Abstract
The substituted thiosemicarbazide moiety was placed at the C-2 position and 2-methylphenyl group at N-3 position of quinazoline ring and obtained compounds were tested for their antitubercular activities and antibacterial activities against selected gram-positive and gram-negative bacteria. The target compounds 1-(3-(2-methylphenyl)-4-oxo-3H-quinazolin-2-yl)-4-(substituted) thiosemicarbazides were obtained by the reaction of 2-hydrazino-3-(2-methylphenyl) quinazolin-4(3H)-one with different dithiocarbamic acid methyl ester derivatives. All synthesized compounds were also screened for their antimicrobial activity against selective gram-positive and gram-negative bacteria by agar dilution method. Among the series, 1-[3-(2-methylphenyl)-4-oxo-3H-quinazolin-2-yl]-4-[4-chlorophenyl]-thiosemicarbazide exhibited the most potent activity against S. typhi, E. coli, and B. subtilis, while 1-[3-(2-methylphenyl)-4-oxo-3H-quinazolin-2-yl]-4-[4-nitrophenyl]-thiosemicarbazide was the most potent against E. coli, B. subtilis, P. aeruginosa, S. typhi, and S. flexneri. These two compounds exhibited the antitubercular activity at the minimum concentration (3 μg/mL) that offered potential for further optimization and development of new antitubercular agents. The obtained results demonstrated promising antimicrobial and antitubercular activities of the synthesized quinazoline compounds which could be used as new scaffolds for improving their antimicrobial activity.
Similar content being viewed by others
References
Houben, E.N., Nguyen, L., and Pieters, J., Curr. Opin. Microbiol., 2001, vol. 9, pp. 76–85.
Venuti, M.C., Principles and Practice, in Burger’s Medicinal Chemistry and Drug Discovery, 5th ed., Wolff, M.E., Ed., New York: John Wiley and Sons, 1995.
World Health Organization. Fact sheet no. 104, Reviewed March, 2014. http://www.who.int/mediacentre/factsheets/fs104/en
Zia-ur-Rehman, M., Choudary, J.A., Ahmad, S., and Siddiqui, H.L., Chem. Pharm. Bull., 2006, vol. 54, pp. 1175–1178.
Pattan, S.R., Reddy, V.V.K., Manvi, F.V., Desai, B.G., and Bhat. A.R., Indian J. Chem., 2006, vol. 45B, pp. 1778–1781.
Pavan, F.R., da S Maia, P.I., Leite, S.R., Deflon, V.M., Batista, A.A., Sato, D.N., Franzblau, S.G., and Leite, C.Q., Eur. J. Med. Chem., 2010, vol. 45, pp. 1898–1905.
Güzel, O., Karali, N.,and Salman, A., Bioorg. Med. Chem., 2008, vol. 16, pp. 8976–8987.
Karali, N., Gursoy, A., Kandemirli, F., Shvets, N., Kaynak, F.B., Ozbey, S., Kovalishyn, V., and Dimoglo, A., Bioorg. Med. Chem., 2007, vol. 15, pp. 5888–5904.
Sriram, D., Yogeeswari, P., Thirumurugan, R., and Pavana, R.K., J. Med. Chem., 2006, vol. 49, pp. 3448–3450.
Sriram, D., Yogeeswari, P., Dhakla, P., Senthilkumar, P., Banerjee, D., and Manjashetty, T.H., Bioorg. Med. Chem. Lett., 2009, vol. 19, pp. 1152–1154.
Saripinar, E., Guzel, Y., Patat, S., Yildirim, I., Akçamur, Y., and Dimoglo, A.S., Arzneimittelforschung, 1996, vol. 46, pp. 824–828.
Milczarska, B., Foks, H., Sokołowska, J., Janowiec, M., Zwolska, Z., and Andrzejczyk, Z., Acta Pol. Pharm., 1999, vol. 56, pp. 121–126.
Turan-Zitouni, G., Ozdemir, A., Kaplancikli, Z.A. Benkli, K., Chevallet, P., and Akalin, G., Eur. J. Med. Chem., 2008, vol. 43, pp. 981–988.
Pandeya, S.N., Smitha, S., Jyoti, M., and Sridhar, S.K., Acta Pharmaceutica, 2005, vol. 55, pp. 27–46.
Meunier, B., Acc. Chem. Res., 2008, vol. 41, pp. 69–77.
Alagarsamy, V., Solomon, V.R., Sheorey, R.V., and Jayakumar R., Chem.Biol Drug. Des., 2009, vol. 73, pp. 471–479.
Alagarsamy, V., Shankar, D., Solomon, V.R., Sheorey, R.V., and Parthiban, P., Acta Pharm., 2009, vol. 59, pp. 75–79.
Alagarsamy, V. Solomon, V.R. Meena, R. Ramaseshu, K.V., Thirumurugan, K., and Murugesan, S., Med. Chem., 2007, vol. 3, pp. 67–73.
Barry, A., Antibiotics in Laboratory Medicine, 5th ed., Baltimore, MD: William and Wilkins, 1991, vol. 1.
Pandeya, S.N., Sriram, D., Nath, G., and De Clercq, E., IL Farmaco, 1999, vol. 54, pp. 624–628.
Sriram, D., Yogeeswari, P., Basha, J.S., Radha, D.R., and Nagaraja, V., Bioorg. Med. Chem., 2005, vol. 13, pp. 5774–5778.
Shanmugavelan, P., Nagarajan, S., Sathishkumar, M., Ponnuswamy, A., Yogeeswari, P., and Sriram, D., Bioorg. Med. Chem. Lett., 2011, vol. 21, pp. 7273–7278.
Kunes, J., Bazant, J., Pour, M., Waisser, K., Slosárek, M., and Janota, J., IL Farmaco, 2000, vol. 55, pp. 725–729.
Alagarsamy, V., Parthiban, P., Sheorey, R.V., and Solomon, V.R., Anti-Infective Agents, 2012, vol. 10, pp. 105–110.
Author information
Authors and Affiliations
Corresponding author
Additional information
The article is published in the original.
Rights and permissions
About this article
Cite this article
Alagarsamy, V., Anjana, G.V., Sulthana, M.T. et al. Antimicrobial activities of some synthesized 1-(3-(2-methylphenyl)-4-Oxo-3H-quinazolin-2-yl-4-(substituted)thiosemicarbazide derivatives. Russ J Bioorg Chem 42, 332–339 (2016). https://doi.org/10.1134/S106816201603002X
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S106816201603002X