Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Multicomponent Synthesis of Novel 2-Aryl-5-((1-aryl-1H-1,2,3-triazol-4-yl)methylthio)-1,3,4-oxadiazoles using CuI as Catalyst and their Antimicrobial Evaluation

Jayant Sindhu A , Harjinder Singh A , Jitender Mohan Khurana A C , Chetan Sharma B and Kamal Rai Aneja B

A Department of Chemistry, Delhi University, Delhi 110007, India.

B Department of Microbiology, Kurukshetra University Kurukshetra, Kurukshetra 136119, Haryana, India.

C Corresponding author. Email: jmkhurana@chemistry.du.ac.in

Australian Journal of Chemistry 66(6) 710-717 http://dx.doi.org/10.1071/CH13082
Submitted: 19 February 2013  Accepted: 2 April 2013   Published: 27 May 2013

Abstract

A series of novel 2-aryl-5-((1-aryl-1H-1,2,3-triazol-4-yl)methylthio)-1,3,4-oxadiazoles have been synthesised by C–S bond formation and azide–alkyne cyclocondensation between [5-(aryl)-[1,3,4]oxadiazol-2-yl]methanethiol, propargyl bromide, and substituted aryl azides in one pot with an aim to explore their effect on the in vitro growth of microorganisms causing microbial infection. In vitro antibacterial activity was determined against four strains, namely Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa and antifungal activity against two fungal strains, namely Aspergillus niger and Aspergillus flavus.

Graphical Abstract Image


References

[1]  M. Grare, M. Mourer, S. Fontanay, J. B. Regnouf-de-Vains, C. Finance, R. E. Duval, J. Antimicrob. Chemother. 2007, 60, 575.
         | CrossRef | 1:CAS:528:DC%2BD2sXpt1Cmur0%3D&md5=e155c873edd4228e6218125bf8707c52CAS | 17626025PubMed | open url image1

[2]  (a) C. Viegas-Junior, A. Danuello, V. S. Bolzani, E. J. Barreiro, C. A. M. Fraga, Curr. Med. Chem. 2007, 14, 1829.
         | CrossRef | 1:CAS:528:DC%2BD2sXnvFanuro%3D&md5=f018f415b4ff4167d9a87cc982cfe856CAS | 17627520PubMed | open url image1
      (b) J. J. Walsh, A. Bell, Curr. Pharm. Des. 2009, 15, 2970.
         | CrossRef | open url image1

[3]  (a) C. Biot, K. Chibale, Infect. Disord. Drug Targets 2006, 6, 173.
         | CrossRef | 1:CAS:528:DC%2BD28XmtFersL0%3D&md5=07eaa7c5f067b64bd2d98bc1d4ad4616CAS | 16789878PubMed | open url image1
      (b) L. F. Tietze, H. P. Bell, S. Chandrasekhar, Angew. Chem. Int. Ed. 2003, 42, 3996.
         | CrossRef | open url image1

[4]  J. E. Biggs-Houck, A. Younai, J. T. Shaw, Curr. Opin. Chem. Biol. 2010, 14, 371.
         | CrossRef | 1:CAS:528:DC%2BC3cXmvVWqsLk%3D&md5=38ea3a3b1e4cd703b544a2711b1ca540CAS | 20392661PubMed | open url image1

[5]  L. A. Marcaurelle, M. A. Foley, Curr. Opin. Chem. Biol. 2010, 14, 285.
         | CrossRef | 1:CAS:528:DC%2BC3cXmvVWqs7k%3D&md5=049ede86d700f7e87112e530824304b1CAS | 20472491PubMed | open url image1

[6]  N. Dahan-Farkas, C. Langley, A. L. Rousseau, D. B. Yadav, H. Davids, C. B. de Koning, Eur. J. Med. Chem. 2011, 46, 4573.
         | CrossRef | 1:CAS:528:DC%2BC3MXhtV2rtbzP&md5=d40712c2e29d4d9a47e57a3629abffeeCAS | 21843907PubMed | open url image1

[7]  R. Huisgen, 1,3-Dipolar Cycloaddition Chemistry 1984, 1–176. (Wiley: New York, NY).

