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Docking and Qsar Studies of Some Quinazolinone Derivatives as Possible Inhibitors of Thyrosine Kinase

Yıl 2022, Cilt: 6 Sayı: 2, 1 - 10, 15.12.2022

Fahimeh Ghasemi , Elham Jafari , Mahmoud Mırzaeı , Karim Mahnam

Öz

Quinazolinones are bicyclic fused heterocyclics that have been shown cytotoxic effects through different mechanisms inparticular thyrozin kinase enzyme inhibition. Based on this, a series of quinazolinone derivatives were subjected to a quantitative structure activity relationship (QSAR) analysis, by using statistical tool, such as principal components analysis (PCA) and genetic algorithm (G.A). It was shown that GA_PLS is reliable to predict activities of new design compounds. Besides, the compounds were docked into the active site of the protein thyrozin kinase (PDB entry code:1M17) to identify the binding interactions. Among the thirty two studied compounds, five compounds showed convenient inhibitory effect. The most active compound of the studied derivatives , Q19, had a ∆Gbind of-9.52kcal/mol.

Anahtar Kelimeler

Quinazolinone; Thyrosin kinase GA_PLS

Kaynakça

  • [1] S. Ranjbar, N. Edraki, M. Khoshneviszadeh, A. Foroumadi, R. Miri, M. Khoshneviszadeh.. Design, synthesis, cytotoxicity evaluation and docking studies of 1, 2, 4-triazine derivatives bearing different arylidene-hydrazinyl moieties as potential mTOR inhibitors, Res. Pharm. sci. 13(1), (2018) 1-11.
  • [2] X. Qin, Z .Li, L. Yang, P. Liu, L. Hu, C. Zeng, Z. Pan. Discovery of new [1, 4] dioxino [2, 3-f] quinazoline-based inhibitors of EGFR including the T790M/L858R mutant, Bioorg & Med Chem. 24 (2016) 2871-2881.
  • [3] X. Qin, Y. Lv, P. Liu, Z .Li, L. Hu, C. Zeng, L. Yang. Novel morpholin-3-one fused quinazoline derivatives as EGFR tyrosine kinase inhibitors Bioorg & Medl Chem Lett. 26 (2016) 1571-5.
  • [4] A.S. Shaw, A.P. Kornev, J. Hu, L.G. Ahuja, S.S. Taylor. Kinases and pseudokinases: lessons from RAF. Mol. Cell. Biol.34 (2014) 1538-1546.
  • [5] G. Vaseghi, E. Jafari, F. Hassanzadeh, S. Haghjooy-Javanmard, N. Dana, M. Rafieian-Kopaei.Cytotoxic evaluation of some fused pyridazino-and pyrrolo-quinazolinones derivatives on melanoma and prostate cell lines. Adv. Biomed. Res.6 ( 2017):1-4.
  • [6] T. Elavarasan, D. Bhakiarajand, M. Gopalakrishnan. Antimicrobial screening and molecular docking studies of some novel triazoloquinazolinone derivatives. Der Pharm. Chem.6 (2014) 391-400.
  • [7] E. Jafari, G.A. Khodarahmi, F. Hassanzadeh, G.H. Hakimelahi, F. Tsai. Synthesis of some new tricyclic 4 (3H)-quinazolinone derivatives. Res. Pharm. Scie .6 (2011) 93-100.
  • [8] M.A. Mohamed, H.M. Ghanem, N.F .Abd El-Ghaffar, S.S .Mohamed. Biological evaluation and molecular docking of substituted quinazolinones as antimicrobial agents. Aust J Basic Appl Sci. 7 (2013) 263-274.
  • [9] G.A. Khodarahmi, M.R. Khajouei, G.H. Hakimelahi, D. Abedi, E. Jafari, F. Hassanzadeh Antibacterial, antifungal and cytotoxic evaluation of some new 2, 3-disubstituted 4 (3H)-quinazolinone derivatives. Res. Pharm. Scie 7 (2012) 151-158.
  • [10] F. Hassanzadeh, M.R. Khajouei, G.H. Hakimelahi, E. Jafari, G.A. Khodarahmi. Synthesis of some new 2, 3-disubstituted-4 (3H) quinazolinone derivatives. Res. Pharm. Scie 7 (2012) 23-30.
