European Journal of Chemistry 2019, 10(3), 209-217. doi:10.5155/eurjchem.10.3.209-217.1850

Synthesis, reactions and biological evaluation of some novel thienothiophene derivatives


Mounir Abbas Ali Mohamed (1,*) orcid , Hanan Salah (2) orcid , Ahmed Mohamed Mohamed El-Saghier (3) orcid

(1) Chemistry Department, Faculty of Science, Sohag University, Sohag 82524, Egypt
(2) Chemistry Department, Faculty of Science, Sohag University, Sohag 82524, Egypt
(3) Chemistry Department, Faculty of Science, Sohag University, Sohag 82524, Egypt
(*) Corresponding Author

Received: 18 Mar 2019, Accepted: 28 May 2019, Published: 30 Sep 2019

Abstract


Synthesis of some new bis(chalcones)-based thienothiophene derivatives and study of their synthetic utilities as building blocks for new bis(thiazole), bis(dihydropyran), bis(dihydro pyridine), bis(isoxazoles), bis(pyrazoles), bis(hydropyrimidinethiones), bis(tetrahydro diazepines, oxazepines) and bis(dihydrobenzodiazepnies, benzoxazepines) each linked to a thienothiophene core, is reported. Biological evaluation of the obtained compounds as antibacterial agents was achieved. Compounds 4b, 4c, 7a, 6a, 9a and 11b were found to be very potent against P. aeruginosa, E. coli and K. pneumonia.


Keywords


Chalcone; Isoxazole; Diazepine; Oxazepine; Thienothiophene; Antibacterial activity

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.10.3.209-217.1850

Get Citation | Scilit | GrowKudos | ResearchGate | Publons | Microsoft Academic

WorldCat | Dimensions | SemanticScholar | PlumX Metrics | Kopernio | Zotero | Mendeley

Article Metrics


This Abstract was viewed 197 times | PDF Article downloaded 66 times


References

[1]. Bhat, B. A.; Dhar, K. L.; Saxena, A. K.; Shanmugavel, M.; Qazi, G. N. Bioorg. Med. Chem. 2005, 15, 3177-3180.
https://doi.org/10.1016/j.bmcl.2005.03.121

[2]. Konieczny, M. T.; Konieczny, W.; Sabisz, M.; Skladanowski, A.; Wakiec, R.; Augustynowicz-Kopec, E.; Zwolska, Z. Eur. J. Med. Chem. 2007, 42, 729-733.
https://doi.org/10.1016/j.ejmech.2006.12.014

[3]. Kumar, D.; Kumar, N. M.; Akamatsu, K.; Kusaka, E.; Harada, H.; Ito, T. Bioorg. Med. Chem. Lett. 2010, 20, 3916-3919.
https://doi.org/10.1016/j.bmcl.2010.05.016

[4]. Biradar, J. S.; Sasidhar, B. S.; Parveen, R. Eur. J. Med. Chem. 2010, 45, 4074-4078.
https://doi.org/10.1016/j.ejmech.2010.05.067

[5]. Singh, P.; Anand, A.; Kumar, V. Eur. J. Med. Chem. 2014, 85, 758-777.
https://doi.org/10.1016/j.ejmech.2014.08.033

[6]. Singh, S.; Sharma, P. K.; Verma, N. K.; Dudhe, R. Asian J. Pharm. Biol. Res. 2011, 1, 412-418.

[7]. Ritter, M.; Martins, R. M.; Dias, D.; Pereira, C. M. P. Lett. Org. Chem. 2011, 11, 498-508.
https://doi.org/10.2174/1570178611666140218004421

[8]. Bukhari, S. N. A.; Jasamai, M.; Jantan, I.; Ahmad, W. Mini-Rev. Org. Chem. 2013, 10, 73-83.
https://doi.org/10.2174/1570193X11310010006

[9]. Xu, J.; Wang, C.; Zhang, Q. Heteroat. Chem. 2001, 6, 557-559.
https://doi.org/10.1002/hc.1085

[10]. Albuquerque, H. M. T.; Santos, C. M. M.; Cavaleiro, J. A. S.; Silva, A. M. S. Curr. Org. Chem. 2014, 18, 2750-2775.
https://doi.org/10.2174/1385272819666141013224253

