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Structural analogs of umifenovir 2*. The synthesis and antiHIV activity study of new regioisomeric (trans-2-phenylcyclopropyl)-1Н-indole derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

We report new carboanalogs of umifenovir – regioisomeric derivatives of ethyl 5-hydroxy-(trans-2-phenylcyclopropyl)-1Н-indole-3-carboxylate. The inhibition of HIV replication by umifenovir and its carboanalogs at micromolar concentration range has been demonstrated for the first time.

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Notes

  1. The unambiguous assignment is not possible due to the proximity of the signals for protons H-6 and H-7 of the indole moiety.

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This work received financial support from the Russian Foundation for Basic Research (grants NK 13-03-00144/14 and MD-1658.2014.3, for the preparation and study of compound rac-МС-1501).

The authors would like to acknowledge the contribution by graduate student E. K. Zakharova at the Organic Chemistry Department of Volgograd State Technical University in isolation and purification of the target compounds.

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Authors and Affiliations

  1. Rega Institute for Medical Research, 10 Minderbroederstraat, Leuven, 3000, Belgium

    Dominique Schols

  2. Closed Joint Stock Company “Farm-Synthesis”, 2-ya, House 2, Build. 9 Kabel’naya St, Moscow, 111024, Russia

    Evsey A. Ruchko

  3. G. F. Gauze Scientific Research Institute of New Antibiotics, 11 Bol’shaya Pirogovskaya St, Moscow, 119021, Russia

    Sergey N. Lavrenov

  4. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119991, Russia

    Vadim V. Kachala

  5. Volgograd State Technical University, 28 Lenina Ave, Volgograd, 400005, Russia

    Maksim B. Nawrozkij & Alexandre S. Babushkin

Authors
  1. Dominique Schols
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  2. Evsey A. Ruchko
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  3. Sergey N. Lavrenov
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  4. Vadim V. Kachala
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  5. Maksim B. Nawrozkij
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  6. Alexandre S. Babushkin
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Corresponding author

Correspondence to Maksim B. Nawrozkij.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(11/12), 978–983

* For Communication 1, see 1.

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Schols, D., Ruchko, E.A., Lavrenov, S.N. et al. Structural analogs of umifenovir 2*. The synthesis and antiHIV activity study of new regioisomeric (trans-2-phenylcyclopropyl)-1Н-indole derivatives. Chem Heterocycl Comp 51, 978–983 (2015). https://doi.org/10.1007/s10593-016-1807-9

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  • DOI: https://doi.org/10.1007/s10593-016-1807-9

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