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Facile One-Pot Approach to the Synthesis of Alkyl Piperazine-1-carbodithioates as Hemolytic and Thrombolytic Agents

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Abstract

A polyethylene glycol (PEG)-promoted methodology has been utilized for synthesis of piperazine-based dithiocarbamates. One-pot reaction of N-methylpiperazine and N-Boc-piperazine with various substituted arylmethyl bromides or 2-bromo-1-phenylethanone and carbon disulfide using PEG as solvent afforded the target S-alkyl piperazine-1-carbodithioates in high yields (80–90%). The synthesized compounds were charac­terized by 1H and 13C NMR and FT-IR spectroscopy. Furthermore, cytotoxic potential of these piperazine derivatives was evaluated via hemolysis and thrombolysis. The synthesized compounds displayed hemolytic potential in the range from 0.1±0.004 to 9.63±0.249% and thrombolytic activity in the range from 48.17±0.016 to 63.56±0.124%.

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REFERENCES

  1. Getty, K.E., Ye, Z., and Dai, M., Synthesis, 2017, vol. 49, p. 2589. https://doi.org/10.1055/s-0036-1589491

    Article  CAS  Google Scholar 

  2. Akhtar, R., Zahoor, A.F., Rasul, A., Ahmad, M., Anjum, M.N., Ajmal, M., and Raza, Z., Pak. J. Pharm. Sci., 2019, vol. 32, p. 2215.

    PubMed  Google Scholar 

  3. Zahoor, A.F., Yousaf, M., Siddique, R., Ahmad, S., Naqvi, S.A.R., and Rizvi, S.M.A., Synth. Commun., 2017, vol. 47, p. 1021. https://doi.org/10.1080/00397911.2017.1300921

    Article  CAS  Google Scholar 

  4. Hafeez, F., Zahoor, A.F., Ahmad, S., Ahmad, M., and Faiz, S., Synth. Commun., 2019, vol. 49, p. 325. https://doi.org/10.1080/00397911.2018.1515367

    Article  CAS  Google Scholar 

  5. Akhtar, R., Zahoor, A.F., Rasul, A., Khan, S.G., and Ali, K.G., Pak. J. Pharm. Sci., 2021, vol. 34, p. 1143. https://doi.org/10.36721/PJPS.2021.34.3.SUP.11431148.1

    Article  CAS  PubMed  Google Scholar 

  6. Taha, M., Irshad, M., Imran, S., Chigurupati, S., Selvaraj, M., Rahim, F., Ismail, N.H., Nawaz, F., and Khan, K.M., Eur. J. Med. Chem., 2017, vol. 141, p. 530. https://doi.org/10.1016/j.ejmech.2017.10.028

    Article  CAS  PubMed  Google Scholar 

  7. Todorovic, A. and Haskell-Luevano, C., Peptides, 2005, vol. 26, p. 2026. https://doi.org/10.1016/j.peptides.2004.11.024

    Article  CAS  PubMed  Google Scholar 

  8. Akhtar, R., Yousaf, M., Naqvi, S.A.R., Irfan, M., Zahoor, A.F., Hussain, A.I., and Chatha, S.A.S., Synth. Commun., 2016, vol. 46, p. 1849. https://doi.org/10.1080/00397911.2016.1234622

    Article  CAS  Google Scholar 

  9. Asadipour, A., Shams, Z., Eskandari, K., Moshafi, M.H., Faghih-Mirzaei, E., and Pourshojaei, Y., Res. Chem. Intermed., 2018, vol. 44, p. 1295. https://doi.org/10.1007/s11164-017-3167-1

    Article  CAS  Google Scholar 

  10. Hayat, F., Ali, R.F., Rehman, Z., and BѐlangerGarlepy, F., Inorg. Chem. Commun., 2020, vol. 121, article ID 108190. https://doi.org/10.1016/j.inoche.2020.108190

  11. Oliveira, J.W.F., Rocha, H.A.O., Medeiros, W.M.T.Q., and Silva, M.S., Molecules, 2019, vol. 24, article no. 2806. https://doi.org/10.3390/molecules24152806

  12. Veignie, E., Ceballos, C., Len, C., and Rafin, C., ACS Omega, 2019, vol. 4, p. 4779. https://doi.org/10.1021/acsomega.8b03685

    Article  CAS  Google Scholar 

  13. Hafeez, F., Zahoor, A.F., Rasul, A., Ahmad, S., and Mansha, A., Pak. J. Pharm. Sci., 2021, vol. 34, p. 353. https://doi.org/10.36721/PJPS.2021.34.1.SUP.353-357.1

    Article  CAS  PubMed  Google Scholar 

  14. Kamal, A., Sreekanth, K., Shankaraiah, N., Sathish, M., Nekkanti, S., and Srinivasulu, V., Bioorg Chem., 2015, vol. 59, p. 23. https://doi.org/10.1016/j.bioorg.2015.01.002

    Article  CAS  PubMed  Google Scholar 

  15. Wong, R. and Dolman, S.J., J. Org. Chem., 2007, vol. 72, p. 3969. https://doi.org/10.1021/jo070246n

    Article  CAS  PubMed  Google Scholar 

  16. Jamir, L., Sinha, U.P., Nath, J., and Patel, B.K., Synth. Commun., 2012, vol. 42, p. 951. https://doi.org/10.1080/00397911.2010.532276