[11]. Mabkhot, Y. N. Molecules 2010, 15, 3329-3337.
https://doi.org/10.3390/molecules15053329

[12]. Mabkhot, Y. N.; Kheder, N. A.; Al-Majid, A. M. Molecules 2010, 15, 9418-9426.
https://doi.org/10.3390/molecules15129418

[13]. Mabkhot, Y. N. Molecules 2009, 14, 1904-1914.
https://doi.org/10.3390/molecules14051904

[14]. Mabkhot, Y. N.; Barakat, A.; Al-Majid, A. M.; Alshahrani, S. A. Int. J. Mol. Sci. 2012, 13, 2263-2275.
https://doi.org/10.3390/ijms13022263

[15]. Jarak, I.; Kralj, M.; Piantanida, I.; Suman, L.; Zinic, M.; Pavelic, K.; Karminski-Zamola, G. Bioorg. Med. Chem. 2006, 14, 2859-2868.

[16]. Mashraqui, S. H.; Sangvikar, Y. S.; Meetsma, A. Tetrahedron Lett. 2006, 47, 5599-5602.
https://doi.org/10.1016/j.tetlet.2006.05.098

[17]. Wang, C.; Jung, G. Y.; Hua, Y.; Pearson, C.; Bryce, M. R.; Petty, M. C.; Batsanov, A. S.; Gaeta, A. E.; Howard, J. A. K. Chem. Mater. 2001, 13, 1167-1173.
https://doi.org/10.1021/cm0010250

[18]. Wang, C.; Jung, G. Y.; Batsanov, A. S.; Bryce, M. R.; Petty, M. C. J. Mater. Chem. 2002, 12, 173-180.
https://doi.org/10.1039/b106907c

[19]. Salem, M. E.; Darweesh, A. F.; Mekky, A. E. M.; Farag, A. M.; Elwahy, A. H. M. J. Heterocyclic Chem. 2017, 54, 226-234.
https://doi.org/10.1002/jhet.2571

[20]. Thurston, D. E.; Bose, D. S.; Thompson, A. S.; Howard, P. W.; Leoni, A.; Croker, S. J.; Jenkins, T. C.; Neidle, S.; Hartley, J. A.; Hurley, L. H. J. Org. Chem. 1996, 61, 8141-8147.
https://doi.org/10.1021/jo951631s

[21]. Shaker, R. M. Phosphorus, Sulfur Silicon Relat Elem. 1999, 149, 7-14.
https://doi.org/10.1080/10426509908037017

[22]. Kamal, A.; Laxman, N.; Ramesh, G.; Neelima, K.; Anand, K. K. Chem Commun. 2001, 437-438.
https://doi.org/10.1039/b009195m

[23]. Raasch, A.; Scharfenstein, O.; Trankle, C.; Holzgrabe, U.; Mohr, K. J. Med. Chem. 2002, 45, 3809-3812.
https://doi.org/10.1021/jm020871e

[24]. Jain, M.; Khanna, P.; Saxena, A.; Bhagat, S.; Olsen, C. E.; Jain, S. C. Synth. Commun. 2006, 36, 1863-1872.
https://doi.org/10.1080/00397910600602560

[25]. Jain, M.; Sakhuja, R.; Khanna, P.; Bhagat, S.; Jain, S. C. Arkivoc 2008, 15, 54-64.

[26]. Yang, G. Y.; Oh, K. A.; Park, N. J.; Jung, Y. S. Bioorg. Med. Chem. 2007, 15, 7704-7710.
https://doi.org/10.1016/j.bmc.2007.08.056

[27]. Giacomo, B. D.; Bedini, A.; Spadoni, G.; Tarzia, G.; Fraschini, F.; Pannaccib, M.; Lucinib, V. Bioorg. Med. Chem. 2007, 15, 4643-4650.
https://doi.org/10.1016/j.bmc.2007.03.080

[28]. Holla, B. S.; Gonsalves, R.; Shenoy, S. Eur. J. Med. Chem. 2000, 35, 267-271.

