Synthesis of 4-(2-ethylphenyl)-1-substituted[1,2,4] triazoloquinazolin-5(4H)-ones for their H1-Antihistamine Activity

Alagarsamy V.; Shankar D.; Raja Solomon V.; Parthiban P; Hanish Singh J.C.

doi:10.37285/ijddd.1.1.6

Articles

Vol. 1 No. 1 (2010): January-March 2010

Synthesis of 4-(2-ethylphenyl)-1-substituted[1,2,4] triazoloquinazolin-5(4H)-ones for their H1-Antihistamine Activity

Alagarsamy V.^▸^▾
Shankar D.^▸^▾
Raja Solomon V.^▸^▾
Parthiban P^▸^▾
Hanish Singh J.C.^▸^▾

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DOI: https://doi.org/10.37285/ijddd.1.1.6
Submitted: November 19, 2024
Published: 2010-02-15

Abstract

This study describes the synthesis of novel 4-(2-ethyl phenyl)-1-substituted-4H-[1,2,4]triazolo [4,3-a] quinazolin-5-ones and evaluation of their H1 antihistamine activity. The in vivo H1-antihistaminic activity of these compounds was evaluated on male Dunkin Hartley guinea pigs; all the test compounds significantly protected the animals from histamine induced bronchospasm. Compound 4-(2-ethyl phenyl)-1-methyl-4H-[1,2,4] triazolo [4,3-a] quinazolin-5-one (8) emerged as the most active compound of the series and it is more potent (74.39 % protection) when compared to the reference standard, chlorpheniramine maleate (71% protection), it showed negligible sedation (10%) when compared to chlorpheniramine maleate (30%). Therefore compound 8 can serve as a lead molecule for further development as a new class of H1-antihistamines.

References

[1] Simons, F. E.; Simons, K. J. N. Engl. J .Med. 1994, 330, 1663-1670.
[2] Van der Goot, H.; Bast, A.; Timmerman, H. Structural Requirements for Histamine H2 Agonists and H2 Antagonists. In Histamine and Histamine Antagonists; Uvniis, B., Ed.; Handbook of Experiment Pharmacology,Vol. 97; Springer: Berlin Heidelberg, 1991, pp 573-748.
[3] Carr, A. A.; Meyer, D. R. Arzneimittelforschung. 1982, 32, 1157-1159.
[4] Hopp, R. J.; Bewtra, A.; Nair, N. M.; Townley, R. G. J. Allergy Clin. Immunol. 1985, 76, 609.
[5] Chairungsrilerd, N.; Furukawa, K.; Ohta, T.; Nozoe, S.; Ohizumi, Y. Eur J Pharmacol. 1996, 314, 351.
[6] Estelle, F.; Simons, R.; Simons, K. Clin. Pharmacokinet. 1991, 21, 372–393.
[7] Renner, H.; Schnitzler, S. ; Hagen, V. ; Kottke, K.; Kuehmstedt, H. Pharmazie 1980, 35, 801-802.
[8] Alagarsamy, V.; Venkatesaperumal, R.; Vijayakumar, S.; Angayarkanni, T.; Pounammal, P.; Senthilganesh, S.; Kandeeban, S. Pharmazie. 2002, 57, 306-307.
[9] Alagarsamy, V. Pharmazie. 2004, 59, 753-755.
[10] Van Arman, C. G.; Miller, L. M.; O'Malley, M. P. J. Pharmacol. Exp. Ther. 1961, 133, 90-95.
[11] Shah, G. B.; Parmar, N. S. Phytother Res. 2003, 17, 1092–1097.
[12] Suhagia, B. N.; Chhabria, M. T.; Makwana, A. G. J Enzyme Inhib Med Chem. 2006, 21, 681-691.

Keywords

Triazoloquinazoline
1,2,4-Triazole
Quinazolin-5-ones
Sedation
H1-Antihistaminic agent

How to Cite

V., A., D., S., V., R. S., P, P., & J.C., H. S. (2010). Synthesis of 4-(2-ethylphenyl)-1-substituted[1,2,4] triazoloquinazolin-5(4H)-ones for their H1-Antihistamine Activity . International Journal of Drug Design and Discovery, 1(1), 49–56. https://doi.org/10.37285/ijddd.1.1.6

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[1] [1] Simons, F. E.; Simons, K. J. N. Engl. J .Med. 1994, 330, 1663-1670.

[2] [2] Van der Goot, H.; Bast, A.; Timmerman, H. Structural Requirements for Histamine H2 Agonists and H2 Antagonists. In Histamine and Histamine Antagonists; Uvniis, B., Ed.; Handbook of Experiment Pharmacology,Vol. 97; Springer: Berlin Heidelberg, 1991, pp 573-748.

[3] [3] Carr, A. A.; Meyer, D. R. Arzneimittelforschung. 1982, 32, 1157-1159.

[4] [4] Hopp, R. J.; Bewtra, A.; Nair, N. M.; Townley, R. G. J. Allergy Clin. Immunol. 1985, 76, 609.

[5] [5] Chairungsrilerd, N.; Furukawa, K.; Ohta, T.; Nozoe, S.; Ohizumi, Y. Eur J Pharmacol. 1996, 314, 351.

[6] [6] Estelle, F.; Simons, R.; Simons, K. Clin. Pharmacokinet. 1991, 21, 372–393.

[7] [7] Renner, H.; Schnitzler, S. ; Hagen, V. ; Kottke, K.; Kuehmstedt, H. Pharmazie 1980, 35, 801-802.

[8] [8] Alagarsamy, V.; Venkatesaperumal, R.; Vijayakumar, S.; Angayarkanni, T.; Pounammal, P.; Senthilganesh, S.; Kandeeban, S. Pharmazie. 2002, 57, 306-307.

[9] [9] Alagarsamy, V. Pharmazie. 2004, 59, 753-755.

[10] [10] Van Arman, C. G.; Miller, L. M.; O'Malley, M. P. J. Pharmacol. Exp. Ther. 1961, 133, 90-95.

[11] [11] Shah, G. B.; Parmar, N. S. Phytother Res. 2003, 17, 1092–1097.

[12] [12] Suhagia, B. N.; Chhabria, M. T.; Makwana, A. G. J Enzyme Inhib Med Chem. 2006, 21, 681-691.