European Journal of Chemistry

Synthesis, spectroscopic characterization, crystal structure and pharmacological properties of some novel thiophene-thiourea core derivatives



Main Article Content

Sohail Saeed
Naghmana Rashid
Muhammad Ali
Rizwan Hussain
Peter G. Jones

Abstract

This article presents our research concerning the synthesis of new thiophene-thiourea derivatives (1-12) and their pharmacological properties. These novel thiophene-thiourea derivatives were synthesized and characterized by IR, 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis. The crystal structure of N,N-diphenyl-N'-(thiophene-2-carbonyl)-thiourea was determined from single crystal X-ray diffraction data. It crystallizes in the monoclinic space group P21 with unit cell dimensions of a=11.7469(5) Å, b=6.0849(2) Å, c=12.5792(6) Å, β= 117.736(7) ° and V = 795.8(6) Å3. The mass fragmentation pattern has also been discussed. The synthesized compounds were screened for their in vitro antifungal activities against the standard strains: C. Albicans, C. Glabrata, and C. Tropicalis. The compounds N-thiophene-N',N'-bis(dimethyl-phosphinoylmethyl)thiourea, N-[(4-nitro-1H-imidazol-2-yl)carbamothioyl]thiophene-2-carboxamide and N,N-diethyl-N'-(thiophene-2-carbonyl)-thiourea showed significant antifungal activities against microbial species.

1_3_221_227_800


icon graph This Abstract was viewed 4439 times | icon graph Article PDF downloaded 1028 times

How to Cite
(1)
Saeed, S.; Rashid, N.; Ali, M.; Hussain, R.; Jones, P. G. Synthesis, Spectroscopic Characterization, Crystal Structure and Pharmacological Properties of Some Novel Thiophene-Thiourea Core Derivatives. Eur. J. Chem. 2010, 1, 221-227.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Verma, R. K.; Verma, L.; Ranjan, M.; Verma, B. P.; Mojumdar, S. C. J. Therm. Anal. Cal. 2008, 94, 27-31.
doi:10.1007/s10973-008-9183-z

[2]. Stiffel, E. I.; George, G. N.; Bertini, I.; Gray, H. B.; Lippard, S. J.; Valentine, J. S. Bioinorganic Chemistry, University Science Books, 1998.

[3]. Cotton, F. A.; Wilkinson, G.; Murillo, A.; Bochman, M. Advanced Inorganic Chemistry, 6th edition, John Wiley & Sons, 1999.

[4]. D’hooghe, M.; Waterinckx, A.; De Kimpe, N. J. Org. Chem. 2005, 70, 227-232.
doi:10.1021/jo048486f
PMid:15624926

[5]. Handerson, W.; Nicholson, B. K.; Dinger, M. B.; Bennett, R. L. Inorg. Chim. Acta 2002, 338, 210-218.
doi:10.1016/S0020-1693(02)01017-4

[6]. Sacht, C.; Datt, M. S.; Otto, S.; Roodt, A. J. Chem. Soc. Dalton Trans. 2000, 24, 4579-4586.
doi:10.1039/b007589m

[7]. Lipowska, M.; Hayes, B. L.; Hansen, L.; Taylor, A.; Marzilli, L. G. Inorg. Chem. 1996, 35, 4227-4231.
doi:10.1021/ic9514657
PMid:11666632

[8]. Zuckerman, R. L.; Bergman, R. G. Organometallics 2000, 19, 4795-4809.
doi:10.1021/om000614c

[9]. Henderson, W.; Kemmitt, R. D. W.; Mason, S.; Moore, M. R.; Fawcett, J.; Russell, D. R. J. Chem. Soc. Dalton Trans. 1992, 1, 59-66.
doi:10.1039/dt9920000059

[10]. Arslan, H.; Külcü, N.; Flörke, U. Trans. Metal Chem. 2003, 32(7), 816-819.
doi:10.1023/A:1026064232260

[11]. Binzet, G.; Arslan, H.; Flörke, U.; Külcü, N.; Duran, N. J. Cood. Chem. 2006, 59(12), 1395-1406.
doi:10.1080/00958970500512633

[12]. Ugur, D.; Arslan, H.; Külcü, N. Russ. J. Coord. Chem. 2006, 32(9), 669-675.
doi:10.1134/S1070328406090089

[13]. Emen, M. F.; Arslan, H.; Külcü, N.; Flörke, U.; Duran, N. Polish. J. Chem. 2005, 79(10), 1615-1626.

[14]. Yesilkaynak, T.; Binzet, G.; Emen, F. M.; Flörke, U.; Külcü, N.; Arslan, H. Eur. J. Chem. 2010, 1(1), 1-5.

[15]. Koch, K. R.; Sacht, C.; Grimmbacher, T.; Bourne, S. S. Afr. J. Chem. 1995, 48 (1-2), 71-77.

