Izvestiya of Saratov University.

Chemistry. Biology. Ecology

ISSN 1816-9775 (Print)
ISSN 2541-8971 (Online)

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Rogov D. A., Krivenko A. P. Cycvalone in the synthesis of nitrogen-, oxygen-containing heterocycles. Izvestiya of Saratov University. Chemistry. Biology. Ecology, 2023, vol. 23, iss. 2, pp. 159-165. DOI: 10.18500/1816-9775-2023-23-2-159-165, EDN: BUMKGQ

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Cycvalone in the synthesis of nitrogen-, oxygen-containing heterocycles

Rogov Danila A., Saratov State University
Krivenko Adel P., Saratov State University

Cycvalone is an analogue of curcumin (EE conformation), exhibits a wide range of biological activity (antioxidant, hepatoprotective, membrane stabilizing, anti-ulcer) and is used in medical practice as a choleretic. Numerous methods of producing cycvalone are known, including industrial ones, but its reactions have been studied much less. Some reactions of cycvalone with N, C-nucleophiles (hydrazines, malononitrile) have been carried out. Reactions with getarylamines that could lead to the synthesis of compounds including pharmacophore fragments remained completely unexplored. We have used cycvalone as a substrate for the synthesis of nitrogen-, oxygen-containing heterosystems of a number of chromenopyrimidine, aminochromencarbonitrile, indazole, triazoloquinazoline. The structure of the obtained new substances has been established by spectral methods (IR, NMR). Schemes of formation of reaction products have been proposed.

  1. Машковский М. Д. Лекарственные средства : в 2 т. М. : Медицина, 1986. Т. 1. 624 с.
  2. Dinkova-Kostova A. T., Abeygunawardana C., Talalay P. Chemoprotective properties of phenylpropenoids, bis (benzylidene) cycloalkanones, and related Michael reaction acceptors: Correlation of potencies as phase 2 enzyme inducers and radical scavengers // J. Med. Chem. 1998. Vol. 41, № 26. P. 5287–5296. https://doi.org/10.1021/jm980424s
  3. Carlson G. L., Hall I. H., Abernethy G. S., Piantadosi C. Cycloalkanones. Antifertility activity // J. Med. Chem. 1973. Vol. 17, № 12. P. 154–159. https://doi.org/ 10.1021/jm00258a004
  4. Gafner S., Lee S. K., Cuendet M., Barthelemy S., Vergnes L., Labidalle S. Biologic evaluation of curcumin and structural derivatives in cancer chemoprevention model // Phytochemistry. 2004. Vol. 65, № 21. P. 2849–2859. https://doi.org/10.1016/j.phytochem. 2004.08.008
  5. Симонян М. А., Диб Х., Пашков А. Н., Симонян А. В., Мячина О. В., Островский О. В. Синтез, антирадикальная и антиоксидантная активность циквалона и его аналогов // Хим. фарм. журнал. 2007. Т. 41, № 8. C. 7–10. https://doi.org/10.30906/0023-1134-2007-41-8-7-10
  6. Патент 2088569 Российская Федерация, МПК С07С49/743, С07С49/747 (2006.01) тема: №94033536: заявл. 12.09.1994: опубл. 27.08.1997 / Симонян А. В. – 1 с. : ил. – Текст: непосредственный
  7. Bayomi S. M., El-Kashef H. A., El-Ashmawy M. B. Synthesis and biological evalua-tion of new curcumin derivatives as antioxidant and antitumor agents // Med. Chem. Res. 2013. Vol. 22, № 3. P. 1147–1162. https://doi.org/ 10.1016/j.ejmech.2015.07.014
  8. Moutafa A. H., Mohammed S. M., Abd El-Salam E. A., El-Sayed H. A. Synthesis and Antimicrobial Activity of New 3H-Chromeno[2,3-d]pyrimidines Derivatives // Russ. J. Gen. Chem. 2020. Vol. 90, № 8. P. 1566– 1672. https://doi.org/10.1134/S1070363220080277
  9. Fayed A. A., El-Manawaty M. A., Yousif N. M. Synthesis and cytotoxic evaluation of novel chromenes and chromene(2,3-d)pyrimidines // J. Appl. Pharm. Science. 2020. Vol. 10, № 12. P. 35–43. https://doi.org/10.7324/ JAPS.2020.101205
  10. Karimi N., Davoodnia A. Synthesis of new 3Hchromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement // Heterocyclic Communications. 2018. Vol. 24, № 1. P. 31–35. https://doi.org/10.1515/hc-2017-0228
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