  • [11] G.A. Khodarahmi, E. Jafari, G.H. Hakimelahi, D. Abedi, M.R. Khajouei, F. HassanzadeSynthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities. Iran. J. Pharm. Sci. 11.( 2012)789-797.
  • [12] E. Jafari, M.R. Khajouei, F. Hassanzadeh, G.H. Hakimelahi, G.A. Khodarahmi.. Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities Res. Pharm. Scie11 (2016) 1-14.
  • [13] M.E. Sahu, A.G. Nerkar. In silico screening, synthesis and in vitro evaluation of some quinazolinone derivatives as dihydrofolate reductase inhibitors for anticancer activity: Part-I. International . Int. J Pharm & . Pharm. Sci 6 (2014) 193-199.
  • [14] V. Srivastava, S.P. Gupta, M.I. Siddiqi, B.N. Mishra. Molecular docking studies on quinazoline antifolate derivatives as human thymidylate synthase inhibitors. Bioinformation. 4 (2010) 357-365.
  • [15] P.M. Chandrika, T. Yakaiah, B. Narsaiah, V. Sridhar, G .Venugopal, J .Venkateshwara rao, et al.. Synthesis leading to novel 2, 4, 6-trisubstituted quinazoline derivatives, their antibacterial and cytotoxic activity against THP-1, HL-60 and A375 cell line. Indian J. Chem. 48B( 2009) 840-847.
  • [16] K. Srivalli, K. Satish. Synthesis, In Vitro Evaluation of Some Novel Quinazolin-4 (3H)-one Derivatives as Anti-Tumor Agents. Chem. Sci. Trans. 1( 2012) 624-631.
  • [17] L. Hosseinzadeh, A. Aliabadi, M. Rahnama, H.M. Sadeghi, M.R .Khajouei Synthesis and cytotoxic evaluation of some new 3-(2-(2-phenylthiazol-4-yl) ethyl)-quinazolin-4 (3H) one derivatives with potential anticancer effects. Res. Pharm. Scie 12(2017) 290-298.
  • [18] F. Hassanzadeh, E. Jafari, G.H. Hakimelahi, M.R. Khajouei, M. Jalali, G.A. Khodarahmi. A. Antibacterial, antifungal and cytotoxic evaluation of some new quinazolinone derivatives. Res. Pharm. Scie7 .( 2012) 87-94.
  • [19] F. Hassanzadeh, H. Sadeghi-Aliabadi, E. Jafari, A. Sharifzadeh, N. Dana. Synthesis and cytotoxic evaluation of some quinazolinone-5-(4-chlorophenyl) 1, 3, 4-oxadiazole conjugates. Res. Pharm. Scie,14 ( 2019) 408-413.
  • [20] F. Hassanzadeh, H. Sadeghi-Aliabadi, S. Nikooei, E. Jafari, G. Vaseghi. Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids. Res. Pharm. Scie 14 (2019) 130-137.
  • [21] F. Ghasemi, A. Mehridehnavi, A. Perez-Garrido, H .Perez-Sanchez,, Neural network and deep-learning algorithms used in QSAR studies: merits and drawbacks, Drug Discov. 23 (2018)1784-1790.
  • [22] T. Mostashari-Rad, R. Arian, H. Sadri, A. Mehridehnavi, M. Mokhtari, F. Ghasemi, A. Fassihi, Study of CXCR4 chemokine receptor inhibitors using QSPR and molecular docking methodologies, J. Theor. Comput. Chem. 18 ( 2019)
  • [23] F. Ghasemi, A. Mehri, J. Peña-García, H. den-Haan, A. Pérez-Garrido, A. Fassihi, H. Péréz-Sánchez, Improving Activity Prediction of Adenosine A2B Receptor Antagonists by Nonlinear Models, Int. Conf. Bioinform. Biomed. Eng.(2015) 635-644
  • [24] F. Hassanzadeh, E. Jafari, M. Zarabi, G. Khodarahmi, G. Vaseghi Synthesis, cytotoxic evaluation, and molecular docking studies of some new 1, 3, 4-oxadiazole-based compounds. Res. Pharm. Scie.15 (2020) 454-462.
  • [25] A Ousaa.QSAR and docking studies on the pyrimidine derivatives analogs with antileishmanial activity. RHAZES: Green. App. Chem.1 (2018) 50-63.
  • [26] A.Y. Helali, M.T. Sarg, M.M. Koraa, M.S. El-Zoghbi.,. Utility of 2-methyl-quinazolin-4 (3H)-one in the synthesis of heterocyclic compounds with anticancer activity. Open. J. Medi. Chem 28(2014) 12-37.

