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



Main Article Content

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.


icon graph This Abstract was viewed 2187 times | icon graph Article PDF downloaded 908 times

How to Cite
(1)
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.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

Supporting Agencies

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).