Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
Synthesis and antioxidant evaluation of novel sophisticated carboxamides based on 3-(ethoxycarbonyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-amine
Moustafa Ahmed Gouda (1,*)
, Serry Atta Atta El Bialy (2) (1) Chemistry Department, Faculty of Science, Mansoura University, Mansoura 35516, Egypt
(2) Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
(*) Corresponding Author
Received: 18 Jul 2014 | Revised: 01 Aug 2014 | Accepted: 23 Aug 2014 | Published: 31 Dec 2014 | Issue Date: December 2014
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.
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF
DOI: 10.5155/eurjchem.5.4.644-651.1125
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics
This Abstract was viewed 849 times |
PDF Article downloaded 590 times
Funding information
Department of Chemistry, Faculty of Science and Arts, Taibah University, Ulla, 41411, Kingdom of Saudi Arabia
Citations
[1]. Rangappa S. Keri, Karam Chand, Srinivasa Budagumpi, Sasidhar Balappa Somappa, Siddappa A. Patil, Bhari Mallanna Nagaraja
An overview of benzo [b] thiophene-based medicinal chemistry
European Journal of Medicinal Chemistry 138, 1002, 2017
DOI: 10.1016/j.ejmech.2017.07.038
[2]. Moustafa A. Gouda, Belal H.M. Hussein, Amr El-Demerdash, Mona E. Ibrahim, Mohammed A. Salem, Mohamed H. Helal, Wafaa S. Hamama
A Review: Synthesis and Medicinal Importance of Coumarins and their Analogues (Part II)
Current Bioactive Compounds 16(7), 993, 2020
DOI: 10.2174/1573407215666191111120604
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.
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.5.4.644-651.1125
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2014, 5(4), 644-651 | doi: https://doi.org/10.5155/eurjchem.5.4.644-651.1125 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.