European Journal of Chemistry

Synthesis of some new fluorine substituted thiobarbituric acid derivatives as anti HIV1 and cyclin-dependent kinase 2 (CDK2) for cell tumor division: Part I



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Abdulrahman Salim Al-Harbi
Reda Mohammady Abdel-Rahman
Abdullah Mohamed Asiri

Abstract

New potential enzyme inhibitors, fluorine-substituted thiobarbituric acid derivatives (2, 3, 9, 8 and 12) and their fused/isolated heterocyclic nitrogen systems (5, 6, 10 and 14) have been obtained from heterocyclization of fluorinated N, Nʹ-disubstituted thiourea (1, 7 and 11) with malonic acid followed by ring closure reactions with primary nitrogen reagents. Structures of the synthesized products have been deduced from their elemental analysis and spectral data. Anti-HIV-1 and inhibition of cyclin-dependent kinase2 (CDK2) for cell tumor division for the synthesized compounds were also evaluated.


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Al-Harbi, A. S.; Abdel-Rahman, R. M.; Asiri, A. M. Synthesis of Some New Fluorine Substituted Thiobarbituric Acid Derivatives As Anti HIV1 and Cyclin-Dependent Kinase 2 (CDK2) for Cell Tumor Division: Part I. Eur. J. Chem. 2015, 6, 63-70.

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References

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

[2]. DeClercq, E. Biochi. Biophys. Acta 2002, 1587, 258-275.
http://dx.doi.org/10.1016/S0925-4439(02)00089-3

[3]. Gulnik, S. V.; Elena, A.; Micheal, E. HIV-1 Protease Inhibitors as Antiretroviral Agents. Enzyme Inhibition in Drug Discovery and Development: The Good and the Bad. Chuang Lu and Albert P. Li, Wiley, OU 143 E605. 2009.

[4]. Sabir, S. M.; Salman, S. M.; Rbcha, J. B. T. Toxicol. Appl. Pharm. 2012, 34, 446-453.

[5]. Fernandez, J.; Perez-Alvarez, J. A.; Fernandez-Lopez, A. Food Chem. 1997, 59(3), 345-353.
http://dx.doi.org/10.1016/S0308-8146(96)00114-8

[6]. Castrejon, S. E.; Yatsimirsky, A. K. Talanta 1977, 44, 951-957.
http://dx.doi.org/10.1016/S0039-9140(96)02141-8

[7]. Vyncke, W. Fett. Wiss. Technol. 1970, 72, 1084-1087.

[8]. Lee, J. H.; Lee, S.; Park, M. Y.; Man, H. Virol. J. 2011, 8, 18-21.
http://dx.doi.org/10.1186/1743-422X-8-18

[9]. Ma, L.; Li, S.; Zheng, H.; Chen, J.; Lin, L.; Ye, X.; Chen, Z.; Xu, Q.; Chen, T.; Yang, J.; Qiu, N.; Wang, G.; Peng, A.; Ding, Y.; Wei, Y.; Chen, L. Eur. J. Med. Chem. 2011, 46, 2003-2010.
http://dx.doi.org/10.1016/j.ejmech.2011.02.033

[10]. Srivastava, A. V. K.; Kumar, A. Bioorg. Med. Chem. 2004, 12, 1257-1264.
http://dx.doi.org/10.1016/j.bmc.2003.08.035

[11]. Pothiwong, W.; Laorpaksa, A.; Pirarat, N.; Sirisawadi, S.; Intarapaya, J.; Jianmongkol, S. J. Pharmacol. Toxicol. 2007, 56, 336-338.
http://dx.doi.org/10.1016/j.vascn.2007.08.004

[12]. Zhang, D.; Zhang, J.; Li, M.; Li, W.; Aimaite, G.; Tuersun, G.; Ye, J. Food. Chem. 2011, 129, 206-212.
http://dx.doi.org/10.1016/j.foodchem.2011.04.025

[13]. Rajamaki, S.; Innitzer, A.; Falciani, C.; Tantori, C.; Christ, F.; Witvrouw, M.; Debyser, Z.; Massa, S.; Botta, M. Bioorg. Med. Chem. Lett. 2009, 19, 3615-3618.
http://dx.doi.org/10.1016/j.bmcl.2009.04.132

[14]. Haddad, E.; Jambazian, P.; Karunia, M.; Tanzman, J.; Sabate, J. Nutr. Res. 2006, 26, 397-402.
http://dx.doi.org/10.1016/j.nutres.2006.06.022

[15]. Lapenna, D.; Ciofani, G.; Pierdonenico, S. D.; Giamberardino, M. A.; Cuccurullo, F. Free Radical Bio. Med. 2001, 31(3), 331-335.
http://dx.doi.org/10.1016/S0891-5849(01)00584-6

[16]. Samir, B.; Abd El-Gaber, T.; Ahmed, A. F. Phosphorus Sulfur 2007, 182, 1915-1936.
http://dx.doi.org/10.1080/10426500701415907

[17]. Makki, M. S. T.; Abdel-Rahman, R. M. Int. J. Chem. 2011, 3, 181-192.
http://dx.doi.org/10.5539/ijc.v3n1p181

[18]. Smart, B. E. J. Fluorine Chem. 2001, 109, 3-11.
http://dx.doi.org/10.1016/S0022-1139(01)00375-X

[19]. Yonrtoku, Y.; Kubota, H.; Okamoto, Y.; Toyoshima, A.; Funtsu, M.; Ishikawa, J.; Takeuchi, M.; Ohta, M.; Tsukamoto, S. Bioorgan. Med Chem. 2006, 14, 4750-4760.

