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Synthesis of polyether macrodiolides based on acetylenic derivatives of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid

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Abstract

The stereoselective synthesis of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid was carried out using Ti-catalyzed homo-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran. Intermolecular esterification of this dicarboxylic acid with polyether acetylenic alcohols in the presence of carbodiimides was used to synthesize the corresponding monoesters and symmetric diesters. Using the intramolecular oxidative coupling of terminal triple bonds of the latter compounds, polyether macrodiolides containing 1Z,5Z-diene and 1,3-diyne fragments were synthesized.

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References

  1. T. N. Makarieva, E. A. Santalova, I. A. Gorshkova, A. S. Dmitrenok, A. G. Guzii, V. I. Gorbach, V. I. Svetashev, V. A. Stonik, Lipids, 2002, 37, 75–80; DOI: https://doi.org/10.1007/s11745-002-0866-6

    Article  PubMed  CAS  Google Scholar 

  2. P. M. Mishra, A. Sree, S. Baliarsingh, Chem. Nat. Compd, 2009, 45, 621–624; DOI: https://doi.org/10.1007/s10600-009-9445-4.

    Article  CAS  Google Scholar 

  3. N. M. Carballeira, Prog. Lipid Res., 2008, 47, 50–61; DOI: https://doi.org/10.1016/j.plipres.2007.10.002.

    Article  PubMed  CAS  Google Scholar 

  4. Y. Pommier, Chem. Rev., 2009, 109, 2894–2902; DOI: https://doi.org/10.1021/cr900097c.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  5. N. M. Carballeira, N. Montano, L. A. Amador, A. D. Rodríguez, M. Y. Golovko, S. A. Golovko, R. M. Reguera, R. Álvarez-Velilla, R. Balaña-Fouce, Lipids, 2016, 51, 245–256; DOI: https://doi.org/10.1007/s11745-015-4114-9.

    Article  PubMed  CAS  Google Scholar 

  6. J. L. Nitiss, Nat. Rev. Cancer., 2009, 9, 327–337; DOI: https://doi.org/10.1038/nrc2608.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  7. S. L. Wethington, J. D. Wright, T. J. Herzog, Expert Rev. Anticancer Ther., 2008, 8, 819–831; DOI: https://doi.org/10.1586/14737140.8.5.819.

    Article  PubMed  CAS  Google Scholar 

  8. V. A. D’yakonov, A. A. Makarov, A. R. Mulyukova, U. M. Dzhemilev, L. U. Dzhemileva, D. S. Baev, T. G. Tolstikova, E. K. Khusnutdinova, Med. Chem. Res., 2016, 25, 30–39; DOI: https://doi.org/10.1007/s00044-015-1446-1.

    Article  Google Scholar 

  9. V. A. D’yakonov, Dzhemilev Reactions in Organic and Organometallic Synthesis, NOVA Sci. Publishers, New York, 2010, 96 pp.

    Google Scholar 

  10. V. A. D’yakonov, L. U. Dzhemileva, A. A. Makarov, E. Kh. Makarova, E. K. Khusnutdinova, U. M. Dzhemilev, Chem. Commun., 2013, 49, 8401–8403; DOI: https://doi.org/10.1039/C3CC44926B.

    Article  Google Scholar 

  11. A. A. Makarov, L. U. Dzhemileva, A. R. Salimova, E. Kh. Makarova, I. R. Ramazanov, V. A. D’yakonov, U. M. Dzhemilev, Bioorg. Chem., 2020, 104, 104303, DOI: https://doi.org/10.1016/j.bioorg.2020.104303.

    Article  PubMed  CAS  Google Scholar 

  12. A. R. Tuktarov, L. L. Khuzina, A. A. Akhmetov, R. A. Tuktarova, S. R. Ishmukhametova, L. U. Dzhemileva, V. A. D’yakonov, U. M. Dzhemilev, Bioorg. Med. Chem. Lett., 2020, 30, 127289; DOI: https://doi.org/10.1016/j.bmcl.2020.127289.

    Article  PubMed  CAS  Google Scholar 

  13. V. A. D’yakonov, R. A. Tuktarova, L. U. Dzhemileva, S. R. Ishmukhametova, M. M. Yunusbaeva, U. M. Dzhemilev, Steroids, 2018, 138, 6–13; DOI: https://doi.org/10.1016/j.steroids.2018.06.004.

    Article  PubMed  Google Scholar 

  14. V. A. D’yakonov, R. A. Tuktarova, L. U. Dzhemileva, S. R. Ishmukhametova, M. M. Yunusbaeva, I. R. Ramazanov, U. M. Dzhemilev, Anti-Cancer Agents Med. Chem., 2017, 17, 1126–1135; DOI: 0.2174/1871520616666161207154850.

    Google Scholar 

  15. V. A. D’yakonov, R. A. Tuktarova, L. U. Dzhemileva, S. R. Ishmukhametova, U. M. Dzhemilev, Pharmaceuticals, 2021, 14, 84; DOI: https://doi.org/10.3390/ph14020084.