[8]  (a) D. J. Ramon, M. Yus, Angew. Chem. Int. Ed. 2005, 44, 1602.
         | CrossRef | 1:CAS:528:DC%2BD2MXisFWkur8%3D&md5=930bd697208ff6ad8ef121b0689b3632CAS | open url image1
      (b) C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51.
         | CrossRef | open url image1

[9]  (a) P. Salehi, D. I. MaGee, M. Dabiri, L. Torkian, J. Donahue, Mol. Divers. 2012, 16, 231.
         | CrossRef | 1:CAS:528:DC%2BC38Xot1egsb8%3D&md5=ab9bae1ff289d25b837110db9cd64344CAS | 22161122PubMed | open url image1
      (b) P. Salehi, M. Dabiri, M. Koohshari, S. K. Movahed, M. Bararjanian, Mol. Divers. 2011, 15, 833.
         | CrossRef | open url image1

[10]  S. J. Dolman, F. Gosselin, P. D. OShea, I. W. Davies, J. Org. Chem. 2006, 71, 9548.
         | CrossRef | 1:CAS:528:DC%2BD28Xht1WhsLzK&md5=2c1a3f0eac142f6a2a77c2ae70cd3164CAS | 17137395PubMed | open url image1

[11]  (a) C. R. W. Guimarães, D. L. Boger, W. L. Jorgensen, J. Am. Chem. Soc. 2005, 127, 17377.
         | CrossRef | open url image1
      (b) V. P. M. Rahman, S. Mukhtar, W. H. Ansari, G. Lemiere, Eur. J. Med. Chem. 2005, 40, 173.
         | CrossRef | open url image1

[12]  F. A. Omar, N. M. Mehfouz, M. A. Rahman, Eur. J. Med. Chem. 1996, 31, 819.
         | CrossRef | 1:CAS:528:DyaK28XmvFOrtbs%3D&md5=f64709c55ee62812dc13e2fbe5a60e06CAS | open url image1

[13]  E. Palaska, G. Sahin, P. Kelicen, N. T. Durlu, G. Altinok, Il Farmaco 2002, 57, 101.
         | CrossRef | 1:CAS:528:DC%2BD38XhsFCrurg%3D&md5=ab062d04ac2a469dd4780e10553eccb8CAS | 11902651PubMed | open url image1

[14]  T. Ramalingam, P. B. Sattur, Eur. J. Med. Chem. 1990, 25, 541.
         | CrossRef | 1:CAS:528:DyaK3MXhsVeht7g%3D&md5=08de4a79a0cd8d2d0676ceb73fa89144CAS | open url image1

[15]  K. Raman, K. H. Singh, S. K. Satzman, S. S. Parmar, J. Pharm. Sci. 1993, 82, 167.
         | CrossRef | 1:CAS:528:DyaK3sXisFCrsLs%3D&md5=7bfcddf35a430688408d1d8c9c528572CAS | 8445529PubMed | open url image1

[16]  M. M. Girges, Arzneimittelforschung 1994, 44, 490.
         | 1:CAS:528:DyaK2MXltFOlsw%3D%3D&md5=1cef0e216a495018f322f9ba39193fb7CAS | 8011002PubMed | open url image1

[17]  M. I. Husain, A. Kumar, R. C. Srivastava, Curr. Sci. 1986, 55, 644.
         | 1:CAS:528:DyaL2sXjt12nsw%3D%3D&md5=9b0ae01f55095218b476c72a926ff227CAS | open url image1

[18]  M. Harfenist, D. J. Heuser, C. T. Joyner, J. F. Batchelor, H. L. White, J. Med. Chem. 1996, 39, 1857.
         | CrossRef | 1:CAS:528:DyaK28XitVaqs74%3D&md5=741f7261105689cc41552c95f1f59351CAS | 8627609PubMed | open url image1

[19]  K. M. Lokanatha Rai, N. Linganna, Il Farmaco 2000, 55, 389.
         | CrossRef | open url image1

[20]  S. Giri, H. Singh, L. D. S. Yadav, Agric. Biol. Chem. 1976, 40, 17.
         | CrossRef | 1:CAS:528:DyaE28Xht1Wksbg%3D&md5=7f13ff0962176d7ef1e5a2c11e044364CAS | open url image1

[21]  I. Mir, M. T. Siddiqui, A. M. Comrie, J. Chem. Soc. 1971, 16, 2798.
         | 1:STN:280:DyaE387htlKmsQ%3D%3D&md5=63f317a9c631f273834522a151a193f8CAS | open url image1

