Synthesis of β-Octaethylporphyrin Conjugates with Nitrogen and Sulfur Containing Heterocycles

Alena O. Shkirdova,^a Ekaterina A. Orlova,^a Gelii V. Ponomarev,^b Vladimir S. Tyurin,^a Ilya A. Zamilatskov,^a@ and Aleksey K. Buryak^a

^aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 119071 Moscow, Russia

^bV.N. Orekhovich Institute of Biomedical Chemistry, 119121 Moscow, Russian Federation

^@Corresponding author E-mail: joz@mail.ru

DOI: 10.6060/mhc211046z
Macroheterocycles 2021 14(3) 204-208

Сonjugates of Ni(II) b-octaethylporphyrin with nitrogen and sulfur containing heterocycles were obtained by meso-functionalization of the porphyrin. The meso-functionalization of Ni(II) b-octaethylporphyrin was performed by the Vilsmeier-Haack formylation reaction, followed by the Knoevenagel reaction of Ni(II) meso-formyl- b-octaethylporphyrin with CH-acids: malonic ester, thiohydantoin, and thiobarbituric acid. The product of condensation of the porphyrin with malonic ester was cyclized with hydrazine to the corresponding porphyrin conjugate with pyrazolidine-3,5-dione. The optical spectra of the obtained new dyes are modified compared to that of the initial compounds. The spectral changes of the porphyrin conjugate with thiobarbituric acid are particularly dramatic reflecting the considerable interaction between tetrapyrrolic and heterocyclic chromophores in the molecule.

References:

Click here to expand or collapse this section

1. Stich M. I.J., Fischer L.H., Wolfbeis O.S. Chem. Soc. Rev. 2010, 39, 3102-3114.
https://doi.org/10.1039/b909635n

2. Ferrick D.A., Neilson A., Beeson C. Drug Discovery Today 2008, 13, 268-274.
https://doi.org/10.1016/j.drudis.2007.12.008

3. Zhdanov A.V., Favre C., O'Flaherty L., Adam J., O'Connor R., Pollard P.J., Papkovsky D.B. Integr. Biol. 2011, 3, 1135-1142.
https://doi.org/10.1039/c1ib00050k

4. Papkovsky D. B., Dmitriev R. I. Chem. Soc. Rev. 2013, 42, 8700-8732.
https://doi.org/10.1039/c3cs60131e

5. Fercher A., Ponomarev G.V., Yashunski D., Papkovsky D. Analyt. Bioanalyt. Chem. 2010, 396, 1793-1803.
https://doi.org/10.1007/s00216-009-3399-z

6. Paolesse R., Nardis S., Monti D., Stefanelli M., Di Natale C. Chem. Rev. 2017, 117, 2517-2583.
https://doi.org/10.1021/acs.chemrev.6b00361

7. Gupta V., Chauhan D., Saini V., Agarwal S., Antonijevic M., Lang H. Sensors 2003, 3, 223-235.
https://doi.org/10.3390/s30700223

8. Lei J., Ju H., Ikeda O. Sensors 2005, 5, 171-184.
https://doi.org/10.3390/s5040171

9. Norvaiša K., Kielmann M., Senge M. O. ChemBioChem 2020, 21, 1793-1807.
https://doi.org/10.1002/cbic.202000067

10. Rathee P., Tonk R.K., Dalal A., Ruhil M.K., Kumar A. Cellular and Molecular Biology 2016, 62, 141-145,
https://www.omicsonline.org/open-access/synthesis-and-application-of-thiobarbituric-acid-derivatives-as-antifungalagents-1165-158X-1000141.pdf

11. Zhang X.-Y., Gu Y.-F., Chen T., Yang D.-X., Wang X.-X., Jiang B.-L., Shao K.-P., Zhao W., Wang C., Wang J.-W., Zhang Q.-R., Liu H.-M. MedChemComm 2015, 6, 1781-1786.
https://doi.org/10.1039/C5MD00240K

12. Cho S., Kim S.-H., Shin D. Eur. J. Med. Chem. 2019, 164, 517-545.
https://doi.org/10.1016/j.ejmech.2018.12.066

13. Lee S. Y., Slagle-Webb B., Sharma A.K., Connor J.R. Anticancer Research 2020, 40, 6039-6049.
https://doi.org/10.21873/anticanres.14625

14. Deng G., Li W., Shen J., Jiang H., Chen K., Liu H. Bioorg. Med. Chem. Lett. 2008, 18, 5497-5502.
https://doi.org/10.1016/j.bmcl.2008.09.027

15. Mousapour K., Hajizadeh S., Farhadi K. Analyt. Methods 2020, 12, 2484-2490.
https://doi.org/10.1039/D0AY00160K

16. Yin R., Yu L., S, P., Liu G., Ge H., Wang S. Analytical Sciences 2021, Article ID: 21P218.
https://doi.org/10.2116/analsci.21P218

17. Yong X., Su M., Wan W., You W., Lu X., Qu J., Liu R. New J. Chem. 2013, 37, 1591-1594.
https://doi.org/10.1039/c3nj41134f

