Skip to main content
Log in

Synthesis and Evaluation of Antibacterial Activity of 1,2,4-Oxadiazole-Containing Biphenylcarboxylic Acids

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A one-pot method for the synthesis of biphenylcarboxylic acids containing 1,2,4-oxadiazole ring in the NaOH–DMSO system was developed. The results of in vitro experiments showed that the synthesized compounds exhibit antibacterial activity against susceptible strains of E. coli and S. aureus.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Pace, A., Buscemi, S., Piccionello, A.P., and Pibiri, I., Adv. Heterocycl. Chem., 2015, vol. 116, p. 85. https://doi.org/10.1016/bs.aihch.2015.05.001

    Article  CAS  Google Scholar 

  2. Piccionello, A.P., Pace, A., and Buscemi, S., Chem. Heterocycl. Compd., 2017, vol. 53, p. 936. https://doi.org/10.1007/s10593-017-2154-1

    Article  CAS  Google Scholar 

  3. Schramm, S. and Weiß, D., Adv. Heterocycl. Chem., 2019, p. 103. https://doi.org/10.1016/bs.aihch.2018.10.003

  4. Boström, J., Hogner, A., Llinàs, A., Wellner, E., and Plowright, A.T., J. Med. Chem., 2012, vol. 55, p. 1817. https://doi.org/10.1021/jm2013248

    Article  CAS  PubMed  Google Scholar 

  5. Salassa, G. and Terenzi, A., Int. J. Mol. Sci., 2019, vol. 20, p. 3483. https://doi.org/10.3390/ijms20143483

    Article  CAS  PubMed Central  Google Scholar 

  6. Welch, E.M., Barton, E.R., Zhuo, J., Tomizawa, Y., Friesen, W.J., Trifillis, P., Paushkin, S., Patel, M., Trotta, C.R., Hwang, S., Wilde, R.G., Karp, G., Takasugi, J., Chen, G., Jones, S., Ren, H., Moon, Y.-C., Corson, D., Turpoff, A.A., Campbell, J.A., Conn, M.M., Khan, A., Almstead, N.G., Hedrick, J., Mollin, A., Risher, N., Weetall, M., Yeh, S., Branstrom, A.A., Colacino, J.M., Babiak, J., Ju, W.D., Hirawat, S., Northcutt, V.J., Miller, L.L., Spatrick, P., He, F., Kawana, M., Feng, H., Jacobson, A., Peltz, S.W., and Sweeney, H.L., Nature, 2007, vol. 447, p. 87. https://doi.org/10.1038/nature05756

    Article  PubMed  Google Scholar 

  7. Lanier, G., Sankholkar, K., and Aronow, W.S., Am. J. Ther., 2014, vol. 21, p. 419. https://doi.org/10.1097/MJT.0b013e31824a0ed7

    Article  PubMed  Google Scholar 

  8. Scott, L.J., Drugs, 2016, vol. 76, p. 1293. https://doi.org/10.1007/s40265-016-0623-y

    Article  CAS  PubMed  Google Scholar 

  9. Kumar, R. and Gupta, D., Chem. Biol. Drug Des., 2016, vol. 88, p. 730. https://doi.org/10.1111/cbdd.12803

    Article  CAS  PubMed  Google Scholar 

  10. Kawashima, M., Nemoto, O., Honda, M., Watanabe, D., Nakayama, J., Imafuku, S., Kato, T., and Katsuramaki, T., J. Dermatol., 2017, vol. 44, p. 1219. https://doi.org/10.1111/1346-8138.13948

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Hale, M., Wild, J., Reddy, J., Yamada, T., and Arjona Ferreira, J.C., Lancet Gastroenterol. Hepatol., 2017, vol. 2, p. 555. https://doi.org/10.1016/S2468-1253(17)30105-X

    Article  PubMed  Google Scholar 

  12. Boudreau, M.A., Ding, D., Meisel, J.E., Janardhanan, J., Spink, E., Peng, Z., Qian, Y., Yamaguchi, T., Testero, S.A., O’Daniel, P.I., Leemans, E., Lastochkin, E., Song, W., Schroeder, V.A., Wolter, W.R., Suckow, M.A., Mobashery, S., and Chang, M., ACS Med. Chem. Lett., 2020, vol. 11, p. 322. https://doi.org/10.1021/jm501661f