[22]  H. K. Misra, Arch. Pharm 1983, 316, 487.
         | CrossRef | 1:CAS:528:DyaL3sXkvVyisL0%3D&md5=c9b536fb31ec5df2f7679cc2631c8c0fCAS | open url image1

[23]  G. Sahin, E. Palaska, M. Ekizoglu, M. Ozalp, Il Farmaco 2002, 57, 539.
         | CrossRef | 1:CAS:528:DC%2BD38Xlt12rsb0%3D&md5=a1a416243666e056482e0c79ac31bb67CAS | 12164209PubMed | open url image1

[24]  H. Singh, L. D. S. Yadav, Agric. Biol. Chem. 1976, 40, 759.
         | CrossRef | 1:CAS:528:DyaE28XktVGmtLY%3D&md5=3f47cd7bdf421440a5f082c4e9a6bb97CAS | open url image1

[25]  L. Cafici, T. Pirali, F. Condorelli, E. Del Grosso, A. Massarotti, G. Sorba, P. L. Canonico, G. C. Tron, A. A. Genazzani, J. Comb. Chem. 2008, 10, 732.
         | CrossRef | 1:CAS:528:DC%2BD1cXptl2gsbw%3D&md5=19047a51e5aaceef0c0217ed96cb2824CAS | 18681482PubMed | open url image1

[26]  F. Lenda, F. Guenoun, J. Martinez, F. Lamaty, Tetrahedron Lett. 2007, 48, 805.
         | CrossRef | 1:CAS:528:DC%2BD2sXlsFCltA%3D%3D&md5=1ad7f5123fa9bab18653678295cf67dbCAS | open url image1

[27]  M. Whiting, J. C. Tripp, Y. C. Lin, W. Lindstrom, A. J. Olson, J. H. Elder, K. B. Sharpless, V. V. Fokin, J. Med. Chem. 2006, 49, 7697.
         | CrossRef | 1:CAS:528:DC%2BD28Xht1GjsbjL&md5=e2c15963836a0f74b5700f3892d60470CAS | 17181152PubMed | open url image1

[28]  T. Liebert, C. Ha¨nsch, T. Heinze, Macromol. Rapid Commun. 2006, 27, 208.
         | CrossRef | 1:CAS:528:DC%2BD28Xhs1ensbk%3D&md5=cebe84d5cf802c90c40997d96bc897f1CAS | open url image1

[29]  H. Gallardo, G. Conte, F. Bryk, M. C. S. Lourenço, M. S. Costa, V. F. Ferreira, J. Braz. Chem. Soc. 2007, 18, 1285.
         | CrossRef | 1:CAS:528:DC%2BD2sXhtl2rurnO&md5=87dc260db4e76f136bcfae8080d4e74cCAS | open url image1

[30]  M. S. Alam, J. Huang, F. Ozoe, F. Matsumura, Y. Ozoe, Bioorg. Med. Chem. 2007, 15, 5090.
         | CrossRef | 1:CAS:528:DC%2BD2sXmtlahtr4%3D&md5=d73fc177eb0502dacc06462be6b31a24CAS | 17544280PubMed | open url image1

[31]  R. Périon, V. Ferrières, M. I. García-Moreno, C. O. Mellet, R. Duval, J. M. G. Fernández, D. Plusquellec, Tetrahedron 2005, 61, 9118.
         | CrossRef | open url image1

[32]  V. D. Bock, D. Speijer, H. Hiemstra, J. H. van Maarseveen, Org. Biomol. Chem. 2007, 5, 971.
         | CrossRef | 1:CAS:528:DC%2BD2sXisV2gtL8%3D&md5=9c572d3f34e0e3babc2c4d8c4d0fd5a7CAS | 17340013PubMed | open url image1

[33]  H. C. Kolb, K. B. Sharpless, Drug Discov. Today 2003, 8, 1128.
         | CrossRef | 1:CAS:528:DC%2BD3sXpvVWkuro%3D&md5=dd837ae1458ae8ae2cf907fc9aff0052CAS | 14678739PubMed | open url image1

