SpringerLink
Log in

Synthesis of chalcones with methylenedioxypolymethoxy fragments based on plant metabolites and study of their antiproliferative properties

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Natural allylpolyalkoxybenzenes were used to synthesize polyalkoxychalcones featuring various conformations, including β-methyl-substituted S-trans-conformers and tetralone derivatives with restricted S-cis conformation. Antiproliferative antitubulin activity and cyto-toxicity of these compounds were studied using a sea urchin embryo model and human cancer cell lines. S-trans-Restricted chalcone 3y was found to exhibit high activity in the inhibition of cancer cell growth by microtubule destabilization with IC50 = 0.02–0.04 µmol L−1.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Germany)

Instant access to the full article PDF.

Institutional subscriptions

References

  1. M. L. Go, X. Wu, X. L. Liu, Curr. Med. Chem., 2005, 12, 481; DOI: https://doi.org/10.2174/0929867053363153.

    Article  CAS  PubMed  Google Scholar 

  2. M. Cabrera, M. Simoens, G. Falchi, M. L. Lavaggi, O. E. Piro, E. E. Castellano, A. Vidal, A. Azqueta, A. Monge, A. L. de Ceráin, G. Sagrera, G. Seoane, H. Cerecetto, M. González, Bioorg. Med. Chem., 2007, 15, 3356; DOI: https://doi.org/10.1016/j.bmc.2007.03.031.

    Article  CAS  PubMed  Google Scholar 

  3. A. Boumendjel, J. Boccard, P.-A. Carrupt, E. Nicolle, M. Blanc, A. Geze, L. Choisnard, D. Wouessidjewe, E.-L. Matera, C. Dumontet, J. Med. Chem., 2008, 51, 2307; DOI: https://doi.org/10.1021/jm0708331.

    Article  CAS  PubMed  Google Scholar 

  4. S. Ducki, D. Rennison, M. Woo, A. Kendall, J. F. Chabert, A. T. McGown, N. J. Lawrence, Bioorg. Med. Chem., 2009, 17, 76984; DOI: https://doi.org/10.1016/j.bmc.2009.09.039.

    Google Scholar 

  5. S. Ducki, G. Mackenzie, B. Greedy, S. Armitage, J. F. D. Chabert, E. Bennett, J. Nettles, J. P. Snyder, N. J. Lawrence, Bioorg. Med. Chem., 2009, 17, 7711; DOI: https://doi.org/10.1016/j.bmc.2009.09.044.

    Article  CAS  PubMed  Google Scholar 

  6. C. W. Mai, M. Yaeghoobi, N. Abd-Rahman, Y. B. Kang, M. R. Pichika, Eur. J. Med. Chem., 2014, 77, 378; DOI: https://doi.org/10.1016/j.ejmech.2014.03.002.

    Article  CAS  PubMed  Google Scholar 

  7. Y. Ouyang, J. Li, X. Chen, X. Fu, S. Sun, Q. Wu, Biomolecules, 2021, 11, 894; DOI: https://doi.org/10.3390/biom11060894.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. N. J. Lawrence, A. T. McGown, S. Ducki, J. A. Hadfield, Anticancer Drug Des., 2000, 15, 135.

    CAS  PubMed  Google Scholar 

  9. S. Ducki, G. Mackenzie, N. J. Lawrence, J. P. Snyder, J. Med. Chem., 2005, 48, 457; DOI: https://doi.org/10.1021/jm049444m.

    Article  CAS  PubMed  Google Scholar 

  10. V. V. Semenov, M. N. Semenova, Russ. Chem. Rev., 2015, 84, 134; DOI: https://doi.org/10.1070/RCR4449.

    Article  CAS  Google Scholar 

  11. Z. Rozmer, P. Perjési, Phytochem. Rev., 2016, 15, 87; DOI: https://doi.org/10.1007/s11101-014-9387-8.

    Article  CAS  Google Scholar 

  12. Y. Alias, K. Awang, A. H. Hadi, O. Thoison, T. Sévenet, M. Païs, J. Nat. Prod., 1995, 58, 1160; DOI: https://doi.org/10.1021/np50122a002.

