Synthesis and antioxidant evaluation of novel sophisticated carboxamides based on 3-(ethoxycarbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-amine

Moustafa Ahmed Gouda; Serry Atta Atta El Bialy

doi:10.5155/eurjchem.5.4.644-651.1125

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Published: Dec 31, 2014

DOI: https://doi.org/10.5155/eurjchem.5.4.644-651.1125

Keywords:

Thiocarbamoyl, Cyanoacetylation, 2-Aminothiophene, Antioxidant evaluation, 3, 5-Dimethyl-1H-pyrazole, 3-(Ethoxycarbonyl)-4, 5, 6, 7-tetrahydro-1-benzothiophen-2-amine

Section

Research Article

Issue

Vol. 5 No. 4 (2014): December 2014

Dates

Received 2014-07-18
Accepted 2014-08-23
Published 2014-12-31

Moustafa Ahmed Gouda

Chemistry Department, Faculty of Science, Mansoura University, Mansoura 35516, Egypt

Serry Atta Atta El Bialy

Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt

Abstract

Condensation of cyanoacetamide 3 with cycloalkanones and elemental sulfur in the presence of morpholine yielded the bisthiophenes 4 and 5. Also, its (3) condensation with terphthalaldehyde or coupling with p-phenylenedidiazonium chloride afforded compound 13 and 14, respectively. Furthermore, cyanoacetylation of compound 4 or 5 afforded the cyanoacetamides 6 and 7, respectively. Knoevenagel condensation of compound 7 with aromatic aldehyde afforded the arylidenes 10, 11 and coumarin 12, respectively. Treatment of compound 3 with CS₂ in DMF/KOH followed by alkylation reaction with ethyl bromoacetate afforded the triester derivative 16, which gave 3-aminothiophene 17 upon heating in DMF/TEA. Moreover, refluxing of compound 23 with α-haloketones afforded 3-aminothiophenes 24 and 25. Identity of newly synthesized compounds was established by the spectral data and novel compounds were evaluated as antioxidant agents.

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Gouda, M. A.; El Bialy, S. A. A. Synthesis and Antioxidant Evaluation of Novel Sophisticated Carboxamides Based on 3-(ethoxycarbonyl)-4,5,6,7-Tetrahydro-1-Benzothiophen-2-Amine. Eur. J. Chem. 2014, 5, 644-651.

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References

[1]. Lutjens, H.; Zickgraft, A.; Figler, H.; Linden, J.; Olsson, R. A.; Scammels, P. J. J. Med. Chem. 2003, 46, 1870-1877.
http://dx.doi.org/10.1021/jm020295m

[2]. Nikolakopoulos, G.; Figler, H.; Linden, J.; Scammels P. J. Bioorg. Med. Chem. 2006, 14, 2358-2365.
http://dx.doi.org/10.1016/j.bmc.2005.11.018

[3]. Pillai, A. D.; Rani, S.; Rathod, P. R.; Xavier, F. P.; Vasu, K. K.; Padh, H.; Sudarsanam, V. Bioorg. Med. Chem. 2005, 13, 1275-1283.
http://dx.doi.org/10.1016/j.bmc.2004.11.016

[4]. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. J. Heterocycl. Chem. 1999, 36, 333-345.
http://dx.doi.org/10.1002/jhet.5570360203

[5]. Ried, W.; Schleimer, B. Angew. Chem. 1958, 70, 164-169.

[6]. Stetinova, J.; Kada, R.; Lesko, J. Molecules 1996, 1, 251-254.

[7]. Gorobets, N. Y; Yousefi, B. H.; Belaj, F.; Kappe, C. O. Tetrahedron 2004, 60, 8633-8644.
http://dx.doi.org/10.1016/j.tet.2004.05.100

[8]. Gouda, M. A.; Abu-Hashem, A. A. Arch. Pharm. 2011, 11, 170-177.
http://dx.doi.org/10.1002/ardp.201000165

[9]. Gutteridge, J. M. C. Free Radic. Res. Commun. 1993, 19, 141-158.
http://dx.doi.org/10.3109/10715769309111598

[10]. Kehrer, J. P. Crit. Rev. Toxicol. 1993, 23, 21-48.
http://dx.doi.org/10.3109/10408449309104073

[11]. Becker, L. B. Cardiovasc Res. 2004, 61, 461-470.
http://dx.doi.org/10.1016/j.cardiores.2003.10.025

[12]. Hayes, J. D.; McLellan, L. I. Free Radic. Res. 1999, 31, 273-300.
http://dx.doi.org/10.1080/10715769900300851

[13]. Masella, R.; Di Benedetto, R.; Vari, R.; Filesi, C.; Giovannini, C. J. Nutr. Biochem. 2005, 16, 577-586.
http://dx.doi.org/10.1016/j.jnutbio.2005.05.013

[14]. Hartmann, R. E.; Shah, A.; Fagan, A. M.; Schwetye, K. E.; Parsadanian, M.; Schulman, R. N.; Finn, M. B.; Holtzman, D. M. Neurobiol Dis. 2006, 24, 506-515.
http://dx.doi.org/10.1016/j.nbd.2006.08.006

[15]. Hollman, P. C.; van Trijp, J. M.; Buysman, M. N.; van Der Gaag, M. S.; Mengelers, M. J.; de Vries, J. H.; Katan, M. B. FEBS Lett. 1997, 418, 152-156.
http://dx.doi.org/10.1016/S0014-5793(97)01367-7

[16]. Abu-Hashem, A. A.; El-Shehry, M. F.; Badria, F. A. Acta Pharm. 2010, 60, 311-323.
http://dx.doi.org/10.2478/v10007-010-0027-6

[17]. Gewald, K. Chem. Ber. 1965, 98, 3571-3577.
http://dx.doi.org/10.1002/cber.19650981120

[18]. Gorobets, N. Y.; Yousefi, B. H.; Belaj, F.; Kappe, C. O. Tetrahedron 2004, 60, 8633-8644.
http://dx.doi.org/10.1016/j.tet.2004.05.100

[19]. Nishimiki, M.; Rao, N. A.; Yagi, K. Biochem. Biophys. Res. Comm. 1972, 46, 849-853.
http://dx.doi.org/10.1016/S0006-291X(72)80218-3

[20]. Aeschbach, R.; Löliger, J.; Scott, B. C.; Murcia, A.; Butler, J.; Halliwell, B.; O.; Aruoma, I. Food Chem. Toxicol. 1994, 32, 31-36
http://dx.doi.org/10.1016/0278-6915(84)90033-4

[21]. Farghaly, T. A.; Abdallah, Zeinab A. Arkivoc 2008, 17, 295-305

[22]. Darwish, Elham S.; Abdel Fattah, Azza M.; Attaby F. A.; Al-Shayea, Oqba N. Int. J. Mol. Sci. 2014, 15, 1237-1254.
http://dx.doi.org/10.3390/ijms15011237

[23]. Ammar, Y. A.; Aly, M. M.; Salem, M. A.; Al-Sehemi, Abd Allah G.; El-Gaby, M. S. A. J. Chin. Chem. Soc-TAIP 2009, 56, 1064- 1071.

Supporting Agencies

Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia

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