[34]  (a) J. N. Sangshetti, A. R. Chabukswar, D. B. Shinde, Biol. Med. Chem. Lett. 2011, 21, 444.
         | CrossRef | 1:CAS:528:DC%2BC3cXhs1SqsbvP&md5=d97411c4e052dc53356ec9f193d339bbCAS | open url image1
      (b) J. N. Sangshetti, D. B. Shinde, Eur. J. Med. Chem. 2011, 46, 1040.
         | CrossRef | open url image1
      (c) Q. Chen, X. L. Zhu, L. L. Jiang, Z. M. Liu, G. F. Yang, Eur. J. Med. Chem. 2008, 43, 595.
         | CrossRef | open url image1

[35]  (a) S. Shafi, M. M. Alam, N. Mulakayala, C. Mulakayala, G. Vanaja, A. M. Kalle, R. Pallu, M. S. Alam, Eur. J. Med. Chem. 2012, 49, 324.
         | CrossRef | 1:CAS:528:DC%2BC38XisFOrsL4%3D&md5=d32c8d872ebb6d73ffe3151b1d6b8909CAS | 22305614PubMed | open url image1
      (b) C. C. Ciocoiu, N. Nikolic, H. Nguyen, G. H. Thoresen, A. J. Aasen, T. V. Hansen, Eur. J. Med. Chem. 2010, 45, 3047.
         | CrossRef | open url image1

[36]  (a) D. Kumar, G. Patel, E. O. Johnson, K. Shah, Bioorg. Med. Chem. Lett 2009, 19, 2739.
         | CrossRef | 1:CAS:528:DC%2BD1MXltl2rs7Y%3D&md5=1bba013c02433dc7c70de30618e685daCAS | 19376704PubMed | open url image1
      (b) M. Farooqui, R. Bora, C.R. Patil, Eur. J. Med. Chem 2009, 44, 794. open url image1
      (c) C. L. L. Ana, F. V. Renata, R. F. Antonio, G. W. Almir, A. Parviz, P. A. X. Eula’lia Camelo, M. S. Rajendra, F. O. Claudia, M. V. Medeiros, A. Edson, J. B. Dalci, II Farmaco 2000, 55, 719. open url image1

[37]  H. S. Chen, Z. M. Li, Y. F. Han, J. Agric. Food Chem. 2000, 48, 5312.
         | CrossRef | 1:CAS:528:DC%2BD3cXnsVaksbo%3D&md5=3a247c9f64853188e200ce506c7feda3CAS | open url image1

[38]  (a) K. K. Jha, A. Samad, Y. Kumar, M. Shaharyar, R. L. Khosa, J. Jain, V. Kumar, P. Singh, Eur. J. Med. Chem. 2010, 45, 4963.
         | CrossRef | 1:CAS:528:DC%2BC3cXht1KrtrvI&md5=c9efc5b2eea4a08e433ab6a31e07e49dCAS | 20817328PubMed | open url image1
      (b) H. Cheng, J. Wan, M.-I. Lin, Y. Liu, X. Lu, J. Liu, Y. Xu, J. Chen, Z. Tu, Y.-S. E. Cheng, K. Ding, J. Med. Chem. 2012, 55, 2144.
         | CrossRef | open url image1

[39]  S. Joshi, A. V. Karnik, Synth. Commun. 2002, 32, 111.
         | CrossRef | 1:CAS:528:DC%2BD38Xht1Ont7w%3D&md5=f3c7279a14cf1fafd35bfa15724e8c92CAS | open url image1

[40]  S. Giri, H. Singh, L. D. S. Yadav, Agric. Biol. Chem. 1976, 40, 17.
         | CrossRef | 1:CAS:528:DyaE28Xht1Wksbg%3D&md5=7f13ff0962176d7ef1e5a2c11e044364CAS | open url image1

[41]  K. R. Aneja, C. Sharma, R. Joshi, Int. J. Pediatr. Otorhinolaryngol. 2010, 74, 604.
         | CrossRef | 1:STN:280:DC%2BC3czjt1Gnug%3D%3D&md5=04ff6d9b1c64308aeaf66dd96d1917c8CAS | 20347163PubMed | open url image1

[42]  K. R. Aneja, C. Sharma, R. Joshi, Jundishapur J. Microbiol. 2011, 4, 175. open url image1

[43]  S. K. S. Al-Burtamani, M. O. Fatope, R. G. Marwah, A. K. Onifade, S. H. Al-Saidi, J. Ethnopharmocol. 2005, 96, 107.
         | CrossRef | 1:CAS:528:DC%2BD2cXhtVaqsLfO&md5=81ae15aa6ffed73d33a7c9cb1456f2c8CAS | open url image1



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