[16]. Saeed, S.; Rashid, N.; Hussain, R.; Ali, M.; Jones, P. G. Eur. J. Med. Chem. 2010, 45, 1323-1331.
doi:10.1016/j.ejmech.2009.12.016
PMid:20056520

[17]. Zhang, Y. M.; Wei, T. B.; Xian, L.; Gao, L. M. Phosphorus Sulfur Silicon Relat. Elem. 2004, 179, 2007-2013.
doi:10.1080/10426500490473456

[18]. Arslan, H.; Duran, N.; Borekci, G.; Ozer, C. K.; Akbay, C. Molecules 2009, 14, 519-527.
doi:10.3390/molecules14010519
PMid:19169199

[19]. Gu, C. L .; Liu, L.; Zhao, J. L.; Wang, D.; Chen, Y. J. Tetrahedron 2007, 18, 455-463.
doi:10.1016/j.tetasy.2007.02.016

[20]. Saeed, S.; Bhatti, M. H.; Yunus, U.; Jones, P. G. Acta Crystallogr. E 2008, 64, o1369-o1369.
doi:10.1107/S1600536808017868

[21]. D’hooghe, M.; Waterinckx, A.; De Kimpe, N. J. Org. Chem. 2005, 70, 227-232.
doi:10.1021/jo048486f
PMid:15624926

[22]. Jain, V. K.; Rao, J. T. J. Institute Chem. (India), 2003, 75, 24-28.

[23]. Lakhan, R.; Ral, B. J. J. Chem. Eng. Data 1986, 31, 501-508.
doi:10.1021/je00046a035

[24]. Saeed, A.; Parvez, M. Cent. Eur. J. Chem. 2005, 3(4), 780-791.
doi:10.2478/BF02475204

[25]. Nie, L.; Li, Z.; Han, J.; Zhang, X.; Yang, R.; Liu, W. X.; Wu, F. Y.; Xie, J. W.; Zhao, Y. F.; Jiang, Y. B. J. Org. Chem. 2004, 69, 6449-6454.
doi:10.1021/jo049088f
PMid:15357607

[26]. Park, H.; Choi, J.; Choi, S.; Park, M.; Lee, J.; Suh, J. Y.; Cho, H.; Oh, H. U.; Lee, J.; Kang, S. U.; Lee, J.; Kim, H. D.; Park, Y. H.; Jeong, Y. S.; J. K. Choi, J. K.; Jew, J. S. Bioorg. Med. Chem. Lett. 2004, 14, 787-791.
doi:10.1016/j.bmcl.2003.11.019

[27]. Maquoi, E.; Sounni, N. E.; Devy, L.; Olivier, F.; Frankenne, F.; Krell, H. W.; Grams, F.; Foidart, J. M. Agnes. Noel. Clin. Cancer Res. 2004, 10, 4038-4042.
doi:10.1158/1078-0432.CCR-04-0125
PMid:15217936

[28]. Merck Index, 13th Edition, Merck &Co, Inc., Whitehouse Station, New Jersery, 2001.

[29]. Varbanov, S.; Tosheva, T.; Russeva, E. Phosphorus Sulfur Silicon Relat. Elem. 1997, 127, 27-35.
doi:10.1080/10426509708040493

[30]. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122.
doi:10.1107/S0108767307043930
PMid:18156677

[31]. National Committee for Clinical Laboratory Standards, M7-A4 (NCCLS, Viallanova, PA, USA, 1997).

[32]. National Committee for Clinical Laboratory Standards, M27-A2 (NCCLS, Wayne, PA, USA, 2002).

[33]. Saeed, S.; Rashid, N; Jones, P. G.; Hussain, R.; Bhatti, M. H. Cent. Eur. J. Chem. 2010, 8(3), 550-558.
doi:10.2478/s11532-010-0014-2

[34]. Saeed, S.; Rashid, N.; Wong, W. T. Acta Crystallogr. E 2010, 66, o980-o980.
doi:10.1107/S1600536810011116

[35]. Sacht, C.; Datt, M. S. Polyhedron 2000, 19, 1347-1355.
doi:10.1016/S0277-5387(00)00419-8

[36]. Zhang, Y. M.; Wei, T. B.; Xian, L.; Gao, L. M. Phosphorus Sulfur Silicon Relat. Elem. 2007, 179, 2007-2013.
doi:10.1080/10426500490473456

[37]. Allen, F. H. Acta Crystallogr. B 2002, 58, 380-388.
doi:10.1107/S0108768102003890

[38]. Hoey, A. J.; Jackson, C. M.; Pegg, G. G.; Sillence, M. N. Br. J. Pharmacol. 1996, 119, 564-571.
PMid:8894179    PMCid:1915720

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).