Skip to main content

Advertisement

SpringerLink
Log in

Synthesis and biological evaluation of new 2-aryl-4-((4-aryl-1H-1,2,3-triazol-1-yl)methyl)thiazole derivatives

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A series of 2-aryl-4-((4-aryl-1H-1,2,3-triazol-1-yl)methyl)thiazole derivatives (8a–p) have been synthesized. The structure of the newly synthesized compounds was determined by spectral analysis. The title compounds were screened for their preliminary antitubercular activity against Mycobacterium tuberculosis H37Ra (MTB, ATCC 25177) and Mycobacterium bovis BCG (BCG, ATCC 35743). Further, the synthesized compounds were screened for antimicrobial activity against standard Gram-negative bacteria Escherichia coli (NCIM 2576) and Pseudomonas flurescence (NCIM 2059) and Gram-positive bacteria Staphylococcus aureus (NCIM 2602) and Bacillus subtilis (NCIM 2162). Among all the synthesized compounds, 8a–c, f–h, m exhibited good activity against dormant M. bovis BCG strain. Compounds 8h, j exhibited good activity against all tested bacterial strains. All active compounds were screened for cytotoxicity and found inactive. Their high potency and promising antimycobacterial activity suggest that these compounds could serve as good leads for further optimization and development.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1

Similar content being viewed by others

References

  1. World Health Organization, Tuberculosis Fact Sheet (2016), http://www.who.int/tb/publications/global_report/en/

  2. Q. Wang, F. Song, X. Xiao, P. Huang, L. Li, A. Monte, W.M. Abdel-Mageed, J. Wang, H. Guo, W. He, F. Xie, H. Dai, M. Liu, C. Chen, H. Xu, M. Liu, A.M. Piggott, X. Liu, R.J. Capon, L. Zhang, Angew. Chem. Int. Ed. 52, 1231–1234 (2013)

    Article  CAS  Google Scholar 

  3. R. Ramesh, R.D. Shingare, V. Kumar, A. Anand, B. Swetha, S. Veeraraghavan, S. Viswanadha, R. Ummanni, R. Gokhale, D.S. Reddy, Eur. J. Med. Chem. 122, 723–730 (2016)

    Article  CAS  Google Scholar 

  4. V.U. Jeankumar, S.R. Rudraraju, R. Vats, R. Janupally, S. Saxena, P. Yogeeswari, D. Sriram, Eur. J. Med. Chem. 122, 216–231 (2016)

    Article  CAS  Google Scholar 

  5. M.D. Chen, S.J. Lu, G.P. Yuag, S.Y. Yang, X.L. Du, Heterocycl. Commun. 6, 421–426 (2000)

    Article  CAS  Google Scholar 

  6. B.S. Holla, M. Mahalinga, M.S. Karthikeyen, B. Poojary, P.M. Akberali, N.S. Kumari, Eur. J. Med. Chem. 40, 1173–1178 (2005)

    Article  CAS  Google Scholar 

  7. H.N. Hafez, H.A. Abbas, A.R. El-Gazzar, Acta Pharm. 58, 359–378 (2008)

    Article  CAS  Google Scholar 

  8. A. Passannanti, P. Diana, P. Barraja, F. Mingooia, A. Lauria, G. Cirrincine, Heterocycles 48, 1229–1235 (1998)

    Article  CAS  Google Scholar 

  9. L.P. Guan, Q.H. Jin, G.R. Tian, K.Y. Chai, Z.S. Quan, J. Pharm. Sci. 10, 254–262 (2007)

    CAS  Google Scholar 

  10. S. Manfredini, C.B. Vicentini, M. Manfrini, N. Bianchi, C. Rustigliano, C. Mischiati, R. Gambari, Bioorg. Med. Chem. 8, 2343–2346 (2000)

    Article  CAS  Google Scholar 

  11. V. Dmitry, A.V. Demchuk, N.B. Samet, V.I. Chernysheva, G.A. Ushkarov, L.D. Stashina, M.M. Konyushkin, S.I. Raihstat, A.A. Firgang, M.P. Philchenkov, L.M. Zavelevich, V.F. Kuiava, D.Y. Chekhun, A.S. Blokhin, M.N. Kiselyov, V.V. Semenova, Bioorg. Med. Chem. 22, 738–755 (2014)

    Article  Google Scholar 

  12. R. Gujjar, A. Marwaha, J. White, L. White, S. Creason, D.M. Shackleford, J. Baldwin, W.N. Charman, F.S. Buckner, S. Charman, P.K. Rathod, M.A. Phillips, J. Med. Chem. 52, 1864–1872 (2009)

    Article  CAS  Google Scholar 

  13. B.A. Johns, J.G. Weatherhead, S.H. Allen, J.B. Thompson, E.P. Garvey, S.A. Foster, Bioorg. Med. Chem. Lett. 19, 1802–1806 (2009)

