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The Pharmaceutical Society of Korea (대한약학회)
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Antibacterial, Antifungal and Anticonvulsant Evaluation of Novel Newly Synthesized 1-[2-(1H-Tetrazol-5-yl)ethyl]-1H-benzo[d][1,2,3]triazoles

  • Published : 2006.07.01
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Abstract

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 their in 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 against Bacillus subtilis and moderate antifungal activity against Candida albicans. Compounds 5-(2-(1 H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(4-aminophenyl)methanone 3d and 5-(2-(1 H-benzo[d][1,2,3]triazo-1-yl)ethyl)-1H-tetrazol-1-yl)(2-aminophenyl)methanone 3e elicited excellent anticonvulsant activity.

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References

  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) https://doi.org/10.1002/ardp.200400967
  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) https://doi.org/10.1046/j.1432-1033.2003.03540.x
  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, antitumoral 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 oxadiazolylbenzotriazole 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) https://doi.org/10.1002/bip.10078
  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) https://doi.org/10.1016/0920-1211(94)90012-4
  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) https://doi.org/10.1016/j.ejmech.2003.11.016
  14. Rajasekaran, A., Rajamanickam, V., Thirupathy Kumaresan, P., Murugesan, S., and Sivakumar, V., Analgesic and Anti-Epileptic activity of N-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) https://doi.org/10.1016/j.ejmech.2005.07.013
  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) https://doi.org/10.1016/j.ejmech.2004.03.004
  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)