Antibacterial, antifungal and anticonvulsant evaluation of novel newly synthesized 1-[2-(1H-tetrazol-5-yl)ethyl]-1H-benzo[d][1,2,3]triazoles

  • 256 Accesses

  • 30 Citations


Several novel 1-[2-(1H-tetrazol-5-yl) ethyl]-1H-benzo[d][1,2,3]triazoles (3a-h) have been synthesized by the condensation of 1-[2-(1H-tetrazol-5-yl)-ethyl]-1H-benzotriazole (2) and appropriate acid chlorides. 1-[2-(1H-tetrazol-5-yl)-ethyl]-1H-benzotriazole (2) was synthesized by reacting 3-(1H-benzo[d][1,2,3]triazol-1-yl)propanenitrile with sodium azide and ammonium chloride in the presence of dimethylformamide. The synthesized compounds were characterized by IR and PMR analysis. The titled compounds were evaluated for theirin vitro antibacterial and antifungal activity by the cup plate method and anticonvulsant activity evaluated by the maximal electroshock induced convulsion method in mice. All synthesized compounds exhibited moderate antibacterial activity againstBacillus subtilis and moderate antifungal activity againstCandida albicans. Compounds 5-(2-(1H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(4-aminophenyl)methanone3d and 5-(2-(1H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(2-aminophenyl)methanone3e elicited excellent anticonvulsant activity.

This is a preview of subscription content, log in to check access.


  1. Adamec, J., Waisser, K., Kunes, J., and Kaustova, J., A note on the antitubercular activities of 1 aryl-5-benzylsulfanyltetrazoles.Arch Pharm., 338, 385–389 (2005).

  2. Borowski, P., Deinert, J., Schalinski, S., Bretner, M., Ginalski, K., Kulikowski, T., and Shugar, D., Halogenated benzimidazoles and benzotriazoles as inhibitors of the NTPase/helicase activities of hepatitis C and related viruses.Eur J Biochem., 270, 1645–1653 (2003)

  3. Calvino, R., Mortarini, V., and Serafino, A., Study of some derivatives of the benzotriazole nucleus.Farmaco., 35, 240–247 (1980).

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

  5. Habib, N. S., Fahmy, S., El-Khawass, S. M., and Abel Aziem, T. A., Novel thiazolinyl, thiazolidinonyl, thiadiazolyl and oxadiazolyl-benzotriazole derivatives with potential antiinflammatory activity and minimum ulcerogenic effect.Pharmazie., 55, 900–906 (2000).

  6. Kaczmarek, K., Jankowski, S., Siemion, I. Z., Wieczorek, Z., Benedetti, E., Di Lello, P., Isernia, C., Saviano, M., and Zabrocki, J., Tetrazole analogues of cyclolinopeptide A: synthesis, conformation, and biology.Biopolymers., 63, 343–357 (2002).

  7. Kulkarni, S. K., In Handbook of Experimental Pharmacology, (2nd ed.); Vallabh. Prakashan, New Delhi, 2004, pp 125–127.

  8. Loscher, W. and Schmidt, D., Strategies in antiepileptic drug development: is rational drug design superior to random screening and structural variation.Epilepsy Res., 17, 95–134 (1994).

  9. Lin, C. Y., Ho, A. C., Chiang, H. C., Sun, J. S., and Sheu, S. Y., Reactive oxygen scavenger effect of pyrimidines, benzotriazoles and related compounds.Anticancer Res., 22, 937–942 (2002).

  10. Misra, A. K., Dandiya, P. C., and Kulkarni, S. K., Anticonvulsant activity of some trimethoxy-benzylidene-2-Thiohydantion derivatives.Indian J. Pharmacol., 5, 449–450 (1973).

  11. Mukerjee, K. L., In Medical Laboratory Technology; (1st ed.); Mcraw Hill: New Delhi, 1996; Vol. 2, pp. 674–675.

  12. Rajasekaran, A. and Thampi, P. P., Synthesis and Anti-Inflammatory activity of some 10-[(1-Acyl-1h-Tetrazol-5-yl)Ethyl]-10h-Phenothiazines.Acta Pharm. Turc., 45, 235–240 (2003).

  13. Rajasekaran, A. and Thampi P. P., Synthesis and analgesic evaluation of some 5-[beta-(10-phenothiazinyl)ethyl]-1-(acyl)-1,2,3,4-tetrazoles.Eur. J. Med. Chem., 39, 273–279 (2004).

  14. Rajasekaran, A., Rajamanickam, V., Thirupathy Kumaresan, P., Murugesan, S., and Sivakumar, V., Analgesic and Anti-Epileptic activity ofN-Mannich bases of Some Substituted Benztriazoles.International Journal of Chemical Sciences., 2, 445–449 (2004).

  15. Rajasekaran, A. and Thampi, P. P., Synthesis and antinociceptive activity of some substituted-{5-[2-(1,2,3,4-tetrahydrocarbazol-9-yl)ethyl]tetrazol-1-yl}alkanones.Eur. J. Med. Chem., 40, 1359–1364 (2005).

  16. Upadhayaya, R. S., Jain, S., Sinha, N., Kishore, N., Chandra, R., and Arora, S. K., Synthesis of novel substituted tetrazoles having antifungal activity.Eur. J. Med. Chem., 39, 579–592 (2004).

  17. Yoshikawa, T., Mine, Y., Morikage, K., and Yoshida N., Pharmacological profile of AS-9705, a novel benzotriazolecarboxamide derivative, as a gastroprokinetic agent with potent anti-emetic activity.Arzneimittelforschung., 53, 98–106 (2003).

  18. Zubrzak, P., Kociolek, K., Smoluch, M., Silberring, J., Kowalski, M. L., Szkudlinska, B., and Zabrocki, J., Search for new synthetic immunosuppressants II. Tetrazole analogues of hymenistatin I.Acta Biochim Pol., 48, 1151–1154 (2001).

Download references

Author information

Correspondence to Aiyalu Rajasekaran.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

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

Download citation

Key words

  • Synthesis
  • 1-[2-(1H-tetrazol-5-yl)ethyl]-1H-benzo[d][1,2,3]triazoles
  • Antibacterial activity
  • Antifungal activity
  • Anticonvulsant activity