Skip to main content

Advertisement

SpringerLink
Log in

Synthesis of 5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-phenyl-1H-tetrazoles

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

Abstract

A series of novel 5-(1,2,3-triazolylmethylsulfanyl)tetrazole derivatives were synthesized by the click reaction from 1-phenyl-5-(prop-2-yn-1-ylsulfanyl)-1H-tetrazole and the corresponding azide. The reaction optimization results showed that higher yields are obtained using CuSO4 and sodium ascorbate in DMF–water (2:1). The product structures were established on the basis of various spectral data, and their evaluation for antimicrobial activity showed moderate to good results compared to standard drugs.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Scheme

Similar content being viewed by others

REFERENCES

  1. Singh, R.P., Verma, R.D., Meshri, D.T., and Shreeve, J.M., Angew. Chem., 2006, vol. 118, p. 3664. https://doi.org/10.1002/ange.200504236

    Article  Google Scholar 

  2. Miyata, Y., Kanou, H., Date, S., and Hasue, K., Sci. Technol. Energ. Mater., 2005, vol. 66, p. 233.

    CAS  Google Scholar 

  3. Derek, N.W., Robert, J.G., Michael, E.K., Perez-Medrano, A., Voight, E.A., Wang, Y., Grayson, G., Namovic, M.T., Donnelly-Roberts, D.L., Niforatos, W., Honore, P., Jarvis, M.F., Faltynek, C.R., and Carroll, W.A., J. Med. Chem., 2006, vol. 49, p. 3659. https://doi.org/10.1021/jm051202e

    Article  CAS  Google Scholar 

  4. Arno, K., Frank, O., and Roland, F., J. Org. Chem., 1999, vol. 64, p. 6425. https://doi.org/10.1021/jo990830z

    Article  CAS  Google Scholar 

  5. Boland, Y., Hertsens, P., and Marchand-Brynaert, J., Synthesis, 2006, vol. 2006, no. 9, p. 1504. https://doi.org/10.1055/s-2006-926439

    Article  CAS  Google Scholar 

  6. Okabayashi, T., Kano, H., and Makisumi, Y., Chem. Pharm. Bull., 1960, vol. 8, p. 157. https://doi.org/10.1248/cpb.8.157

    Article  CAS  Google Scholar 

  7. Sangal, S.K. and Ashok Kumar, A., J. Indian Chem. Soc., 1986, vol. 63, p. 351.

    CAS  Google Scholar 

  8. Tsov, K.C. and Su, H.C.F., J. Med. Chem., 1963, vol. 6, p. 693. https://doi.org/10.1021/jm00342a014

    Article  Google Scholar 

  9. Rajasekaran, A. and Thampi, P P., Eur. J. Med. Chem., 2004, vol. 39, no. 3, p. 273. https://doi.org/10.1016/j.ejmech.2003.11.016

    Article  PubMed  CAS  Google Scholar 

  10. Lamie, P.F., Philoppes, J.N., Azouz, A.A., and Safwat, N.M., J. Enzyme Inhib. Med. Chem., 2017, vol. 32, no. 1, p. 805. https://doi.org/10.1080/14756366.2017.1326110

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  11. Esplin, D.W. and Woodbuy, D.M., J. Pharmacol. Exp. Ther., 1956, vol. 118, p. 129.

    PubMed  CAS  Google Scholar 

  12. Beletskaya, I.P. and Ananikov, V.P., Chem. Rev., 2011, vol. 111, p. 1596. https://doi.org/10.1021/cr100347k

    Article  PubMed  CAS  Google Scholar 

  13. Kharasch, N. and Arora, A.S., Phosphorus Sulfur Relat. Elem., 1976, vol. 2, p. 1. https://doi.org/10.1080/03086647608078930

    Article  CAS  Google Scholar 

  14. Parveen, S., Khan, M.O.F., Austin, S.E., Croft, S.L., Yardly, V., Rock, P., and Douglas, K.T., J. Med. Chem., 2005, vol. 48, p. 8087. https://doi.org/10.1021/jm050819t

    Article  PubMed  CAS  Google Scholar 

  15. Wang, Y., Chackalamannil, S., Hu, Z., Clader, J.W., Greenlee, W., Billard, W, Binch, H., Crosby, G., Ruperto, V., Duffy, R.A., McQuade, R., and Lachowicz, J.E., Bioorg. Med. Chem. Lett., 2000, vol. 10, p. 2247. https://doi.org/10.1016/s0960-894x(00)00457-1

    Article  PubMed  CAS  Google Scholar 

  16. Nielsen, S.F., Nielsen, E.O., Oslen, G.M., Liljefors, T., and Peters, D., J. Med. Chem., 2000, vol. 43, p. 2217. https://doi.org/10.1021/jm990973d