    Article  CAS  PubMed  Google Scholar 

  13. Spink, E., Ding, D., Peng, Z., Boudreau, M.A., Leemans, E., Lastochkin, E., Song, W., Lichtenwalter, K., O’Daniel, P.I., Testero, S.A., Pi, H., Schroeder, V.A., Wolter, W.R., Antunes, N.T., Suckow, M.A., Vakulenko, S., Chang, M., and Mobashery, S., J. Med. Chem., 2015, vol. 58, p. 1380. https://doi.org/10.1021/jm501661f

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Leemans, E., Mahasenan, K.V., Kumarasiri, M., Spink, E., Ding, D., O’Daniel, P.I., Boudreau, M.A., Lastochkin, E., Testero, S.A., Yamaguchi, T., Lee, M., Hesek, D., Fisher, J.F., Chang, M., and Mobashery, S., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 1011. https://doi.org/10.1016/j.bmcl.2015.12.041

    Article  CAS  PubMed  Google Scholar 

  15. O’Daniel, P.I., Peng, Z., Pi, H., Testero, S.A., Ding, D., Spink, E., Leemans, E., Boudreau, M.A., Yamaguchi, T., Schroeder, V.A., Wolter, W.R., Llarrull, L.I., Song, W., Lastochkin, E., Kumarasiri, M., Antunes, N.T., Espahbodi, M., Lichtenwalter, K., Suckow, M.A, Vakulenko, S., Mobashery, S., and Chang, M., J. Am. Chem. Soc., 2014, vol. 136, p. 3664. https://doi.org/10.1021/ja500053x

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Carter, G.P., Harjani, J.R., Li, L., Pitcher, N.P., Nong, Y., Riley, T.V., Williamson, D.A., Stinear, T.P., Baell, J.B., and Howden, B.P., J. Antimicrob. Chemother., 2018, vol. 73, p. 1562. https://doi.org/10.1093/jac/dky064

    Article  CAS  PubMed  Google Scholar 

  17. Janardhanan, J., Meisel, J.E., Ding, D., Schroeder, V.A., Wolter, W.R., Mobashery, S., and Chang, M., Antimicrob. Agents Chemother., 2016, vol. 60, p. 5581. https://doi.org/10.1128/AAC.00787-16

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Early, J.V., Casey, A., Martinez-Grau, M.A., Valcarcel, I.C.G., Vieth, M., Ollinger, J., Bailey, M.A., Alling, T., Files, M., Ovechkina, Y., and Parish, T., Antimicrob. Agents Chemother., 2016, vol. 60, p. 3608. https://doi.org/10.1128/AAC.02896-15

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Shruthi, N., Poojary, B., Kumar, V., Hussain, M.M., Rai, V.M., Pai, V.R., Bhat, M., and Revannasiddappa, B.C., RSC Adv., 2016, vol. 6, p. 8303. https://doi.org/10.1039/C5RA23282A

    Article  CAS  Google Scholar 

  20. Gold, B., Smith, R., Nguyen, Q., Roberts, J., Ling, Y., Lopez Quezada, L., Somersan, S., Warrier, T., Little, D., Pingle, M., Zhang, D., Ballinger, E., Zimmerman, M., Dartois, V., Hanson, P., Mitscher, L.A., Porubsky, P., Rogers, S., Schoenen, F.J., Nathan, C., and Aubé, J., J. Med. Chem., 2016, vol. 59, p. 6027. https://doi.org/10.1021/acs.jmedchem.5b01833

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Ventola, C.L., Pharm. Ther., 2015, vol. 40, p. 277.

