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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Synthesis and Antimicrobial Evaluation of Quinazoline-4[3H]-one Derivatives

Author(s): Cheenu Chaudhary*, Sushil Kumar, Surendra Kumar and S. Riaz Hashim

Volume 18, Issue 7, 2021

Published on: 18 August, 2020

Page: [547 - 554] Pages: 8

DOI: 10.2174/1570178617999200818205800

Price: $65

Abstract

The present investigation aimed to synthesize quinazoline-4(3H)-one derivatives (B1-10) and evaluated their antimicrobial activity. The test compounds (B1-10) were obtained by reaction of 2- phenyl-4H-benzo[d] [1, 3]oxazin-4-one (1) with 4-aminophenol (2) to afford 3-(4-hydroxyphenyl)-2- phenylquinazoline-4(3H)-one (3) which were further reacted with different N-phenylacetamide (4) in the presence of anhydrous potassium carbonate and a catalytic amount of potassium iodide in ethylmethylketone. The test compounds (B1-10) were characterized by the spectroscopic method and evaluated for their antimicrobial activity using the cup plate method by measuring the zone of inhibition. Among the compounds, compound B1, B2, B4, B6, and B8 showed maximum zone of inhibition as compared to standard drug ciprofloxacin and fluconazole against Bacillus subtilis, Escherichia coli and Aspergillus niger. Molecular docking was also performed for test compounds to predict their binding affinities in the target protein and results showed good drug-like properties.

Keywords: Quinazoline-4[3H]-one, N-Phenylacetamides, 4-Aminophenol, Zone of inhibition, antimicrobial activity, protein preparation, molecular docking.

