Direct synthesis of a new hybrid molecules based on isomerically pure 5Z,9Z-dienoic acids and monocarbonyl derivatives of curcuminoids
- Authors: Islamov I.I1, Yusupova A.V1, Dyakonov V.A2, Dzhemilev U.M2
- 
							Affiliations: 
							- Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
 
- Issue: Vol 59, No 5 (2023)
- Pages: 679-686
- Section: Articles
- URL: https://kld-journal.fedlab.ru/0514-7492/article/view/666298
- DOI: https://doi.org/10.31857/S0514749223050166
- EDN: https://elibrary.ru/EDBEPX
- ID: 666298
Cite item
Abstract
Synthesis of previously undescribed hybrid compounds based on monocarbonyl derivatives of curcumin and 5 Z ,9 Z -dienoic acids with yields of 61-67% was carried out for the first time. Unsaturated acids are synthesized using at the key stage of stereoselective reaction of intermolecular cross-cyclomagnesiation of aliphatic and O-containing 1,2-dienes catalyzed by Cp2TiCl2.
			                About the authors
I. I Islamov
Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences
														Email: iislamovi@gmail.com
				                					                																			                												                														
A. V Yusupova
Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences
														Email: iislamovi@gmail.com
				                					                																			                												                														
V. A Dyakonov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
														Email: iislamovi@gmail.com
				                					                																			                												                														
U. M Dzhemilev
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
														Email: iislamovi@gmail.com
				                					                																			                												                														
References
- Shishodia S., Sethi G., Aggarwal B.B. Ann. N.Y. Acad. Sci. 2005, 1056, 206-217. doi: 10.1196/annals.1352.010
- Zhang Y., Khan A. R., Fu M., Zhai Y., Ji J., Bobrovskaya L., Zhai G. J. Drug Target. 2019, 27, 917-931. doi: 10.1080/1061186X.2019.1572158
- Ashrafizadeh M., Ahmadi Z., Mohamamdinejad R., Yaribeygi H., Serban M.C., Orafai H.M., Sahebkar A. Curr. Pharm. Biotechnol. 2020, 21, 1006-1015. doi: 10.2174/1389201021666200305115101
- Hatcher H., Planalp R., Cho J., Torti F.M., Torti S.V. Cell. Mol. Life Sci. 2008, 65, 1631-1652. doi: 10.1007/s00018-008-7452-4
- Wilken R., Veena M.S., Wang M.B., Srivatsan E.S. Mol. Cancer. 2011, 10, 12. doi: 10.1186/1476-4598-10-12
- Wang K., Fan H., Chen Q., Ma G., Zhu M., Zhang X., Zhang Y., Yu J. Anti-Cancer Drugs. 2015, 26, 15-24. doi: 10.1097/CAD.0000000000000132
- Tomeh M.A., Hadianamrei R., Zhao X. Int. J. Mol. Sci. 2019, 20, 1033. doi: 10.3390/ijms20051033
- Bairwa K., Grover J., Kania M., Jachak S.M. RSC Adv. 2014, 4, 13946-13978. doi: 10.1039/c4ra00227j
- Anand P., Kunnumakkara A.B., Newman R.A., Aggarwal B.B. Mol. Pharm. 2007, 4, 807-818. doi: 10.1021/mp700113r
- Liu Z., Smart J.D., Pannala A.S. J. Drug Deliv. Sci. Technol. 2020, 60, 102082. doi: 10.1016/j.jddst.2020.102082
- Sohn S.-I., Priya A., Balasubramaniam B., Muthuramalingam P., Sivasankar C., Selvaraj A., Valliammai A., Jothi R., Pandian S. Pharmaceutics. 2021, 13, 2102. doi: 10.3390/pharmaceutics13122102
- Liang G., Shao L., Wang Y., Zhao C., Chu Y., Xiao J., Zhao Y., Li X., Yang S. Bioorg. Med. Chem. 2009, 17, 2623-2631. doi: 10.1016/j.bmc.2008.10.044
- Leow P.C., Bahety P., Boon C.P., Lee C.Y., Tan K.L., Yang T., Ee P.L. Eur. J. Med. Chem. 2014, 71, 67-80. doi: 10.1016/j.ejmech.2013.10.073