    Google Scholar 

  22. Ventola, C.L., Pharm. Ther., 2015, vol. 40, p. 344.

    Google Scholar 

  23. Qiao, M., Ying, G.G., Singer, A.C., and Zhu, Y.G., Environ. Int., 2018, vol. 110, p. 160. https://doi.org/10.1016/j.envint.2017.10.016

    Article  CAS  PubMed  Google Scholar 

  24. Arias, C.A. and Murray, B.E., N. Engl. J. Med., 2009, vol. 360, p. 439. https://doi.org/10.1056/NEJMp0804651

    Article  CAS  PubMed  Google Scholar 

  25. Martens, E. and Demain, A.L., J. Antibiot., 2017, vol. 70, p. 520. https://doi.org/10.1038/ja.2017.30

    Article  CAS  PubMed  Google Scholar 

  26. MacGowan, A. and Macnaughton, E., Medicine, 2017, vol. 45, p. 622. https://doi.org/10.1016/j.mpmed.2017.07.006

    Article  Google Scholar 

  27. Sharonova, T., Pankrat’eva, V., Savko, P., Baykov, S., and Shetnev, A., Tetrahedron Lett., 2018, vol. 59, p. 2824. https://doi.org/10.1016/j.tetlet.2018.06.019

    Article  CAS  Google Scholar 

  28. Baykov, S., Sharonova, T., Osipyan, A., Rozhkov, S., Shetnev, A., and Smirnov, A., Tetrahedron Lett., 2016, vol. 57, p. 2898. https://doi.org/10.1016/j.tetlet.2016.05.071

    Article  CAS  Google Scholar 

  29. Pankrat’eva, V.E., Sharonova, T.V., Tarasenko, M.V., Baikov, S.V., and Kofanov, E.R., Russ. J. Org. Chem., 2018, vol. 54, p. 1250. https://doi.org/10.1134/S1070428018080213

    Article  Google Scholar 

  30. Baykov, S., Sharonova, T., Shetnev, A., Rozhkov, S., Kalinin, S., and Smirnov, A.V., Tetrahedron, 2017, vol. 73, p. 945. https://doi.org/10.1016/j.tet.2017.01.007

    Article  CAS  Google Scholar 

  31. Baykov, S., Tarasenko, M., Zelenkov, L.E., Kasatkina, S., Savko, P., and Shetnev, A., Eur. J. Org. Chem., 2019, p. 5685. https://doi.org/10.1002/ejoc.201900843

  32. Krasavin, M., Shetnev, A., Sharonova, T., Baykov, S., Kalinin, S., Nocentini, A., Sharoyko, V., Poli, G., Tuccinardi, T., Presnukhina, S., Tennikova, T.B., and Supuran, C.T., Eur. J. Med. Chem., 2019, vol. 164, p. 92. https://doi.org/10.1016/j.ejmech.2018.12.049

    Article  CAS  PubMed  Google Scholar 

  33. Shetnev, A., Osipyan, A., Baykov, S., Sapegin, A., Chirkova, Z., Korsakov, M., Petzer, A., Engelbrecht, I., and Petzer, J.P., Bioorg. Med. Chem. Lett., 2019, vol. 29, p. 40. https://doi.org/10.1016/j.bmcl.2018.11.018

    Article  CAS  PubMed  Google Scholar 

  34. Krasavin, M., Shetnev, A., Sharonova, T., Baykov, S., Tuccinardi, T., Kalinin, S., Angeli, A., and Supuran, C.T., Bioorg. Chem., 2017, vol. 76, p. 88. https://doi.org/10.1016/j.bioorg.2017.10.005

    Article  CAS  PubMed  Google Scholar 

  35. Thacker, P.S., Angeli, A., Argulwar, O.S., Tiwari, P.L., Arifuddin, M., and Supuran, C.T., Bioorg. Chem., 2020, vol. 98, p. 103739. https://doi.org/10.1016/j.bioorg.2020.103739

    Article  CAS  PubMed  Google Scholar 

  36. Sucu, B.O., Ipek, O.S., Kurtulus, S.O., Yazici, B.E., Karakas, N., and Guzel, M., Bioorg. Chem., 2019, vol. 91, p. 103146. https://doi.org/10.1016/j.bioorg.2019.103146

