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

PDF

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 2014-08-13
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.

This Abstract was viewed 946 times |

Article PDF downloaded 645 times

How to Cite

(1)

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.

Links for Article

Crossref - Scopus - Google - European PMC

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.

Most read articles by the same author(s)

Moustafa Ahmed Gouda, Majed Musallam Mutlaq Al‐Balawi, Ameen Ali Abu-Hashem, One-pot pseudo five-component synthesis and antioxidant evaluation of 4,4'-(aryl-methylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol) , European Journal of Chemistry: Vol. 7 No. 3 (2016): September 2016
Moustafa Ahmed Gouda, Meshal Abdulrahim Sabah, Waled Khaled Aljuhani, Ahmed Saleh El-Gahani, Snad Abd El-Karem El-Enazi, Salem Atalleh Al Enizi, Majed Musallam Al-Balawi, Utility of 2-cyano-N-(2-hydroxyethyl) acetamide in heterocyclic synthesis , European Journal of Chemistry: Vol. 6 No. 2 (2015): June 2015
Moustafa Ahmed Gouda, Hadeer Fakhr Eldien, Margret Mansour Girges, Moged Ahmed Berghot, Synthesis and antioxidant evaluation of some new sulphadimidine incorporating thiophene moiety , European Journal of Chemistry: Vol. 5 No. 4 (2014): December 2014
Moustafa Ahmed Gouda, Mohamed Hamdy Helal, Synthesis and antioxidant evaluation of some new pyridines , European Journal of Chemistry: Vol. 6 No. 1 (2015): March 2015

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).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics