European Journal of Chemistry 2015, 6(4), 444-450. doi:10.5155/eurjchem.6.4.444-450.1316

Design and synthesis of new thiophene derivatives together with their antitumor evaluations


Mahmoud Ali Abdelaziz Mahmoud (1,*)

(1) Department of Chemistry, Faculty of Science, University of Tabuk, Tabuk, 71491, P.O. Box 741, Kingdom of Saudi Arabia
(*) Corresponding Author

Received: 09 Sep 2015, Accepted: 04 Oct 2015, Published: 31 Dec 2015

Abstract


A series of new thiophene derivatives (3a,b) have been prepared by the reaction of acetylacetone with either cyanoacetanilide or 2-cyano-N-(p-tolyl)acetamide and elemental sulfur in the presence of triethylamine as basic catalyst. The two synthesized compounds were used to further synthesize new thiophene derivatives. The structures of all the newly synthesized products have been established on the basis of analytical and spectral data. The antitumor activity of the newly thiophene derivatives was evaluated against six human cancer cell lines, namely gastric cancer (NUGC), colon cancer (DLD1), liver cancer (HA22T and HEPG2), nasopharyngeal carcinoma (HONE1), breast cancer (MCF) and normal fibroblast cells (WI38).


Keywords


Pyrazole; Thiophene; Cytotoxicity; Breast cancer; Antitumor activity; Benzo[b]thiophene

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.6.4.444-450.1316

Get Citation | Scilit | GrowKudos | ResearchGate | Publons | Microsoft Academic

WorldCat | Dimensions | SemanticScholar | PlumX Metrics | Kopernio | Zotero | Mendeley

Article Metrics


This Abstract was viewed 531 times | PDF Article downloaded 246 times


References

[1]. Romagnoli, R.; Baraldi, P. G.; Lopez-Cara, C.; Cruz-Lopez, O.; Moorman, A. R.; Massink, A.; IJzerman, A. P.; Vincenzi, F.; Borea, P. A.; Varani, K. Eur. J. Med. Chem. 2015, 101, 185-204.
http://dx.doi.org/10.1016/j.ejmech.2015.06.041

[2]. Romagnoli, R.; Baraldi, P. G.; Lopez-Cara, C.; Salvador, M. K.; Preti, D.; Tabrizi, M. A.; Balzarini, J.; Nussbaumer. P.; Bassetto, M.; Brancale, A.; Fu, X. H.; Yang-Gao, Li. J.; Zhang, S. Z.; Hamel, E.; Bortolozzi, R.; Basso, G.; Viola, G. Bioorg. Med. Chem. 2014, 22(18), 5097-5109.
http://dx.doi.org/10.1016/j.bmc.2013.12.030

[3]. Zhang, Q.; Luo, J.; Ye, L.; Wang, H.; Huang, B.; Zhang, J.; Wu, J.; Zhang, S.; Tian, Y. J. Mol. Struct. 2014, 1074, 33-42.
http://dx.doi.org/10.1016/j.molstruc.2014.04.058

[4]. Mohareb, R. M.; Abbas, N. S.; Ibrahim, R. A. Acta Chim. Slov. 2013, 60, 583-594.

[5]. Lu, X.; Wan, B.; Franzblau, S. G.; You, Q. Eur. J. Med. Chem. 2011, 46(9), 3551-3563.
http://dx.doi.org/10.1016/j.ejmech.2011.05.018

[6]. Dalvie, D. K.; Kalgutkar, A. S.; Khojasteh-Bakht, S. C.; Obach, R. S.; O'Donnell, J. P. Chem. Res. Toxicol. 2002, 15, 269-299.
http://dx.doi.org/10.1021/tx015574b

[7]. Kagan, J.; Arora, S. K.; Prakash, I.; Ustunol, A. Heterocycles 1983, 20, 1341-1345.
http://dx.doi.org/10.3987/R-1983-07-1341

[8]. Gribble, G. W.; Saulnier, M. G.; Sibi, M. P.; Obaza-Nutaitis, J. A. J. Org. Chem. 1984, 49, 4518-4523.
http://dx.doi.org/10.1021/jo00197a039

[9]. Bakker, J.; Gommers, F. J.; Nieuwenhuis, I.; Wynberg, H. J. Biol. Chem. 1979, 254, 1841-1844.

[10]. Iyengar, S.; Arnason, J. T.; Philogene, B. J.; Murand, P.; Werstink, N. H.; Timmins, G. P. Pestic. Biochem. Physiol. 1987, 29(1), 1-9.
http://dx.doi.org/10.1016/0048-3575(87)90078-2

[11]. Matsuura, H.; Saxena, G.; Farmer, S. W.; Hancock, R. E. W.; Towers, G. H. N. Planta Med. 1996, 62, 256-259.
http://dx.doi.org/10.1055/s-2006-957872

[12]. Chan, G. F. Q.; Towers, G. H. N.; Mitchell, J. C. Phytochem. 1975, 14, 2295-2296.
http://dx.doi.org/10.1016/S0031-9422(00)91121-X

[13]. Hudson, J. B.; Graham, E. A.; Miki, N.; Towers, G. H. N.; Hudson, L. L.; Rossi, R.; Carpita, A.; Neri, D. Chemosphere 1989, 19, 1329-1343.
http://dx.doi.org/10.1016/0045-6535(89)90080-5

[14]. Malmstrom, J.; Jonsson, M.; Cotgreave, I. A.; Hammarström, L.; Sjodin, M.; Engman, L. J. Am. Chem. Soc. 2001, 123, 3434-3440.
http://dx.doi.org/10.1021/ja0035811

[15]. Nobles, W. L.; Blanton, D. W.; Jr, C. J. Pharm. Sci. 1964, 53, 115-129.
http://dx.doi.org/10.1002/jps.2600530202

[16]. Meotti, F. C.; Silva, D. O.; dos Santos, A. R. S.; Zeni, G.; Rocha, J. B. T.; Nogueira, C. W. Env. Toxicol. Pharm. 2003, 15(1), 37-44.
http://dx.doi.org/10.1016/j.etap.2003.08.008


How to cite


Mahmoud, M. Eur. J. Chem. 2015, 6(4), 444-450. doi:10.5155/eurjchem.6.4.444-450.1316
Mahmoud, M. Design and synthesis of new thiophene derivatives together with their antitumor evaluations. Eur. J. Chem. 2015, 6(4), 444-450. doi:10.5155/eurjchem.6.4.444-450.1316
Mahmoud, M. (2015). Design and synthesis of new thiophene derivatives together with their antitumor evaluations. European Journal of Chemistry, 6(4), 444-450. doi:10.5155/eurjchem.6.4.444-450.1316
Mahmoud, Mahmoud. "Design and synthesis of new thiophene derivatives together with their antitumor evaluations." European Journal of Chemistry [Online], 6.4 (2015): 444-450. Web. 9 Dec. 2019
Mahmoud, Mahmoud. "Design and synthesis of new thiophene derivatives together with their antitumor evaluations" European Journal of Chemistry [Online], Volume 6 Number 4 (31 December 2015)

DOI Link: https://doi.org/10.5155/eurjchem.6.4.444-450.1316

| | | | |

| | | | | |

. OPEN ACCESS PEER-REVIEWED Research Article

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.