    Article  CAS  Google Scholar 

  14. S.C. Beasley, N. Cooper, L. Gowers, J.P. Gregory, A.A.F. Haughan, P.G. Hellewell, D. Macar, J. Miotla, J.G. Montana, T. Morgan, R. Taylor, K.A. Runcie, B. Tuladhar, J.B.H. Warneck, Bioorg. Med. Chem. Lett. 8, 2629–2634 (1998)

    Article  CAS  Google Scholar 

  15. C.E. De, Clin. Microbiol. Rev. 10, 674–693 (1997)

    Google Scholar 

  16. T. Weide, S.A. Saldanha, D. Minond, T.P. Spicer, J.R. Fotsing, M. Spaargaren, J. Frere, C. Bebrone, K.B. Sharpless, P.S. Hodder, V.V. Fokin, A.C.S. Med, Chem. Lett. 1, 150–154 (2010)

    CAS  Google Scholar 

  17. G. Heubach, B. Sachse, H. Buerstell, Ger. Offen 2, 760–826 (1979)

    Google Scholar 

  18. B. Chaia, X. Qianb, S. Caoa, H. Liua, G. Song, ARKIVOC ii, 141-145, (2003)

  19. A.R. Bhat, G.V. Bhat, G.G. Shenoy, J. Pharm. Pharmacol. 53, 267–272 (2001)

    Article  CAS  Google Scholar 

  20. N.B. Patel, I.H. Khan, S.D. Rajani, Eur. J. Med. Chem. 45, 4293–4299 (2010)

    Article  CAS  Google Scholar 

  21. G.R. Jadhav, M.U. Shaikh, R.P. Kale, M.R. Shiradkar, C.H. Gill, Eur. J. Med. Chem. 44, 2930–2935 (2009)

    Article  CAS  Google Scholar 

  22. H. Foks, M. Janowiec, Z. Zwolska, E. Augustynowicz-Kopeć, Phosphorus Sulfur Silicon Relat. Elem. 180, 537–543 (2005)

    Article  CAS  Google Scholar 

  23. D. Castagnolo, M. Radi, F. Dessi, F. Manetti, M. Saddi, R. Meleddu, A.D. Logu, M. Botta, Bioorg. Med. Chem. Lett. 19, 2203–2205 (2009)

    Article  CAS  Google Scholar 

  24. M. Shiradkar, S. Kumar, V. Dasari, S. Tatikonda, K.C. Akula, R. Shah, Eur. J. Med. Chem. 42, 807–816 (2007)

    Article  CAS  Google Scholar 

  25. S.R. Patpi, L. Pulipati, P. Yogeeswari, D. Sriram, N. Jain, B. Sridhar, R. Murthy, A.T. Devi, S.V. Kalivendi, S. Kantevari, J. Med. Chem. 55, 3911–3922 (2012)

    Article  CAS  Google Scholar 

  26. M.H. Shaikh, D.D. Subhedar, L. Nawale, D. Sarkar, F.A. Kalam Khan, J.N. Sangshetti, B.B. Shingate, Med. Chem. Commun 6, 1104–1116 (2015)

    Article  CAS  Google Scholar 

  27. P. Shanmugavelan, S. Nagarajan, M. Sathishkumar, A. Ponnuswamy, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 21, 7273–7276 (2011)

    Article  CAS  Google Scholar 

  28. N. Boechat, V.F. Ferreira, S.B. Ferreira, M.L.G. Ferreira, F.C. da Silva, M.M. Bastos, M.S. Costa, M.C.S. Lourenço, A.C. Pinto, A.U. Krettli, A.C. Aguiar, B.M. Teixeira, N.V. da Silva, P.R.C. Martins, F.A.F.M. Bezerra, A.L.S. Camilo, G.P. da Silva, C.C.P. Costa, J. Med. Chem. 54, 5988–5999 (2011)

    Article  CAS  Google Scholar 

  29. G.R. Labadie, A. de la Iglesia, H.R. Morbidoni, Mol. Divers. 15, 1017–1024 (2011)

    Article  CAS  Google Scholar 

  30. C. Gill, G. Jadhav, M. Shaikh, R. Kale, A. Ghawalkar, D. Nagargoje, M. Shiradkar, Bioorg. Med. Chem. Lett. 18, 6244–6247 (2008)

    Article  CAS  Google Scholar 

  31. S.R. Patpi, L. Pulipati, P. Yogeeswari, D. Sriram, N. Jain, B. Sridhar, R. Murthy, T. Anjana Devi, S.V. Kalivendi, S. Kantevari, J. Med. Chem. 55, 3911–3922 (2012)

