European Journal of Chemistry

A series of 1,3-imidazoles and triazole-3-thiones based thiophene-2-carboxamides as anticancer agents: Synthesis and anticancer activity

Crossmark


Main Article Content

Reda Ahmed Haggam
Mohamed Gomma Assy
Mohamed Hassan Sherif
Mohamed Mohamed Galahom

Abstract

By addition of semicarbazide or phenylhydrazine hydrochloride to thienoylisothiocyanate (1) resulted in building of thiosemicarbazide derivative (2), triazole derivative (4) and thiophene-2-carboxamide (5), respectively. Basic cyclization of compound 2 led to formation of oxadiazine (3). Synthesis of thiadiazine derivative (6) was achieved via reaction of compound 5 and maleic anhydride in triethyl amine. Heating of compound 5 with ethyl chloroacetate or sodium ethoxide produced thiadiazine derivative (7) and triazolethione (8), respectively. Thiosemicarbazide derivative 11 was synthesized by addition of nicotinic hydrazide to compound 1. Refluxing of compound 11 with lead acetate afforded triazole (13). Moreover, acid and base mediated cyclizations of compound 11 gave thiadiazole (12) and 1,2,4-triazolethione (14) throughout thiophene intermediate, respectively. Addition of ethyl 2-aminothiophene-3-carboxylate to compound 1 formed thiourea (15) which was refluxed with ethoxide giving thiophene-3-carboxylic acid (16). Lastly, nucleophilic addition of amino phenol or ethylene diamine to compound 1 yielded oxazine structure (18) and imidazole derivative (19), respectively. The yields of the synthesized compounds were 61-95%. The detailed synthesis and spectroscopic data of the new compounds are reported.


icon graph This Abstract was viewed 1791 times | icon graph Article PDF downloaded 709 times

How to Cite
(1)
Haggam, R. A.; Assy, M. G.; Sherif, M. H.; Galahom, M. M. A Series of 1,3-Imidazoles and Triazole-3-Thiones Based Thiophene-2-Carboxamides As Anticancer Agents: Synthesis and Anticancer Activity. Eur. J. Chem. 2018, 9, 99-106.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Barbuceanu, S. F.; Saramet, G.; Almajan, G. L.; Draghici, C.; Barbuceanu, F.; Bancescu, G. Bioorg. Med. Chem. 2012, 49, 417-423.

[2]. Sharma, R.; Misra, G. P.; Sainy, J.; Chaturvedi, S. C. Med. Chem. Res. 2011, 20, 245-253.
https://doi.org/10.1007/s00044-010-9308-3

[3]. Khan, I.; Ali, S.; Hameed, S.; Rama, N. H.; Hussain, M. T.; Wadood, A.; Uddin, R.; Ul-Haq, Z.; Khan, A.; Choudhary, M. I. Eur. J. Med. Chem. 2010, 45, 5200-5207.
https://doi.org/10.1016/j.ejmech.2010.08.034

[4]. Li, Y. F.; Wang, G. F.; Luo, Y.; Huang, W. G.; Tang, W.; Feng, C. L.; Shi, L. P.; Ren, Y. D.; Zuo, J. P.; Lu, W. Eur. J. Med. Chem. 2007, 42, 1358-1364.
https://doi.org/10.1016/j.ejmech.2007.03.005

[5]. Young, W. B.; Sprengeler, P.; Shrader, W. D.; Li, Y.; Rai, R.; Verner, E.; Jenkins, T.; Fatheree, P.; Kolesnikov, A.; Janc, J. W.; Cregar, L.; Elrod, K.; Katz, B.; Bioorg. Med. Chem. Lett. 2006, 16, 710-713.
https://doi.org/10.1016/j.bmcl.2005.10.023

[6]. Ramla, M. M.; Omar, M. A.; Tokuda, H.; El-Diwani, H. I. Bioorg. Med. Chem. 2007, 15, 6489-6496.
https://doi.org/10.1016/j.bmc.2007.04.010

[7]. Blaszczak-Swiatkiewic, K.; Olszewska, P. Pharmacol. Rep. 2014, 66, 100-106.
https://doi.org/10.1016/j.pharep.2014.01.001