    Article  CAS  PubMed  Google Scholar 

  13. J. Lee, H. W. Chun, T. H. Pham, J. H. Yoon, J. Lee, M. K. Choi, H. W. Ryu, S. R. Oh, J. Oh, D. Y. Yoon, J. Microbiol. Biotechnol., 2020, 30, 279; DOI: https://doi.org/10.4014/jmb.1909.09059.

    Article  PubMed  Google Scholar 

  14. J. Rathore, S. Garg, S. Gupta, Phytochemistry, 1981, 20, 1755; DOI: https://doi.org/10.1016/S0031-9422(00)98577-7.

    Article  CAS  Google Scholar 

  15. W. Baker, J. Chem. Soc., 1941, 662; DOI: https://doi.org/10.1039/JR9410000662.

  16. C. Nanjala, W. O. Odago, P. C. Rono, E. N. Waswa, E. S. Mutinda, M. A. Oulo, F. W. Muema, V. O. Wanga, E. M. Mkala, J. Kuja, M. M. Njire, G.-W. Hu, J. Ethnopharmacol., 2022, 295, 115404; DOI: https://doi.org/10.1016/j.jep.2022.115404.

    Article  CAS  PubMed  Google Scholar 

  17. N. B. Chernysheva, D. V. Tsyganov, A. A. Philchenkov, M. P. Zavelevich, A. S. Kiselyov, R. V. Semenov, M. N. Semenova, V. V. Semenov, Bioorg. Med. Chem. Lett., 2012, 22, 2590; DOI: https://doi.org/10.1016/j.bmcl.2012.01.128.

    Article  CAS  PubMed  Google Scholar 

  18. D. V. Demchuk, A. V. Samet, N. B. Chernysheva, V. I. Ushkarov, G. A. Stashina, L. D. Konyushkin, M. M. Raihstat, S. I. Firgang, A. A. Philchenkov, M. P. Zavelevich, L. M. Kuiava, V. F. Chekhun, D. Y. Blokhin, A. S. Kiselyov, M. N. Semenova, V. V. Semenov, Bioorg. Med. Chem., 2014, 22, 738; DOI: https://doi.org/10.1016/j.bmc.2013.12.015.

    Article  CAS  PubMed  Google Scholar 

  19. M. N. Semenova, D. V. Tsyganov, O. R. Malyshev, O. V. Ershov, I. N. Bardasov, R. V. Semenov, A. S. Kiselyov, V. V. Semenov, Bioorg. Med. Chem. Lett., 2014, 24, 3914; DOI: https://doi.org/10.1016/j.bmcl.2014.06.043.

    Article  CAS  PubMed  Google Scholar 

  20. M. N. Semenova, D. V. Demchuk, D. V. Tsyganov, N. B. Chernysheva, A. V. Samet, E. A. Silyanova, V. P. Kislyi, A. S. Maksimenko, A. E. Varakutin, L. D. Konyushkin, M. M. Raihstat, A. S. Kiselyov, V. V. Semenov, ACS Comb. Sci., 2018, 20, 700; DOI: https://doi.org/10.1021/acscombsci.8b00113.

    Article  CAS  PubMed  Google Scholar 

  21. S. Ducki, R. Forrest, J. A. Hadfield, A. Kendall, N. J. Lawrence, A. T. McGown, D. Rennison, Bioorg. Med. Chem. Lett., 1998, 8, 1051; DOI: https://doi.org/10.1016/s0960-894x(98)00162-0.

    Article  CAS  PubMed  Google Scholar 

  22. E. Królicka, K. Kieć-Kononowicz, D. Łażewska, Pharmaceuticals (Basel), 2022, 15, 847; DOI: https://doi.org/10.3390/ph15070847.

    Article  PubMed  Google Scholar 

  23. P. Mailliet, C. Combeau, M.-C. Bissery, T. Caulfield, G. Tiraboschi, M.-P. Cherrier, US Pat. US 2003/0153611 A1, 2003.

  24. J. Hu, J. Yan, J. Chen, Y. Pang, L. Huang, X. Li, Med. Chem. Commun., 2015, 6, 1318; DOI: https://doi.org/10.1039/C5MD00139K.

    Article  CAS  Google Scholar 

  25. W. D. Ollis, B. T. Redman, I. O. Sutherland, O. R. Gottlieb, Phytochemistry, 1978, 17, 1379; DOI: https://doi.org/10.1016/S0031-9422(00)94593-X.