18. Johnson A.W., Oldfield D. J. Chem. Soc. C: Organic 1966, 794-798.
https://doi.org/10.1039/J39660000794

19. Shkirdova A.O., Zamilatskov I.A., Stanetskaya N.M., Tafeenko V.A., Tyurin V.S., Chernyshev V.V., Ponomarev G.V., Tsivadze A.Y. Macroheterocycles 2017, 10, 480-486.
https://doi.org/10.6060/mhc171148z

20. Cerqueira A.F.R., Moura N.M.M., Serra V.V., Faustino M.A.F., Tomé A.C., Cavaleiro J.A.S., Neves M.G.P.M.S. Molecules 2017, 22, 1269.
https://doi.org/10.3390/molecules22081269

21. Ponomarev G.V. Chem. Heterocycl. Cmpds 1994, 30, 1444-1465.
https://doi.org/10.1007/BF01172868

22. Arnold D.P., Johnson A.W., Mahendran M. J. Chem. Soc., Perkin Trans. 1 1978, 366-370.
https://doi.org/10.1039/p19780000366

23. Runge S., Senge M.O. Tetrahedron 1999, 55, 10375-10390.
https://doi.org/10.1016/S0040-4020(99)00579-7

24. Dahms K., Senge M.O., Bakri Bakar M. Eur. J. Org. Chem. 2007, 3833-3848.
https://doi.org/10.1002/ejoc.200700380

25. Erzina D.R., Zamilatskov I.A., Stanetskaya N.M., Tyurin V.S., Kozhemyakin G.L., Ponomarev G.V., Chernyshev V.V., Fitch A.N. Eur. J. Org. Chem. 2019, 2019, 1508-1522.
https://doi.org/10.1002/ejoc.201801659

26. Tyurin V.S., Erzina D.R., Zamilatskov I.A., Chernyadyev A.Y., Ponomarev G.V., Yashunskiy D.V., Maksimova A.V., Krasnovskiy A.A., Tsivadze A.Y. Macroheterocycles 2015, 8, 376-383.
https://doi.org/10.6060/mhc151199z

27. Volov A.N., Zamilatskov I.A., Mikhel I.S., Erzina D.R., Ponomarev G.V., Koifman O.I., Tsivadze A.Y. Macroheterocycles 2014, 7, 256-261.
https://doi.org/10.6060/mhc140274z

28. Kozhemyakin G.L., Tyurin V., Shkirdova A.O., Belyaev E., Kirinova E., Ponomarev G., Chistov A.A., Aralov A., Tafeenko V., Zamilatskov I. Org. Biomol. Chem. 2021, 19, 9199-9210.
https://doi.org/10.1039/D1OB01626A

29. Belyaev E.S., Shkirdova A.O., Kozhemyakin G.L., Tyurin V.S., Emets V.V., Grinberg V.A., Cheshkov D.A., Ponomarev G.V., Tafeenko V.A., Radchenko A.S., Kostyukov A.A., Egorov A.E., Kuzmin V.A., Zamilatskov I.A. Dyes Pigm. 2021, 191, 109354.
https://doi.org/10.1016/j.dyepig.2021.109354

30. Dox A.W., Plaisance G.P. J. Am. Chem. Soc. 1916, 38, 2164-2166.
https://doi.org/10.1021/ja02267a027

31. Witte L., Fuhrhop J.-H. Angew. Chemie Int. Ed. 1975, 14, 361-363.
https://doi.org/10.1002/anie.197503612

32. Haleem K.Z., Sabet Y.A., Ali K.A., Ali A.-H. A., Foaad A.R. Bull. Chem. Soc. Japan 1988, 61, 1345-1349.
https://doi.org/10.1246/bcsj.61.1345

33. Singh A.K., Usman M., Sciortino G., Garribba E., Rath S.P. Chemistry - A Eur. J. 2019, 25, 10098-10110.
https://doi.org/10.1002/chem.201901731

34. Locos O., Bašić B., McMurtrie J.C., Jensen P., Arnold D.P. Chemistry - A Eur. J. 2012, 18, 5574-5588.
https://doi.org/10.1002/chem.201102995

35. Hsiao J.-S., Krueger B.P., Wagner R.W., Johnson T.E., Delaney J.K., Mauzerall D.C., Fleming G.R., Lindsey J.S., Bocian D.F., Donohoe R.J. J. Am. Chem. Soc. 1996, 118, 11181-11193.
https://doi.org/10.1021/ja961612f

36. Senthilkumar M., Amaresan N., Sankaranarayanan A. In: Plant-Microbe Interactions: Laboratory Techniques, New York: Springer US, 2021. p. 103-105.
https://doi.org/10.1007/978-1-0716-1080-0_25

37. Wang X.-F.,Tamiaki H. Energy Environ. Sci. 2010, 3, 94-106.
https://doi.org/10.1039/B918464C

38. Fiedor L., Zbyradowski M., Pilch M. Tetrapyrrole pigments of photosynthetic antennae and reaction centers of higher plants: Structures, biophysics, functions, biochemistry, mechanisms of regulation, applications. In: Advances in Botanical Research, Vol. 90 (Grimm B., Ed.), London: Academic Press, 2019., Ch. 1, p. 1-33.
https://doi.org/10.1016/bs.abr.2019.04.001

Attachment	Size
mhc211046z.pdf	693.79 KB
mhc211046z-supp.pdf	41.08 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Synthesis of β-Octaethylporphyrin Conjugates with Nitrogen and Sulfur Containing Heterocycles

References: