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Synthesis and antioxidant screening of Novel indole amines

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Abstract

Novel indoles amines have been synthesized and screened for antioxidant activity. Chiron approach is used to synthesis enantiopure heterocycles. Newly synthesized indole amines showed good antioxidant potential as compared to standard drugs. Novel indole amines (1317) were synthesized and showed promising DPPH scavenging activity, The H2O2 inhibition potential and the Ferric ion (Fe3+) reducing antioxidant power assay. The pharmacological activity is tested by targeting indolic diazepines derivatives.

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Data availability

Samples of the compounds 4–17 are available from the authors.

Code availability

DPI = Compound no:4, LR89F = Compound no:6, LR_III_83A = Compound no:7 LR-89C = Compound no:9, LR-89D = Compound no:10, LR_SJ_I = Compound no:11, LR_SJ_V = Compound no:11, LR-52 = Compound no:13, LR_III_45B = Compound no:14, LR_III_60E = Compound no:15,, 2R = Compound no:16, LR-5R = Compound no:17.

References

  1. L. Yu, B. Gao, Y. Li, T.T. Wang, Y. Luo, J. Wang, L.L. Yu, Food Funct. 9(1), 585–593 (2018)

    Article  CAS  Google Scholar 

  2. S. Lee, K.Y. Yi, S.K. Kim, J. Suh, N.J. Kim, S.E. Yoo, B.H. Lee, H.W. Sao, S.O. Kim, H. Lim, Eur. J. Med. Chem. 38, 459 (2003)

    Article  CAS  Google Scholar 

  3. F. Zhang, Y. Zhao, L. Sun, L. Ding, Y. Gu, P. Gong, Eur. J. Med. Chem. 46, 3149 (2011)

    Article  CAS  Google Scholar 

  4. N. Gilhotra, D. Dhingra, Nat. Prod. Radiance 5, 476 (2008)

    Google Scholar 

  5. M.R. Karekal, B.H. Mathada, Turkish J. Chem. 37, 775 (2013)

    Article  CAS  Google Scholar 

  6. S. Shanavas, J. Duraimurugan, G. Suresh Kumar, R. Ramesh, R. Acevedo, P.M. Anbarasan, P. Maadeswaran, Mater. Res. Express 6, 105098 (2019)

    Article  CAS  Google Scholar 

  7. S.K. Bhati, A. Kumar, Eur. J. Med. Chem. 43, 2323 (2008)

    Article  CAS  Google Scholar 

  8. I.A. Leneva, R.J. Russell, Y.S. Boriskin, A.J. Hay, Antivir. Res. 81, 132 (2009)

    Article  CAS  Google Scholar 

  9. B.B. Mishra, K.R. Singh, A. Srivastava, V.J. Tripathi, V.K. Tiwari, Mini. Rev. Med. Chem. 9, 107 (2009)

    Article  CAS  Google Scholar 

  10. S. Shanavas, T. Ahamad, S.M. Alshehri, A. Sultan, R. Acevedo, P.M. Anbarasan, Opt. Laser Technol. 123, 105902 (2020)

    Article  CAS  Google Scholar 

  11. A. Flake, R.D. Scalley, A.G. Bailey, Am. Fam. Phys. 69, 1169 (2004)

    Google Scholar 

  12. H.Y.A. Enein, I. Kruk, K. Lichszteld, T. Michalska, A. Kiadna, S. Marczynski, S. Olgen, Luminescence 19, 1 (2004)

    Article  Google Scholar 

  13. M.L. Mohler, Y. He, Z. Wu, D.J. Hwang, D.D. Miller, Med. Res. Rev. 29, 125 (2009)

    Article  CAS  Google Scholar 

  14. European Food Safety Authority, EFSA J. 10, 2686 (2012)

    Article  Google Scholar 

  15. S. Süzen, Top. Heterocycl. Chem. 11, 145 (2007)

    Article  Google Scholar 

  16. L.X. Cheng, J.J. Tang, H. Luo, X.L. **, F. Dai, J. Yang, Y.P. Qian, X. Li, B. Zhou, Bioorg. Med. Chem. Lett. 20, 2417 (2010)

    Article  CAS  Google Scholar 

  17. S. Shanavas, A. Priyadharsan, S. Karthikeyan, K. Dharmaboopathi, I. Ragavan, C. Vidya, R. Acevedo, P.M. Anbarasan, Mat. Today: Proc. 26, 3531 (2020)

