European Journal of Chemistry

Synthesis and pharmacological evaluation of new fluorine substituted pyrimido[1,2-b][1,2,4]triazines and [1,3,5]-triazino-[1,2-b][1,2,4]triazines derived as CDK2 potential inhibitors

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Dina Bakhotmah
Fatimah Alotaibi

Abstract

New fluorine-substituted polyfunctional pyrimido-[1,2-b]-[1,2,4]triazines and [1,3,5]-triazino[1,2-b]-[1,2,4]triazines were synthesized via the reaction between 3-amino-6-(2-aminophenyl)-1,2,4-triazin-5(2H)-one with polyfunctional oxygen/sulfur/nitrogen reagents under different conditions. Structures of the target compounds were deduced by elemental analysis and spectral measurements (IR, 1H/13C NMR, and mass spectra). According to the obtained inhibitor assay results, the inhibition activity of the new fluorine-substituted 1,2,4-triazines toward CDK2 decreased in the order of compounds 3 > 8 > 9 > 6 > 13 > 15.


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Bakhotmah, D.; Alotaibi, F. Synthesis and Pharmacological Evaluation of New Fluorine Substituted pyrimido[1,2-b][1,2,4]triazines and [1,3,5]-Triazino-[1,2-b][1,2,4]triazines Derived As CDK2 Potential Inhibitors. Eur. J. Chem. 2020, 11, 198-205.

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References

[1]. Abdel-Rahman, R. M.; Angawi, R. F.; Al-Mehmadi, A. R. J. Saudi Chem. Soc. 2017, 21(4), 495-503
https://doi.org/10.1016/j.jscs.2016.11.004

[2]. Bakhotmah, D. A. Polycycl. Aromat. Comp. 2019, in press, DOI: 10.1080/10406638.2019.1625066
https://doi.org/10.1080/10406638.2019.1625066

[3]. Abdel-Rahman, R. M.; Alharbi, A. S.; Alshammari, N. A.; Adnan, Y. O. Lett. Org. Chem. 2020, 17(3), 184-190.
https://doi.org/10.2174/1570178616666190718120953

[4]. Makki, M. S.; Abdel-Rahman, R. M.; Alharbi, A. S. Curr. Org. Synth. 2019, 16(1), 165-172.
https://doi.org/10.2174/1570179415666181105142247

[5]. Makki, M. S.; Dina, A. B.; Abdel-Rahman, R. M.; Aqlan, F. M. Curr. Org. Synth. 2018, 15(1), 116-125.
https://doi.org/10.2174/1570179414666170509151123

[6]. Tib, L. A.; Adibani, S. A. Int. J. Org. Chem. 2018, 8, 176-189.
https://doi.org/10.4236/ijoc.2018.81013

[7]. Makki, M. S. T.; Abdel-Rahman, R. M.; Ali, O. A. A. Asian. J. Chem. 2016, 28(4), 917-920.
https://doi.org/10.14233/ajchem.2016.19555

[8]. Makki, M. S.; Abdel-Rahman, R. M.; Aqlan, F. M. Int. J. Org. Chem. 2015, 5(3), 200-211.
https://doi.org/10.4236/ijoc.2015.53020

[9]. Makki, M. S.; Abdel-Rahman, R. M.; Khan, K. A. J. Chem. 2014, 430573, 1-14.
https://doi.org/10.1155/2014/430573

[10]. Al-Romaizan, A. N. Mediterr. J. Chem. 2019, 9(3), 249-257.
https://doi.org/10.13171/mjc93191014920aar

[11]. Aqlan, F. M.; Makki, M. S.; Abdel‐Rahman, R. M. J. Heterocyclic. Chem. 2016, 53(4), 1310-1317.
https://doi.org/10.1002/jhet.2386

[12]. Abdel-Rahman, R. M.; Makki, M. S.; Bawazir, W. A. J. Chem. 2011, 8(1), 405-414.
https://doi.org/10.1155/2011/586063

[13]. Leyla, Y. L.; Demirayak, S.; Ilgin, S.; Atli, O. Bioorg. Med. Chem. 2014, 22, 6313-6323.
https://doi.org/10.1016/j.bmc.2014.10.002

[14]. Abdel-Rahman, R. M. Farmaco 1992, 47(3), 319-326.
https://doi.org/10.1007/BF02137667

[15]. Tomachin, A. B.; Krylova, I. Zh. Org. Khim. 1986, 22, 2420-2434.

[16]. Abdel-Rahman, R. M.; Morsy, J. M.; Hanafy, F.; Amene, H. A. Pharmazie 1999, 54(9), 667-671.

[17]. Abdel-Rahman, R. M. Pharmazie 2001, 56, 18-22.

