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Synthesis of 9-bromocotarnine and its recyclization into 4-acyl-9-bromo-7,8-methylenedioxy-1,2-dihydro-3-benzazepines with anti-infective activity

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Abstract

9-Bromocotarnine in the stable perchlorate form has been obtained by the interaction of cotarnine with bromine. The reaction of 9-bromocotarnine with α-haloketones is accompanied by the extension of the six-membered hetero-ring to seven-membered ring and led to previously unknown 4-acyl-9-bromo-3-methyl-6-methoxy-7,8-methylendioxy-1,2-dihydro-3-benzazepines. Some of these compounds have been shown to have only moderate antibacterial (against Staphylococcus aureus, Escherichia coli) and fungistatic (Penicillium italicum) activities, but none of them has been shown to have a pronounced protistocidal activity against Colpoda steinii.

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Authors and Affiliations

  1. Institute of Organic and Physical Chemistry, South Federal University, Rostov-on-Don, 344090, Russia

    L. N. Divaeva & A. S. Morkovnik

  2. North-Caucasian Zonal Scientific Research Veterinary Institute, Novocherkassk, Russia

    A. A. Zubenko, Y. D. Drobin, N. M. Serbinovskaya, L. N. Fetisov, A. N. Bodryakov, M. A. Bodryakova & L. A. Lyashenko

  3. InterBioScreen Ltd, Moscow oblast, Chernogolovka, Russia

    V. G. Kartsev

Authors
  1. A. A. Zubenko
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  2. L. N. Divaeva
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  3. A. S. Morkovnik
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  4. V. G. Kartsev
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  5. Y. D. Drobin
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  6. N. M. Serbinovskaya
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  7. L. N. Fetisov
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  8. A. N. Bodryakov
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  9. M. A. Bodryakova
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  10. L. A. Lyashenko
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Corresponding author

Correspondence to L. N. Divaeva.

Additional information

Original Russian Text © A.A. Zubenko, L.N. Divaeva, A.S. Morkovnik, V.G. Kartsev, Y.D. Drobin, N.M. Serbinovskaya, L.N. Fetisov, A.N. Bodryakov, M.A. Bodryakova, L.A. Lyashenko, 2017, published in Bioorganicheskaya Khimiya, 2017, Vol. 43, No. 3, pp. 311–316.

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Zubenko, A.A., Divaeva, L.N., Morkovnik, A.S. et al. Synthesis of 9-bromocotarnine and its recyclization into 4-acyl-9-bromo-7,8-methylenedioxy-1,2-dihydro-3-benzazepines with anti-infective activity. Russ J Bioorg Chem 43, 311–316 (2017). https://doi.org/10.1134/S1068162017030189

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  • DOI: https://doi.org/10.1134/S1068162017030189

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