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Synthesis of New 2-(N'-Allylidene-hydrazino)quinazolinones and 2-(4,5-Dihydropyrazolyl)-quinazolinones and Their Antimicrobial and Antifungal Activity Screening
Corresponding Author(s) : Nezire Saygili
Asian Journal of Chemistry,
Vol. 26 No. 11 (2014): Vol 26 Issue 11
Abstract
Novel 2-[N'-(1,3-disubstituted-phenyl)allylidene]hydrazine-3-ethyl-3H-quinazolin-4-one (8) and 2-(3,5-disubstituted-phenyl-4,5-dihydro-pyrazol-1-yl)-3-ethyl-3H-quinazolin-4-one (9) compounds have been prepared and tested for antibacterial and antifungal activities. 1H NMR, 13C NMR, elemental analysis and mass spectroscopy methods have been used to identify molecular structures of the newly synthesized compounds. For screening antibacterial and antifungal activities of the new compounds, minimum inhibitory concentration (MIC) values were evaluated against the Staphylococcus aureus, Escherichia. coli, Pseudomonas aeruginosa, Enterococcus faecalis, Candida albicans, Candida parapsilosis and Candida krusei using microdilution broth method. Compounds 8a-8h exhibited the best antibacterial activity against E. faecalis.
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- R. Rajput and A.P. Mishra, Int. J. Pharm. Pharm. Sci., 4, 66 (2012).
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- K. Butler and M.W. Partridge, J. Chem. Soc., 1512 (1959); doi:10.1039/jr9590001512.
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A.S. El-Azab, Phosphorus, Sulfur, Silicon Rel. Elem., 182, 333 (2007); doi:10.1080/10426500600919207.
N.A. Santagati, E. Bousquet, A. Spadaro and G. Ronsisvalle, IL Farmaco, 54, 780 (1999); doi:10.1016/S0014-827X(99)00102-0.
C. Parkanyi and D.S. Schmidt, J. Heterocycl. Chem., 37, 725 (2000); doi:10.1002/jhet.5570370409.
I. Philipova, G. Dobrikov, K. Krumova and J. Kaneti, J. Heterocycl. Chem., 43, 1057 (2006); doi:10.1002/jhet.5570430436.
M.B. Deshmukh, S.S. Patil, S.S. Patil and S.D. Jadhav, J. Heterocycl. Chem., 47, 1144 (2010); doi:10.1002/jhet.440.
M. Wang, Z. Song and T. Zhang, J. Heterocycl. Chem., 47, 468 (2010); doi:10.1002/jhet.330.
R.S. Giri, H.M. Thaker, T. Giordano, J. Williams, D. Rogers, V. Sudersanam and K.K. Vasu, Eur. J. Med. Chem., 44, 2184 (2009); doi:10.1016/j.ejmech.2008.10.031.
S.K. Kundu, M. P. D. Mahindaratne, M. V. Quintero, A. Bao, G. R. Negrete, ARKIVOC, 33 (2008).
V. Alagarsamy, S. Murugesan, K. Dhanabal, M. Murugan and E. De Clercq, Indian J. Pharm. Sci., 69, 304 (2007); doi:10.4103/0250-474X.33167.
M.S. Mohamed, M.M. Kamel, E.M.M. Kassem, N. Abotaleb, S.I. Abd El-moez and M.F. Ahmed, Eur. J. Med. Chem., 45, 3311 (2010); doi:10.1016/j.ejmech.2010.04.014.
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H. Georgey, N. Abdel-Gawad and S. Abbas, Molecules, 13, 2557 (2008); doi:10.3390/molecules13102557.
S. Eguchi, T. Suzuki, T. Okawa, Y. Matsushita, E. Yashima and Y. Okamoto, J. Org. Chem., 61, 7316 (1996); doi:10.1021/jo9609283.
S. Hayao, H.J. Havera, W.G. Strycker, T.J. Leipzig, R.A. Kulp and H.E. Hartzler, J. Med. Chem., 8, 807 (1965); doi:10.1021/jm00330a017.
A. Rahman and A.A. Siddiqui, Int. J. Pharm. Sci. Drug Res., 2, 165 (2010).
M.A. Khalil, R. Soliman, A.M. Farghaly and A.A. Bekhit, Arch. Pharm., 327, 27 (1994); doi:10.1002/ardp.19943270105.
A. Yesilada, S. Koyunoglu, N. Saygilia, E. Kupeli, E. Yesilada, E. Bedir and I. Khanc, Arch. Pharm. Pharm. Med. Chem., 337, 96 (2004); doi:10.1002/ardp.200200752.
W. Gaüss, H. J. Kabbe, W. Paülüs, H. J. Rosslenbroich and W. Brandes, US Patent 4,644,000 (1987).
A.A. El-Helby and M.H. Abdel Wahab, Egyptian J. Biomed. Sci., 11, 297 (2003).
Z. Li, H. Huang, H. Sun, H. Jiang and H. Liu, J. Comb. Chem., 10, 484 (2008); doi:10.1021/cc800040z.
G.N. Vassilev and N.G. Vassilev, Oxid. Commun., 30, 228 (2007).
I. Yavari and S. Beheshti, Helv. Chim. Acta, 94, 1825 (2011); doi:10.1002/hlca.201100071.
R. Murdoch, W.R. Tully and R. Westwood, J. Heterocycl. Chem., 23, 833 (1986); doi:10.1002/jhet.5570230335.
K. Butler and M.W. Partridge, J. Chem. Soc., 1512 (1959); doi:10.1039/jr9590001512.
K. Kottke, H. Kühmstedt and G. Griesner, Pharmazie, 38, 367 (1983).
W. Fathalla, M. Cajan and P. Pazdera, Molecules, 6, 557 (2001); doi:10.3390/60600557.
R. Jacquier and G. Maury, Bull. Soc. Chim. Fr., 306 (1967).
A. Hassner and M.J. Michelson, J. Org. Chem., 27, 298 (1962); doi:10.1021/jo01048a513.
Clinical and Laboratory Standards Institute. Methods for Dilution Anti-microbial Susceptibility Tests for Bacteria that Grow Aerobically: Approved Standard, M07-A8, edn 8, Clinical and Laboratory Standards Institute, Wayne, PA (2008).
Clinical and Laboratory Standards Institute, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts: Approved Standard, M27-A3, edn 3, Clinical and Laboratory Standards Institute, Wayne, PA (2008).