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Synthesis and Anticholinesterase Activity of 3-{[4-Methyl-3-(4-methylpiperazin-1-yl)]pent-1-en-1-yl}-4H-chromen-4-ones

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Abstract

A procedure has been developed and optimized for the synthesis of 3-{[4-methyl-3-(4-methylpiperazin-1-yl)]pent-1-en-1-yl}-4H-chromen-4-ones (as dihydrochlorides) by an unusual version of the Morita–Baylis–Hillman reaction. A number of the title compounds with various substituents in the chromene fragment and their deamination products have been synthesized, and their inhibitory activity against butyrylcholinesterase has been studied.

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References

  1. Sharma, S.K., Kumar, S., Chand, K., Kathuria, A., Gupta, A., and Jain, R., Curr. Med. Chem., 2011, vol. 18, no. 25, p. 3825. https://doi.org/10.2174/092986711803414359

    Article  CAS  Google Scholar 

  2. Gaspar, A., Matos, M.J., Garrido, J., Uriarte, E., and Borges, F., Chem. Rev., 2014, vol. 114, no. 9, p. 4960. https://doi.org/10.1021/cr400265z

    Article  CAS  Google Scholar 

  3. Santos, C.M.M., Silva, V.L.M., and Silva, A.M.S., Molecules, 2017, vol. 22, no. 10, p. 1665. https://doi.org/10.3390/molecules22101665

    Article  Google Scholar 

  4. Bornadiego, A., Díaz, J., and Marcos, C.F., J. Org. Chem., 2015, vol. 80, no. 12, p. 6165. https://doi.org/10.1021/acs.joc.5b00658

    Article  CAS  Google Scholar 

  5. Chernov, N.M., Shutov, R.V., Sharoyko, V.V., Kuz’mich, N.N., Belyakov, A.V., and Yakovlev, I.P., Eur. J. Org. Chem., 2017, vol. 2017, no. 19, p. 2386. https://doi.org/10.1002/ejoc.201700310

    Article  Google Scholar 

  6. Bodwell, G.J., Hawco, K.M., and da Silva, R.P., Synlett, 2003, no. 2, p. 179. https://doi.org/10.1055/s-2003-36800

    Google Scholar 

  7. Chernov, N.M., Shutov, R.V., Barygin, O.I., Dron, M.Y., Starova, G.L., Kuz’mich, N.N., and Yakovlev, I.P., Eur. J. Org. Chem., 2018, vol. 2018, no. 45, p. 6034. https://doi.org/10.1002/ejoc.201801159

    Article  Google Scholar 

  8. Gupta, R.C. and Dekundy, A., Drug Dev. Res., 2017, vol. 68, no. 5, p. 253. https://doi.org/10.1002/ddr.20186

    Article  Google Scholar 

  9. Francis, P.T., Palmer, A.M., Snape, M., and Wilcock, G.K., J. Neurol. Neurosurg. Psychiatry, 1999, vol. 66, no. 2, p. 137. https://doi.org/10.1136/jnnp.66.2.137

    Article  CAS  Google Scholar 

  10. Ciro, A., Park, J., Burkhard, G., Yan, N., and Geula, C., Curr. Alzheimer Res., 2012, vol. 9, no. 1, p. 138. https://doi.org/10.2174/156720512799015127

    Article  CAS  Google Scholar 

  11. Ellman, G.L., Courtney, K.D., Andres, V., and Featherstone, R.M., Biochem. Pharmacol., 1961, vol. 7, p. 88. https://doi.org/10.1016/0006-2952(61)90145-9

    Article  CAS  Google Scholar 

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Funding

This study was supported by the scholarship from the council for Grants at the President of the Russian Federation (competition no. SP-2019).

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Authors and Affiliations

  1. St. Petersburg State Chemical Pharmaceutical University, St. Petersburg, 197376, Russia

    P. V. Filippova, N. M. Chernov, R. V. Shutov & I. P. Yakovlev

Authors
  1. P. V. Filippova
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  2. N. M. Chernov
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  3. R. V. Shutov
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  4. I. P. Yakovlev
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Correspondence to N. M. Chernov.

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Filippova, P.V., Chernov, N.M., Shutov, R.V. et al. Synthesis and Anticholinesterase Activity of 3-{[4-Methyl-3-(4-methylpiperazin-1-yl)]pent-1-en-1-yl}-4H-chromen-4-ones. Russ J Gen Chem 89, 2471–2479 (2019). https://doi.org/10.1134/S1070363219120235

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  • DOI: https://doi.org/10.1134/S1070363219120235

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