Skip to main content
Log in

Cu(I)-Promoted Regioselective Synthesis of Some New Benzimidazole-1,2,3-Triazole Frameworks as In Vitro Anticancer Agents

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

Abstract

The regioselective synthesis of twelve new benzimidazole-1,2,3-triazole hybrids through the Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction between 1-(3-azidopropyl)-1H-benzo[d]imidazole and several terminal alkynes was described herein. All the synthesized compounds were further evaluated for their in vitro anticancer activity against three human cancer cell lines like PC3, A549, and MCF-7 using etoposide as standard drug. Four compounds named by 1-(3-(4-(3,5-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl)propyl)-1H-benzo[d]imidazole,1-(3-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)propyl)-1H benzo[d]imidazole,4-(1-(3-(1H-benzo[d]imidazol-1-yl)propyl)-1H-1,2,3-triazol-4-yl) benzonitrile and 1-(3-(4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)propyl)-1H-benzo[d]imidazole were displayed promising activity, in those the compound was shown outstanding activity against PC3, A549, and MCF-7 with IC50 values of 3.01, 3.82, and 2.91 μM respectively.

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.

Fig. 1.

Similar content being viewed by others

REFERENCES

  1. Neelima, M., Javed Naim, Md., Jahangir Alam, Md., Nawaz, F., Shujauddin, Ah., and Alam, O., Arch. Pharm. Chem. Life Sci., 2017, vol. 350, pp. 1–80. https://doi.org/10.1002/ardp.201700040

    Article  CAS  Google Scholar 

  2. Tonelli, M.S., Matteo, T., Bruno, N., Federica, S., Giuseppina, S., Fabio, P., Giuseppe, P., Sabrina, B., Vito, G., Gabriele, B., Sylvain, I., Cristina, L., Roberta, L., and Paolo, C., Bioorg. Med. Chem., 2010, vol. 18. pp. 2937–2953. https://doi.org/10.1016/j.bmc.2010.02.037

    Article  CAS  PubMed  Google Scholar 

  3. Ravishankara, D.K. and Chandrashekara, P.G., Eur. J. Chem., 2012, vol. 3, pp. 359–362. https://doi.org/10.5155/eurjchem.3.3.359-362.607

    Article  CAS  Google Scholar 

  4. Love Kumar, S., Narsinghani, T., and Anand, S., Med. Chem. Res., 2012, vol. 21, pp. 4330–4334. https://doi.org/10.1007/s00044-012-9976-2

    Article  CAS  Google Scholar 

  5. Deepkumar, J. and Kalpesh, P., Med. Chem. Res., 2014, vol. 23, pp. 1290–1299. https://doi.org/10.1007/s00044-013-0732-z

    Article  CAS  Google Scholar 

  6. Galal, S.A., Abdelsamie, A.S., Rodriguez, M.L., Kerwin, S.M., and El Diwani, H.I., Eur. J. Chem., 2010, vol. 1, pp. 67–72. https://doi.org/10.5155/eurjchem.1.2.67-72.1

    Article  CAS  Google Scholar 

  7. Kaushik, D., Ahmed Khan, S., and Gita, C., Med. Chem. Res., 2012, vol. 21, pp. 459–467. https://doi.org/10.1007/s00044-011-9552-1

    Article  CAS  Google Scholar 

  8. Kolb, H.C. and Sharpless, K.B., Drug Discov. Today, 2009, vol. 8, pp. 1128–1137. https://doi.org/10.1016/S1359-6446(03)02933-7

    Article  CAS  Google Scholar 

  9. Agalave, S.G., Maujan, S.R., and Pore, V.S., Chem. Asian J., 2011, vol. 6, pp. 2696–2718. https://doi.org/10.1080/00397911.2019.1616301

    Article  CAS  PubMed  Google Scholar 

  10. Rostovtsev, V.V. and Sharpless, K.B., Angew. Chem. Int. Ed., 2002, vol. 41, pp. 2596–2599. https://doi.org/10.1002/1521-3757 (20020715)114:14<2708::AID ANGE2708>3.0.CO;2-0

  11. Saqlain, H., Mohammad, S.A., Hinna, H., Syed, S., Abhijeet, D., Firasat, H., Perwez, A., Sadiq, U., Pasha, M.A.Q., Sameena, B., Syed, N., Yakub, A., and Chetna, K., Eur. J. Med. Chem., 2014, vol. 81. pp. 204–217. https://doi.org/10.1016/j.ejmech.2014.05.012

    Article  CAS  Google Scholar 

  12. Jin-Mei, X., En, Z., Xiao-Jing, S., Yan-Cha, W., Bin, Y., Wei-Wei, J., Ya-Zhuo, G., and Hong-Min, L., Eur. J. Med. Chem., 2014, vol. 80, pp. 593–604. https://doi.org/10.1016/j.ejmech.2014.03.022

    Article  CAS  Google Scholar 

  13. Narasimha Swamy Thirukovela, Shravan Kumar, K., Ranjith Kumar, K., Suresh, P., Mohan Rao, G., Chandra Sekhar, V., and Ravinder, V., Med. Chem. Res., 2017, vol. 26, pp. 2190–2195. https://doi.org/10.1007/s00044-017-1926-6

    Article  CAS  Google Scholar 

  14. Reddy, D.M., Srinivas, J., Chashoo, G., Saxena, A.K., and Kumar, H.M.S., Eur. J. Med. Chem., 2011, vol. 46, pp. 1983–1991. https://doi.org/10.1016/j.ejmech.2011.02.016

    Article  CAS  PubMed  Google Scholar 

  15. Odlo, K., Hentzen, J., Chabert, J.F.D., Ducki, S., and Gani, I., Bioorg.Med. Chem., 2008, vol. 16, pp. 4829–4838. https://doi.org/10.1016/j.bmc.2008.03.049

    Article  CAS  PubMed  Google Scholar 

  16. Singh, P., Raj, R., Kumar, V., Mahajan, M.P., Bedi, P.M.S., Kaur, T., and Saxena, A.K., Eur. J. Med. Chem., 2012, vol. 47, pp. 594–600. https://doi.org/10.1016/j.ejmech.2011. 10.033

  17. Stefely, J.A., Palchaudhuri, R., Miller, P.A., Peterson, R.J., Moraski, G.C., Hergenrother, P.J., and Miller, M.J., J. Med. Chem., 2010, vol. 53, pp. 3389–3395. https://doi.org/10.1021/jm1000979

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Vinod D. Jadhav.

Ethics declarations

COMPLIANCE WITH ETHICAL STANDARDS

This article does not contain any studies involving animals or human participants performed by any of the authors.

Conflict of Interests

The authors declare that they have 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

Manmohan Reddy Depa, Potla, S., Narkhede, U.C. et al. Cu(I)-Promoted Regioselective Synthesis of Some New Benzimidazole-1,2,3-Triazole Frameworks as In Vitro Anticancer Agents. Russ J Bioorg Chem 47, 1028–1033 (2021). https://doi.org/10.1134/S1068162021050228

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162021050228

Keywords:

Navigation