    Article  CAS  Google Scholar 

  26. M. Iinuma, T. Tanaka, S. Matsuura, Chem. Pharm. Bull., 1984, 32, 3354; DOI: https://doi.org/10.1248/cpb.32.3354.

    Article  CAS  Google Scholar 

  27. K. Vongdeth, P. Han, W. Li, Q.-A. Wang, Chem. Nat. Compd., 2019, 55, 11; DOI: https://doi.org/10.1007/s10600-019-02605-x.

    Article  CAS  Google Scholar 

  28. V. V. Semenov, V. V. Rusak, E. M. Chartov, M. I. Zaretskii, L. D. Konyushkin, S. I. Firgang, A. O. Chizhov, V. V. Elkin, N. N. Latin, V. M. Bonashek, O. N. Stas’eva, Russ. Chem. Bull., 2007, 56, 2448; DOI: https://doi.org/10.1007/s11172-007-0389-1.

    Article  CAS  Google Scholar 

  29. V. V. Semenov, D. V. Tsyganov, M. N. Semenova, R. N. Chuprov-Netochin, M. M. Raihstat, L. D. Konyushkin, P. B. Volynchuk, E. I. Marusich, V. V. Nazarenko, S. V. Leonov, A. S. Kiselyov, J. Nat. Prod., 2016, 79, 1429; DOI: https://doi.org/10.1021/acs.jnatprod.6b00173.

    Article  CAS  PubMed  Google Scholar 

  30. V. V. Semenov, A. S. Kiselyov, I. Y. Titov, I. K. Sagamanova, N. N. Ikizalp, N. B. Chernysheva, D. V. Tsyganov, L. D. Konyushkin, S. I. Firgang, R. V. Semenov, I. B. Karmanova, M. M. Raihstat, M. N. Semenova, J. Nat. Prod., 2010, 73, 1796; DOI: https://doi.org/10.1021/np1004278.

    Article  CAS  PubMed  Google Scholar 

  31. D. V. Tsyganov, M. N. Semenova, L. D. Konyushkin, V. I. Ushkarov, M. M. Raihstat, V. V. Semenov, Mendeleev Commun., 2019, 29, 163; DOI: https://doi.org/10.1016/j.mencom.2019.03.015.

    Article  CAS  Google Scholar 

  32. N. A. Zefirov, A. V. Mamaeva, A. I. Krasnoperova, Y. A. Evteeva, E. R. Milaeva, O. N. Zefirova, S. A. Kuznetsov, Russ. Chem. Bull., 2021, 70, 549; DOI: https://doi.org/10.1007/s11172-021-3123-5.

    Article  CAS  Google Scholar 

  33. D. V. Tsyganov, A. V. Samet, E. A. Silyanova, V. I. Ushkarov, A. E. Varakutin, N. B. Chernysheva, R. N. Chuprov-Netochin, A. A. Khomutov, A. S. Volkova, S. V. Leonov, M. N. Semenova, V. V. Semenov, ACS Omega, 2022, 7, 3369; DOI: https://doi.org/10.1021/acsomega.1c05515.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. H. P. Hemantha, R. Ramanujam, M. Majeed, K. Nagabhushanam, Nat. Prod. Res., 2019, 35, 1413; DOI: https://doi.org/10.1080/14786419.2019.165035.

    Article  PubMed  Google Scholar 

  35. C. Pain, S. Celanire, G. Guillaumet, B. Joseph, Tetrahedron, 2003, 59, 9627; DOI: https://doi.org/10.1016/j.tet.2003.09.094.

    Article  CAS  Google Scholar 

  36. M. Waser, H. Falk, Monatsh. Chem., 2005, 136, 609; DOI: https://doi.org/10.1007/s00706-004-0263-x.

    Article  CAS  Google Scholar 

  37. M. Bougault, Ann. Chim. Phis. Ser. 7, 1902, 25, 483.

    CAS  Google Scholar 

  38. S. Messaoudi, B. Tréguier, A. Hamze, O. Provot, J.-F. Peyrat, J. R. De Losada, J.-M. Liu, J. Bignon, J. Wdzieczak-Bakala, S. Thoret, J. Dubois, J.-D. Brion, M. Alami, J. Med. Chem., 2009, 52, 4538; DOI: https://doi.org/10.1021/jm900321u.