[20]. Dlavi, V. H.; Rossky, P. J. P. Natl. Acad. Sci. USA 2010, 107, 13603-13607.
http://dx.doi.org/10.1073/pnas.0915169107

[21]. Brassard, J. D.; Sakar, D.; Perron, J. Appl. Sci. 2012, 2, 453-464.
http://dx.doi.org/10.3390/app2020453

[22]. Mutlib, A.; Shockcor, J.; Chen, S. Y.; Espina, R.; Lin, J.; Graciani, N.; Prakash, S.; Gan, L. S. Drug Metab. Dispos. 2001, 29, 1296-1306.

[23]. Abdel-Rahman, R. M.; Makki, M. S. T.; Ali, T. E.; Ibrahim, M. A. Curr. Org. Synth. 2009, 10, 136-160.

[24]. Al-Harbi, A. S.; Abdel-Rahman, R. M.; Asiri A. M. Int. J. Org. Chem. 2014, 4, 142-153.
http://dx.doi.org/10.4236/ijoc.2014.42016

[25]. Abdel-Rahman, R. M.; Makki, M. S. T.; Bawazir, W. A. E-J. Chem. 2010, 7(S1), S93-S102.

[26]. Abdel-Rahman, R. M.; Makki, M. S. T.; Bawazir, W. A. E-J. Chem. 2011, 8(1), 405-414.

[27]. Makki, M. S. T.; Bakhotmah, D. A.; Abdel-Rahman, R. M. Int. J. Org. Chem. 2012, 2, 49-55.
http://dx.doi.org/10.4236/ijoc.2012.21009

[28]. Fikry, R. M. Indian J. Heterocy. Ch. 1995, 4, 265-268.

[29]. Makki, M. S. T.; Abdel-Rahman, R. M.; El-Shahawy, M. S. Int. J. Chem. 2011, 3(1), 181-192.
http://dx.doi.org/10.5539/ijc.v3n1p181

[30]. Makki, M. S. T.; Bakhotmah, D. A.; Abdel-Rahman, R. M.; El-Shahawy, M. S. Int. J. Org. Chem. 2012, 2, 311-320.
http://dx.doi.org/10.4236/ijoc.2012.223043

[31]. Makki, M. S. T.; Abdel-Rahman; R. M.; El-Shahawi, M. S. C. R. Chem. 2012, 15, 617-626.
http://dx.doi.org/10.1016/j.crci.2012.05.004

[32]. Abdel-Rahman, R. M.; El-Mahdy, K. Heterocycles 2012, 85(10), 2391-2414.
http://dx.doi.org/10.3987/REV-12-745

[33]. Ali, T. E.; Abdel-Rahman, R. M.; Hanafy, F. I.; El-Edfawy, S. M. Phosphorus Sulfur 2008, 183, 2565-2577.
http://dx.doi.org/10.1080/10426500801967864

[34]. Ibrahim, M. A.; Abdel-Rahman, R. M; Abdel-Halim, A. M.; Ibrahim, S. S.; Allimony, H. A. J. Braz. Chem. Soc. 2009, 20(7), 1275-1286.
http://dx.doi.org/10.1590/S0103-50532009000700012

[35]. Rael, L. T.; Thomas, G. W.; Craun, M. L.; Curtis, C. G.; Bar-Or, R.; Bar-Or, D. J. Biochem. Mol. Biol. 2004, 37(6), 749-752.
http://dx.doi.org/10.5483/BMBRep.2004.37.6.749

[36]. Tomei, L.; Altamura, S.; Bartholomew, L.; Bioccio, A.; Ceccacci, A.; Pacini, L.; Narjes, F.; Gennari, N.; Bisbocci, M.; Incitti, I.; Orsatti, L.; Harper, S.; Stansfield, I.; Rowley, M.; De Francesco, R.; Migliaccio, G. J. Virol. 2003, 77, 13225-13231.
http://dx.doi.org/10.1128/JVI.77.24.13225-13231.2003

[37]. Seefl, L. B.; Hoofnagle, J. H. Clin. Liver Dis. 2003, 7(1), 261-287.
http://dx.doi.org/10.1016/S1089-3261(02)00078-8

[38]. Lee, S.; Lee, G.; Kee, Y.; Park, M.; Myung, H. Virus Res. 2005, 114, 158-163.
http://dx.doi.org/10.1016/j.virusres.2005.06.010

[39]. Beaulieu, P. L. Curr. Opin. Invest. Dr. 2007, 8(8), 614-634.

[40]. Weislow, O. W.; Kiser, R.; Fine, D. L.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. J. Natl. Cancer. I 1989, 81(8), 577-586.
http://dx.doi.org/10.1093/jnci/81.8.577

[41]. Balas, V. I.; Verginadis, I. I.; Geromichalos, G. D.; Kourkoumelis, N.; Male, L.; Hursthouse, M. B.; Repana, K. H.; Yiannaki, E.; Charalabopoulos, K.; Bakas, T.; Hadjikakou, S. K. Eur. J. Med. Chem. 2001, 46, 2835-2844.
http://dx.doi.org/10.1016/j.ejmech.2011.04.005

[42]. Krystof, V.; Cankar, P.; Frysova, I.; Slouka, J.; Kontopidis, G.; Dzubak, P.; Hajduch, M.; Srovnal, J.; DeAzevedoJr, W. F.; Orsag, M.; Paprskarova, M.; Rolcik, J.; Latr, A.; Fischer, P. M.; Strnad., M. J. Med. Chem. 2006, 49, 6500-6509.

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

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