[29]. Holla, B. S.; Gonsalves, R.; Rao, B. S.; Shenoy, S.; Gopalakrishna, H. N. Il Farmaco 2001, 56, 899-903.
https://doi.org/10.1016/S0014-827X(01)01119-3

[30]. Holla, B. S.; Poojary, K. N.; Rao, B. S.; Shivananda, M. K. Eur. J. Med. Chem. 2002, 37, 511-517.
https://doi.org/10.1016/S0223-5234(02)01358-2

[31]. Li, J. T.; Sun, M. X.; He, G. Y.; Xu, X. Y. Ultrason. Sonochem. 2011, 18, 412-414.
https://doi.org/10.1016/j.ultsonch.2010.07.016

[32]. Wang, Z.; Zhao, C.; Zhao, D.; Li, C.; Ahang, J.; Wang, H. Tetrahedron 2010, 66, 2168-2174.
https://doi.org/10.1016/j.tet.2010.01.056

[33]. Diana, P.; Carbone, A.; Barraja, P.; Kelter, G.; Fiebig, H.; Cirrincione, G. Bioorg. Med. Chem. 2010, 18, 4524-4529.
https://doi.org/10.1016/j.bmc.2010.04.061

[34]. Toyota, K.; Okada, K.; Katsuta, H.; Morita, N. Tetrahedron 2009, 65, 145-151.
https://doi.org/10.1016/j.tet.2008.10.088

[35]. Todd, E. M.; Zimmerman, S. C. Tetrahedron 2008, 64, 8558-8570.
https://doi.org/10.1016/j.tet.2008.05.076

[36]. Diana, P.; Carbone, A.; Barraja, P.; Montalbano, A.; Martorana, A.; Dattolo, G.; Gia, O.; Dalla Via, L.; Cirrincione, G. Bioorg Med. Chem. Lett. 2007, 17, 2342-2346.
https://doi.org/10.1016/j.bmcl.2007.01.065

[37]. Blanco, G.; Quintela, J. M.; Peinador, C. Tetrahedron 2007, 63, 2034-2041.
https://doi.org/10.1016/j.tet.2006.12.049

[38]. Promarak, V.; Punkvuang, A.; Jungsuttiwong, S.; Saengsuwan, S.; Sudyoadsuk, T.; Keawin, T. Tetrahedron Lett. 2007, 48, 3661-3665.
https://doi.org/10.1016/j.tetlet.2007.03.131

[39]. Gomha, S. M.; Edrees, M. M.; Ezz El-Arabb, E. J. Heterocyclic Chem. 2017, 54, 641647.
https://doi.org/10.1002/jhet.2869

[40]. Gomha, S. M.; El-Hashash, M. A.; Mastoura, M.; Edrees, M. M.; El-Arab, E. J. Heterocyclic Chem. 2017, 54, 2686-2695.
https://doi.org/10.1002/jhet.2869

[41]. Murru, S.; Nefzi, A. ACS Comb. Sci. 2014, 16, 39-45.
https://doi.org/10.1021/co400133a

[42]. Dolle, R. E. J. Comb. Chem. 2005, 7, 739-798.
https://doi.org/10.1021/cc050082t

[43]. Dolle, R. E. J. Comb. Chem. 2004, 6, 623-679.
https://doi.org/10.1021/cc0499082

[44]. Helal, J.; Sanner, M. A.; Cooper, C. B.; Gant, T.; Adam, M.; Lucas, J. C.; Kang, Z.; Kupchinsky, S.; Ahlijanian, M. K.; Tate, B.; Menniti, F. S.; Kelly, K.; Peterson, M. Bioorg. Med. Chem. Lett. 2004, 14, 5521-5525.
https://doi.org/10.1016/j.bmcl.2004.09.006

[45]. Soural, M.; Bouillon, I.; Krchnak, V. J. Comb. Chem. 2008, 10, 923-933.
https://doi.org/10.1021/cc8001074

[46]. El-Fatah, N. A. A.; Darweesh, A. F.; Mohamed, A. A.; Abdelhamid, I. A.; Elwahy, A. H. M. Monatsh. Chemie-Chem. Mon. 2017, 148, 2107-2122.
https://doi.org/10.1007/s00706-017-2040-7

