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Synthesis of New N-Mono- and N,N-Dialkylated Imidazole Derivatives and Their Antiplatelet and Anticoagulation Activity

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Currently there are several effective synthetic methods for preparing various N-mono- and N,N-dialkylated imidazole derivatives with a very wide variety of biological activities including antiplatelet and anticoagulation effects. The present work reports N-mono- and N,N-dialkylation of 2-methyl-, 2-ethyl-, and 4-nitroimidazoles using (adamantyl-1)bromomethylketone. The synthesized compounds were identified by elemental analyses and PMR and IR spectroscopy. Five compounds having antiplatelet properties were found in in vitro investigations of the antiplatelet and anticoagulation activity in blood of healthy volunteers. The anticoagulation effects of these compounds on the maximum aggregation amplitude were comparable with that of acetylsalicylic acid and even exceeded it with respect to the duration of inhibition of the platelet release reaction.

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References

  1. X.-Q. Wang, P.-T. Ye, M.-J. Bai, et al., Bioorg. Med. Chem. Lett., 30, 127210 (2020).

    Article  Google Scholar 

  2. M. Nakazawa, K. Iizuka, A. Ujiie, et al., J. Pharm. Soc. Jpn., 114(12), 911 – 933 (1994).

    Article  CAS  Google Scholar 

  3. J. J. Baldwin, D. C. Remy, and A. Claremon, US Pat. 5,098,707, Merck & Co., Inc., Mar. 24, 1992.

  4. A. J. Bojarski, M. J. Mokrosz, et al., Bioorg. Med. Chem., 50(1), 87 – 95 (2002).

    Article  Google Scholar 

  5. V. A. Klimova, Principal Microanalytical Methods for Organic Compounds [in Russian], Khimiya, Moscow (1975), pp. 51 – 56.

  6. A. F. Pozharskii, V. A. Anisimova, and E. B. Tsupak, Practical Works in the Chemistry of Heterocycles [in Russian], RGU (1988) p. 98.

  7. D. Li, H. Bao, Q. Tan, et al., Synth. Commun., 35(8), 1017 – 1026 (2005).

    Article  CAS  Google Scholar 

  8. G. V. R. Born, J. Physiol., 162, 67 – 68 (1962).

    Google Scholar 

  9. D. A. Abaimov, L. R. Spavronskaya, A. A. Shabalina, et al., Khim.-farm. Zh., 53(1), 52 – 57 (2019); Pharm. Chem. J., 53(1), 65 – 70 (2019); https://doi.org/10.1007/s11094-019-01957-6.

  10. A. N. Mironov (ed.), Handbook for Preclinical Drug Trials [in Russian], Vol. 1, Grif i K, Moscow (2013).

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Authors and Affiliations

  1. A. I. Evdokimov Moscow State University of Medicine and Dentistry, 20/1 Delegatskaya St., Moscow, 127473, Russia

    K. G. Gurevich

  2. Izhevsk State Medical Academy, Ministry of Health of the RF, 281 Kommunarov St., Izhevsk, Udmurtia, 426034, Russia

    A. L. Urakov & I. I. Bashirov

  3. Institute of Natural Sciences, S. P. Korolev Samara National Research University, 34 Moskovskoe Shosse, Samara, 443086, Russia

    A. V. Basantsev, A. A. Danilin, P. P. Purygin & N. A. Klenova

  4. Bashkir State Medical University, Ministry of Health of the RF, 3 Lenina St., Ufa, Bashkortostan, 450008, Russia

    A. V. Samorodov, L. I. Bashirova, V. I. Korunas & D. O. Lipatov

  5. Togliatti State University, 14 Belorusskaya St., Togliatti, 445020, Russia

    A. A. Golovanov

Authors
  1. K. G. Gurevich
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  2. A. L. Urakov
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  3. A. V. Basantsev
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  4. A. V. Samorodov
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  5. A. A. Danilin
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  6. P. P. Purygin
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  7. N. A. Klenova
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  8. I. I. Bashirov
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  9. L. I. Bashirova
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  10. A. A. Golovanov
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  11. V. I. Korunas
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  12. D. O. Lipatov
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Corresponding author

Correspondence to A. L. Urakov.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 55, No. 2, pp. 8 – 12, February, 2021.

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Gurevich, K.G., Urakov, A.L., Basantsev, A.V. et al. Synthesis of New N-Mono- and N,N-Dialkylated Imidazole Derivatives and Their Antiplatelet and Anticoagulation Activity. Pharm Chem J 55, 119–122 (2021). https://doi.org/10.1007/s11094-021-02395-z

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  • DOI: https://doi.org/10.1007/s11094-021-02395-z

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