Yıl 2022, Cilt: 6 Sayı: 2, 1 - 10, 15.12.2022

Fahimeh Ghasemi , Elham Jafari , Mahmoud Mırzaeı , Karim Mahnam

Öz

Kaynakça

  • [1] S. Ranjbar, N. Edraki, M. Khoshneviszadeh, A. Foroumadi, R. Miri, M. Khoshneviszadeh.. Design, synthesis, cytotoxicity evaluation and docking studies of 1, 2, 4-triazine derivatives bearing different arylidene-hydrazinyl moieties as potential mTOR inhibitors, Res. Pharm. sci. 13(1), (2018) 1-11.
  • [2] X. Qin, Z .Li, L. Yang, P. Liu, L. Hu, C. Zeng, Z. Pan. Discovery of new [1, 4] dioxino [2, 3-f] quinazoline-based inhibitors of EGFR including the T790M/L858R mutant, Bioorg & Med Chem. 24 (2016) 2871-2881.
  • [3] X. Qin, Y. Lv, P. Liu, Z .Li, L. Hu, C. Zeng, L. Yang. Novel morpholin-3-one fused quinazoline derivatives as EGFR tyrosine kinase inhibitors Bioorg & Medl Chem Lett. 26 (2016) 1571-5.
  • [4] A.S. Shaw, A.P. Kornev, J. Hu, L.G. Ahuja, S.S. Taylor. Kinases and pseudokinases: lessons from RAF. Mol. Cell. Biol.34 (2014) 1538-1546.
  • [5] G. Vaseghi, E. Jafari, F. Hassanzadeh, S. Haghjooy-Javanmard, N. Dana, M. Rafieian-Kopaei.Cytotoxic evaluation of some fused pyridazino-and pyrrolo-quinazolinones derivatives on melanoma and prostate cell lines. Adv. Biomed. Res.6 ( 2017):1-4.
  • [6] T. Elavarasan, D. Bhakiarajand, M. Gopalakrishnan. Antimicrobial screening and molecular docking studies of some novel triazoloquinazolinone derivatives. Der Pharm. Chem.6 (2014) 391-400.
  • [7] E. Jafari, G.A. Khodarahmi, F. Hassanzadeh, G.H. Hakimelahi, F. Tsai. Synthesis of some new tricyclic 4 (3H)-quinazolinone derivatives. Res. Pharm. Scie .6 (2011) 93-100.
  • [8] M.A. Mohamed, H.M. Ghanem, N.F .Abd El-Ghaffar, S.S .Mohamed. Biological evaluation and molecular docking of substituted quinazolinones as antimicrobial agents. Aust J Basic Appl Sci. 7 (2013) 263-274.
  • [9] G.A. Khodarahmi, M.R. Khajouei, G.H. Hakimelahi, D. Abedi, E. Jafari, F. Hassanzadeh Antibacterial, antifungal and cytotoxic evaluation of some new 2, 3-disubstituted 4 (3H)-quinazolinone derivatives. Res. Pharm. Scie 7 (2012) 151-158.
  • [10] F. Hassanzadeh, M.R. Khajouei, G.H. Hakimelahi, E. Jafari, G.A. Khodarahmi. Synthesis of some new 2, 3-disubstituted-4 (3H) quinazolinone derivatives. Res. Pharm. Scie 7 (2012) 23-30.
  • [11] G.A. Khodarahmi, E. Jafari, G.H. Hakimelahi, D. Abedi, M.R. Khajouei, F. HassanzadeSynthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities. Iran. J. Pharm. Sci. 11.( 2012)789-797.
  • [12] E. Jafari, M.R. Khajouei, F. Hassanzadeh, G.H. Hakimelahi, G.A. Khodarahmi.. Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities Res. Pharm. Scie11 (2016) 1-14.
  • [13] M.E. Sahu, A.G. Nerkar. In silico screening, synthesis and in vitro evaluation of some quinazolinone derivatives as dihydrofolate reductase inhibitors for anticancer activity: Part-I. International . Int. J Pharm & . Pharm. Sci 6 (2014) 193-199.