- Baldwin P.R., Reeves A.Z., Powell K.R., Napier R.J., Swimm A.I., Sun A., Giesler K., Bommarius B., Shinnick T.M., Snyder J.P., Liotta D.C., Kalman D. Eur. J. Med. Chem. 2015, 92, 693-699. doi: 10.1016/j.ejmech.2015.01.020
- Pan Z., Chen C., Zhou Y., Xu F., Xu Y. Drug Dev. Res. 2016, 77, 43-49. doi: 10.1002/ddr.21291
- Kohyama A., Yamakoshi H., Hongo S., Kanoh N., Shibata H., Iwabuchi Y. Molecules. 2015, 20, 15374-15391. doi: 10.3390/molecules200815374
- Kumar P., Kandi S.K., Manohar S., Mukhopadhyay K., Rawat D.S. ACS Omega. 2019, 4, 675-687. doi: 10.1021/acsomega.8b02625
- Carapina da Silva C., Pacheco B.S., das Neves R.N., Di� Alves M.S., Sena-Lopes �., Moura S., Borsuk S., de Pereira C.M.P. Biomed. Pharmacother. 2019, 111, 367-377. doi: 10.1016/j.biopha.2018.12.058
- Teiten M.-H., Dicato M., Diederich M. Molecules. 2014, 19, 20839-20863. doi: 10.3390/molecules191220839
- Noureddin S.A., El-Shishtawy R.M., Al-Footy K.O. Eur. J. Med. Chem. 2019, 182, 111631. doi: 10.1016/j.ejmech.2019.111631
- Sanabria-Rios D. J., Rivera-Torres Y., Rosario J., Gutierrez R., Torres-Garc�a Y., Montano N., Ort�z-Soto G., Rios-Olivares E., Rodriguez J. W., Carballeira N. M. Bioorg. Med. Chem. Lett. 2015, 25, 5067-5071. doi: 10.1016/j.bmcl.2015.10.022
- Dias K.S.T., de Paula C.T., dos Santos T., Souza I.N.O., Boni M.S., Guimar�es M.J.R., da Silva F.M.R., Castro N.G., Neves G., Veloso C.C., Coelho M.M., de Melo I.S.F., Vilela F.C., Giusti-Paiva A., da Silva M.L., Dardenne L.E., Guedes I., Pruccoli L., Morroni F., Tarozzi A., Viegas Jr. C. Eur. J. Med. Chem. 2017, 130, 440-457. doi: 10.1016/j.ejmech.2017.02.043
- Sharma S., Gupta M.K., Saxena A.K., Bedi P.M.S. Bioorg. Med. Chem. 2015, 23, 7165-7180. doi: 10.1016/j.bmc.2015.10.013
- Allegra A., Innao V., Russo S., Gerace D., Alonci A., Musolino C. Canc. Invest. 2017, 35, 1-22. doi: 10.1080/07357907.2016.1247166
- Singh A., Singh J.V., Rana A., Bhagat K., Gulati H.K., Kumar R., Salwan R., Bhagat K., Kaur G., Singh N., Kumar R., Singh H., Sharma S., Bedi P.M.S. ACS Omega. 2019, 4, 11673-11684. doi: 10.1021/acsomega.9b01109
- D'yakonov V.A., Dzhemileva L.U., Makarov A.A., Makarova E.Kh., Khusnutdinova E.K., Dzhemilev U.M. Chem. Commun. 2013, 49, 8401-8403. doi: 10.1039/C3CC44926B
- 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, 2405-2408. doi: 10.1016/j.bmcl.2015.04.011
- 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, 30-39. doi: 10.1007/s00044-015-1446-1
- D'yakonov V.A., Dzhemileva L.U., Tuktarova R.A., Makarov A.A., Islamov I.I., Mulyukova A.R., Dzhemilev U.M. Steroids. 2015, 102, 110-117. doi: 10.1016/j.steroids.2015.08.006
- D'yakonov V.A., Tuktarova R.A., Dzhemileva L.U., Ishmukhametova S.R., Yunusbaeva M.M., Dzhemilev U.M. Steroids. 2018, 138, 6-13. doi: 10.1016/j.steroids.2018.06.004
- D'yakonov V.A., Tuktarova R.A., Dzhemileva L.U., Ishmukhametova S.R., Yunusbaeva M.M., Dzhemilev U.M. Steroids. 2018, 138, 14-20. doi: 10.1016/j.steroids.2018.06.002
- D'yakonov V.A., Dzhemileva L.U., Dzhemilev U.M. Phytochem. Rev. 2021, 20, 325-342. doi: 10.1007/s11101-020-09685-6
- Kuang J., Ma S., J. Org. Chem. 2009, 74, 1763-1765. doi: 10.1021/jo802391x
- Sanabria-Rios D.J., Rivera-Torres Y., Rosario J., Rios C., Gutierrez R., Carballeira N. M., Velez C., Zayas B., Alvarez-Colon F., Ortiz-Soto G., Serrano V., Altieri-Rivera J., Rios-Olivares E., Rodriguez J.W. Bioorg. Med. Chem. Lett. 2015, 25, 2174. doi: 10.1016/j.bmcl.2015.03.065
- Masuda T., Jitoe A., Isobe J., Nakatani N., Yonemori S. Phytochemistry. 1993, 32, 1557-1560. doi: 10.1016/0031-9422(93)85179-u
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