European Journal of Chemistry

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

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Moustafa Ahmed Gouda
Serry Atta Atta El Bialy


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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[1]. Lutjens, H.; Zickgraft, A.; Figler, H.; Linden, J.; Olsson, R. A.; Scammels, P. J. J. Med. Chem. 2003, 46, 1870-1877.

[2]. Nikolakopoulos, G.; Figler, H.; Linden, J.; Scammels P. J. Bioorg. Med. Chem. 2006, 14, 2358-2365.

[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.

[4]. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. J. Heterocycl. Chem. 1999, 36, 333-345.

[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.

[8]. Gouda, M. A.; Abu-Hashem, A. A. Arch. Pharm. 2011, 11, 170-177.

[9]. Gutteridge, J. M. C. Free Radic. Res. Commun. 1993, 19, 141-158.

[10]. Kehrer, J. P. Crit. Rev. Toxicol. 1993, 23, 21-48.

[11]. Becker, L. B. Cardiovasc Res. 2004, 61, 461-470.

[12]. Hayes, J. D.; McLellan, L. I. Free Radic. Res. 1999, 31, 273-300.

[13]. Masella, R.; Di Benedetto, R.; Vari, R.; Filesi, C.; Giovannini, C. J. Nutr. Biochem. 2005, 16, 577-586.

[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.

[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.

[16]. Abu-Hashem, A. A.; El-Shehry, M. F.; Badria, F. A. Acta Pharm. 2010, 60, 311-323.

[17]. Gewald, K. Chem. Ber. 1965, 98, 3571-3577.

[18]. Gorobets, N. Y.; Yousefi, B. H.; Belaj, F.; Kappe, C. O. Tetrahedron 2004, 60, 8633-8644.

[19]. Nishimiki, M.; Rao, N. A.; Yagi, K. Biochem. Biophys. Res. Comm. 1972, 46, 849-853.

[20]. Aeschbach, R.; Löliger, J.; Scott, B. C.; Murcia, A.; Butler, J.; Halliwell, B.; O.; Aruoma, I. Food Chem. Toxicol. 1994, 32, 31-36

[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.

[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.

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