  • [14] V. Srivastava, S.P. Gupta, M.I. Siddiqi, B.N. Mishra. Molecular docking studies on quinazoline antifolate derivatives as human thymidylate synthase inhibitors. Bioinformation. 4 (2010) 357-365.
  • [15] P.M. Chandrika, T. Yakaiah, B. Narsaiah, V. Sridhar, G .Venugopal, J .Venkateshwara rao, et al.. Synthesis leading to novel 2, 4, 6-trisubstituted quinazoline derivatives, their antibacterial and cytotoxic activity against THP-1, HL-60 and A375 cell line. Indian J. Chem. 48B( 2009) 840-847.
  • [16] K. Srivalli, K. Satish. Synthesis, In Vitro Evaluation of Some Novel Quinazolin-4 (3H)-one Derivatives as Anti-Tumor Agents. Chem. Sci. Trans. 1( 2012) 624-631.
  • [17] L. Hosseinzadeh, A. Aliabadi, M. Rahnama, H.M. Sadeghi, M.R .Khajouei Synthesis and cytotoxic evaluation of some new 3-(2-(2-phenylthiazol-4-yl) ethyl)-quinazolin-4 (3H) one derivatives with potential anticancer effects. Res. Pharm. Scie 12(2017) 290-298.
  • [18] F. Hassanzadeh, E. Jafari, G.H. Hakimelahi, M.R. Khajouei, M. Jalali, G.A. Khodarahmi. A. Antibacterial, antifungal and cytotoxic evaluation of some new quinazolinone derivatives. Res. Pharm. Scie7 .( 2012) 87-94.
  • [19] F. Hassanzadeh, H. Sadeghi-Aliabadi, E. Jafari, A. Sharifzadeh, N. Dana. Synthesis and cytotoxic evaluation of some quinazolinone-5-(4-chlorophenyl) 1, 3, 4-oxadiazole conjugates. Res. Pharm. Scie,14 ( 2019) 408-413.
  • [20] F. Hassanzadeh, H. Sadeghi-Aliabadi, S. Nikooei, E. Jafari, G. Vaseghi. Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids. Res. Pharm. Scie 14 (2019) 130-137.
  • [21] F. Ghasemi, A. Mehridehnavi, A. Perez-Garrido, H .Perez-Sanchez,, Neural network and deep-learning algorithms used in QSAR studies: merits and drawbacks, Drug Discov. 23 (2018)1784-1790.
  • [22] T. Mostashari-Rad, R. Arian, H. Sadri, A. Mehridehnavi, M. Mokhtari, F. Ghasemi, A. Fassihi, Study of CXCR4 chemokine receptor inhibitors using QSPR and molecular docking methodologies, J. Theor. Comput. Chem. 18 ( 2019)
  • [23] F. Ghasemi, A. Mehri, J. Peña-García, H. den-Haan, A. Pérez-Garrido, A. Fassihi, H. Péréz-Sánchez, Improving Activity Prediction of Adenosine A2B Receptor Antagonists by Nonlinear Models, Int. Conf. Bioinform. Biomed. Eng.(2015) 635-644
  • [24] F. Hassanzadeh, E. Jafari, M. Zarabi, G. Khodarahmi, G. Vaseghi Synthesis, cytotoxic evaluation, and molecular docking studies of some new 1, 3, 4-oxadiazole-based compounds. Res. Pharm. Scie.15 (2020) 454-462.
  • [25] A Ousaa.QSAR and docking studies on the pyrimidine derivatives analogs with antileishmanial activity. RHAZES: Green. App. Chem.1 (2018) 50-63.
  • [26] A.Y. Helali, M.T. Sarg, M.M. Koraa, M.S. El-Zoghbi.,. Utility of 2-methyl-quinazolin-4 (3H)-one in the synthesis of heterocyclic compounds with anticancer activity. Open. J. Medi. Chem 28(2014) 12-37.
Toplam 26 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Research Article
Yazarlar