    Article  CAS  Google Scholar 

  32. L. Chen, D.J. Wilson, Y. Xu, C.C. Aldrich, K. Felczak, Y.Y. Sham, K.W. Pankiewicz, J. Med. Chem. 53, 4768–4778 (2010)

    Article  CAS  Google Scholar 

  33. R.S. Upadhayaya, G.M. Kulkarni, N.R. Vasireddy, J.K. Vandavasi, S.S. Dixit, V. Sharma, J. Chattopadhyaya, Bioorg. Med. Chem. 17, 4681–4692 (2009)

    Article  CAS  Google Scholar 

  34. C. Menendez, S. Gau, C. Lherbet, F. Rodriguez, C. Inard, M.R. Pasca, M. Baltas, Eur. J. Med. Chem. 46, 5524–5531 (2011)

    Article  CAS  Google Scholar 

  35. S.P. Pardeshi, S.S. Patil, V.D. Bobade, Bioorg. Med. Chem. Lett. 21, 6559–6562 (2011)

    Article  CAS  Google Scholar 

  36. T. Tomasic, S. Katsamakas, Z. Hodnik, J. Ilas, M. Brvar, T. Solmajer, S. Montalvao, P. Tammela, M. Banjanac, G. Ergovic, M. Anderluh, L.P. Masic, D. Kikelj, J. Med. Chem. 58, 5501–5521 (2015)

    Article  CAS  Google Scholar 

  37. Z.Y. Liu, Y.M. Wang, Z.R. Li, J.D. Jiang, D.W. Boykin, Bioorg. Med. Chem. Lett. 19, 5661–5664 (2009)

    Article  CAS  Google Scholar 

  38. S.A.F. Rostom, I.M. El-Ashmawy, H.A. Abd El Razik, M.H. Badr, H.M.A. Ashour, Bioorg. Med. Chem. Lett. 17, 882–895 (2009)

    Article  CAS  Google Scholar 

  39. D. Sampson, X.Y. Zhu, S.V.K. Eyunni, J.R. Etukala, E. Ofori, B. Bricker, N.S. Lamango, V. Setola, B. Roth, S.Y. Ablordeppey, Bioorg. Med. Chem. Lett. 22, 3105–3114 (2014)

    Article  CAS  Google Scholar 

  40. G.S. Inamdar, A.N. Pandya, H.M. Thakar, V. Sudarsanam, S. Kachler, S. Moro, D. Sabbadin, K.N. Klotz, K.K. Vasu, Eur. J. Med. Chem. 63, 924–934 (2013)

    Article  CAS  Google Scholar 

  41. Y.S. Lee, H. Kim, Y.H. Kim, E.J. Roh, H. Han, K.J. Shin, Bioorg. Med. Chem. Lett. 22, 7555–7561 (2012)

    Article  CAS  Google Scholar 

  42. Y.K. Abhale, K.K. Deshmukh, A.V. Sasane, A.P. Chavan, P.C. Mhaske, J. Heterocycl. Chem. 53, 229–233 (2016)

    Article  CAS  Google Scholar 

  43. P.C. Mhaske, S.H. Shelke, M. Bhoye, V.D. Bobade, J. Heterocycl. Chem. 54, 1590–1597 (2017)

    Article  CAS  Google Scholar 

  44. S. Malik, R.S. Bahare, S.A. Khan, Eur. J. Med. Chem. 67, 1–13 (2013)

    Article  CAS  Google Scholar 

  45. M.F. Arshad, N. Siddiqui, A. Elkerdasy, H. Abdulmohsen, A.L. Rohaimi, S.A.A. Khan, J. Pharmacol. Toxicol. 9, 132–138 (2014)

    Article  Google Scholar 

  46. J.L. Falco, A. Palomer, A. Guglietta, US 2008/0200473 A12008

  47. F. Hayat, E. Yoo, H. Rhim, H.Y.P. Choo, Bull. Korean Chem. Soc. 34, 495–499 (2013)

    Article  CAS  Google Scholar 

  48. R.B. Clark, D. Lamppu, L. Libertine, A. McDonough, A. Kumar, G.L. Rosa, R. Rush, D. Elbaum, J. Med. Chem. 57, 3966–3983 (2014)

    Article  CAS  Google Scholar 

  49. J.A. Shiran, A. Yahyazadeh, M. Mamaghani, M. Rassa, J. Mol. Struct. 1039, 113–118 (2013)

    Article  Google Scholar 

  50. M. Brvar, A. Perdith, G. Anderluh, D. Turk, T. Solmajer, J. Med. Chem. 55, 6413–6426 (2012)

    Article  CAS  Google Scholar 

  51. C. Araniciu, A.E. Parvu, B. Tiperciuc, M. Palage, S. Oniga, P. Verite, O. Oniga, J Nanomater. Biostruct. 8, 699–709 (2013)