    Article  CAS  PubMed  Google Scholar 

  37. Shetnev, A., Baykov, S., Kalinin, S., Belova, A., Sharoyko, V., Rozhkov, A., Zelenkov, L., Tarasenko, M., Sadykov, E., Korsakov, M., and Krasavin, M., Int. J. Mol. Sci., 2019, vol. 20, p. 1699. https://doi.org/10.3390/ijms20071699

    Article  CAS  PubMed Central  Google Scholar 

  38. Geyl, K., Baykov, S., Tarasenko, M., Zelenkov, L.E., Matveevskaya, V., and Boyarskiy, V.P., Tetrahedron Lett., 2019, vol. 60, p. 151108. https://doi.org/10.1016/j.tetlet.2019.151108

    Article  CAS  Google Scholar 

  39. Strelnikova, J.O., Rostovskii, N.V., Starova, G.L., Khlebnikov, A.F., and Novikov, M.S., J. Org. Chem., 2018, vol. 83, p. 11232. https://doi.org/10.1021/acs.joc.8b01809

    Article  CAS  PubMed  Google Scholar 

  40. Tarasenko, M., Duderin, N., Sharonova, T., Baykov, S., Shetnev, A., and Smirnov, A.V., Tetrahedron Lett., 2017, vol. 58, p. 3672. https://doi.org/10.1016/j.tetlet.2017.08.020

    Article  CAS  Google Scholar 

  41. Ohemeng, K.A., Podlogar, B.L., Nguyen, V.N., Bernstein, J.I., Krause, H.M., Hilliard, J.J., and Barrett, J.F., J. Med. Chem., 1997, vol. 40, p. 3292. https://doi.org/10.1021/jm9701583

    Article  CAS  PubMed  Google Scholar 

  42. Husain, A., Chen, S., Wilson, D.B., and Ganem, B., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 2485. https://doi.org/10.1016/s0960-894x(01)00485-1

    Article  CAS  PubMed  Google Scholar 

  43. De, R., Sarkar, A., Ghosh, P., Ganguly, M., Karmakar, B.C., Saha, D.R., Halder, A., Chowdhury, A., and Mukhopadhyay, A.K., J. Antimicrob. Chemother., 2018, vol. 73, p. 1595. https://doi.org/10.1093/jac/dky079

    Article  CAS  PubMed  Google Scholar 

  44. Srivastava, R.M., Pereira, M.C., Faustino, W.W.M., Coutinho, K., Dos Anjos, J.V., and De Melo, S.J., Monat. Chem., 2009, vol. 140, p. 1319. https://doi.org/10.1007/s00706-009-0186-7

    Article  CAS  Google Scholar 

  45. Atkinson, E.R. and Lawler, H.J., Org. Synth., 1927, vol. 7, p. 30. https://doi.org/10.15227/orgsyn.007.0030

    Article  Google Scholar 

  46. Dar’in, D., Bakulina, O., Chizhova, M., and Krasavin, M., Org. Lett., 2015, vol. 17, p. 3930. https://doi.org/10.1021/acs.orglett.5b02014

    Article  CAS  PubMed  Google Scholar 

  47. Tsiulin, P.A., Sosnina, V.V., Krasovskaya, G.G., Danilova, A.S., Baikov, S.V., and Kofanov, E.R., Russ. J. Org. Chem., 2011, vol. 47, p. 1874. https://doi.org/10.1134/S1070428011120153

    Article  CAS  Google Scholar 

  48. Gangloff, A.R., Litvak, J., Shelton, E.J., Sperandio, D., Wang, V.R., and Rice, K.D., Tetrahedron Lett., 2001, vol. 42, p. 1441. https://doi.org/10.1016/S0040-4039(00)02288-7

    Article  CAS  Google Scholar 

  49. Otaka, H., Ikeda, J., Tanaka, D., and Tobe, M., Tetrahedron Lett., 2014, vol. 55, p. 979. https://doi.org/10.1002/chin.201427151

    Article  CAS  Google Scholar 

  50. Kumpan, K., Nathubhai, A., Zhang, C., Wood, P.J., Lloyd, M.D., Thompson, A.S., Haikarainen, T., Lehtiö, L., and Threadgill, M.D., Bioorg. Med. Chem., 2015, vol. 23, p. 3013. https://doi.org/10.1016/j.bmc.2015.05.005

