Skip to main content

Advertisement

SpringerLink
Log in

Synthesis and Biological Evaluation of Novel Fused [1,2,3]Triazolo[4',5':3,4] pyrrolo[2,1-f]purines as Potent Anti-Proliferative Agents

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

Abstract

In search of the best anticancer agents, a series of novel fused [1,2,3]triazolo[4',5':3,4] pyrrolo[2,1-f]purine derivatives in one vessel was synthesized using 8-bromo-1,3-dimethyl-7-(prop-2-yn-1-yl)-1H-purine-2,6(3H,7H)-dione and various arylazides. The newly synthesized derivatives were evaluated for their in vitro anti-proliferative activity against four human cancer cell lines (MCF-7, HeLa, A-549 and U-87MG). 3-(3,5-dichlorophenyl)-5,7-dimethyl-7,10-dihydro-[1,2,3]triazolo[4',5':3,4]pyrrolo[2,1-f]purine-6,8(3H,5H)-dione and 5,7-dimethyl-3-(4-nitrophenyl)-3,10-dihydro-[1,2,3]triazolo[4',5':3.4]pyrrolo[2,1-f]purine-6,8 (5H,7H)-dione are showed stronger activity against MCF-7 and A-549 with IC50 values ranging from 11.5 ± 0.64 to 15.3 ± 0.81 μM, which are comparable to the standard drug doxorubicin. Molecular docking studies have also been conducted to complement the experimental results.

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.
Fig. 2.
Fig. 3.
Fig. 4.

Similar content being viewed by others

REFERENCES

  1. Nivedita, S., Ashwinee, K.S., Thakur, M.S., and Sanjukta, P., Heliyon, 2018, vol. 4, no. 10, e00829. https://doi.org/10.1016/j.heliyon.2018.e00829

    Article  Google Scholar 

  2. Allwood, M.B., Cannan, B., Van Aalten, D.M.F., and Eggleston, I.M., Tetrahedron., 2007, vol. 63, pp. 12294–12302. https://doi.org/10.1016/j.tet.2007.09.067

    Article  CAS  Google Scholar 

  3. Hayallah, A. M., Elgaher, W.A., Salem, O. I., and Abdel Alim, A.A.M., Arch. Pharm. Res., 2011, vol. 34, pp. 3–21. https://doi.org/10.1007/s12272-011-0101-8

    Article  CAS  PubMed  Google Scholar 

  4. Matthias, E., Elke, L., Michael, M., Moh, T., Leo, T., Herbert, N., Waldemar, P., Brian, G., Ralf, L., Peter, S., Holger, F., and Frank, H., J. Med. Chem., 2007, vol. 50, pp. 6450–6453. https://doi.org/10.1021/jm701280z

    Article  CAS  Google Scholar 

  5. Gang, L., Yi, H., Baokun, Y., Jin, W., Qian, J., Ziyun, L., Zhufang, S., and Haihong, H., Eur. J. Med. Chem., 2016, vol. 124, pp. 103–116. https://doi.org/10.1016/j.ejmech.2016.08.023

    Article  CAS  Google Scholar 

  6. Yiwen, H., Xiaoqing, H., Taizhi, W., and Fuli, Z., Molecules, 2016, vol. 21, pp.1041. https://doi.org/10.3390/molecules21081041

    Article  CAS  Google Scholar 

  7. Yan, R., Heying, P., Mingfeng, S., and Lijuan, C., Chem. Biol. Drug. Des., 2016, vol. 87, pp. 290–295. https://doi.org/10.1111/cbdd.12663

    Article  CAS  Google Scholar 

  8. Sirassu, N., Kumara, S.B., Ravinder, M., Reddy, Y.N., and Vasudeva, R.N., J. Chem. Sci., 2020, vol. 132, pp. 59. https://doi.org/10.1007/s12039-020-1760-0

    Article  CAS  Google Scholar 

  9. Glennon, R.A., Gaines, J.J., and Rogers, M.E., J. Med. Chem., 1981, vol. 24, pp. 766–769. https://doi.org/10.1021/jm00138a027

    Article  CAS  PubMed  Google Scholar 

  10. Wong, E.H.-A. and Ooi, S.-O., Biochem. Pharmacol., 1985, vol. 34, pp. 2891–2896. https://doi.org/10.1016/0006-2952(85)90012-7

    Article  CAS  PubMed  Google Scholar 

  11. Haginaka, J., Wakai, J., Yasuda, H., and Kimura, Y., J. Chromatogr. B Biomed. Sci. Appl., 1990, vol. 529, pp. 455–461. https://doi.org/10.1016/s0378-4347(00)83854-2