[18]. Krystof, V.; Cankar, P.; Frysova, I.; Slouka, J.; Kontopidis, G.; Dzubak, P.; Hajduch, M.; Srovnal, J.; de Azevedo, W. F.; Orsag, M.; Paprskarova, M.; Rolcik, J.; Latr, A.; Fischer, P. M.; Strnad, M. J. Med. Chem. 2006, 49(22), 6500-6509.
https://doi.org/10.1021/jm0605740

[19]. Gucky, T.; Reznickova, E.; Dzubak, P.; Hajduch, M.; Krystof, V. Monatsh. Chemie-Chem. Monthly 2010, 141(6), 709-714.
https://doi.org/10.1007/s00706-010-0314-4

[20]. Lazzaro, F.; Giannattasio, M.; Puddu, F.; Granata, M.; Pellicioli, A.; Plevani, P.; Muzi-Falconi, M. DNA Repair 2009, 8(9), 1055-1067.
https://doi.org/10.1016/j.dnarep.2009.04.022

[21]. Wohlbold, L.; Fisher, R. P. DNA Repair 2009, 8(9), 1018-1024.
https://doi.org/10.1016/j.dnarep.2009.04.009

[22]. Saloutina, L. V.; Zapevalov, A. Y.; Kodess, M. I.; Slepukhin, P. A.; Ganebnykh, I. N.; Saloutin, V. I.; Chupakhin, O. N, J. Fluorine Chem. 2019, 227, 109362, 1-9.
https://doi.org/10.1016/j.jfluchem.2019.109362

[23]. Isanbor, C.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303-319.
https://doi.org/10.1016/j.jfluchem.2006.01.011

[24]. Abdel-Rahman, R. M.; Abdel-Monem, W. R. Indian J. Chem. B 2007, 46, 838-846.

[25]. Abdel-Rahman, R. M.; Abdel-Monem, W. R. Int. J. Chem. 2006, 16, 1-14.

[26]. Javid, A.; Heravi, M. M.; Bamoharram, F.; Nikpour, M. J. Chem. 2011, 8(2), 547-552.
https://doi.org/10.1155/2011/980546

[27]. Abrahams, S. L.; Hazen, R. J.; Batson, A. G.; Phillips, A. P. J. Pharmacol. Exp. Ther. 1989, 249(2), 359-365.

[28]. Tanigawara, Y.; Aoyama, N.; Kita, T.; Shirakawa, K.; Komada, F.; Kasuga, M.; Okumura, K. Clin. Pharmacol. Ther. 1999, 66(5), 528-534.
https://doi.org/10.1016/S0009-9236(99)70017-2

[29]. Chowdhury, S.; Mohan, R. S.; Scott, J. L. Tetrahedron 2007, 63(11), 2363-2389.
https://doi.org/10.1016/j.tet.2006.11.001

[30]. Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang, Y.; Zhao, Z.; Lindsley, C. W. Org. Lett. 2004, 6(9), 1453-1456.
https://doi.org/10.1021/ol049682b

[31]. Abdel-Rahman, R. M.; El-Gendy, Z. Indian. J. Chem. B 1989, 28, 1072-1076.

[32]. Jindal, A.; Pandya, K.; Khan, I. Med. J. Armed Forces India 2015, 71(2), 178-181.
https://doi.org/10.1016/j.mjafi.2014.04.011

[33]. Tsvetkova, E.; Goss, G. Curr. Oncol. 2012, 19(Suppl 1), S45 -S51.

[34]. Maeda, H.; Khatami, M. Clin. Trans. Med. 2018, 7(1), 11-11.

[35]. Okasha, R. M.; Alsehli, M.; Ihmaid, S.; Althagfan, S. S.; El-Gaby, M. S. A.; Ahmed, H. E. A.; Afifi, T. H. Bioorg. Chem. 2019, 92, 103262, 1-15
https://doi.org/10.1016/j.bioorg.2019.103262

[36]. Roskoski, J, R. Pharmacol. Res. 2019, 139, 471-488.
https://doi.org/10.1016/j.phrs.2018.11.035

[37]. Sanchez-Martinez, C.; Lallena, M. J.; Sanfeliciano, S. G.; de Dios, A. Bioorg. Med. Chem. Lett. 2019, 29(20), 126637, 1-18.
https://doi.org/10.1016/j.bmcl.2019.126637

[38]. Liu, Q.; Gao, J.; Zhao, C.; Guo, Y.; Wang, S.; Shen, F.; Xing, X.; Luo, Y. DNA Repair 2020, 85, 102702, 1-15.
https://doi.org/10.1016/j.dnarep.2019.102702

[39]. Matthews, D. J.; Gerritsen, M. E., Targeting Protein kinases for Cancer Therapy, John Wiley & Sons Inc., Hoboken, New Jersey, 2010.
https://doi.org/10.1002/9780470555293

[40]. Senderowicz, A. M., Inhibitors of cyclin-dependent kinase modulators for cancer therapy, In Advances in Targeted Cancer Therapy, Springer, 2005.
https://doi.org/10.1201/9781420005400.ch8

[41]. Chandrappa, S.; Kavitha, C. V.; Shahabuddin, M. S.; Vinaya, K.; Ananda Kumar, C. S.; Ranganatha, S. R.; Raghavan, S. C.; Rangappa, K. S. Bioorg. Med. Chem. 2009, 17(6), 2576-2584.
https://doi.org/10.1016/j.bmc.2009.01.016

[42]. Bakhotmah, D. A. Am. J. Heterocyclic. Chem. 2019, 5(4), 76-80.

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