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Synthesis, Characterization and Biological Evaluation of N-3 Substituted Quinazolin-4(3H)-ones
Corresponding Author(s) : J.P. Jini
Asian Journal of Chemistry,
Vol. 38 No. 9 (2026): Vol 38 Issue 9 Year 2026
Abstract
A series of 3-substituted-2-phenylquinazolin-4(3H)-one derivatives (4a-g) were designed and synthesized to examine the effect of different steric and electronic substituents on their chemical and biological properties. The target compounds were obtained in good yields of 64-78% by reacting 2-phenyl-4H-benzo[d][1,3]oxazin-4-one with substituted aromatic and heteroaromatic primary amines in glacial acetic acid. Structural characterization was carried out using FT-IR, 1H NMR and 13C NMR spectroscopy. The FT-IR data established the characteristic carbonyl stretching vibration of the quinazolinone moiety within the 1682-1670 cm−1 range, consistent with the resonance effects of the heterocyclic ring. The synthesized derivatives exhibited moderate to good concentration-dependent antioxidant activity in the DPPH assay, while their anti-inflammatory potential was assessed through the protein denaturation assay.
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- R. Karan, P. Agarwal, M. Sinha and N. Mahato, ChemEngineering, 5, 73 (2021); https://doi.org/10.3390/chemengineering5040073
- K. Chen, S. Wang, S. Fu, J. Kim, P. Park, R. Liu and K. Lei, Int. J. Mol. Sci., 26, 2473 (2025); https://doi.org/10.3390/ijms26062473
- S. Gatadi, T. V. Lakshmi and S. Nanduri, Eur. J. Med. Chem., 170, 157 (2019); https://doi.org/10.1016/j.ejmech.2019.03.018
- J. Mravljak, L. Slavec and M. Hrast, Molecules, 26, 6585 (2021); https://doi.org/10.3390/molecules26216585
- M.A. El-Hashash, K.M. Darwish, S.A. Rizk and F.A. El-Bassiouny, Molecules, 4, 1032 (2011); https://doi.org/10.3390/ph4071032
- V. Alagarsamy and U.S. Pathak, Bioorg. Med. Chem., 15, 3457 (2007); https://doi.org/10.1016/j.bmc.2007.03.007
- R. Bouley, D. Ding, Z. Peng, M. Bastian, E. Lastochkin, W. Song, M.A. Suckow, V.A. Schroeder, W.R. Wolter, S. Mobashery and M. Chang, J. Med. Chem., 59, 5011 (2016); https://doi.org/10.1021/acs.jmedchem.6b00372
- S.C. Khadse, M.B. Karade, S.P.P. Patel, A.S.M. Tripathi and R.S.P. Singh, Future J. Pharm. Sci., 5, 11 (2019); https://doi.org/10.1186/s43094-019-0012-y
- P. Verma, L.Z. Xiang, U. Chaube and G. Natesan, ChemistrySelect, 9, e202403009 (2024); https://doi.org/10.1002/slct.202403009
- H.T.B. Bui, K.M. Do, H.T.D. Nguyen, H.V. Mai, T.L.D. Danh, D.Q. Tran and H. Morita, Tetrahedron, 98, 132426 (2021); https://doi.org/10.1016/j.tet.2021.132426
- H.I. El-Subbagh and M.A. Sabry, Mini Rev. Med. Chem., 21, 2249 (2021); https://doi.org/10.2174/1389557521666210304105736
- D.A. Patil, P.O. Patil, G.B. Patil and S.J. Surana, Mini Rev. Med. Chem., 11, 633 (2011); https://doi.org/10.2174/138955711796268778
- N. Manhas, G. Kumar, S. Dhawan, T. Makhanya and P. Singh, ChemistryOpen, 14, e202400439 (2025); https://doi.org/10.1002/open.202400439
- X.-F. Shang, S. L. Morris-Natschke, G.-Z. Yang, Y.-Q. Liu, X. Guo, X.-S. Xu, M. Goto, J.-C. Li, J.-Y. Zhang, and K.-H. Lee, Med. Res. Rev., 38, 1614 (2018); https://doi.org/10.1002/open.202400439
- Z. Li, L. Zhao, Y. Bian, Y. Li, J. Qu, and F. Song, Curr. Top. Med. Chem., 22, 1035 (2022); https://doi.org/10.2174/1568026622666220307144015
- H.A.M. Gomaa, Chem. Biol. Drug Des., 100, 639 (2022); https://doi.org/10.1111/cbdd.14129
- M.J. Mphahlele, Molecules, 27, 7985 (2022); https://doi.org/10.3390/molecules27227985
- M.M. Rahman, M.B. Islam, M. Biswas and A.H.M. Khurshid Alam, BMC Res. Notes, 8, 621 (2015); https://doi.org/10.1186/s13104-015-1618-6
- S.M.A. El-Banna, M.A.A. El-Sayed, M.A.M. El-Monem and A.A. El-Batal, Beni-Suef Univ. J. Basic Appl. Sci., 11, 89 (2022); https://doi.org/10.1186/s43088-022-00297-x
- S. Dharmadeva, L.S. Galgamuwa, C. Prasadinie and N. Kumarasinghe, Ayu, 39, 239 (2018); https://doi.org/10.4103/ayu.AYU_27_18
- O.A.E.M. Fathalla, E.M.M. Kassem, N.M. Ibrahem and M.M. Kamel, Acta Pol. Pharm. Drug Res., 65, 11 (2008).
- T.P. Selvam, P.V. Kumar and A.S. Kumar, Res. Biotechnol., 1, 38 (2010).
- E.Y. Mendogralo, L.Y. Nesterova, E.R. Nasibullina, R.O. Shcherbakov, A.G. Tkachenko, R.Y. Sidorov, M.A. Sukonnikov, D.A. Skvortsov and M.G. Uchuskin, Molecules, 28, 5348 (2023); https://doi.org/10.3390/molecules28145348
- V. Alagarsamy, U.S. Pathak, S.N. Pandeya, D. Sriram and E. De Clercq, Indian J. Pharm. Sci., 62, 433 (2000).
- R. Rohini, P. Muralidhar Reddy, K. Shanker, A. Hu and V. Ravinder, Eur. J. Med. Chem., 45, 1200 (2010); https://doi.org/10.1016/j.ejmech.2009.11.038
- P.M. Chandrika, T. Yakaiah, B. Narsaiah, V. Sridhar, G. Venugopal, J.V. Rao, K.P. Kumar, U.S.N. Murthy and A.R.R. Rao, Indian J. Chem., 48B, 840 (2009).
- C. Balakumar, P. Lamba, D. Pran Kishore, B. Lakshmi Narayana, K. Venkat Rao, K. Rajwinder, A. Raghuram Rao, B. Shireesha and B. Narsaiah, Eur. J. Med. Chem., 45, 4904 (2010); https://doi.org/10.1016/j.ejmech.2010.07.063
- S.M. Mosaad, K.I. Mohamed, M.A. Ahmed and G.A. Sami, Int. J. Pharmacol., 1, 261 (2005); https://doi.org/10.3923/ijp.2005.261.266
References
R. Karan, P. Agarwal, M. Sinha and N. Mahato, ChemEngineering, 5, 73 (2021); https://doi.org/10.3390/chemengineering5040073
K. Chen, S. Wang, S. Fu, J. Kim, P. Park, R. Liu and K. Lei, Int. J. Mol. Sci., 26, 2473 (2025); https://doi.org/10.3390/ijms26062473
S. Gatadi, T. V. Lakshmi and S. Nanduri, Eur. J. Med. Chem., 170, 157 (2019); https://doi.org/10.1016/j.ejmech.2019.03.018
J. Mravljak, L. Slavec and M. Hrast, Molecules, 26, 6585 (2021); https://doi.org/10.3390/molecules26216585
M.A. El-Hashash, K.M. Darwish, S.A. Rizk and F.A. El-Bassiouny, Molecules, 4, 1032 (2011); https://doi.org/10.3390/ph4071032
V. Alagarsamy and U.S. Pathak, Bioorg. Med. Chem., 15, 3457 (2007); https://doi.org/10.1016/j.bmc.2007.03.007
R. Bouley, D. Ding, Z. Peng, M. Bastian, E. Lastochkin, W. Song, M.A. Suckow, V.A. Schroeder, W.R. Wolter, S. Mobashery and M. Chang, J. Med. Chem., 59, 5011 (2016); https://doi.org/10.1021/acs.jmedchem.6b00372
S.C. Khadse, M.B. Karade, S.P.P. Patel, A.S.M. Tripathi and R.S.P. Singh, Future J. Pharm. Sci., 5, 11 (2019); https://doi.org/10.1186/s43094-019-0012-y
P. Verma, L.Z. Xiang, U. Chaube and G. Natesan, ChemistrySelect, 9, e202403009 (2024); https://doi.org/10.1002/slct.202403009
H.T.B. Bui, K.M. Do, H.T.D. Nguyen, H.V. Mai, T.L.D. Danh, D.Q. Tran and H. Morita, Tetrahedron, 98, 132426 (2021); https://doi.org/10.1016/j.tet.2021.132426
