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p-Tyrosol: a new synthetic method and new types of pharmacological activity

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Abstract

A new method for the synthesis of p-tyrosol, i.e., 2-(4-hydroxyphenyl)ethanol, has been developed, which considerably simplified the process of preparation of this pharmaceutical substance. The method includes nitration of 2-phenylethanol, catalytic hydrogenation of 2-(4nitrophenyl)ethyl nitrate, and nitrosation of 2-(4-aminophenyl)ethanol, followed by acid hydrolysis of the intermediate diazo compound. The method is easily feasible, furnishes the pharmaceutical substance of high quality, and is quite acceptable for commercialization. Antihypertensive and hemorheologic activities of p-tyrosol in spontaneously hypertensive rats were investigated per se and in combination with captopril. p-Tyrosol in the course administration with captopril was found to enhance the antihypertensive effect of the latter and eliminate its negative effect on red blood cell aggregation.

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Authors and Affiliations

  1. Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, 1 ul. Sotsialisticheskaya, 659322, Biisk, Russian Federation

    S. V. Sysolyatin, Yu. A. Kryukov, V. V. Malykhin & K. K. Muradov

  2. E. D. Gol’dberg Institute of Pharmacology and Regenerative Medicine, 3 prosp. Lenina, 634028, Tomsk, Russian Federation

    G. A. Chernysheva, O. I. Aliev, V. I. Smol’yakova, A. M. Anishchenko, A. V. Sidekhmenova, A. Yu. Shamanaev & M. B. Plotnikov

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  1. S. V. Sysolyatin
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  2. Yu. A. Kryukov
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  3. V. V. Malykhin
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  4. K. K. Muradov
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  5. G. A. Chernysheva
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  6. O. I. Aliev
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  7. V. I. Smol’yakova
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  8. A. M. Anishchenko
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  9. A. V. Sidekhmenova
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  10. A. Yu. Shamanaev
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  11. M. B. Plotnikov
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Corresponding authors

Correspondence to Yu. A. Kryukov or M. B. Plotnikov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2210–2214, September, 2015.

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Sysolyatin, S.V., Kryukov, Y.A., Malykhin, V.V. et al. p-Tyrosol: a new synthetic method and new types of pharmacological activity. Russ Chem Bull 64, 2210–2214 (2015). https://doi.org/10.1007/s11172-015-1140-y

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  • DOI: https://doi.org/10.1007/s11172-015-1140-y

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