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Synthesis of methylsulfanyl analogs of Kaede protein chromophore

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Chemistry of Heterocyclic Compounds Aims and scope

A Correction to this article was published on 01 August 2020

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5-Arylidene-1-methyl-2-[2-(methylsulfanyl)-2-phenylethenyl]-1H-imidazol-5(4H)-ones were synthesized as a result of the reaction of 5-arylidene-1-methyl-2-(methylsulfanyl)-1H-imidazol-5(4H)-ones with terminal acetylenes in the presence of a palladium catalyst and copper iodide. This reaction presents a rare example of the formation of a compound with a methylsulfanylethenyl group. A study of the optical properties of the obtained compounds showed that they are characterized by a significant bathochromic shift of spectral maxima in comparison with similar derivatives of the GFP chromophore.

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  • 29 September 2020

    To the article ���Synthesis of methylsulfanyl analogs of Kaede protein chromophore��� by Elvira R. Zaitseva, Alexander Yu. Smirnov, Sofya I. Shcerbinina, Vlada V. Zasedateleva, Konstantin S. Mineev, Mikhail S. Baranov

References

  1. Walker, C. L.; Lukyanov, K. A.; Yampolsky, I. V; Mishin, A. S.; Bommarius, A. S.; Duraj-Thatte, A. M.; Azizi, B.; Tolbert, L. M.; Solntsev, K. M. Curr. Opin. Chem. Biol. 2015, 27, 64.

    Article  CAS  Google Scholar 

  2. Ge, S.; Deng, H.; Su, Y.; Zhu, X. RSC Adv. 2017, 7, 17980.

    Article  CAS  Google Scholar 

  3. Povarova, N. V; Bozhanova, N. G.; Sarkisyan, K. S.; Gritcenko, R.; Baranov, M. S.; Yampolsky, I. V; Lukyanov, K. A.; Mishin, A. S. J. Mater. Chem. C 2016, 4, 3036.

  4. Povarova, N. V; Zaitseva, S. O.; Baleeva, N. S.; Smirnov, A. Y.; Myasnyanko, I. N.; Zagudaylova, M. B.; Bozhanova, N. G.; Gorbachev, D. A.; Malyshevskaya, K. K.; Gavrikov, A. S.; Mishin A. S.; Baranov, M. S. Chem.–Eur. J. 2019, 25, 9592.

    Article  CAS  Google Scholar 

  5. Ermakova, Y. G.; Bogdanova, Y. A.; Baleeva, N. S.; Zaitseva, S. O.; Guglya, E. B.; Smirnov, A. Y.; Zagudaylova, M. B.; Baranov, M. S. Dyes Pigm. 2019, 170, 107550.

    Article  CAS  Google Scholar 

  6. Cheng, H.-G.; Chen, H.; Liu, Y.; Zhou, Q. Asian J. Org. Chem. 2018, 7, 490.

    CAS  Google Scholar 

  7. Mehta, V. P.; Sharma, A.; Van der Eycken, E. Org. Lett. 2008, 10, 1147.

    Article  CAS  Google Scholar 

  8. Arambasic, M.; Majhail, M. K.; Straker, R. N.; Neuhaus, J. D.; Willis, M. C. Chem. Commun. 2019, 55, 2757.

    Article  CAS  Google Scholar 

  9. Iwasaki, M.; Topolovčan, N.; Hu, H.; Nishimura, Y.; Gagnot, G.; Na nakorn, R.; Yuvacharaskul, R.; Nakajima, K.; Nishihara, Y. Org. Lett. 2016, 18, 1642.

    Article  CAS  Google Scholar 

  10. Hooper, J. F.; Chaplin, A. B.; González-Rodríguez, C.; Thompson, A. L.; Weller, A. S.; Willis, M. C. J. Am. Chem. Soc. 2012, 134, 2906.

    Article  CAS  Google Scholar 

  11. Gosling, S.; Rollin, P.; Tatibouët, A. Synthesis 2011, 3649.

  12. Oumouch, S.; Bourotte, M.; Schmitt, M.; Bourguignon, J.-J. Synthesis 2005, 25.

  13. Saxena, G.; Chaudhary, A.; Naqvi, A.; Khan, S.; Seth, D. S. Orient. J. Chem. 2008, 24, 347.

    CAS  Google Scholar 

  14. Mendgen, T.; Steuer, C.; Klein, C. D. J. Med. Chem. 2012, 55, 743.

    Article  CAS  Google Scholar 

  15. Kadry, A. M.; Mansour, S. A. J. Heterocycl. Chem. 1985, 22, 155.

    Article  CAS  Google Scholar 

  16. Zaitseva, S. O.; Golodukhina, S. V; Baleeva, N. S.; Levina, E. A.; Smirnov, A. Y.; Zagudaylova, M. B.; Baranov, M. S. ChemistrySelect 2018, 3, 8593.

    Article  CAS  Google Scholar 

  17. Baranov, M. S.; Solntsev, K. M.; Lukyanov, K. A.; Yampolsky, I. V. Chem. Commun. 2013, 49, 5778.

    Article  CAS  Google Scholar 

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The study was carried out with the financial support of the Russian Foundation for Basic Research within the framework of the scientific project No. 20-33-70266.

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Authors and Affiliations

  1. D. Mendeleyev University of Chemical Technology of Russia, 9 Miusskaya Sq, Moscow, 125047, Russia

    Elvira R. Zaitseva

  2. Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St, Moscow, 117997, Russia

    Elvira R. Zaitseva, Alexander Yu. Smirnov, Sofya I. Shcerbinina, Vlada V. Zasedateleva, Konstantin S. Mineev & Mikhail S. Baranov

  3. Pirogov Russian National Research Medical University, 1 Ostrovitianova St, Moscow, 117997, Russia

    Mikhail S. Baranov

Authors
  1. Elvira R. Zaitseva
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  2. Alexander Yu. Smirnov
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  3. Sofya I. Shcerbinina
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  4. Vlada V. Zasedateleva
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  5. Konstantin S. Mineev
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  6. Mikhail S. Baranov
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Corresponding author

Correspondence to Alexander Yu. Smirnov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(3), 399–402

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Zaitseva, E.R., Smirnov, A.Y., Shcerbinina, S.I. et al. Synthesis of methylsulfanyl analogs of Kaede protein chromophore. Chem Heterocycl Comp 56, 399–402 (2020). https://doi.org/10.1007/s10593-020-02673-w

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  • DOI: https://doi.org/10.1007/s10593-020-02673-w

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