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Design, Synthesis and Pharmacological Evaluation of 2-Phenyl Quinazolin-4-one Derivatives as Anticolorectal Cancer and Anti-Inflammatory Agent
Corresponding Author(s) : T.P. Aneesh
Asian Journal of Chemistry,
Vol. 30 No. 12 (2018): Vol 30 Issue 12
Abstract
Quinazoline derivatives are heterocyclic compounds that acts as important structural lead for the discovery of effective therapeutic agents. The anti-inflammatory activity along with cytotoxicity helps to reduce the inflammation and pain associated with carcinoma. Derivatives of quinazoline-4-one were preliminary screened and in silico molecular modelling studies using Autodock were performed. In the docking study, ligands were docked against anticancer and anti-inflammatory targets. In silico analysis revealed that the compounds with aromatic substitution at 3rd and halogen substitution at 6th or 7th positions possess lesser side effects and have more potent antitumor activity. Based upon these results 12 compounds were selected, synthesized, characterized and screened for their in vitro, anti-inflammatory, antioxidant and anticancer activities. From the in vitro studies, compounds QA4, QA7 and QB1 showed good anticancer, anti-inflammatory and anti-oxidant activity when compared to the standard.
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- V. Chandregowda, A.K. Kush and G. Chandrasekara Reddy, Eur. J. Med. Chem., 44, 3046 (2009); https://doi.org/10.1016/j.ejmech.2008.07.023.
- V. Alagarsamy, V. Raja Solomon and K. Dhanabal, Bioorg. Med. Chem., 15, 235 (2007); https://doi.org/10.1016/j.bmc.2006.09.065.
- A. Baba, N. Kawamura, H. Makino, Y. Ohta, S. Taketomi and T. Sohda, J. Med. Chem., 39, 5176 (1996); https://doi.org/10.1021/jm9509408.
- A. Jose, A.B. Chittethu, S. Sankaran, S.T. Suja and K. Prem Ekambaram, J. Pharm. Res., 6, 933 (2013); https://doi.org/10.1016/j.jopr.2013.07.033.
- H. Liu, R. Huang, D. Qiu, Z. Yang and X. Liu, Prog. Nat. Sci., 8, 359 (1998).
- 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).
- G. Saravanan, V. Alagarsamy and C.R. Prakash, Int. J. Pharm. Pharm. Sci., 2, 83 (2010).
- M.S. Malamas and J. Millen, J. Med. Chem., 34, 1492 (1991); https://doi.org/10.1021/jm00108a038.
- S.B. Mhaske and N.P. Argade, Tetrahedron, 62, 9787 (2006); https://doi.org/10.1016/j.tet.2006.07.098.
- P.C. Sharma, G. Kaur, R. Pahwa, A. Sharma and H. Rajak, Curr. Med. Chem., 18, 4786 (2011); https://doi.org/10.2174/092986711797535326.
- K. Manasa, R.V. Sidhaye, G. Radhika and C.N. Nalini, Curr. Pharm. Res., 1, 101 (2011).
- N.A. Salih, J. Al-Nahrain University, 11, 16 (2008); https://doi.org/10.22401/JNUS.11.2.03.
- A.K. Nanda, S. Ganguli and R. Chakraborty, Molecules, 12, 2413 (2007); https://doi.org/10.3390/12102413.
- N. Thomas and S.M. Zachriah, Int. J. Pharm. Sci. Rev. Res., 22, 50 (2013).
- F. Denizot and R.J. Lang, Immunomethods, 89, 271 (1986).
- H.A. Ali, N.H.A. Orooba and W.A. Khulood, J. Assn. Arab. Univ. Basic Appl. Sci., 14, 87 (2013).
- P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney and M.R. Boyd, J. Natl. Cancer Inst., 82, 1107 (1990); https://doi.org/10.1093/jnci/82.13.1107.
- A.B. Chittethu, S. Sathianarayanan, A. Nair, E. Varghese, R.V. Gopal, and K.S. Sreelakshmi, Int. J. Pharmacol. Biol. Sci., 5, 75 (2011).
References
V. Chandregowda, A.K. Kush and G. Chandrasekara Reddy, Eur. J. Med. Chem., 44, 3046 (2009); https://doi.org/10.1016/j.ejmech.2008.07.023.
V. Alagarsamy, V. Raja Solomon and K. Dhanabal, Bioorg. Med. Chem., 15, 235 (2007); https://doi.org/10.1016/j.bmc.2006.09.065.
A. Baba, N. Kawamura, H. Makino, Y. Ohta, S. Taketomi and T. Sohda, J. Med. Chem., 39, 5176 (1996); https://doi.org/10.1021/jm9509408.
A. Jose, A.B. Chittethu, S. Sankaran, S.T. Suja and K. Prem Ekambaram, J. Pharm. Res., 6, 933 (2013); https://doi.org/10.1016/j.jopr.2013.07.033.
H. Liu, R. Huang, D. Qiu, Z. Yang and X. Liu, Prog. Nat. Sci., 8, 359 (1998).
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).
G. Saravanan, V. Alagarsamy and C.R. Prakash, Int. J. Pharm. Pharm. Sci., 2, 83 (2010).
M.S. Malamas and J. Millen, J. Med. Chem., 34, 1492 (1991); https://doi.org/10.1021/jm00108a038.
S.B. Mhaske and N.P. Argade, Tetrahedron, 62, 9787 (2006); https://doi.org/10.1016/j.tet.2006.07.098.
P.C. Sharma, G. Kaur, R. Pahwa, A. Sharma and H. Rajak, Curr. Med. Chem., 18, 4786 (2011); https://doi.org/10.2174/092986711797535326.
K. Manasa, R.V. Sidhaye, G. Radhika and C.N. Nalini, Curr. Pharm. Res., 1, 101 (2011).
N.A. Salih, J. Al-Nahrain University, 11, 16 (2008); https://doi.org/10.22401/JNUS.11.2.03.
A.K. Nanda, S. Ganguli and R. Chakraborty, Molecules, 12, 2413 (2007); https://doi.org/10.3390/12102413.
N. Thomas and S.M. Zachriah, Int. J. Pharm. Sci. Rev. Res., 22, 50 (2013).
F. Denizot and R.J. Lang, Immunomethods, 89, 271 (1986).
H.A. Ali, N.H.A. Orooba and W.A. Khulood, J. Assn. Arab. Univ. Basic Appl. Sci., 14, 87 (2013).
P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney and M.R. Boyd, J. Natl. Cancer Inst., 82, 1107 (1990); https://doi.org/10.1093/jnci/82.13.1107.
A.B. Chittethu, S. Sathianarayanan, A. Nair, E. Varghese, R.V. Gopal, and K.S. Sreelakshmi, Int. J. Pharmacol. Biol. Sci., 5, 75 (2011).