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

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 photopharmacol...

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Bibliographic Details
Published in:Russian chemical bulletin 2021-07, Vol.70 (7), p.1388-1393
Main Authors: Ozhogin, I. V., Zolotukhin, P. V., Tkachev, V. V., Pugachev, A. D., Kozlenko, A. S., Belanova, A. A., Aldoshin, S. M., Lukyanov, B. S.
Format: Article
Language:English
Subjects:
Biological activity
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Chlorine
Cytotoxicity
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Infrared spectroscopy
Inorganic Chemistry
Lipoic acid
Mass spectrometry
NMR
Nuclear magnetic resonance
Organic Chemistry
Spiropyrans
Synthesis
Toxicity
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Summary: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.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-021-3228-x