[8]. Wu, J.; Liu, X.; Cheng, X.; Cao, Y.; Wang, D.; Li, Z.; Xu, W.; Pannecouque, C.; Witvrouw, M.; Declereq, E. Molecules 2007, 12, 2003-2016.
https://doi.org/10.3390/12082003

[9]. Holla, B. S.; Veerendra, B.; Shivananda, M. K.; Poojary, B. Eur. J. Med. Chem. 2003, 38, 759-767.
https://doi.org/10.1016/S0223-5234(03)00128-4

[10]. Jubie, S.; Sikdar, P.; Antony, S.; Kalirajan, R.; Gowramma, B.; Gomathy, S.; Elango, K. Pak. J. Pharm. Sci. 2011, 24, 109-112.

[11]. Heindel, N. D.; Reid, J. R. J. Heterocycl. Chem. 1980, 17, 1087-1088.
https://doi.org/10.1002/jhet.5570170547

[12]. Holla, B. S.; Kalluraya, B.; Sridhar, K. R.; Drake, E.; Thomas, L. M.; Bhandary, K. K.; Levine, M. S. Eur. J. Med. Chem. 1994, 29, 301-308.
https://doi.org/10.1016/0223-5234(94)90100-7

[13]. Demirbas, N.; Ugurluoglu, D. A.; Bioorg. Med. Chem. 2002, 10, 3717-3723.
https://doi.org/10.1016/S0968-0896(02)00420-0

[14]. Kiran, S.; Singh, B. M.; Parikshit, T. Eur. J. Med. Chem. 2006, 41, 147-153.
https://doi.org/10.1016/j.ejmech.2005.06.006

[15]. Almajan, L. G.; Saramet, I.; Barbuceanu, S. F.; Draghici, C.; Bancescu, G. Rev. Chem. (Bucharest) 2009, 60, 896-901.

[16]. Dymock, B. W.; Jones, P. S.; Wilson, F. X. Antiviral Chemother. 2000, 11, 79-96.
https://doi.org/10.1177/095632020001100201

[17]. Moustafa, A. H.; Haggam, R. A.; Younes, M. E.; El Ashry, E. S. H. Nucleos. Nucleot. Nucleic Acids 2005, 24, 1885-1894.
https://doi.org/10.1080/15257770500268962

[18]. Moustafa, A. H.; Haggam, R. A.; Younes, M. E.; El Ashry, E. S. H. Phosphorus, Sulfur and Silicon 2006, 181, 2361-2371.
https://doi.org/10.1080/10426500600634681

[19]. Haggam, R. A.; Res. Chem. Intermed. 2015, 41, 1135-1148.
https://doi.org/10.1007/s11164-013-1259-0

[20]. Haggam, R. A.; Res. Chem. Intermed. 2016, 41, 7313-7328.
https://doi.org/10.1007/s11164-016-2538-3

[21]. Sherif, M. H.; Assy, M. G.; Yousif, N.; Galahom, M. M. J. Iran. Chem. Soc. 2013, 10, 85-91.
https://doi.org/10.1007/s13738-012-0128-x

[22]. Haggam, R. A.; Assy, M. G.; Sherif, M. H.; Galahom, M. M. Res. Chem. Intermed. 2017, 43, 6299-6315.
https://doi.org/10.1007/s11164-017-2990-8

[23]. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D; Warren, J. T.; Bokesch, H.; Kenny, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107-1112.
https://doi.org/10.1093/jnci/82.13.1107

[24]. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A.; Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd, M. J. Natl. Cancer Inst. 1991, 83, 757-766.
https://doi.org/10.1093/jnci/83.11.757

[25]. Kibrom, G. B.; Girija, S. S. Arkivoc 2015, 6, 206-213.

[26]. Mukerjee, A. K.; Ashare, R. Chem. Rev. 1991, 91, 1-24.
https://doi.org/10.1021/cr00001a001

[27]. El-Bahaie, S.; Assy, M. G.; Kadry, A. Collect. Czech. Chem. Commun. 1990, 55, 1049-1054.
https://doi.org/10.1135/cccc19901049

Most read articles by the same author(s)
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).