M. Bretner, Synthesis of new analogs of benzotriazole, benzimidazole and phthalimide potential inhibitors of human protein kinase CK2, Bioorg. Med. Chem. 15 (2009) 1573-1578; DOI: 10.1016/j.bmc.2008.12.071. [CrossRef] [Web of Science]

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