

Synthesis and antimicrobial evaluation of some 1,2,4-triazolo[1,5-a]pyridine, pyrimidine sulfonamides and sulfinyl derivatives
Fatma Fakhry Abdel-Motaal (1)


(1) Botany Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt
(2) Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt
(*) Corresponding Author
Received: 18 Mar 2014 | Accepted: 24 Apr 2014 | Published: 30 Sep 2014 | Issue Date: September 2014
Abstract
Several new substituted sulfonamides and sulfinyl compound derivatives were obtained by the reaction of 2-thioxo-1,2,4-triazolo[1,5-a]pyridine and pyrimidine thiol derivatives with (2-chloromethyl)benzimidazole and/or (2-chloromethyl)benzooxazole. Structures of the newly synthesized products have been deduced on the basis of spectral and analytical data. The synthesized compounds were screened for their antimicrobial activity.
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.5.3.481-487.1054
Links for Article
| | | | | | |
| | | | | | |
| | |
Related Articles
Article Metrics


Funding information
Faculty of Science, Aswan University, 81528 Aswan, Egypt
Citations
[1]. Maria Assunta Chiacchio , Daniela Iannazzo , Roberto Romeo, Salvatore V. Giofrè , Laura Legnani
Pyridine and Pyrimidine Derivatives as Privileged Scaffolds in Biologically Active Agents
Current Medicinal Chemistry 26(40), 7166, 2020
DOI: 10.2174/0929867325666180904125400