    Article  PubMed  CAS  Google Scholar 

  17. Liu, G., Huth, J.R., Olejniczak, E.T., Mendoza, R., De Vries, P., Leitza, S., Reilly, E.B., Okasinski, G.F., Fesik, S.W., and von Geldern, T.W., J. Med. Chem., 2001, vol. 44, p. 1202. https://doi.org/10.1021/jm000503f

    Article  PubMed  CAS  Google Scholar 

  18. Smith, G. Mikkelsen, G., Eskildsen, J., and Bundgaard, C., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 3981. https://doi.org/10.1016/j.bmcl.2006.05.017

    Article  PubMed  CAS  Google Scholar 

  19. Liu, G., Link, J.T., Pei, Z., Reilly, E.B., Leitza, S., Nguyen, B., Marsh, G K.C., Okasinski, F., von Geldern, T.W., Ormes, M., Fowler, K., and Gallatin, M., J. Med. Chem., 2000, vol. 43, p. 4025. https://doi.org/10.1021/jm0002782

    Article  PubMed  CAS  Google Scholar 

  20. Tremblay, L.W., Xu, H., and Blanchard, J.S., Biochemistry, 2010, vol. 49, p. 9685. https://doi.org/10.1021/bi1015088

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  21. Ostrovskii, V.A., Koldobskii, G.I., and Trifonov, R.E., Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier, 2008, vol. 6, p. 257 https://doi.org/10.1016/B978-008044992-0.00517-4

  22. Brown, M., Br. J. Hosp. Med., 1998, vol. 59, p. 808.

    CAS  Google Scholar 

  23. Genin, M.J., Allwine, D.A., and Anderson, A., J. Med. Chem., 2000, vol. 43, p. 953. https://doi.org/10.1021/jm990373e

    Article  PubMed  CAS  Google Scholar 

  24. Wamhoff, H., Comprehensive Heterocyclic Chemistry, Katritzky, A.R. and Rees, C.W., Eds., Oxford: Pergamon, 1984, vol. 5, p. 669. https://doi.org/10.1016/B978-008096519-2.00079-5

  25. Buckle, D.R., Rockell, C.J.M., Smith, H., and Spicer, B.A., J. Med. Chem., 1986, vol. 29, p. 2262. https://doi.org/10.1021/jm00161a022

    Article  PubMed  CAS  Google Scholar 

  26. Alvarez, R., Velazquez, S., San Felix, S., Aquaro, A., De Clercq, E., Perno, C.F., Karlsson, A., Balzarini, J., and Camarasa, M.J., J. Med. Chem., 1994, vol. 37, p. 4184. https://doi.org/10.1021/jm00050a015

    Article  Google Scholar 

  27. Chen, H., Zuo, S., Wang, X., Tang, X., Zhao, M., Lu, Y., Chen, L., Liu, J., Liu, Y., Liu, D., Zhang, S., and Li, T., Eur. J. Med. Chem., 2011, vol. 46, p. 4709. https://doi.org/10.1016/j.ejmech.2011.07.024

    Article  PubMed  CAS  Google Scholar 

  28. Khan, I., Ali, S., Hameed, S., Rama, N.H., Hussain, M.T., Wadood, A., Ul-Haq, Z., Khan, A., Ali, S., and Choudhary, M.I., Eur. J. Med. Chem., 2010, vol. 45, p. 5200. https://doi.org/10.1016/j.ejmech.2010.08.034

    Article  PubMed  CAS  Google Scholar 

  29. Thotla, K., GiriNoole, V., Kedika, B., and Reddy, K., Russ. J. Gen. Chem., 2019, vol. 89, p. 789. https://doi.org/10.1134/S1070363219040248

    Article  CAS  Google Scholar 

  30. Venkatagiri, N., Krishna, T., Thirupathi, P., Bhavani, K., and Reddy, C.K., Russ. J. Gen. Chem., 2018, vol. 88, no. 7, p. 1488. https://doi.org/10.1134/S107036321606027X

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors thank Head of the Department of Chemistry, Osmania University, for providing laboratory facilities and also the director, Central Facilities for Research and Development (CFRD), Osmania University, Hyderabad, India for providing spectral data.

Funding

K. Thotla thanks the Council of Scientific and Industrial Research (CSIR, New Delhi, India) for financial support in the form of fellowship.

Author information

Authors and Affiliations

  1. Department of Chemistry, Osmania University, 500007, Hyderabad, India

    K. Thotla, V. G. Noole, B. Kedika & C. H. Krishna Reddy

Authors
  1. K. Thotla
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. G. Noole
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. Kedika
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. C. H. Krishna Reddy
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to C. H. Krishna Reddy.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Thotla, K., Noole, V.G., Kedika, B. et al. Synthesis of 5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-phenyl-1H-tetrazoles. Russ J Org Chem 56, 1077–1081 (2020). https://doi.org/10.1134/S1070428020060172

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020060172

Keywords:

Search

Navigation