Design and Synthesis of 1-Substituted-4-(4-Nitrophenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones as a New Class of Antihistaminic Agents

Abstract

Some new 1-substituted-4-(4-nitrophenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones were synthesized and screened for their H1-antihistaminic activity. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, and mass spectral data and purity of the compounds was determined by elemental analysis. Antihistaminic activity of synthesized compounds was determined by the protection against histamine-induced bronchospasm on conscious guinea pigs. Percentage protection data showed that all title compounds of the series show significant protection in the range of 68–71.56% when compared to reference drug chlorpheniramine maleate (70.17%). The sedative properties of the compounds were also evaluated and found to be negligible when compared to chlorpheniramine maleate.

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REFERENCES

  1. 1

    Carr, A.A. and Meyer, D.R., Arzneimittelforschung, 1982, vol. 32, pp. 1157–1159.

    CAS  PubMed  Google Scholar 

  2. 2

    E.F. Ellis, N.F. Adkinson, J.W. Yungingen, and W.W. Busso, H1-receptor antagonists, in Musby-Year Book, Inc., 1985, pp. 856–891.

  3. 3

    Mallareddy, V. and Sattur, P.B., Curr. Sci., 1984, vol. 53, pp. 1069–1075.

    Google Scholar 

  4. 4

    Kumar, S., Shrivastava, S.K., and Sarkar, P.C., Indian J. Heterocycl. Chem., 1997, vol. 7, 109–113.

    CAS  Google Scholar 

  5. 5

    Bartroli, J., Turmo, E., and Alguero, M., J. Med. Chem., 1988, vol. 41, pp. 1869–1892.

    Article  Google Scholar 

  6. 6

    Alagarsamy, V., Sharma, H.K., Parthiban, P., Singh, J.C., Murugan, S.T., and Solomon, V.R. Pharmazie, 2009, vol. 64, pp. 5–12.

    CAS  PubMed  Google Scholar 

  7. 7

    Bousquet J., Van Cauwenberge, P., and Khaltaev, N., J. Allergy Clin. Immunol., 2001, vol. 108, pp. 147–152.

    Article  Google Scholar 

  8. 8

    Kuhn, W.L. and Van Maanen, E.F., J. Pharmacol. Exp. Ther., 1961, vol. 134, pp. 60–68.

    CAS  PubMed  Google Scholar 

  9. 9

    Van Arman, C.G., Miller, L.M., and O’Malley, M.P., J. Pharmacol. Exp. Ther., 1961, vol. 133, pp. 90–97.

    CAS  PubMed  Google Scholar 

  10. 10

    Alagarsamy, V., Narendhar, B., Sulthana, M.T., and Solomon, V.R., Med. Chem. Res., 2014, vol. 23, pp. 4692–4299.

    CAS  Article  Google Scholar 

  11. 11

    Nivedhitha, S., Solomon, V.R., Gobinath, M., Subramanian N., and Alagarsamy, V., Trop. J. Pharm. Res., 2015, vol. 14, pp. 271–278.

    Article  Google Scholar 

  12. 12

    Mallareddy, V., Ravinderreddy, P., and Jayamma, Y., Indian Drugs, 1987, vol. 25, pp. 182–186.

    Google Scholar 

  13. 13

    Raghuram Rao, A., Chandrasekhar, V., and Mallareddy, V., Indian Drugs, 1986, vol. 24, pp. 40–48.

  14. 14

    Hopp, R.J., Bewtra, A., Nair, N.M., and Townley, R.G., J. Allergy Clin. Immunol., 1985, vol. 76, pp. 609–614.

    CAS  Article  Google Scholar 

  15. 15

    Raju, V.S.K., Bhagawanraju, M., Bahekar, R.H., Rajan, K.S., and Raghuram Rao, A. Indian Drugs, 1999, vol. 36, pp. 759–764.

    CAS  Google Scholar 

  16. 16

    Chairungsrilerd, N., Furukawa, K., Ohta, T., Nozoe, S., and Ohizumi, Y., Eur. J. Pharmacol., 1996, vol. 314, pp. 351–359.

    CAS  Article  Google Scholar 

  17. 17

    Dews, P. B., Br. J. Pharmacol., 1953, vol. 8, pp. 46–52.

    CAS  Google Scholar 

  18. 18

    Kuhn, W.L. and Van Maanen, E.F., J. Pharmacol. Exp. Ther., 1961, 134, pp. 60–67.

    CAS  PubMed  Google Scholar 

  19. 19

    Mukherji, D.D., Nintiyal, S.R., Prasad, C.R., and Dhawan, B.N. Indian J. Med. Res., 1980, vol. 93, pp. 1426–1467.

    Google Scholar 

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Correspondence to V. Alagarsamy.

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The Institutional Animal Ethics committee approved the protocol adopted for the experimentation of animals. All applicable international, national, and institutional guidelines for the care and use of animals were followed.

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The authors report no conflicts of interest.

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Corresponding author: phone: +91 8455-230690; fax: +91 8455 233888; e-mail: drvalagarsamy@gmail.com.

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Gobinath, M., Subramanian, N., Alagarsamy, V. et al. Design and Synthesis of 1-Substituted-4-(4-Nitrophenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones as a New Class of Antihistaminic Agents. Russ J Bioorg Chem 46, 403–408 (2020). https://doi.org/10.1134/S1068162020030085

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Keywords:

  • histamine
  • triazolo
  • quinazolin-5(4H)-ones
  • antihistaminic activity
  • sedative–hypnotic activity