References
[1]. Lu, X.; Zhang, H.; Chen, G.; Luo, Y.; Ruan, B. F.; Chen, X. W.; Zhu, H. L.; Zhu, H. L. Bioorg. Med. Chem. 2011, 19, 6827-6832.
http://dx.doi.org/10.1016/j.bmc.2011.09.034
[2]. Luo, Y.; Qiu, K. M.; Lu, X.; Liu, K.; Fu, J.; Zhu, H. L. Bioorg. Med. Chem. 2011, 19, 4730-4738.
http://dx.doi.org/10.1016/j.bmc.2011.06.088
[3]. Chandak, N.; Bhardwaj, J. K.; Sharma, R. K.; Sharma, P. K. Eur. J. Med. Chem. 2013, 59, 203-208.
http://dx.doi.org/10.1016/j.ejmech.2012.11.015
[4]. Kamal, A.; Swapna, P.; Shetti, R. V.; Shaik, A. B.; Narasimha Rao, M. P.; Gupta, S. Eur. J. Med. Chem. 2013, 62, 661-669.
http://dx.doi.org/10.1016/j.ejmech.2013.01.034
[5]. Akurathi, V.; Dubois, L.; Lieuwes, N. G.; Chitneni, S. K.; Cleynhens, B. J.; Vullo, D.; Supuran, C. T.; Verbruggen, A. M.; Lambin, P.; Bormans, G. M. Nucl. Med. Biol. 2010, 37, 557-564.
http://dx.doi.org/10.1016/j.nucmedbio.2010.02.006
[6]. Andrighetti-Frohner, C. R.; De Oliveira, K. N.; Gaspar-Silva, D.; Pacheco, L. K.; Joussef, A. C.; Steindel, M.; Simoes, C. M. O.; De Souza, A. M. T.; Magalhaes, U. O.; Afonso, I. F.; Rodrigues, C. R.; Nunes, R. J.; Castro, H. C. Eur. J. Med. Chem. 2009, 44, 755-763.
http://dx.doi.org/10.1016/j.ejmech.2008.04.016
[7]. Gadad, A. K.; Mahajanshetti, C. S.; Nimbalkar, S.; Raichurkar, A. Eur. J. Med. Chem. 2000, 35, 853-857.
http://dx.doi.org/10.1016/S0223-5234(00)00166-5
[8]. Azab, M.; Youssef, M.; El-Bordany, E. Molecules 2013, 18, 832-844.
http://dx.doi.org/10.3390/molecules18010832
[9]. Ezabadi, I. R.; Camoutsis, C.; Zoumpoulakis, P.; Geronikaki, A.; Sokovic, M.; Glamocilija, J.; Ciric, A. Bioorg. Med. Chem. 2008, 16, 1150-1161.
http://dx.doi.org/10.1016/j.bmc.2007.10.082
[10]. Ghorab, M. M.; Ragab, F. A.; Heiba, H. I.; Arafa, R. K.; El-Hossary, E. M. Eur. J. Med. Chem. 2010, 45, 3677-3684.
http://dx.doi.org/10.1016/j.ejmech.2010.05.014
[11]. Ghorab, M. M.; Ragab, F. A.; Hamed, M. M. Eur. J. Med. Chem. 2009, 44, 4211-4217.
http://dx.doi.org/10.1016/j.ejmech.2009.05.017
[12]. Bano, S.; Javed, K.; Ahmad, S.; Rathish, I. G.; Singh, S.; Alam, M. S. Eur. J. Med. Chem. 2011, 46, 5763-5768.
http://dx.doi.org/10.1016/j.ejmech.2011.08.015
[13]. Sondhi, S. M.; Johar, M.; Singhal, N.; Dastidar, S. G.; Raghubir, R. Monatsh. Chem. 2000, 131, 511-520.
http://dx.doi.org/10.1007/s007060050332
[14]. El-Araby, M.; Omar, A.; Hassanein, H. H.; El-Helby, A. G. H.; Abdel-Rahman, A. A. Molecules 2012, 17, 12262-12275.
http://dx.doi.org/10.3390/molecules171012262
[15]. Nanthakumar, R.; Muthurmani, P.; Girija, K. Arab. J. Chem. 2011, doi: 10.1016/j.arabjc.2010.12.035.
http://dx.doi.org/10.1016/j.arabjc.2010.12.035
[16]. Al-Mohammed, N. N.; Alias, Y.; Abdullah, Z.; Shakir, R. M.; M. Taha, E. M.; Hamid, A. A. Molecules 2013, 18, 11978-11995.
http://dx.doi.org/10.3390/molecules181011978
[17]. El-masry, A. H.; Fahmy, H. H.; Abdelwahed, S. H. A. Molecules 2000, 5, 1429-1438.
http://dx.doi.org/10.3390/51201429
[18]. Khalil, M. A. A. J. Heterocycl. Chem. 2012, 49, 806-813.
http://dx.doi.org/10.1002/jhet.867
[19]. Alen, J.; Robeyns, K.; De Borggraeve, W. M. Tetrahedron 2008, 64, 8128-8133.
http://dx.doi.org/10.1016/j.tet.2008.06.056
[20]. Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Change, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J. J. Med. Chem. 1988, 31, 2235-2246.
http://dx.doi.org/10.1021/jm00120a002
[21]. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893-930.
http://dx.doi.org/10.1021/cr020033s
[22]. Siddiqui, N.; Alam, M. S. Der Pharm. Chem. 2010, 2, 163-171.
[23]. Kamder, G. C.; Bhatt, D. J.; Parith, A. R. J. Indian Chem. Soc. 1988, 65, 67-68.
[24]. Pereira, E. R.; Sancelme, M.; Voldoire, A.; Prudhomme, M. Bioorg. Med. Chem. Lett. 1997, 7, 2503-2507.
http://dx.doi.org/10.1016/S0960-894X(97)10007-5
[25]. Viti, G.; Namnicine, R.; Ricci, R.; Pestelline, V.; Abeli, L.; Funo, M. Eur. J. Med. Chem. 1994, 29, 401-406.
http://dx.doi.org/10.1016/0223-5234(94)90066-3
[26]. Abd El Aziz, H. A.; Gomha, S. M. Int. J. Pharm. Pharm. Sci. 2013, 5, 183-189.
[27]. Al-Issa, S. A. Molecules 2012, 17, 10902-10915.
http://dx.doi.org/10.3390/molecules170910902
[28]. Chandrashekhar, C. H.; Latha, K. P.; Vagdevi, H. M.; Vaidya, V. P.; Vijaya Kumar, M. L. Der Chem. Sinica 2013, 4, 75-78.