[47]. Salama, S. K.; Darweesh, A. F.; Abdelhamid, I. A.; Elwahy, A. H. M. J. Heterocyclic Chem. 2017, 54, 305-312.
https://doi.org/10.1002/jhet.2584

[48]. Abd El-Fatah, N. A.; Darweesh, A. F.; Mohamed, A. A.; Abdelhamid, I. A.; Elwahy, A. H. M. Tetrahedron 2017, 73, 1436-1450.
https://doi.org/10.1016/j.tet.2017.01.047

[49]. Salem, M. E.; Darweesh, A. F.; Elwahy, A. H. M. J. Sulfur Chem. 2018, 39, 525-543.
https://doi.org/10.1080/17415993.2018.1471143

[50]. Mabkhot, Y. N.; Al-Majid, A. M.; Alamary, A. M. A. S.; Warad, I.; Sedigi, Y. Molecules 2011, 16, 5142-5148.
https://doi.org/10.3390/molecules16065142

[51]. Mabkhot, Y. N.; Al-Majid, A. M.; Alamary, A. S. Molecules 2011, 16, 7706-7714.
https://doi.org/10.3390/molecules16097706

[52]. Pandey, B.; Ghimire, P.; Agrawal, V. P. Studies on the antibacterial activity of actinomycetes isolated from the Khumbu region of Mt. Everest. A paper presented in the International Conference on the Great Himalayas: Climate, Health, Ecology, Management and Conservation, Kathmandu. Organized by Kathmandu University and the Aquatic Ecosystem Health and Management Society, Canada. 12-15, 2004.

[53]. NCCLS (National Committee for Clinical Laboratory Standards), 3rd Ed.; Approved standard M7-A3, NCCLS, Villanova, PA, 1993.

[54]. Amenu, D. Amer. J. Ethnomed. 2014, 1(1), 18-29.

[55]. Abd Rabou, A.; Yassin, M.; Al-Agha, M.; Madi, M.; Al-Wali, M.; Ali, A.; Hamad, D. The Islamic Univ. J. 2008, 16(1), 31-63.

[56]. El-Shafei, A. K.; Abdel-Ghany, H.; Sultan, A. A.; El-Saghier, A. M. M. Phosphorus Sulfur Silicon Rel. Elem. 1992, 73(1-4), 15-25.
https://doi.org/10.1080/10426509208034426

[57]. Moustafa, H. M.; Khodairy, A.; El-Saghier, A. M. M. Phosphorus Sulfur Silicon Rel. Elem. 2003, 178(6), 1211-1224.
https://doi.org/10.1080/10426500307907

[58]. Khodairy, A.; El-Saghier, A. M. M. Acta Chim. Slov. 2011, 58, 360-366.
https://doi.org/10.5771/0044-3360-2011-3-360


How to cite


Mohamed, M.; Salah, H.; El-Saghier, A. Eur. J. Chem. 2019, 10(3), 209-217. doi:10.5155/eurjchem.10.3.209-217.1850
Mohamed, M.; Salah, H.; El-Saghier, A. Synthesis, reactions and biological evaluation of some novel thienothiophene derivatives. Eur. J. Chem. 2019, 10(3), 209-217. doi:10.5155/eurjchem.10.3.209-217.1850
Mohamed, M., Salah, H., & El-Saghier, A. (2019). Synthesis, reactions and biological evaluation of some novel thienothiophene derivatives. European Journal of Chemistry, 10(3), 209-217. doi:10.5155/eurjchem.10.3.209-217.1850
Mohamed, Mounir, Hanan Salah, & Ahmed Mohamed Mohamed El-Saghier. "Synthesis, reactions and biological evaluation of some novel thienothiophene derivatives." European Journal of Chemistry [Online], 10.3 (2019): 209-217. Web. 9 Dec. 2019
Mohamed, Mounir, Salah, Hanan, AND El-Saghier, Ahmed. "Synthesis, reactions and biological evaluation of some novel thienothiophene derivatives" European Journal of Chemistry [Online], Volume 10 Number 3 (30 September 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.3.209-217.1850

| | | | |

| | | | | |

. OPEN ACCESS PEER-REVIEWED Research Article

Refbacks

  • There are currently no refbacks.




Copyright (c) 2019 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/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 (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© Copyright 2019  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 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.