H.I. El-Subbagh and M.A. Sabry, Mini Rev. Med. Chem., 21, 2249 (2021); https://doi.org/10.2174/1389557521666210304105736
D.A. Patil, P.O. Patil, G.B. Patil and S.J. Surana, Mini Rev. Med. Chem., 11, 633 (2011); https://doi.org/10.2174/138955711796268778
N. Manhas, G. Kumar, S. Dhawan, T. Makhanya and P. Singh, ChemistryOpen, 14, e202400439 (2025); https://doi.org/10.1002/open.202400439
X.-F. Shang, S. L. Morris-Natschke, G.-Z. Yang, Y.-Q. Liu, X. Guo, X.-S. Xu, M. Goto, J.-C. Li, J.-Y. Zhang, and K.-H. Lee, Med. Res. Rev., 38, 1614 (2018); https://doi.org/10.1002/open.202400439
Z. Li, L. Zhao, Y. Bian, Y. Li, J. Qu, and F. Song, Curr. Top. Med. Chem., 22, 1035 (2022); https://doi.org/10.2174/1568026622666220307144015
H.A.M. Gomaa, Chem. Biol. Drug Des., 100, 639 (2022); https://doi.org/10.1111/cbdd.14129
M.J. Mphahlele, Molecules, 27, 7985 (2022); https://doi.org/10.3390/molecules27227985
M.M. Rahman, M.B. Islam, M. Biswas and A.H.M. Khurshid Alam, BMC Res. Notes, 8, 621 (2015); https://doi.org/10.1186/s13104-015-1618-6
S.M.A. El-Banna, M.A.A. El-Sayed, M.A.M. El-Monem and A.A. El-Batal, Beni-Suef Univ. J. Basic Appl. Sci., 11, 89 (2022); https://doi.org/10.1186/s43088-022-00297-x
S. Dharmadeva, L.S. Galgamuwa, C. Prasadinie and N. Kumarasinghe, Ayu, 39, 239 (2018); https://doi.org/10.4103/ayu.AYU_27_18
O.A.E.M. Fathalla, E.M.M. Kassem, N.M. Ibrahem and M.M. Kamel, Acta Pol. Pharm. Drug Res., 65, 11 (2008).
T.P. Selvam, P.V. Kumar and A.S. Kumar, Res. Biotechnol., 1, 38 (2010).
E.Y. Mendogralo, L.Y. Nesterova, E.R. Nasibullina, R.O. Shcherbakov, A.G. Tkachenko, R.Y. Sidorov, M.A. Sukonnikov, D.A. Skvortsov and M.G. Uchuskin, Molecules, 28, 5348 (2023); https://doi.org/10.3390/molecules28145348
V. Alagarsamy, U.S. Pathak, S.N. Pandeya, D. Sriram and E. De Clercq, Indian J. Pharm. Sci., 62, 433 (2000).
R. Rohini, P. Muralidhar Reddy, K. Shanker, A. Hu and V. Ravinder, Eur. J. Med. Chem., 45, 1200 (2010); https://doi.org/10.1016/j.ejmech.2009.11.038
P.M. Chandrika, T. Yakaiah, B. Narsaiah, V. Sridhar, G. Venugopal, J.V. Rao, K.P. Kumar, U.S.N. Murthy and A.R.R. Rao, Indian J. Chem., 48B, 840 (2009).
C. Balakumar, P. Lamba, D. Pran Kishore, B. Lakshmi Narayana, K. Venkat Rao, K. Rajwinder, A. Raghuram Rao, B. Shireesha and B. Narsaiah, Eur. J. Med. Chem., 45, 4904 (2010); https://doi.org/10.1016/j.ejmech.2010.07.063
S.M. Mosaad, K.I. Mohamed, M.A. Ahmed and G.A. Sami, Int. J. Pharmacol., 1, 261 (2005); https://doi.org/10.3923/ijp.2005.261.266
