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Synthesis and study of new indoline spiropyran and its derivative with α-lipoic acid exhibiting low cytotoxicity

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Abstract

New indoline spiropyran was synthesized by the cyclocondensation of 5-chlorine-substituted Fischer base with 2,7-dihydroxy-1-naphthaldehyde. This spiropyran was used to prepare a new derivative of α-lipoic acid with potential biological activity, which can be considered as a promising photopharmacological agent. The structures of the synthesized compounds were determined by NMR and IR spectroscopy and mass spectrometry and were confirmed by X-ray diffraction. Biological assays using HeLa cells showed that the spirocyclic compounds possess low cytotoxicity even at relatively high concentrations.

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    I. V. Ozhogin, A. D. Pugachev, A. S. Kozlenko & B. S. Lukyanov

  2. Academy of Biology and Biotechnology, Southern Federal University, 194/1 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    P. V. Zolotukhin & A. A. Belanova

  3. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    V. V. Tkachev & S. M. Aldoshin

Authors
  1. I. V. Ozhogin
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  2. P. V. Zolotukhin
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  3. V. V. Tkachev
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  4. A. D. Pugachev
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  5. A. S. Kozlenko
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  6. A. A. Belanova
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  7. S. M. Aldoshin
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  8. B. S. Lukyanov
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Corresponding author

Correspondence to I. V. Ozhogin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1388–1393, July, 2021.

This work was financially supported by the Russian Science Foundation (Project No. 19-73-00224). The X-ray diffraction studies were performed within the framework of the state assignment (registration number AAAAA19-119092390076-7, V. V. Tkachev and S. M. Aldoshin).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Ozhogin, I.V., Zolotukhin, P.V., Tkachev, V.V. et al. Synthesis and study of new indoline spiropyran and its derivative with α-lipoic acid exhibiting low cytotoxicity. Russ Chem Bull 70, 1388–1393 (2021). https://doi.org/10.1007/s11172-021-3228-x

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  • DOI: https://doi.org/10.1007/s11172-021-3228-x

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