Abstract
A series of fused pyranopyrazole and pyranoimidazole, namely 5-(3,6-diamino-4-aryl-5-carbonitrile-pyrano(2,3-c)pyrazol-2-yl)sulphonyl-8-hydroxyquinolines (5a–e), 5-(6-amino-4-aryl-5-carbonitrile-pyrano(2,3-c)pyrazol-3-yl)sulphonamido-8-hydroxyquinolines (6a-e), 5-(2-thioxo-4-aryl-5-carbonitrile-6-amino-pyrano(2,3-d)imidazol-2-yl)sulphonyl-8-hydroxyquinolines (10a-e), and 5-(2-oxo-4-aryl-5-carbonitrile-6-amino-pyrano(2,3-d)imidazol-2-yl) sulphonyl-8-hydroxyquinolines (11a-e), have been prepared via condensation of some arylidine malononitriles with 5-sulphonamido-8-hydroxyquinoline derivatives 3, 4, 8 and 9. All the synthesized compounds were screened for their antimicrobial activities, and most of the tested compounds showed potent inhibition growth activity towards Escherichia coli, Pseudomonas aeruginosa (Gramnegative bacteria). Furthermore, six selected compounds were tested for their antiviral activity against avian paramyxovirus type1 (APMV-1) and laryngotracheitis virus (LTV), and the results showed that a concentration range of 3-4 μg per mL of compounds 2, 3, and 4 showed marked viral inhibitory activity for APMV-1 of 5000 tissue culture infected dose fifty (TCID50) and LTV of 500 TCID50 in Vero cell cultures based on their cytopathic effect. Chicken embryo experiments show that compounds 2, 3, and 4 possess high antiviral activity in vitro with an inhibitory concentration fifty (IC50) range of 3–4 μg per egg against avian APMV-1 and LTV and their toxic concentration fifty (CC50) of 200–300 μg per egg.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bankovskis, J., Cirule, M., Brusilovskii, P. I., and Tsilinskaya, I. A., Synthesis of 5-alkylthio-8-hydroxyquinolines. Khim. Geterotsiklicheskikh Soedin., 11, 1501–1504 (1979).
Barry, A. L. and Thornsberry, C., Susceptibility Testing: Diffusion Test Procedures, in Manual of Clinical Microbiology. Lennette, E. H., Balows, A., Hausler, W. J., Jr., and Truant, J. P. (Eds.), 3rd ed. American Society for Microbiology, Washington (DS), pp. 463–474, (1980).
Callejo, M. J., Lafuente, P., Martín-León, N., Quinteiro, M., Seoane, C., and Soto, J. L., A convenient preparation of [1, 2,4]triazolo[1,5-a]pyridines from acetohydrazide derivatives. Synthetic and mechanistic aspects. J. Chem. Soc. Perkin Trans. I, 1687–1690 (1990).
Chen, S., Chen, R., He, M., Pang, R., Tan, Z., and Yang, M., Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat-TAR interaction inhibitors. Bioorg. Med. Chem., 17, 1948–1956 (2009).
Corson, B. B. and Stoughton, R. W., Reactions of alpha, betaunsaturated dinitriles. J. Am. Chem. Soc., 50, 2825–2837 (1928).
Cox, S., Buontempo, P. J., Wright-Minogue, J., DeMartino, J. L., Skelton, A. M., Ferrari, E., Schwartz, J., Rozhon, E. J., Linn, C. C., Girijavallabhan, V., and O’Connell, J. F., Antipicornavirus activity of SCH 47802 and analogs: in vitro and in vivo studies. Antiviral. Res., 32, 71–79 (1996).
Graham, G., Porter, H. D., and Weissberger, A., Synthesis and acylation of pyrazolines derived from hydrazine and methyl hydrazine. J. Am. Chem. Soc., 71, 983 (1949).
Heibron, I., Dictionary of Organic Compounds, 4th ed. Oxford University press, New York, p. 1374, (1965).
Hoemann, M. Z., Xie, R. L., Rossi, R. F., Meyer, S., Sidhu, A., Cuny, G. D., and Hauske, J. R., Potent in vitro methicillinresistant Staphylococcus aureus activity of 2-(1H-indol-3-yl)tetrahydroquinoline derivatives. Bioorg. Med. Chem. Lett., 12, 129–132 (2002).
Hussein, M. A., Kafafy, A. H., Abdel-Moty, S. G., and Abou-Ghadir, O. M., Synthesis and biological activities of new substituted thiazoline-quinoline derivatives. Acta Pharm., 59, 365–382 (2009).
Jia, W., Liu, Y., Li, W., Liu, Y., Zhang, D., Zhang, P., and Gong, P., Synthesis and in vitro anti-hepatitis B virus activity of 6H-[1]benzothiopyrano[4,3-b]quinolin-9-ols. Bioorg. Med. Chem., 17, 4569–4574 (2009).
Kouznetsov, V. V., Vargas Mendez, L. Y., Milena Leal, S., Mora Cruz, U., Andres Coronado, C., Melendez Gomez, C. M., Romero Bohorquez, A. R., and Escobar Rivero, P., Targetoriented synthesis of antiparasitic 2-hetaryl substituted quinolines based on imino Diels-Alder reactions. Lett. Drug Des. Discov., 4, 293–296 (2007).
Lilienkampf, A., Mao, J., Wan, B., Wang, Y., Franzblau, S. G., and Kozikowski, A. P., Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculo-sis. J. Med. Chem., 52, 2109–2118 (2009).
Meléndez Gómez, C. M., Kouznetsov, V. V., Sortino, M. A., Alvarez, S. L., and Zacchino, S. A., In vitro antifungal activity of polyfunctionalized 2-(hetero)arylquinolines prepared through imino Diels-Alder reactions. Bioorg. Med. Chem., 16, 7908–7920 (2008).
Meyyanathan, S. N., Murali, K. E., Chandrashekhar, H. R., Godavarthi, A., Dhanaraj, S. A., Vijayan, P., and Suresh, B., Synthesis of some amino acids incorporated 4(3H)-quinazolinones as possible antiherpes viral agents. Ind. Drugs, 43, 497–502 (2006).
Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods., 65, 55–63 (1983).
Reed, L. J. and Muench, H., A simple method of estimating 50 percent endpoint. Am. J. Hyg., 27, 493–497 (1938).
Takatsy, G. X., The use of spiral loops in serological and virological method. Acta Microbial. Hung., 3, 191–194 (1956).
Vargas, M. L. Y., Castelli, M. V., Kouznetsov, V. V., Urbina, G. J. M., López, S. N., Sortino, M., Enriz, R. D., Ribas, J. C., and Zacchino, S., In vitro antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers. Bioorg. Med. Chem., 11, 1531–1550 (2003).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kassem, E.M., El-Sawy, E.R., Abd-Alla, H.I. et al. Synthesis, antimicrobial, and antiviral activities of some new 5-sulphonamido-8-hydroxyquinoline derivatives. Arch. Pharm. Res. 35, 955–964 (2012). https://doi.org/10.1007/s12272-012-0602-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-012-0602-0