    Article  PubMed  PubMed Central  Google Scholar 

  16. G. Casillas-Vargas, C. Ocasio-Malavé, S. Medina, C. Morales-Guzmán, R. G. Del Valle, N. M. Carballeira, D. J. Sanabria-Ríos, Prog. Lipid Res., 2021, 82, 101093, DOI: https://doi.org/10.1016/j.plipres.2021.101093.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  17. Y. Lu, Y. Chen, Y. Wu, H. Hao, W. Liang, J. Liu, R. Huang, RSC Adv., 2019, 9, 35312; DOI: https://doi.org/10.1039/c9ra08119d.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  18. I. I. Islamov, A. A. Makarov, E. Kh. Makarova, A. V. Yusupova, V. A. D’yakonov, U. M. Dzhemilev, Russ. Chem. Bull., 2023, 72, 925–931; DOI: https://doi.org/10.1007/s11172-023-3855-1.

    Article  CAS  Google Scholar 

  19. A. A. Makarov, I. V. Ishbulatov, E. Kh. Makarova, U. M. Dzhemilev, V. A. D’yakonov, Russ. Chem. Bull., 2023, 72, 689–696, DOI: https://doi.org/10.1007/s11172-023-3833-6.

    Article  CAS  Google Scholar 

  20. U. M. Dzhemilev, L. U. Dzhemileva, V. A. D’yakonov, Russ. Chem. Bull., 2023, 72, 404–414, DOI: https://doi.org/10.1007/s11172-023-3808-8.

    Article  CAS  Google Scholar 

  21. S. Svedhem, C. Å. Hollander, J. Shi, P. Konradsson, B. Liedberg, S. C. Svensson, J. Org. Chem., 2001, 66, 4494–4503; DOI: https://doi.org/10.1021/jo0012290.

    Article  PubMed  CAS  Google Scholar 

  22. V. A. D’yakonov, L. U. Dzhemileva, R. A. Tuktarova, A. A. Makarov, I. I. Islamov, A. R. Mulyukova, U. M. Dzhemilev, Steroids, 2015, 102, 110–117; DOI: https://doi.org/10.1016/j.steroids.2015.08.006.

    Article  PubMed  Google Scholar 

  23. V. A. D’yakonov, I. I. Islamov, L. U. Dzhemileva, M. M. Yunusbaeva, U. M. Dzhemilev, Mend. Commun., 2019, 29, 613–615; DOI: https://doi.org/10.1016/j.mencom.2019.11.002.

    Article  Google Scholar 

  24. M. Marjanovic, M. Kralj, F. Supek, L. Frkanec, I. Piantanida, T. Smuc, L. Tusek-Bozic, J. Med. Chem., 2007, 50, 1007–1018; DOI: https://doi.org/10.1021/jm061162u.

    Article  PubMed  CAS  Google Scholar 

  25. A. Roy, P. Talukdar, ChemBioChem., 2021, 22, 2925–2940; DOI: https://doi.org/10.1002/cbic.202100112.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  26. I. Alfonso, R. Quesada, Chem. Sci., 2013, 4, 3009–3019; DOI: https://doi.org/10.1039/C3SC50882J.

    Article  CAS  Google Scholar 

  27. H. Zhang, R. Ye, Y. Mu, T. Li, H. Zeng, Nano Lett., 2021, 21, 1384–1391; DOI: https://doi.org/10.1021/acs.nanolett.0c04134.

    Article  PubMed  CAS  Google Scholar 

  28. M. B. Patel, E. Garrad, J. W. Meisel, S. Negin, M. R. Gokel, G. W. Gokel, RSC Adv., 2019, 9, 2217–2230; DOI: https://doi.org/10.1039/c8ra07641c.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  29. T. Yokoyama, M. Mizuguchi, J. Med. Chem., 2019, 62, 2076–2082; DOI: https://doi.org/10.1021/acs.jmedchem.8b01700.

    Article  PubMed  CAS  Google Scholar 

  30. A.-C. Bedard, S. K. Collins, J. Am. Chem. Soc., 2011, 133, 19976; DOI: https://doi.org/10.1021/ja208902t.

    Article  PubMed  CAS  Google Scholar 

  31. Yamamoto, K. Kurihara, A. Yamada, M. Takahashi, Y. Takahashi, N. Miyaura, Tetrahedron, 2003, 59, 537–542; DOI: https://doi.org/10.1016/S0040-4020(02)01557-0.

    Article  CAS  Google Scholar 

  32. J. A. Nieman, S. K. Nair, S. E. Heasley, B. L. Schultz, H. M. Zerth, R. A. Nugent, K. Chen, K. J. Stephanski, T. A. Hopkins, M. L. Knechtel, N. L. Oien, J. L. Wieber, M. W. Wathen, Bioorg. Med. Chem. Lett., 2010, 20, 3039–3042; DOI: https://doi.org/10.1016/j.bmcl.2010.03.115.

    Article  PubMed  CAS  Google Scholar 

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Funding

This work was performed under financial support of the Russian Science Foundation (Project No. 22-73-10164).

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    I. I. Islamov & A. V. Yusupova

  2. N. D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. A. D’yakonov & U. M. Dzhemilev

Authors
  1. I. I. Islamov
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  2. A. V. Yusupova
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  3. V. A. D’yakonov
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  4. U. M. Dzhemilev
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Corresponding author

Correspondence to I. I. Islamov.

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No human or animal subjects were used in this research.

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The authors declare no competing interests.

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Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2473–2483, October, 2023.

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Islamov, I.I., Yusupova, A.V., D’yakonov, V.A. et al. Synthesis of polyether macrodiolides based on acetylenic derivatives of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid. Russ Chem Bull 72, 2473–2483 (2023). https://doi.org/10.1007/s11172-023-4049-x

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  • DOI: https://doi.org/10.1007/s11172-023-4049-x

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