    Article  CAS  Google Scholar 

  17. Halimehjani, A.Z., Pourshojaei, Y., and Saidi, M.R., Tetrahedron Lett., 2009, vol. 50, p. 32. https://doi.org/10.1016/j.tetlet.2008.10.063

    Article  CAS  Google Scholar 

  18. Anastas, P.T. and Kirchhoff, M.M., Acc. Chem. Res., 2002, vol. 35, p. 686. https://doi.org/10.1021/ar010065m

    Article  CAS  PubMed  Google Scholar 

  19. Cernasky, R., Nature, 2015, vol. 519, p. 379. https://doi.org/10.1038/nj7543-379a

    Article  Google Scholar 

  20. Horvàth, I.T. and Anastas, P.T., Chem. Rev., 2007, vol. 107, p. 2169. https://doi.org/10.1021/cr078380v

    Article  CAS  PubMed  Google Scholar 

  21. Li, C. and Trost, B.M., Proc. Natl. Acad. Sci. U. S. A., 2008, vol. 105, p. 13197. https://doi.org/10.1073/pnas.0804348105

    Article  PubMed  PubMed Central  Google Scholar 

  22. Constable, D.J.C., Dunn, P.J., Hayler, J.D., Humph­rey, G.R., Leazer, J.L., Linderman, R.J., Lorenz, K., Manley, J., Pearlman, B.A., Wells, A., Zaks, A., and Zang, T.Y., Green Chem., 2007, vol. 9, p. 411. https://doi.org/10.1039/b703488c

    Article  CAS  Google Scholar 

  23. Sheldon, R.A., Green Chem., 2005, vol. 7, p. 267. https://doi.org/10.1039/b418069k

    Article  CAS  Google Scholar 

  24. Li, Z., Liu, D., Chen, Y., Yin, Y., Wang, Z., and Sun, X., J. Chem. Res., 2017, vol. 40, p. 515. https://doi.org/10.3184/174751916X14682481534021

    Article  CAS  Google Scholar 

  25. Thomas, P.A. and Marvey, B.B., Molecules, 2016, vol. 21, p. 184. https://doi.org/10.3390/molecules21020184

    Article  CAS  PubMed Central  Google Scholar 

  26. Nagarapu, L., Mallepali, R., Arava, G., and Yera­manchi, L., Eur. J. Chem., 2010, vol. 2010, p. 228. https://doi.org/10.5155/eurjchem.1.3.228-231.172

    Article  CAS  Google Scholar 

  27. Soni, J., Sahiba, N., Sethiya, A., and Agarwal, S., J. Mol. Liq., 2020, vol. 315, article ID 113766. https://doi.org/10.1016/j.molliq.2020.113766

  28. Azizi, N. and Gholbeglo, E.A., RSC Adv., 2012, vol. 2, p. 7413. https://doi.org/10.1039/C2RA20615C

    Article  CAS  Google Scholar 

  29. Shahzadi, I., Zahoor, A.F., Rasul, A., Rasool, N., Raza, Z., Faisal, S., Parveen, B., Kamal, S., Rehman, M.Z., and Zahid, F.M., J. Heterocycl. Chem., 2020, vol. 57, p. 2782. https://doi.org/10.1002/jhet.3987

    Article  CAS  Google Scholar 

  30. Hafeez, F., Mansha, A., Zahoor, A.F., Ali, K.G., Khan, S.G., and Naqvi, S.A.R., Pak. J. Pharm. Sci., 2021, vol. 34, p. 1885. https://doi.org/10.36721/PJPS.2021.34.5.SUP.18851890.1

    Article  CAS  PubMed  Google Scholar 

  31. Shahzadi, I., Zahoor, A.F., Rasul, A., Mansha, A., Ahmad, S., and Raza, Z., ACS Omega, 2021, vol. 6, p. 11943. https://doi.org/10.1021/acsomega.1c00424

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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ACKNOWLEDGMENTS

The authors thank Government College University Faisalabad (GCUF) and HEC Pakistan for providing neces­sary facilities.

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Authors and Affiliations

  1. Department of Chemistry, Government College University Faisalabad, 38000, Faisalabad, Pakistan

    F. Hafeez & A. F. Zahoor

  2. Department of Pharmaceutics, Government College University Faisalabad, 38000, Faisalabad, Pakistan

    M. Irfan

  3. Department of Biochemistry, Government College University Faisalabad, 38000, Faisalabad, Pakistan

    S. Kamal

  4. Department of Chemistry, University of Engineering and Technology Lahore, Faisalabad Campus, 38000, Faisalabad, Pakistan

    S. Ahmad

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  1. F. Hafeez
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  2. A. F. Zahoor
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  3. M. Irfan
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  4. S. Kamal
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  5. S. Ahmad
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Correspondence to A. F. Zahoor.

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Hafeez, F., Zahoor, A.F., Irfan, M. et al. Facile One-Pot Approach to the Synthesis of Alkyl Piperazine-1-carbodithioates as Hemolytic and Thrombolytic Agents. Russ J Org Chem 58, 884–890 (2022). https://doi.org/10.1134/S1070428022060197

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  • DOI: https://doi.org/10.1134/S1070428022060197

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