    Article  CAS  PubMed  Google Scholar 

  51. Borg, S., Luthman, K., Nyberg, F., Terenius, L., and Hacksell, U., Eur. J. Med. Chem., 1993, vol. 28, p. 801. https://doi.org/10.1016/0223-5234(93)90115-u

    Article  CAS  Google Scholar 

  52. Yang, C.-T., Han, J., Liu, J., Gu, M., Li, Y., Wen, J., Yu, H.-Z., Hu, S., and Wang, X., Org. Biomol. Chem., 2015, vol. 13, p. 2541. https://doi.org/10.1039/C4OB02456G

    Article  CAS  PubMed  Google Scholar 

  53. Lin, C.-C., Hsieh, T.-H., Liao, P.-Y., Liao, Z.-Y., Chang, C.-W., Shih, Y.-C., Yeh, W.-H., and Chien, T.-C., Org. Lett., 2014, vol. 16, p. 892. https://doi.org/10.1021/ol403645y

    Article  CAS  PubMed  Google Scholar 

  54. He, X., Jiang, Y., Zhang, Y., Wu, S., Dong, G., Liu, N., Liu, Y., Yao, J., Miao, Z., Wang, Y., Zhang, W., and Sheng, C., Med. Chem. Commun., 2015, vol. 6, p. 653. https://doi.org/10.1039/C4MD00505H

    Article  CAS  Google Scholar 

  55. Wang, Z., Zhang, H., Jabeen, F., Gopinathan-Pillai, G., Arami, J.A., Killian, B.J., Stiegler, K.D., Yudewitz, D.S., Thiemann, P.L., Turk, J.D., Zhou, W., Steel, P.J., Hall, C.D., and Katritzky, A.R., Eur. J. Org. Chem., 2015, vol. 34, p. 7468. https://doi.org/10.1002/ejoc.201501056

    Article  CAS  Google Scholar 

  56. Stevanovic, S., Sencanski, M., Danel, M., Menendez, C., Belguedj, R., Bouraiou, A., Nikolic, K., Cojean, S., Loiseau, P., Glisic, S., Baltas, M., and García-Sosa, A., Molecules, 2019, vol. 24, p. 1282. https://doi.org/10.3390/molecules24071282

    Article  CAS  PubMed Central  Google Scholar 

  57. Bulman Page, P.C., Bartlett, C.J., Chan, Y., Allin, S.M., McKenzie, M.J., Lacour, J., and Jones, G.A., Org. Biomol. Chem., 2016, vol. 14, p. 4220. https://doi.org/10.1039/C6OB00542J

    Article  CAS  PubMed  Google Scholar 

  58. Wang, X., Chen, R.-X., Wei, Z.-F., Zhang, C.-Y., Tu, H.-Y., and Zhang, A.-D., J. Org. Chem., 2016, vol. 81, p. 238. https://doi.org/10.1021/acs.joc.5b02506

    Article  CAS  PubMed  Google Scholar 

  59. Gong, H., Zeng, H., Zhou, F., and Li, C.-J., Angew. Chem. Int. Ed., 2015, vol. 54, p. 5718. https://doi.org/10.1002/anie.201500220

    Article  CAS  Google Scholar 

  60. CLSI, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, CLSI document M07-A9. Clinical and Laboratory Standards Institute, Pennsylvania, USA, 2012.

Download references

Funding

This work was financially supported by the Russian Foundation for Basic Research (project no. 19-33-60064) using the equipment of the Resource Centers “Chemical Analysis and Materials Research Center” and “Magnetic Resonance Research Center” of the Research Park of St. Petersburg State University.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. V. Tarasenko.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tarasenko, M.V., Presnukhina, S.I., Baikov, S.V. et al. Synthesis and Evaluation of Antibacterial Activity of 1,2,4-Oxadiazole-Containing Biphenylcarboxylic Acids. Russ J Gen Chem 90, 1611–1619 (2020). https://doi.org/10.1134/S1070363220090042

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363220090042

Keywords:

Navigation