    CAS  Google Scholar 

  18. S.H. Benabadji, R.J. Wen, B. Zheng, X.C. Dong, S.G. Yuan, Acta. Pharmacol. Sin. 25, 666 (2004)

    CAS  PubMed  Google Scholar 

  19. Q.V. Vo, C. Trenerry, S. Rochfort, J. Wadeson, C. Leyton, A.B. Hughes, Bioorg. Med. Chem. 22, 856 (2014)

    Article  CAS  Google Scholar 

  20. S.L. Rubab, B. Nisar, A.R. Raza, N. Ullah, M.N. Tahir, Molecules 19, 139e148 (2013)

    Article  Google Scholar 

  21. B. Nisar, A.R. Raza, D.S. Black, N. Kumar, M.N. Tahir, Chirality 25, 865e870 (2013)

    Article  Google Scholar 

  22. G.M. Ziarani, R. Moradi, T. Ahmadi, N. Lashgari, RSC Adv. 8, 12069 (2018)

    Article  Google Scholar 

  23. G. Yao, Z.X. Zhang, C.B. Zhang, H.H. Xu, R.Y. Tang, Molecules 23, 3317 (2018)

    Article  Google Scholar 

  24. C. Xu, J. Xu, J. Org. Chem. 83, 14733 (2018)

    Article  CAS  Google Scholar 

  25. A.P. Rajput, S.S. Rajput, Int. J. Pharm. Tech. Res. 1, 1605 (2009)

    CAS  Google Scholar 

  26. B. Nisar, S.L. Rubab, A.R. Raza, S. Tariq, A. Sultan, M.N. Tahir, Mol. Diversity 22, 709 (2018)

    Article  CAS  Google Scholar 

  27. S. Tariq, A.R. Raza, M. Khalid, S.L. Rubab, M.U. Khan, A. Ali, M.N. Tahir, A.A.C. Braga, J. Mol. Struc. 1203, 127438 (2019)

    Article  Google Scholar 

  28. M.F. Ismail, A.A. El-sayed, J. Iran. Chem. Soc. 16, 921 (2019)

    Article  CAS  Google Scholar 

  29. S.A. Ibrahim, H.F. Rizk, M.A. El-Borai, M.E. Sadek, J. Iran. Chem. Soc. 18, 1391 (2021)

    Article  CAS  Google Scholar 

  30. D. Azarifar, H. Ebrahimiasl, R. Karamian, A.K. Masoumeh, J. Iran. Chem. Soc. 16, 341 (2019)

    Article  CAS  Google Scholar 

  31. G. Thirupathi, E. Yadaiah Goud, Y. Hemasri, M.D. Suban Ali, Y. Jayaprakash Rao, J. Iran. Chem. Soc. 14, 477 (2017)

    Article  CAS  Google Scholar 

  32. S.U. Tekale, S.S. Kauthale, R.U. Shaikh, R.P. Marathe, R.B. Nawale, R.P. Pawar, J. Iran. Chem. Soc. 11, 717 (2014)

    Article  CAS  Google Scholar 

  33. M.M. Rahman, M.B. Islam, M. Biswas, A.K. Alam, BMC. Res. Notes 8, 1 (2015)

    Article  CAS  Google Scholar 

  34. C. Sanchez-Moreno, Food Sci. Technol. Int. 8, 121 (2002)

    Article  CAS  Google Scholar 

  35. M. Oyaizu, Jpn J Nut. 44, 307–315 (1986)

    Article  CAS  Google Scholar 

  36. M. Jabeen, S. Ali, S. Shahzadi, M. Shahid, Q.M. Khan, S.K. Sharma, K. Qanungo, J. Iran. Chem. Soc. 9, 307 (2012)

    Article  CAS  Google Scholar 

  37. R. Govindarasu, M.K. Subramanian, A. Arunkumar, S. Shanavas, P.M. Anbarasan, T. Ahamad, S.M. Alshehri, J. Iran. Chem. Soc. 18, 1279 (2021)

    Article  CAS  Google Scholar 

  38. S. Shahzadi, S. Ali, J. Iran. Chem. Soc. 5, 16 (2008)

    Article  CAS  Google Scholar 

  39. S. Shanavas, A. Priyadharsan, V. Vasanthakumar, A. Arunkumar, P.M. Anbarasan, S. Bharathkumar, J. Photochem. Photobiol., A 340, 96 (2017)

    Article  CAS  Google Scholar 

  40. İ Gulcin, Arch. Toxicol. 94, 651 (2020)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors acknowledge the Higher Education Commission (HEC) of Pakistan for generous financial support for research funding (HEC-20-3873). We are grateful to the University of Sargodha for the provision of basic instruments and the XRD facility.

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Contributions

SLR: Conception or design of the work, data collection, analysis and interpretation; BN: Conception or design of the work; ARR: Conception or design of the work; MS: Data analysis and interpretation; MNT: Data Collection; NS: Data Collection; SS: Final approval of the version to be published; RA: Final approval of the version to be published.

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Correspondence to Syeda Laila Rubab or Roberto Acevedo.

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Rubab, S.L., Nisar, B., Raza, A.R. et al. Synthesis and antioxidant screening of Novel indole amines. J IRAN CHEM SOC 19, 2693–2704 (2022). https://doi.org/10.1007/s13738-021-02482-8

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