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Synthesis and neurotropic activity of 6,8-diamino derivatives of pyrano[3,4-c]pyridines

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Abstract

New diamino derivatives of pyrano[3,4-c]pyridines were synthesized by the pyridine ring recyclization. The presence of the intramolecular hydrogen bond in 6-[(4-methoxyphenyl)amino]-3,3-dimethyl8-methylamino-3,4-dihydro-1H-pyrano[3,4-c]pyridin-5-carbonitrile was identified by X-ray diffraction. A pharmacological study of the synthesized compounds was carried out in known tests, such as assay for antagonism induced by corazole subcutaneous injection and the open field test. The method of rotating rod was used to evaluate neurotoxicity. The diamino derivatives of pyrano[3,4-c]pyridines were found to possess neutrotropic properties. The synthesized compounds, as well as diazepam, prevent the occurrence of clonic seizures and clonic corazoleinduced convulsions in animals; however, they cause a behavior-depressing sedative effect.

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Authors and Affiliations

  1. Mndzhoyan Institute of Fine Organic Chemistry, Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    E. G. Paronikyan, Sh. Sh. Dashyan, I. A. Dzhagatspanyan, R. G. Paronikyan, I. M. Nazaryan & A. G. Akopyan

  2. Molecular Structure Research Center, Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    N. S. Minasyan, A. G. Ayvazyan & R. A. Tamazyan

  3. Moscow State University, Moscow, 119991, Russia

    E. V. Babaev

Authors
  1. E. G. Paronikyan
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  2. Sh. Sh. Dashyan
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  3. I. A. Dzhagatspanyan
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  4. R. G. Paronikyan
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  5. I. M. Nazaryan
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  6. A. G. Akopyan
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  7. N. S. Minasyan
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  8. A. G. Ayvazyan
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  9. R. A. Tamazyan
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  10. E. V. Babaev
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Corresponding author

Correspondence to Sh. Sh. Dashyan.

Additional information

Original Russian Text © E.G. Paronikyan, Sh.Sh. Dashyan, I.A. Dzhagatspanyan, R.G. Paronikyan, I.M. Nazaryan, A.G. Akopyan, N.S. Minasyan, A.G. Ayvazyan, R.A. Tamazyan, E.V. Babaev, 2016, published in Bioorganicheskaya Khimiya, 2016, Vol. 42, No. 2, pp. 238–246.

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Paronikyan, E.G., Dashyan, S.S., Dzhagatspanyan, I.A. et al. Synthesis and neurotropic activity of 6,8-diamino derivatives of pyrano[3,4-c]pyridines. Russ J Bioorg Chem 42, 215–223 (2016). https://doi.org/10.1134/S1068162016020102

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  • DOI: https://doi.org/10.1134/S1068162016020102

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