Skip to main content
Log in

Synthesis, Antitubercular Activity, and Molecular Docking Studies of Novel 2-(4-Chlorobenzylamino)-4-(cyclohexylmethylamino)-pyrimidine-5-carboxamides

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

Abstract

A novel series of 2-(4-chlorobenzylamino)-4-(cyclohexylmethylamino)-pyrimidine-5-carboxamide derivatives are synthesized and their structures are confirmed by 1H and 13C NMR, and MS spectral data. The compounds are screened for their antitubercular activity, and those with aryl moiety 7o, 7q, and 7r demonstrate potent activity against Mycobacterium tuberculosis. Docking studies suggest a mode of interaction of the products with the binding site of enoyl-CoA hydratase demonstrating that the target compounds were potential anti-TB agents.

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.

Similar content being viewed by others

References

  1. Ouyang, Y., Yang, H., Zhang, P., Wang, Y., Kaur, S., Zhu, S., Wang, Z., Sun, Y., Hong, W., Ngeow, Y.F., and Wang, H., Molecules, 2017, vol. 22, p. 1592. doi https://doi.org/10.3390/molecules22101592

    Article  CAS  PubMed Central  Google Scholar 

  2. Sittikornpaiboon, P., Toochinda, P., Thongpanchang, C., Leartsakulpanich, U., and Lawtrakul, L., Chiang Mai J. Sci., 2016, vol. 43, p. 931.

    CAS  Google Scholar 

  3. Sittikornpaiboon, P., Toochinda, P., and Lawtrakul, L., Sci. Pharm., 2017, vol. 85, p. 31. doi https://doi.org/10.3390/scipharm85030031

    Article  CAS  PubMed Central  Google Scholar 

  4. Roth, B., Aig, E., Lane, K., and Rauckman, B.S., J. Med. Chem., 1980, vol. 23, p. 535. doi https://doi.org/10.1021/jm00179a012

    Article  CAS  PubMed  Google Scholar 

  5. Argiriadi, M.A., Ericsson, A.M., Harris, C.M., Banach, D.L., Borhani, D.W., Calderwood, D.J., Demers, M.D., DiMauro, J., Dixon, R.W., Hardman, J., Biqin Li, S.K., Mankovich, J.A., Marcotte, D., Mullen, K.D., Pietras, B.N.M., Sadhukhan, R., Sousa, S., Tomlinson, M.J., Wang, L., Xiang, T., and Talanian, R.V., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 330. doi https://doi.org/10.1016/j.bmcl.2009.10.102

    Article  CAS  PubMed  Google Scholar 

  6. Zhou, W., Huang, A., Zhang, Y., Lin, Q., Guo, W., You, Z., Yi, Z., Liu, M., and Chen, Y., Eur. J. Med. Chem., 2015, vol, 96, p. 269. doi https://doi.org/10.1016/j.ejmech.2015.04.027

    Article  CAS  PubMed  Google Scholar 

  7. Bodige, S., Ravula, P., Gulipalli, K.C., Endoori, S., Narendra Sharath Chandra, J.N., Cherukumalli, P.K.R., Vanaja, G.R., and Seelam, N.V., Anticancer Agents Med. Chem., 2018, vol, 18, p. 891. doi https://doi.org/10.2174/1871520618666180209151018

    Article  CAS  PubMed  Google Scholar 

  8. Nakazato, A., Kumagai, T., Okubo, T., Tanaka, H., Chaki, S., Okuyama, S., and Tomisawa, K., Bioorg. Med. Chem., 2000, vol. 8, p. 1183. doi https://doi.org/10.1016/S0968-0896.00)00045-6

    Article  CAS  PubMed  Google Scholar 

  9. Nakazato, A., Kumagai, T., Okubo, T., Kataok-Okubo, H., Chaki, S., and Okuyama, S., Bioorg. Med. Chem., 2001, vol. 9, p. 1349. doi https://doi.org/10.1016/S0968-0896(01)00004-9

    Article  PubMed  Google Scholar 

  10. Borowski, T., Krol, M., Broclawik, E., Baranowski, T.C., Strekowski, L., and Mokrosz, M., J. Med. Chem., 2000, vol. 43, p. 1901. doi https://doi.org/10.1021/jm9911332

