Abstract
A series of novel substituted quinazoline derivatives are synthesized. Antibacterial tests demonstrate their high activity against Gram-positive and Gram-negative bacteria. 3-[4-(2-Bromoacetyl)-phenyl]-2-phenylquinazolin-4(3H)-one 2 and 3-oxo-3-{[4-(4-oxo-2-phenylquinazolin-3(4H)-yl]phenyl}propanenitrile 3 are used as intermediates in the synthesis of functionalized heterocyclic derivatives such as 3-[4-(2-amino-thiazol-5-yl)phenyl]-2-phenylquinazolin-4(3H)-one 4, Schiff base 5, 3-{5-(4-[4-oxo-2-phenylquinazolin-3(4H)-yl]phenyl)thiazol-2-yl}-2-phenylthiazolidin-4-one 6, and N-phenyl acetohydrazonoyl derivatives 7a, 7b. The latter react with ethyl cyanoacetate with formation of 9a, 9b. Chalcone 10 is the key intermediate in the synthesis of N-acetylpyrazole derivative 11 and 1-thiocaramoyl pyrazole derivative 12. Treatment of 12 with chloroacetyl chloride and compound 2 leads to formation of compounds 13 and 14, respectively. Treatment of compound 3 with phenyl isothiocyanate affords the corresponding quinazolin-3(4H)-yl acrylonitrile derivative 15, which reacts with phenyl hydrazine to give the corresponding product 16. The synthesized compounds are characterized by IR, MS and 1H NMR spectra.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Bartoli, J., Turmo, E., and Alguero, M., J. Med. Chem., 1998, vol. 41 (11), p. 1869. doi 10.1021/jm9707277
Kurogi, Y., Inoue, Y., Tsutsumi, K., Yoshitsugu, H., and Tuda, Y., J. Med. Chem., 1996, vol. 39, p. 143. doi 10.1021/jm9506938
Sayyed, M.S., Mokle, S.S., and Vibhute, Y.B., Arkivoc, 2006, vol. 11, p. 221.
Mosaad, S.M., Mohammed, K.I., Ahmed, M.A., and Abdel-Hamide, S.G., J. Biol. Sci., 2004, vol. 4(4), p. 504.
Griffin, R.J., Srinivasan, S., Bowman, K., Calvert, A.H., Curtin, N.J., Newell, D.R., Pemberton, L.C., and Golding, B.T., and J. Med. Chem., 1998, vol. 41(26), p. 5247. doi 10.1021/jm980273t
Bhattacharjee, A.K., Hartell, M.G., Nichols, D.A., Hicks, R.P., Stanton, B., Hamont, J.E., and Milhous, W.K. Eur. J. Med. Chem., 2004, vol. 39(1), p. 59. doi 10.1016/j.ejmech.2003.10.004
Salih, N.A., J. Al-Nahrain University, 2008, vol. 11, p. 8. doi 10.1016/j.jtusci.2013.09.003
Oh, S. and Park, S.B. Chem. Comm., 2011, vol. 47, p. 12754. doi 10.1039/C1CC14042F
Tiwaryl, B.K., Pradhan, K., Nanda, A.K., and Chakraborty, R., J. Chem. Bio. Ther., 2015, vol. 1(1), p. 1. doi 10.4172/2572-0406.1000104
El-Shenawy, A.I., Russ. J. Gen. Chem., 2017, vol. 87, no. 9, p. 2067. doi 10.1134/S1070363217090237
El-Shenawy, A.I. and Aly, A.A., Egypt. J. Chem., 2005, vol. 38(6), p. 781.
Aly, A.A., J. Chinese Chem. Soc., 2007, vol. 54, p. 437. doi 10.1002/jccs.200700061
Aly, A.A., Chinese J. Chem., 2003, vol. 21 (3), p. 339. doi 10.1002/cjoc.20030210324
Aly, A.A., Phosphorus. Sulfur, and Silicon, 2003, vol. 178(11), p. 2415. doi 10.1080/714040955
Nassar S.N. and Aly, A.A., Egyptian j Chem., 2002, vol. 45(1), p. 205.
Mahmoud, M.R., and Abdelwahab, S.S., Saied, K.F., Egypt. J. Chem., 2017, vol. 60(6), p. 1059. doi 10.21608/EJCHEM.2017.1819.1152
Chande, M.S. and Ambhaikar, S.B., Indian J. Chem., 1996, vol. 35B, p. 373.
Havera, H.J., J. Med. Chem., 1979, vol. 22(12), p. 1548. doi 10.1021/jm00198a024
Zhang, Y., Xu, C., Houghten, R.A., and Yu, Y., J. Comb. Chem., 2007, vol. 9(1), p. 9. doi 10.1021/cc0601231
Kumara, D., Mariappana, G., Husainb, A., Mongac, J., and Kumard, S., Arabian J. Chem., 2017, vol. 10(3), p. 344. doi 10.1016/j.arabjc.2014.07.001
Waynae, P.A., National Committee for Clinical Laboratory Standards Approved Standards M2–A6. Performance Standards for Antimicrobial Disc Susceptibility Testing, Perseus, Cambridge, 1997, 6 ed.
Author information
Authors and Affiliations
Corresponding author
Additional information
The text was submitted by the author in English.
Rights and permissions
About this article
Cite this article
El-Shenawy, A.I. Synthesis and In Vitro Antibacterial Evaluation of Some Novel Annulated Quinazolinone Derivatives. Russ J Gen Chem 88, 1712–1719 (2018). https://doi.org/10.1134/S107036321808025X
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107036321808025X