[29]. Fotouhi, L.; Hekmatshoar, R.; Heravi, M. M.; Sadjadi, S.; Rasmi, V. Tetrahedron Lett. 2008, 49, 6628-6632.
http://dx.doi.org/10.1016/j.tetlet.2008.09.023
[30]. Bekircan, O.; Bektas, H. Molecules 2006, 11, 469-477.
http://dx.doi.org/10.3390/11060469
[31]. El-Sherief, H. A. H.; Hozien, Z. A.; El-Mahdy, A. F. M.; Sarhan, A. A. O. Arkivoc 2011, 10, 71-84.
http://dx.doi.org/10.3998/ark.5550190.0012.a06
[32]. Mahmoud, M. R.; El-Shahawi, M. M.; Abu El-Azm, F. S. M.; Farahat, S. E. Amer. J. Org. Chem. 2011, 1, 14-20.
http://dx.doi.org/10.5923/j.ajoc.20110101.04
[33]. Singh, T.; Sreenivas, S.; Parameshwar, R.; Abhimanyu, R.; Indira, K.; Vyashnavi, V.; Lavanya, CH.; Srinivas, M. Int. J. Bioassays. 2012, 2, 256-259.
[34]. Fadda, A. A.; Abdel-Rahman, A. A. H.; Hamed, E. A.; Khalil, E. H. Amer. J. Org. Chem. 2012, 2, 7-13.
http://dx.doi.org/10.5923/j.ajoc.20120202.02
[35]. Barsy, M. A.; El-Rady, E. A.; Ismael, M. A. J. Heterocycl. Chem. 2012, 49, 388-393.
http://dx.doi.org/10.1002/jhet.646
[36]. Khalil, M. A.; Sayed, S. M.; Raslan, M. A. J. Korean Chem. Soc. 2013, 57, 612-617.
http://dx.doi.org/10.5012/jkcs.2013.57.5.612
[37]. Singh, I.; Kaur, H.; Kumar, S.; Kumar, A.; Lata, S.; Kumar, A. Int. J. Chem. Tech. Res. 2010, 2, 1745-1752.
[38]. Khafagy, M. M.; Abd El-Wahab, A. H. F.; Eid, F. E.; El-Agrody, A. M. Il Farmaco 2002, 57, 715-722.
http://dx.doi.org/10.1016/S0014-827X(02)01263-6
[39]. Sayed, S. M.; Khalil, M. A.; Raslan, M. A. Amer. J. Org. Chem. 2012, 2, 151-160.
http://dx.doi.org/10.5923/j.ajoc.20120206.05
[40]. Khalil, M. A.; Sayed, S. M.; Raslan, M. A. Amer. J. Org. Chem. 2012, 2, 161-170.
http://dx.doi.org/10.5923/j.ajoc.20120206.06
[41]. Khalil, M. A.; Sayed, S. M.; Raslan, M. A. Amer. J. Org. Chem. 2012, 2, 171-181.
http://dx.doi.org/10.5923/j.ajoc.20120206.07
[42]. Sayed, S. M.; Raslan, M. A.; Khalil, M. A.; Dawood, K. M. Heteroatom Chem. 1999, 10, 385-390.
http://dx.doi.org/10.1002/(SICI)1098-1071(1999)10:5<385::AID-HC8>3.0.CO;2-O
[43]. Raslan, M. A.; Sayed, S. M.; Khalil, M. A.; Farag, A. M. Heteroatom Chem. 2000, 11, 94-101.
http://dx.doi.org/10.1002/(SICI)1098-1071(2000)11:2<94::AID-HC3>3.0.CO;2-U
[44]. Sayed, S. M.; Selim, M. A.; Raslan, M. A.; Khalil, M. A. Heteroatom Chem. 2000, 11, 362-369.
http://dx.doi.org/10.1002/1098-1071(2000)11:5<362::AID-HC7>3.0.CO;2-N
[45]. Sayed, S. M.; Khalil, M. A.; Selim, M. A.; Raslan, M. A. Synth. Commun. 2002, 32, 481-495.
http://dx.doi.org/10.1081/SCC-120002134
[46]. Dawood, K. M.; Raslan, M. A. J. Heterocycl. Chem. 2008, 45, 137-141.
http://dx.doi.org/10.1002/jhet.5570450113
[47]. Raslan, M.; Khalil, M.; Sayed, S. Heterocycles 2013, 87, 2567-2576.
http://dx.doi.org/10.3987/COM-13-12848
[48]. El-Kazak, A. M.; Ibrahim, M. A. Arkivoc 2013, 3, 282-293.
http://dx.doi.org/10.3998/ark.5550190.p007.884
[49]. Gellis, A.; Boutatah, N.; Vanelle, P. Green Chem. 2006, 8, 483-487.
http://dx.doi.org/10.1039/b601452f
[50]. Kristinsson, H. Synthesis 1979, 102-107.
http://dx.doi.org/10.1055/s-1979-28571
[51]. Morton, R.; Chang, H.; Craine, L.; Edwin, H. J. Org. Chem. 1985, 50, 2205-2219.
http://dx.doi.org/10.1021/jo00225a077
[52]. Chauhan, S. M. S.; Junjappa, H. Tetrahadron 1976, 32, 1779-1787.
http://dx.doi.org/10.1016/0040-4020(76)85174-5
[53]. Avinash, P.; Swastike, G.; Jogendra, H.; Santosh, T. Int. J. Pharm. Chem. 2012, 3, 89-92.
[54]. Vogt, R. L.; Dippold, L. Public Health Rep. 2005, 120, 174-178.
[55]. Hollis, D. G.; Wiggins, G. L.; Weaver, R. W. Appl. Microbiol. 1969, 17, 71-77.
[56]. Hudault, S.; Guignot, J.; Servin, A. L. Gut 2001, 49, 47-55.
http://dx.doi.org/10.1136/gut.49.1.47
[57]. Wiest, P.; Kurt, W.; Michael, R. J.; Anne, B. M.; Tom, I. A.; William, W.; Michael, M. L. Rev. Infect. Dis. 1987, 9, 799-803.
http://dx.doi.org/10.1093/clinids/9.4.799
[58]. Shimada, A.; Kusano, M.; Takeuchi, S.; Fujioka, S.; Inokuchi, T.; Kimura, Y. J. Biosciences 2002, 57, 459-464.
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.5.3.481-487.1054

















European Journal of Chemistry 2014, 5(3), 481-487 | doi: https://doi.org/10.5155/eurjchem.5.3.481-487.1054 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2021 • 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 2010-2021 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.