    Google Scholar 

  52. O. Oniga, J.T. Ndongo, C. Moldovan, B. Tiperciuc, S. Oniga, A. Pirnau, L. Vlase, P. Verite, Farmacia 6, 785–797 (2012)

    Google Scholar 

  53. C.B. Mark, J.W. Dale, E.A. Merritt, X. Xin, Chem. Rev. 105, 685–714 (2005)

    Article  Google Scholar 

  54. E. Riego, D. Hernandez, F. Albericio, M. Alvarez, Synthesis 2005, 1907–1922 (2005)

    Article  Google Scholar 

  55. J. Parvate, V.S. Bhagwat, M.M. Doshi, H.L. Mondkar, Indian Drugs 26, 222–226 (1989)

    CAS  Google Scholar 

  56. S.H. Shelke, P.C. Mhaske, P. Hande, V.D. Bobade, Phosphorus Sulfur Silicon Relat. Elem. 188, 1262–1270 (2013)

    Article  CAS  Google Scholar 

  57. M.R. Shiradkar, K.K. Murahari, G.H. Reddy, S. Tatikonda, A.K. Chakravarthy, P. Dolly, R. Kaur, P. Burange, J. Ghogare, V. Mokalec, M. Rautc, Bioorg. Med. Chem. Lett. 15, 3997–4008 (2007)

    Article  CAS  Google Scholar 

  58. Y.K. Abhale, A.V. Sasane, A.P. Chavan, K.K. Deshmukh, S.S. Kotapalli, R. Ummanni, S.F. Sayyad, P.C. Mhaske, Eur. J. Med. Chem. 94, 340–347 (2015)

    Article  CAS  Google Scholar 

  59. Y.K. Abhale, A.V. Sasane, A.P. Chavan, S.H. Shekh, K.K. Deshmukh, S. Bhansali, L. Nawale, D. Sarkar, P.C. Mhaske, Eur. J. Med. Chem. 132, 333–340 (2017)

    Article  CAS  Google Scholar 

  60. A. Khan, D. Sarkar, J. Microbiol. Methods 73, 62–68 (2008)

    Article  CAS  Google Scholar 

  61. R. Singh, L. Nawale, M. Arkile, U. Shedbalkar, S. Wadhwani, D. Sarkar, B. Chopade, Int. J. Antimicrob. Agents 46, 183–188 (2015)

    Article  CAS  Google Scholar 

  62. S. Sarkar, D. Sarkar, J. Biomol. Screen. 17, 966–973 (2012)

    Article  Google Scholar 

  63. U. Singh, S. Akhtar, A. Mishra, D. Sarkar, J. Microbiol. Methods 84, 202–207 (2011)

    Article  CAS  Google Scholar 

  64. A. Khan, S. Sarkar, D. Sarkar, Int. J. Antimicrob. Agents 32, 40–45 (2008)

    Article  CAS  Google Scholar 

  65. T. Mosmann, J. Immunol. Methods 65, 55–63 (1983)

    Article  CAS  Google Scholar 

  66. G. Ciapetti, E. Cenni, L. Pratelli, A. Pizzoferrato, Biomaterials 4, 359–364 (1993)

    Article  Google Scholar 

  67. R.C. Hartkoorn, B. Chandler, A. Owen, S.A. Ward, S.B. Squire, D.J. Back, S.H. Khoo, Tuberculosis 87, 248 (2007)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to CSIR-NCL, Pune for supporting the biological activity investigation. Central Analysis Facility, Savitribai Phule Pune University, Pune is also acknowledged for spectral analysis.

Author information

Authors and Affiliations

  1. School of Chemical Sciences, North Maharashtra University, Jalgaon, India

    Vikas Shinde & Pramod Mahulikar

  2. Post Graduate Department of Chemistry, S. P. Mandali’s Sir Parashurambhau College (Affiliated to Savitribai Phule Pune University), Tilak Road, Pune, 411 030, India

    Pravin C. Mhaske

  3. CombiChemBio Resource Centre, CSIR-National Chemical Laboratory, Pune, 411 008, India

    Laxman Nawale & Dhiman Sarkar

Authors
  1. Vikas Shinde
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Pramod Mahulikar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pravin C. Mhaske
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Laxman Nawale
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Dhiman Sarkar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Pramod Mahulikar or Pravin C. Mhaske.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1218 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shinde, V., Mahulikar, P., Mhaske, P.C. et al. Synthesis and biological evaluation of new 2-aryl-4-((4-aryl-1H-1,2,3-triazol-1-yl)methyl)thiazole derivatives. Res Chem Intermed 44, 1247–1260 (2018). https://doi.org/10.1007/s11164-017-3164-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-017-3164-4

Keywords

Search

Navigation