Graphical Abstract
[1]
Joule, J.A.; Mills, K. Heterocyclic Chemistry, 5th ed; Wiley-Blackwell, 2010.
[2]
Rajput, R.; Mishra, A.P. Int. J. Pharm. Pharm. Sci., 2012, 4, 66-70.
[3]
Werbel, L.M.; Elslager, E.F.; Newton, L.S. J. Heterocycl. Chem., 1987, 24.
[http://dx.doi.org/10.1002/jhet.5570240210]
[4]
Yong, J.; Lu, C.; Wu, X. Anticancer. Agents Med. Chem., 2015, 15(10), 1326-1332.
[http://dx.doi.org/10.2174/1871520615666150526115904] [PMID: 26008189]
[5]
Pandey, V.K.; Misra, D.; Shukla, A. Indian Drugs, 1994, 31(11), 532-536.
[6]
Modh, R.P.; De Clercq, E.; Pannecouque, C.; Chikhalia, K.H. J. Enzyme Inhib. Med. Chem., 2014, 29(1), 100-108.
[http://dx.doi.org/10.3109/14756366.2012.755622] [PMID: 23327639]
[7]
Hajimahdi, Z.; Zabihollahi, R.; Aghasadeghi, M.R.; Zarghi, A. Curr. HIV Res., 2019, 17(3), 214-222.
[http://dx.doi.org/10.2174/1570162X17666190911125359] [PMID: 31518225]
[8]
Patel, N.B.; Lilakar, J.D. J. Heterocycl. Chem., 2001, 11, 85-86.
[9]
F, Zayed M.; H, Hassan M. Saudi Pharm. J., 2014, 22(2), 157-162.
[http://dx.doi.org/10.1016/j.jsps.2013.03.004] [PMID: 24648828]
[10]
Al-Salahi, R.; Abuelizz, H.A. Med. Chem., 2017, 13, 85-92.
[http://dx.doi.org/10.2174/1573406412666160610095706] [PMID: 27306606]
[11]
Alagarsamy, V.; Murugananthan, G.; Venkateshperumal, R. Biol. Pharm. Bull., 2003, 26(12), 1711-1714.
[http://dx.doi.org/10.1248/bpb.26.1711] [PMID: 14646176]
[12]
Bhandari, S.V.; Deshmane, B.J.; Dangare, S. Pharmacologyonline, 2008, 2, 604-613.
[13]
Chandrika, P.M.; Yakaiah, T.; Rao, A.R.; Narsaiah, B.; Reddy, N.C.; Sridhar, V.; Rao, J.V. Eur. J. Med. Chem., 2007, 147-152.
[PMID: 17689837]
[14]
Chaudhari, P.S.; Chitlange, S.S.; Nanda, R.K. Antiinflamm. Antiallergy Agents Med. Chem., 2018, 17(2), 102-114.
[http://dx.doi.org/10.2174/1871523017666180910105609] [PMID: 30198442]
[15]
Al-deeb, O.; Alafeefy, A.M. World Appl. Sci. J., 2008, 5, 94-99.
[16]
Barmak, A.; Niknam, K.; Mohebbi, G. ACS Omega, 2019, 4(19), 18087-18099.
[http://dx.doi.org/10.1021/acsomega.9b01906] [PMID: 31720511]
[17]
Gobinath, M.; Subramanian, N.; Alagarsamy, V.J. Saudi Chem., 2015, 19, 282-286.
[http://dx.doi.org/10.1016/j.jscs.2012.02.006]
[18]
Saravanan, G.; Alagarsamy, V.; Prakash, C.R. Int. J. Pharm. Pharm. Sci., 2010, 2(4), 83-86.
[19]
Kohli, D.; Hashim, S.R.; Vishal, S.; Sharma, M.; Singh, A.K. Int. J. Pharm. Pharm. Sci., 2009, 1(1), 163-169.
[20]
Vijaykumar, K. Ahamed, A.J.; Thiruneelakandan, G. J. Appl. chem., 2013.387191
[21]
Devi, A.K.; Saragapani, M. Int. J. Drug Dev. Res., 2012, 4(3), 324-327.
[22]
Indian Pharmacopoeia, Delhi, 1996, 3, 105-107.
[23]
OEDOCKING 3.4.0.2: OpenEye Scientific Software, Santa Fe, NM, http://www.eyesopen.com
[24]
Kelley, B.P.; Brown, S.P.; Warren, G.L.; Muchmore, S.W. J. Chem. Inf. Model., 2015, 55(8), 1771-1780.
[http://dx.doi.org/10.1021/acs.jcim.5b00142] [PMID: 26151876]
[25]
McGann, M. J. Chem. Inf. Model., 2011, 51(3), 578-596.
[http://dx.doi.org/10.1021/ci100436p] [PMID: 21323318]
[26]
McGann, M. J. Comput. Aided Mol. Des., 2012, 26(8), 897-906.
[http://dx.doi.org/10.1007/s10822-012-9584-8] [PMID: 22669221]
[27]
Labute, P. J. Comput. Chem., 2008, 29(10), 1693-1698.
[http://dx.doi.org/10.1002/jcc.20933] [PMID: 18307169]
[28]
Verma, S.; Kumar, S.; Kumar, S. Arab. J. Chem., 2020, 13, 863-874.
[http://dx.doi.org/10.1016/j.arabjc.2017.08.005]
[29]
Abulkhair, H.S.; El-Gamal, K.M.; El-Adl, K.; Fadl, M.F. Med. Chem., 2016, 6(9), 593-603.
[30]
Strushkevich, N.; Usanov, S.A.; Park, H.W. J. Mol. Biol., 2010, 397(4), 1067-1078.
[http://dx.doi.org/10.1016/j.jmb.2010.01.075] [PMID: 20149798]
[31]
Brvar, M.; Perdih, A.; Renko, M.; Anderluh, G.; Turk, D.; Solmajer, T. J. Med. Chem., 2012, 55(14), 6413-6426.
[http://dx.doi.org/10.1021/jm300395d] [PMID: 22731783]
[32]
Sastry, G.M.; Adzhigirey, M.; Day, T.; Annabhimoju, R.; Sherman, W. J. Comput. Aided Mol. Des., 2013, 27(3), 221-234.
[http://dx.doi.org/10.1007/s10822-013-9644-8] [PMID: 23579614]
[33]
Release, S. 2018-2: LigPrep; Schrödinger, LLC: New York, NY, 2018.
[34]
Hawkins, P.C.D.; Skillman, A.G.; Warren, G.L.; Ellingson, B.A.; Stahl, M.T. J. Chem. Inf. Model., 2010, 50(4), 572-584.
[http://dx.doi.org/10.1021/ci100031x] [PMID: 20235588]

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