    Article  CAS  PubMed  Google Scholar 

  11. Russell, M.G.N., Baker, R.J., Barden, L., Beer, M.S., Bristow, L., Broughton, H.B., Knowles, M., McAllister, G., Patel, S., and Castro, J.L., J. Med. Chem., 2001, vol. 44, p. 3881. doi https://doi.org/10.1021/jm010943m

    Article  CAS  PubMed  Google Scholar 

  12. Chen, H., Chan, B.K., Drummond, J., Estrada, A.A., Gunzer-Toste, J., Liu, X., Liu, Y., Moffat, J., Shore, D., Sweeney, Z.K., Tran, T., Wang, S., Zhao, G., Zhu, H., and Burdick, D.J., J. Med. Chem., 2012, vol. 55, p. 5536. doi https://doi.org/10.1021/jm300452p

    Article  CAS  PubMed  Google Scholar 

  13. Verma, S., Nagarathnam, D., Shao, J., Zhang, L., Zhao, J., Wang, Y., Li, T., Mull, E., Enyedy, I., Wang, C., Zhu, Q., Altieri, M., Jordan, J., Dang, T., and Reddy, S., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 1973. doi https://doi.org/10.1016/j.bmcl.2005.02.076

    Article  CAS  PubMed  Google Scholar 

  14. Mesguiche, V., Hardcastle, I.R., Wang, L.Z., Noble, M.E.M., Newell, D.R., Newell, D.R., Johnson, L.N., Jewsbury, P., Griffin, R.J., Golding, B.T., Gibson, A.E., Endicott, J.A., Davies, T.G., Curtin, N.J., Boyle, F.T., Bentley, J., Arris, C.E., and Parsons, R.J., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 217. doi https://doi.org/10.1016/S0960-894.(02)00884-3

    Article  CAS  PubMed  Google Scholar 

  15. Ludovici, D.W., DeCorte, B.L., Kukla, M.J., Ye, H., Ho, C.Y., Lichtenstein, M.A., Kavash, R.W., Andries, K., De Bethune, M.P., Azijn, H., Pauwels, R., Lewi, P.J., Heeres, J., Koymans, L.M.H., DeJonge, M.R., Van Aken, K.J.A., Daeyaert, F.F.D., Das, K., Arnold, E., and Janssen, P.A.J., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 2235. doi https://doi.org/10.1016/S0960-894X(01)00412-7

    Article  CAS  PubMed  Google Scholar 

  16. Brown, D.J., Chemistry of Heterocyclic Compounds, The Pyrimidines, 1994, vol. 52, p. 371.

    Google Scholar 

  17. Rathod, A.S., Godipurge, S.S., and Biradar, J.S., Russ. J. Gen. Chem., 2018, vol. 88, no. 6, p. 1238. doi https://doi.org/10.1134/S1070363218060324

    Article  CAS  Google Scholar 

  18. Gulipalli, K.C., Bodige, S., Ravula, P., Endoori, S., Vanaja, G.R., Suresh Babu, G., Narendra Sharath Chandra, J.N., and Seelam, N.V., Bioorg. Med. Chem. Lett., 2017, vol, 27, p. 3558. doi https://doi.org/10.1016/j.bmcl.2017.05.047

    Article  CAS  PubMed  Google Scholar 

  19. Parameshwar, R., Harinadha Babu, V., Manichandrika, P., Narendra Sharath Chandra, J.N., and Swetha, K., EXCLI. J., 2016, vol. 15, p. 187. doi https://doi.org/10.17179/excli2016-103

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. Naresh Varma.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Srinu, B., Parameshwar, R., Kali Charan, G. et al. Synthesis, Antitubercular Activity, and Molecular Docking Studies of Novel 2-(4-Chlorobenzylamino)-4-(cyclohexylmethylamino)-pyrimidine-5-carboxamides. Russ J Gen Chem 89, 836–843 (2019). https://doi.org/10.1134/S1070363219040327

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219040327

Keywords

Navigation