Fahimeh Ghasemi 0000-0001-9333-4699

Elham Jafari 0000-0001-6472-0312

Mahmoud Mırzaeı 0000-0001-9346-4901

Karim Mahnam

Erken Görünüm Tarihi 18 Mart 2022
Yayımlanma Tarihi 15 Aralık 2022
Gönderilme Tarihi 27 Aralık 2021
Yayımlandığı Sayı Yıl 2022 Cilt: 6 Sayı: 2

Kaynak Göster

APA Ghasemi, F., Jafari, E., Mırzaeı, M., Mahnam, K. (2022). Docking and Qsar Studies of Some Quinazolinone Derivatives as Possible Inhibitors of Thyrosine Kinase. Turkish Computational and Theoretical Chemistry, 6(2), 1-10.
AMA Ghasemi F, Jafari E, Mırzaeı M, Mahnam K. Docking and Qsar Studies of Some Quinazolinone Derivatives as Possible Inhibitors of Thyrosine Kinase. Turkish Comp Theo Chem (TC&TC). Aralık 2022;6(2):1-10.
Chicago Ghasemi, Fahimeh, Elham Jafari, Mahmoud Mırzaeı, ve Karim Mahnam. “Docking and Qsar Studies of Some Quinazolinone Derivatives As Possible Inhibitors of Thyrosine Kinase”. Turkish Computational and Theoretical Chemistry 6, sy. 2 (Aralık 2022): 1-10.
EndNote Ghasemi F, Jafari E, Mırzaeı M, Mahnam K (01 Aralık 2022) Docking and Qsar Studies of Some Quinazolinone Derivatives as Possible Inhibitors of Thyrosine Kinase. Turkish Computational and Theoretical Chemistry 6 2 1–10.
IEEE F. Ghasemi, E. Jafari, M. Mırzaeı, ve K. Mahnam, “Docking and Qsar Studies of Some Quinazolinone Derivatives as Possible Inhibitors of Thyrosine Kinase”, Turkish Comp Theo Chem (TC&TC), c. 6, sy. 2, ss. 1–10, 2022.
ISNAD Ghasemi, Fahimeh vd. “Docking and Qsar Studies of Some Quinazolinone Derivatives As Possible Inhibitors of Thyrosine Kinase”. Turkish Computational and Theoretical Chemistry 6/2 (Aralık 2022), 1-10.
JAMA Ghasemi F, Jafari E, Mırzaeı M, Mahnam K. Docking and Qsar Studies of Some Quinazolinone Derivatives as Possible Inhibitors of Thyrosine Kinase. Turkish Comp Theo Chem (TC&TC). 2022;6:1–10.
MLA Ghasemi, Fahimeh vd. “Docking and Qsar Studies of Some Quinazolinone Derivatives As Possible Inhibitors of Thyrosine Kinase”. Turkish Computational and Theoretical Chemistry, c. 6, sy. 2, 2022, ss. 1-10.
Vancouver Ghasemi F, Jafari E, Mırzaeı M, Mahnam K. Docking and Qsar Studies of Some Quinazolinone Derivatives as Possible Inhibitors of Thyrosine Kinase. Turkish Comp Theo Chem (TC&TC). 2022;6(2):1-10.

Journal Full Title: Turkish Computational and Theoretical Chemistry


Journal Abbreviated Title: Turkish Comp Theo Chem (TC&TC)