European Journal of Chemistry 2010, 1(3), 221-227 | doi: https://doi.org/10.5155/eurjchem.1.3.221-227.124 | Get rights and content

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


Sohail Saeed (1,*) , Naghmana Rashid (2) , Muhammad Ali (3) , Rizwan Hussain (4) , Peter G. Jones (5)

(1) Department of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad, 44000, Pakistan
(2) Department of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad, 44000, Pakistan
(3) Department of Pharmacy, University of the Punjab, Lahore, 54590, Pakistan
(4) National Engineering & Scientific Commission, P.O. Box 2801, Islamabad, Pakistan
(5) Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Braunschweig, D-38023, Germany
(*) Corresponding Author

Received: 23 May 2010 | Revised: 27 Aug 2010 | Accepted: 19 Jul 2010 | Published: 29 Sep 2010 | Issue Date: September 2010

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.

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Keywords


Thiourea derivatives; Thiophene; Single crystal structure determination; Mass fragmentation; Antifungal activity

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DOI: 10.5155/eurjchem.1.3.221-227.124

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[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


How to cite


Saeed, S.; Rashid, N.; Ali, M.; Hussain, R.; Jones, P. Eur. J. Chem. 2010, 1(3), 221-227. doi:10.5155/eurjchem.1.3.221-227.124
Saeed, S.; Rashid, N.; Ali, M.; Hussain, R.; Jones, P. Synthesis, spectroscopic characterization, crystal structure and pharmacological properties of some novel thiophene-thiourea core derivatives. Eur. J. Chem. 2010, 1(3), 221-227. doi:10.5155/eurjchem.1.3.221-227.124
Saeed, S., Rashid, N., Ali, M., Hussain, R., & Jones, P. (2010). Synthesis, spectroscopic characterization, crystal structure and pharmacological properties of some novel thiophene-thiourea core derivatives. European Journal of Chemistry, 1(3), 221-227. doi:10.5155/eurjchem.1.3.221-227.124
Saeed, Sohail, Naghmana Rashid, Muhammad Ali, Rizwan Hussain, & Peter G. Jones. "Synthesis, spectroscopic characterization, crystal structure and pharmacological properties of some novel thiophene-thiourea core derivatives." European Journal of Chemistry [Online], 1.3 (2010): 221-227. Web. 16 Jun. 2021
Saeed, Sohail, Rashid, Naghmana, Ali, Muhammad, Hussain, Rizwan, AND Jones, Peter. "Synthesis, spectroscopic characterization, crystal structure and pharmacological properties of some novel thiophene-thiourea core derivatives" European Journal of Chemistry [Online], Volume 1 Number 3 (29 September 2010)

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