    Article  CAS  Google Scholar 

  12. Constantin, S., Lupascu, F.G., Apotrosoaei, M., Vasincu, I.M., Lupascu, D., and Buron, F., Chem. Cent. J., 2017, vol.11, p. 12. https://doi.org/10.1186/s13065-017-0241-0

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Dai, Z.-K., Liu, Y.-W., Hsu, J.-H., Yeh, J.-L., Chen, I.-J., and Wu, J.-R., Int. J. Biol. Sci., 2015, vol.11, pp. 633–642. https://doi.org/10.7150/ijbs.11127

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Slattery, M.L. and West, D.W., Cancer Causes Control, 1993, vol. 4, pp. 559–563. https://doi.org/10.1007/BF00052432

    Article  CAS  PubMed  Google Scholar 

  15. Barcz, E., Sommer, E., Janik, P., Marianowski, L., and Skopinska-Rózewska, E., Oncol. Rep., 2000, vol. 7, pp. 1285–1291. https://doi.org/10.3892/or.7.6.1285

    Article  CAS  PubMed  Google Scholar 

  16. Kakuyama, A., and Sadzuka, Y., Curr. Drug Metabol., 2001, vol. 2, pp. 379–395. https://doi.org/10.2174/1389200013338270

    Article  CAS  Google Scholar 

  17. Zhang, Y., Yu, J., Zhang, L., Cai, J., Cai, D., and Lv, C., Tumor Biol., 2016, vol. 37, pp. 2703–2708. https://doi.org/10.1007/s13277-015-4106-7

    Article  CAS  Google Scholar 

  18. Agalave, S.G., Maujan, S.R., and Pore, V.S., Chem. Asian J., 2011, vol. 6, pp. 2696–2718. https://doi.org/10.1002/asia.201100432

    Article  CAS  PubMed  Google Scholar 

  19. El-Sagheer, A.H. and Brown, T., Acc. Chem. Res., 2012, vol. 45, pp. 1258–1267. https://doi.org/10.1021/ar200321n

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Thirumurugan, P., Matosiuk, D., and Jozwiak, K., Chem. Rev., 2013, vol. 113, pp. 4905–4979. https://doi.org/10.1021/cr200409f

    Article  CAS  PubMed  Google Scholar 

  21. Bonandi, E., Christodoulou, M.S., Fumagalli, G., Perdicchia, D., Rastelli, G., and Passarella, D., Drug. Discov. Today., 2017, 2ol. 2, pp. 1572–1581. https://doi.org/10.1016/j.drudis.2017.05.014

  22. Narsimha, S., Kumara, S.B., Satheesh, K. N., Ramesh, G., Yellu, N.R., and Vasudeva, R. N., RSC Adv., 2016, vol. 6, pp. 74332–74339. https://doi.org/10.1039/C6RA12285J

    Article  CAS  Google Scholar 

  23. Narsimha, S., Kumara, S.B., Yellu, N.R., Vasudeva, R.N., Chem. Heterocycl. Compd., 2018, vol. 54, pp. 1161–1167. https://doi.org/10.1007/s10593-019-02408-6

    Article  CAS  Google Scholar 

  24. Senwar, K.R., Sharma, P., Reddy, T.S., Jeengar, M.K., Nayak, V.L., Naidu, V.G., Kamal, A., and Shankaraiah, N., Eur. J. Med. Chem., 2015, vol. 102, pp. 413–424. https://doi.org/10.1016/j.ejmech.2015.08.017

    Article  CAS  PubMed  Google Scholar 

  25. Sheng-Jiao, Y., Yong-Jiang, L., Yu-Lan, C., Lin, L., and Jun, L., Bioorg. Med. Chem. Lett., 2010, vol. 20, pp. 5225–5228. https://doi.org/10.1016/j.bmcl.2010.06.141

    Article  CAS  Google Scholar 

  26. Chen, C.Y., Yang, C.H., Hu, W.P., Vandavasi, J.K., Chung, M.I., and Wang, J.J., RSC Adv., 2013, vol. 3, pp. 2710–2719. https://doi.org/10.1039/C2RA22799A

    Article  CAS  Google Scholar 

  27. Srivari, C., Mallikanti, S., Abhishek, K., Chada, R. R., Suman, K. M., Chityal, G. K., and Sridhar, B., Tetrahedron Lett., 2011, vol. 52, pp. 806–808. https://doi.org/10.1016/j.tetlet.2010.12.040

    Article  CAS  Google Scholar 

  28. Hsin-Yu, H., Wen-Chun, L., Gopal, C.S., WanPing, H., Jium-Jia, L., Tong-Rong, T., Yu-Wei, C., Kung-Kai, K., Chung-Yu, C., and Jeh-Jeng, W., J. Med. Chem., 2013, vol. 56, pp. 5422–5435. https://doi.org/10.1021/jm400394s