    Article  CAS  PubMed  Google Scholar 

  39. F. J. Pond, O. P. Maxwell, G. M. Norman, J. Am. Chem. Soc., 1899, 21, 955; DOI: https://doi.org/10.1021/ja02061a002.

    Article  Google Scholar 

  40. V. Y. Bagirov, M. B. Belyi, F. A. Rasulov, N. M. Ismailov, Chem. Nat. Compd., 1982, 18, 123; DOI: https://doi.org/10.1007/BF00581620.

    Article  Google Scholar 

  41. Z.-T. Du, J. Lu, H.-R. Yu, Y. Xu, A.-P. Li, J. Chem. Res., 2010, 34, 222; DOI: https://doi.org/10.3184/030823410X12708998015900.

    Article  CAS  Google Scholar 

  42. M. Iinuma, T. Tanaka, S. Matsuura, Chem. Pharm. Bull., 1984, 32, 1006; DOI: https://doi.org/10.1248/cpb.32.1006.

    Article  CAS  Google Scholar 

  43. F. Dallacker, R.-D. Maier, R. Morcinek, A. Rabie, R. van Loo, Chem. Ber., 1980, 113, 1320; DOI: https://doi.org/10.1002/cber.19801130411.

    Article  CAS  Google Scholar 

  44. APEX-III, Bruker AXS Inc., Madison (WI), USA, 2019.

  45. L. Krause, R. Herbst-Irmer, G. M. Sheldrick, D. Stalke, J. Appl. Crystallogr., 2015, 48, 3; DOI: https://doi.org/10.1107/S1600576714022985.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  46. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found Adv., 2015, 71, 3; DOI: https://doi.org/10.1107/S2053273314026370.

    Article  Google Scholar 

  47. G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem, 2015, 71, 3; DOI: https://doi.org/10.1107/S2053229614024218.

    Article  Google Scholar 

  48. C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, J. van de Streek, J. Appl. Crystallogr., 2006, 39, 453; DOI: https://doi.org/10.1107/S002188980600731X.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

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

    A. E. Varakutin, E. A. Muravsky, D. V. Tsyganov, I. Yu. Shinkarev, A. I. Samigullina, T. S. Kuptsova & V. V. Semenov

  2. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    E. A. Muravsky & I. Yu. Shinkarev

  3. Moscow Institute of Physics and Technology, 9 Institutskii per., 141701, Dolgoprudny, Moscow Region, Russian Federation

    R. N. Chuprov-Netochin, A. V. Smirnova, A. A. Khomutov & S. V. Leonov

  4. N. K. Kol’tsov Institute of Developmental Biology, Russian Academy of Sciences, 26 ul. Vavilova, 119334, Moscow, Russian Federation

    M. N. Semenova

Authors
  1. A. E. Varakutin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. A. Muravsky
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. V. Tsyganov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. Yu. Shinkarev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. I. Samigullina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. T. S. Kuptsova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. R. N. Chuprov-Netochin
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. A. V. Smirnova
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. A. A. Khomutov
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. S. V. Leonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. M. N. Semenova
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. V. V. Semenov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. A. Muravsky.

Additional information

The crystal structure of chalcone 9b was determined at the Center for Collective Use of the N. D. Zelinsky Institute of Organic Chemistry of the RAS.

This work was financially supported by the Russian Science Foundation (Project No. 18-13-00044-R). The work of M. N. Semenova (the study of the activity of compounds on the sea urchin embryos model) was conducted under the IDB RAS Government basic research program in 2022 No. 0088-2024-0001.

All procedures conducted in the studies involving animals complied with the ethical standards of the institution where the studies were carried out and with the approved legal acts of the Russian Federation and international organizations.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 7, pp. 1632–1647, July, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Varakutin, A.E., Muravsky, E.A., Tsyganov, D.V. et al. Synthesis of chalcones with methylenedioxypolymethoxy fragments based on plant metabolites and study of their antiproliferative properties. Russ Chem Bull 72, 1632–1647 (2023). https://doi.org/10.1007/s11172-023-3943-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3943-6

Keywords

Search

Navigation