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Synthesis and Structure of Dimephosphone Pyridinoylhydrazones with Antimycobacterial Activity

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Pharmaceutical Chemistry Journal Aims and scope

Nicotinoyl- and isonicotinoylhydrazones of 2-dimethoxyphosphoryl-2-methylpentan-4-one (the active ingredient of the medicinal preparation Dimephosphone) were synthesized. It was shown that crystals of both hydrazones contained a single spatial form of the EC=N isomer. The dimephosphone pyridinoylhydrazones existed in slightly polar and polar solvents as a mixture of two amide conformers of a single EC=N isomer. This was due to hindered rotation of the molecular fragments around the (O=)C–N amide bond. The ratio of conformers was determined by the solvent and the time of solution preparation. Both hydrazones possessed low toxicity and high antimycobacterial activity.

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Acknowledgments

The work was supported financially by a joint grant of the Russian Foundation for Basic Research and the Academy of Sciences of the Republic of Tatarstan (Grant 09-03-97007-p_povolzh’e_a).

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Tatarstan, 420088, Russia

    B. I. Buzykin, V. N. Nabiullin & V. F. Mironov

  2. Kazan State Medical University, Kazan, Tatarstan, 420008, Russia

    R. S. Garaev & L. R. Kashapov

  3. Republic Clinical TB Dispensary, Kazan, Tatarstan, 420049, Russia

    R. V. Chestnova & R. Sh. Valeev

Authors
  1. B. I. Buzykin
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  2. V. N. Nabiullin
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  3. R. S. Garaev
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  4. R. V. Chestnova
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  5. L. R. Kashapov
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  6. R. Sh. Valeev
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  7. V. F. Mironov
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Corresponding author

Correspondence to B. I. Buzykin.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 47, No. 1, pp. 36–40, January, 2013.

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Buzykin, B.I., Nabiullin, V.N., Garaev, R.S. et al. Synthesis and Structure of Dimephosphone Pyridinoylhydrazones with Antimycobacterial Activity. Pharm Chem J 47, 35–39 (2013). https://doi.org/10.1007/s11094-013-0891-8

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  • DOI: https://doi.org/10.1007/s11094-013-0891-8

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