Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Syntheses and Cytotoxicity Screening of Some Novel 1,2,4-Triazine Derivatives against Liver Carcinoma Cell Lines

Author(s): Wesam Abd El-Fattah*

Volume 18, Issue 1, 2021

Published on: 24 February, 2020

Page: [2 - 7] Pages: 6

DOI: 10.2174/1570178617666200224104740

Price: $65

Abstract

In this work, 1,2,4-triazine derivatives were synthesized and evaluated for anticancer activities. Series of 1,2,4-triazine derivatives (4a, b) were prepared via the reaction of N-benzoyl glycine (1) with aromatic aldehydes in the presence of fused sodium acetate and acetic anhydride to give 1,3- oxazolinone derivatives (2a, b), followed by condensation with 1-(ethoxycarbonyl) hydrazine (3) in glacial acetic acid. Compounds (4a, b) then reacted with acetic anhydride, ethyl chloroacetate and 2,4- dinitrophenyl hydrazine yielded the corresponding N-acetyl derivatives (5a, b), N-(ethoxycarbonyl) methyl derivative (6) and 1,2-disubstituted hydrazine (7), respectively. The structures of the 1,2,4- triazine derivatives were confirmed by IR, 1H, 13C NMR, MS, and elemental analyses. Anticancer activity of some 1,2,4-triazine derivatives (4-7) has been investigated. The results revealed that compounds 4a (IC50= 2.7μM), 5a (IC50= 1.5μM), and 5b (IC50= 3.9μM) show promising inhibitory growth efficacy compared to a standard antitumor drug (IC50= 4.6μM). These three compounds can be considered as potential agents against human hepatocellular carcinoma cell lines (HepG-2).

Keywords: Cell lines, triazine, antitumor activity, liver cancer, vinblastine, HePG-2, IC50, aromatic aldehydes, benzoyl glycine.

« Previous Next »
Graphical Abstract

[1]
Bruix, J.; Sherman, M. Gastroenterology, 2005, 129(4), 1364.
[http://dx.doi.org/10.1053/j.gastro.2005.08.046] [PMID: 16230100]
[2]
Cheng, A.L.; Kang, Y.K.; Chen, Z.; Tsao, C.J.; Qin, S.; Kim, J.S.; Luo, R.; Feng, J.; Ye, S.; Yang, T.S.; Xu, J.; Sun, Y.; Liang, H.; Liu, J.; Wang, J.; Tak, W.Y.; Pan, H.; Burock, K.; Zou, J.; Voliotis, D.; Guan, Z.; Guan, Z. Lancet Oncol., 2009, 10(1), 25-34.
[http://dx.doi.org/10.1016/S1470-2045(08)70285-7] [PMID: 19095497]
[3]
Chen, K.F.; Chen, H.L.; Tai, W.T.; Feng, W.C.; Hsu, C.H.; Chen, P.J.; Cheng, A.L. J. Pharmacol. Exp. Ther., 2011, 337(1), 155-161.
[http://dx.doi.org/10.1124/jpet.110.175786] [PMID: 21205925]
[4]
Kidwai, M.; Goel, Y.; Kummar, R. Indian J. of Chem., 1998, 37(B), 174-179.
[5]
Holla, B.S.; Gonsalves, R.; Rao, B.S.; Shenoy, S.; Gopalakrishna, H.N. Farmaco, 2001, 56(12), 899-903.
[http://dx.doi.org/10.1016/S0014-827X(01)01119-3 PMID: 11829109]
[6]
Abdel-Rahman, R.M.; Morsy, J.M.; Hanafy, F.; Amene, H.A. Pharmazie, 1999, 54(5), 347-351.
[PMID: 10368828]
[7]
Partridge, M.W.; Stevens, M.F.G. J. Chem. Soc., 1966, 1127-1131.
[8]
Abd, EL-Sami. Z.K. J. Chem. Technol. Biotechnol., 1992, 53, 143-164.
[9]
Hay, M.P.; Pruijn, F.B.; Gamage, S.A.; Liyanage, H.D.; Kovacs, M.S.; Patterson, A.V.; Wilson, W.R.; Brown, J.M.; Denny, W.A. J. Med. Chem., 2004, 47(2), 475-488.
[http://dx.doi.org/10.1021/jm030399c] [PMID: 14711317]
[10]
Heilman, W.P.; Heilman, R.D.; Scozzie, J.A.; Wayner, R.J.; Gullo, J.M.; Ariyan, Z.S. J. Med. Chem., 1979, 22(6), 671-677.
[http://dx.doi.org/10.1021/jm00192a012] [PMID: 458822]
[11]
Erickson, J.G. Chem. Heterocycl. Compd., 1956, 10, 44.
[12]
Jones, R.L.; Kershaw, J.R. Rev. Pure Appl. Chem., 1971, 21, 23.
[13]
Abd El-Moneim, M.A.; El-Deen, I.M.; Abd El-Fattah, W.A. Indian J. Appl. Res., 2013, 3(7), 107-110.
[14]
Bhaskar, S.D.; Shuddhodan, N.K.; Baseer, M.S. Der pharmacia Lett., 2010, 2(4), 126-131.
[15]
Mosmann, T. J. Immunol. Methods, 1983, 65(1-2), 55-63.
[http://dx.doi.org/10.1016/0022-1759(83)90303-4] [PMID: 6606682]
[16]
Vijayan, P.; Raghu, C.; Ashok, G.; Dhanaraj, S.A.; Suresh, B. Indian J. Med. Res., 2004, 120(1), 24-29.
[PMID: 15299228]
[17]
Magdy, I.F.; Somaia, S.A.; Manal, M.A. Afr. J. Chem, 2009, 62, 189-199.

Rights & Permissions Print Cite
Article Metrics
16
1
© 2024 Bentham Science Publishers | Privacy Policy