Synthesis of Amides Based on Biologically Active 5Z,9Z-Eicosadienoic Acid

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

For the first time, amides of (5Z,9Z)-eicosa-5,9-dienoic acid, which exhibits a high inhibitory activity of topoisomerases I and II, were synthesized using aliphatic and O-containing 1,2-dienes at the key stage of the intermolecular cross-cyclomagnesiation reaction, catalyzed by Cp2TiCl2.

Full Text

Restricted Access

About the authors

E. Kh. Makarova

Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences

Author for correspondence.
Email: makarovaelina87@gmail.com
ORCID iD: 0000-0001-7481-0880
Russian Federation, 141, Oktyabr Ave., Ufa, 450075

A. A. Makarov

Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences

Email: makarovaelina87@gmail.com
ORCID iD: 0000-0001-7870-2334
Russian Federation, 141, Oktyabr Ave., Ufa, 450075

U. M. Dzhemilev

Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Email: makarovaelina87@gmail.com
ORCID iD: 0000-0002-7992-6337
Russian Federation, 47, Leninsky Ave., Moscow, 119991

V. A. Dyakonov

Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Email: makarovaelina87@gmail.com
ORCID iD: 0000-0002-7787-5054
Russian Federation, 47, Leninsky Ave., Moscow, 119991

References

  1. Johanss J.R. Synlett 2019, 30, 213–217. doi: 10.1055/s-0037-1611939
  2. Bezuglov V., Bobrov M., Gretskaya N., Gonchar A., Zinchenko G., Melck D., Bisogno T., Marzo V.Di, Kuklev D., Rossi J.-C., Vidald J.-P., Durand T. Bioorg. Med. Chem. Lett. 2001, 11, 447–449.
  3. Dionisi M., Alexander S.P.H., Bennett A.J. Lipids Health Disease 2012, 11, 51. doi: 10.1186/1476-511X-11-51
  4. Mueller G.P., Driscoll W.J. Vitamins & Hormones, 2009, 55–78. doi: 10.1016/s0083-6729(09)81003-0
  5. Sancho R. Mol. Pharmacol. 2003, 63 (2), 429–438. doi: 10.1124/mol.63.2.429
  6. Oz M. Curr. Pharm. Des. 2006, 12, 227–239.
  7. Verme J.L. Molecular Pharmacology 2005, 67 (1), 15–19. doi: 10.1124/mol.104.006353
  8. Petrosino S., Di Marzo V. Brit. J. Pharmacol. 2016, 174 (11), 1349–1365. doi: 10.1111/bph.13580
  9. Takao K., Noguchi K., Hashimoto Y., Shirahat A., Sugita Y. Chem. Pharm. Bull. 2015, 63 (4), 278–285. doi: 10.1248/cpb.c14-00881
  10. Rodriguez de Fonseca F., Navarro M., Gomez R., Escuredo L., Nava F., Fu J., Piomelli D. Nature 2001, 414 (6860), 209–212. doi: 10.1038/35102582
  11. Guzman M., Lo Verme J., Fu J., Oveisi F., Blazquez C., Piomelli D. J. Biol. Chem. 2004, 279 (27), 27849–27854. doi: 10.1074/jbc.m404087200
  12. Petrosino S., Di Marzo V. Handbook Neurochem. Mol. Neurobiol. 2009, 75–98.
  13. Maione S., Petrocellis L., Novellis V., Moriello A. S., Petrosino S., Palazzo E., Marzo V. Brit. J. Pharmacol. 2007, 150 (6), 766–781. doi: 10.1038/sj.bjp.0707145
  14. Ortar G., Cascio M.G., De Petrocellis L., Morera E., Rossi F., Schiano-Moriello A., Di Marzo V. J. Med. Chem. 2007, 50 (26), 6554–6569. doi: 10.1021/jm070678q
  15. Liu Y., Ji L., Eno M., Kudalkar S., Li A., Schimpgen M., Nikas S. P. J. Med. Chem. 2018, 61, 8639−8657. doi: 10.1021/acs.jmedchem.8b00611
  16. Grabiec U., Dehghani F. Cannabis Cannabinoid Res. 2017, 2 (1), 183–196. doi: 10.1089/can.2017.0015
  17. Burstein S., Salmonsen R. Bioorg. Med. Chem. 2008, 16 (22), 9644–9651. doi: 10.1016/j.bmc.2008.10.015
  18. D’yakonov V.A., Makarov A.A., Dzhemileva L.U., Makarova E.Kh., Khusnutdinova E.K., Dzhemilev U.M. Chem. Commun. 2013, 49, 8401–8403. doi: 10.1039/C3CC44926B
  19. D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M. Bioorg. Med. Chem. Lett., 2015, 25 (11), 2405–2408. doi: 10.1016/j.bmcl.2015.04.011
  20. D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M. Curr. Cancer Drug Targets 2015, 15 (6), 504–510. doi: 10.2174/1568009615666150506093155
  21. D’yakonov V.A., Dzhemileva L.U., Makarov A.A., Mulyukova A.R., Baev D.S., Khusnutdinova E.K., Tolstikova T.G., Dzhemilev U.M. Med. Chem. Res., 2016, 25 (1), 30–39. doi: 10.1007/s00044-015-1446-1
  22. Makarov A.A., Dzhemileva L.U., Salimova A.R., Makarova E.Kh., Ramazanov I.R., D'yakonov V.A., Dzhemilev U.M. Bioorg. Chem., 2020, 104, 104303. doi: 10.1016/j.bioorg.2020.104303
  23. Kojima N., Fushimi T., Tatsukawa T., Yoshimitsu T., Tanaka T., Yamori T., Dan S., Iwasaki H., Yamashita M. Eur. J. Med/ Chem. 2013, 63, 833–839. doi: 10.1016/j.ejmech.2013.03.009
  24. Kuang J., Ma S. J. Org. Chem., 2009, 74, 1763. doi: 10.1021/jo802391x

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Scheme

Download (115KB)
Indexing metadata
3. Scheme 1

Download (96KB)
Indexing metadata
4. Scheme 2

Download (57KB)
Indexing metadata

Copyright (c) 2025 Russian Academy of Sciences