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Synthesis and Biological Activity of (Z)-Dialkylaminoalkylamides of N-Benzoyl-α,β-Dehydroamino Acids and Their Iodomethylates

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A series of N,N-(dialkylamino)alkylamides of several N-substituted α,β-dehydroamino acids and their quaternary ammonium salts were synthesized via the reaction of unsaturated 5(4H)-oxazolones with N,N-dialkyldiamines and characterized by physicochemical characteristics. Their reactions with human erythrocytic acetylcholinesterase (ACE) and plasmic butyrylcholinesterase (BuCE) were studied. The IC50 values [concentration at which the hydrolysis rate of cholinesterase was 50% inhibited by acetylthiocholine (0.1 mM)] of all synthesized compounds were determined. It was found that all synthesized compounds possessed anticholinesterase activity and were specific mainly for BuCE.

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References

  1. A. A. Grigoryan, A. A. Ambartsumyan, M. V. Mkrtchyan, et al., Khim.-farm. Zh., 40(3), 18 – 23 (2006); Pharm. Chem. J., 40(3), 135 – 140 (2006).

  2. H. A. Grigoryan, A. A. Hambardzumyan, M. V. Mkrtchyan, et al., NAS RA Electron. J. Nat. Sci., 1(6), 14 – 20 (2006).

    Google Scholar 

  3. H. A. Grigoryan, A. A. Hambardzumyan, M. V. Mkrtchyan, et al., Chem.-Biol. Interact., 171(1), 108 – 116 (2008).

    Article  CAS  PubMed  Google Scholar 

  4. A. A. Spasov, D. S. Yakovlev, and L. F. Suzdalev, Khim.-farm. Zh., 46(10), 14 – 17 (2012); Pharm. Chem. J., 46(10), 584 – 590 (2012).

  5. A. Kawasaki, K. Meakawa, K. Kubo, et al., Tetrahedron, 60(42), 9517 – 9524 (2004).

    Article  CAS  Google Scholar 

  6. V. O. Topuzyan and S. R. Tosunyan, Khim. Zh. Arm., 65(3), 369 – 373 (2012).

    CAS  Google Scholar 

  7. G. Fairbanks, T. L. Stec, and D. F. Wallach, Biochemistry, 10(13), 2606 – 2617 (1971).

    Article  CAS  PubMed  Google Scholar 

  8. B. N. La Du, C. F. Bartels, C. P. Nogueria, et al., Clin. Biochem., 23, 423 – 431 (1990).

    Article  PubMed  Google Scholar 

  9. G. L. Ellman, K. D. Coutney, V. Andres, Jr., et al., Biochem. Pharmacol., 7, 88 – 95 (1961).

    Article  CAS  PubMed  Google Scholar 

  10. P. W. Riddles, R. L. Blakeley, and B. Zerner, Anal. Biochem., 94(1), 75 – 81 (1979).

    Article  CAS  PubMed  Google Scholar 

  11. G. N. Pershin, Methods of Experimental Chemotherapy [in Russian], Meditsina, Moscow (1971), pp. 507 – 522.

    Google Scholar 

  12. M. D. Mashkovskii, Drugs [in Russian], Novaya Volna, Moscow (2010), p. 851.

    Google Scholar 

  13. C. G. Caloran, G. P. Dillon, J. M. Gaynor, et al., J. Med. Chem., 51(20), 6400 – 6409 (2008).

    Article  Google Scholar 

Download references

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Authors and Affiliations

  1. A. L. Mnjoyan Institute of Fine Organic Chemistry, Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, 26 Azatutyan Pr., 0014, Yerevan, 375014, Armenia

    V. O. Topuzyan, S. R. Tosunyan, S. G. Chshmarityan & R. V. Paronikyan

Authors
  1. V. O. Topuzyan
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  2. S. R. Tosunyan
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  3. S. G. Chshmarityan
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  4. R. V. Paronikyan
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Corresponding author

Correspondence to S. R. Tosunyan.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 51, No. 10, pp. 26 – 29, October, 2017.

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Topuzyan, V.O., Tosunyan, S.R., Chshmarityan, S.G. et al. Synthesis and Biological Activity of (Z)-Dialkylaminoalkylamides of N-Benzoyl-α,β-Dehydroamino Acids and Their Iodomethylates. Pharm Chem J 51, 877–880 (2018). https://doi.org/10.1007/s11094-018-1708-6

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  • DOI: https://doi.org/10.1007/s11094-018-1708-6

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