    Article  CAS  Google Scholar 

  29. Ramesh, B.H., Ravinder, M., Narsimha, S., Indian J. Heterocycl. Chem., 2019, vol. 29, pp. 389–395.

    Google Scholar 

  30. Narsimha, S., Kumar, N.S., Kumaraswamy, B., Vasudeva, R.N., Hussain, A.S., and Srinivasa, R.M., Bioorg. Med. Chem. Lett., 2016, vol. 26, pp.1639–1644. https://doi.org/10.1016/j.bmcl.2016.01.055

    Article  CAS  PubMed  Google Scholar 

  31. Swamy, B.K., Narsimha, S., Kumar, T.R., Reddy, Y.N., and Reddy, N.V., Chem. Select., 2017, vol. 2, pp. 9595–9598. https://doi.org/10.1002/slct.201701902

    Article  CAS  Google Scholar 

  32. Narsimha, S., Battula, K.S., and Nagavelli, V.R., Syn. Commun., 2018, vol. 48, pp. 1220–1226. https://doi.org/10.1080/00397911.2018.1440315

    Article  CAS  Google Scholar 

  33. Swamy, B.K., Narsimha, S., Kumar, T.R., Reddy, Y.N., and Reddy, N.V., Chem. Select., 2017, vol. 2, pp. 4001–4005. https://doi.org/10.1002/slct.201700524

    Article  CAS  Google Scholar 

  34. Ramesh, B.H., Narsimha, S., Ravinder, M., Janapatla, U.R., Indian J. Heterocycl. Chem., 2020, vol. 30, pp. 233–238.

    Google Scholar 

  35. Mosmann, T., J. Immunol. Methods, 1983, vol. 65, pp. 55–63. https://doi.org/10.1016/0022-1759(83)90303-4

    Article  CAS  PubMed  Google Scholar 

  36. Botta, M., Armaroli, S., Castagnolo, D., Fontana, G., Pera, P., and Bombardelli, E., Bioorg. Med. Chem. Lett., 2007, vol. 17, pp. 1579–1583. https://doi.org/10.1016/j.bmcl.2006.12.101

    Article  CAS  PubMed  Google Scholar 

  37. Park, J.H. and Lemmon, M.A., Biochem. J., 2012, vol. 448, pp. 417–423. https://doi.org/10.1042/BJ20121513

    Article  CAS  PubMed  Google Scholar 

  38. Sebastian, J., Richards, R.G., Walker, M. P., Wiesen, J.F., Werb, Z., Derynck, R., Hom,Y. K., Cunha, G.R., and DiAugustine, R. P., Cell Grow. Diff., 1998, vol. 9, pp. 777–785.

    CAS  Google Scholar 

  39. McBryan, J., Howlin, J., Napoletano, S., and Martin, F., J. Mammary Gland Biol. Neoplasia, 2008, vol. 13, pp.159–167. https://doi.org/10.1007/s10911-008-9075-7

    Article  PubMed  Google Scholar 

  40. Walker, F., Abramowitz, L., Benabderrahmane, D., Duval, X., Descatoire, V., Henin, D., Lehy, T., and Aparicio, T., Hum. Path., 2009, vol. 40, pp. 1517–1527. https://doi.org/10.1016/j.humpath.2009.05.010

    Article  CAS  PubMed  Google Scholar 

  41. Roskoski, R. Jr., Pharmacol Res., 2014, vol. 79, pp. 34–74. https://doi.org/10.1016/j.phrs.2013.11.002

    Article  CAS  PubMed  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are thankful to the head, Department of Bio-Technology, Kakatiya University, and Warangal for providing data of biological activity.

Author information

Authors and Affiliations

  1. Department of Chemistry, Chaitanya Deemed to be University, TS-506001, Warangal, India

    E. Ramya Sucharitha, N. Satheesh Kumar, M. Ravinder & Sirassu Narsimha

  2. Department of Chemistry, Kakatiya University, TS-506 009, Warangal, India

    N. Vasudeva Reddy

Authors
  1. E. Ramya Sucharitha
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. Satheesh Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Ravinder
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. Vasudeva Reddy
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sirassu Narsimha
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sirassu Narsimha.

Ethics declarations

COMPLIANCE WITH ETHICAL STANDARDS

No animals were involved in this work. No human subjects were involved in this work.

Conflict of Interests

No conflict of interest was declared by the authors.

Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

E. Ramya Sucharitha, Kumar, N.S., Ravinder, M. et al. Synthesis and Biological Evaluation of Novel Fused [1,2,3]Triazolo[4',5':3,4] pyrrolo[2,1-f]purines as Potent Anti-Proliferative Agents. Russ J Bioorg Chem 47, 896–905 (2021). https://doi.org/10.1134/S1068162021040208

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162021040208

Keywords:

Search

Navigation