Abstract:
New macrodiolides incorporating 1Z,5Z-diene and 1,3-diyne moieties were obtained in 55–79% yields and with >98% stereoselectivity by Hf(OTf)4-catalyzed intermolecular cyclocondesation of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid with a,ω-diols. Alternative route included intramolecular oxidative coupling of a,ω-diynes, esterification products of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid with alkynols. The macrodiolides synthesized exhibit in vitro cytotoxic activity toward Jurkat, K562, U937, HL-60, HeLa and Hek293 cell lines.
Citation:
V. A. D'yakonov, I. I. Islamov, L. U. Dzhemileva, M. M. Yunusbaeva, U. M. Dzhemilev, “Stereoselective synthesis and antitumor activity of macrodiolides containing 1Z,5Z-diene and 1,3-diyne moieties”, Mendeleev Commun., 29:6 (2019), 613–615
Linking options:
https://www.mathnet.ru/eng/mendc1605
https://www.mathnet.ru/eng/mendc/v29/i6/p613
This publication is cited in the following 10 articles:
V M Aparna, L Vidya, Aparna Raj, S Neelima, S Vandana, G Anilkumar, E R Anabha, C Sudarsanakumar, “Synthesis, Structural Characterization, Hirshfeld Surface Analysis, and Antibacterial Properties of Ethyl (2E,4Z)-5-(4-bromophenyl)-5-chloro-2-cyanopenta-2,4-dienoate”, Journal of Molecular Structure, 2025, 141762
I. I. Islamov, I. V. Gaisin, U. M. Dzhemilev, V. A. D'yakonov, “Synthesis of macrocyclic mono- and diolides based on new ω-hydroxyalkadienoic acids with (Z,Z)-1,5-diene moiety”, Russ Chem Bull, 73:6 (2024), 1623
I. I. Islamov, A. A. Makarov, E. Kh. Makarova, A. V. Yusupova, V. A. D'yakonov, U. M. Dzhemilev, “Synthesis of macrocyclic and linear compounds with 1Z,5Z-diene and alkynylcarbinol fragments based on (5Z,9Z)-tetradeca-5,9-diene-1,14-diol”, Russ Chem Bull, 72:4 (2023), 925
Ilgiz Islamov, Ilgam Gaisin, Usein Dzhemilev, ECSOC 2023, 2023, 70
I. I. Islamov, A. V. Yusupova, V. A. D'yakonov, U. M. Dzhemilev, “Synthesis of polyether macrodiolides based on acetylenic derivatives of (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid”, Russ Chem Bull, 72:10 (2023), 2473
Ilgiz Islamov, Adelya Yusupova, Lilya U. Dzhemileva, Usein Dzhemilev, The 25th International Electronic Conference on Synthetic Organic Chemistry, 2021, 6
Vladimir A. D'yakonov, Lilya U. Dzhemileva, Usein M. Dzhemilev, “Natural compounds with bis-methylene-interrupted Z-double bonds: plant sources, strategies of total synthesis, biological activity, and perspectives”, Phytochem Rev, 20:1 (2021), 325
Airat R. Tuktarov, Liliya L. Khuzina, Zarema R. Sadretdinova, Elina Kh. Makarova, Lilya U. Dzhemileva, Vladimir A. D'yakonov, Usein M. Dzhemilev, “Synthesis and cytotoxic activity of unsaturated macrolides and their hybrid molecules with a C60 fullerene”, Org. Biomol. Chem., 19:8 (2021), 1847
Ilgiz Islamov, Adelya Yusupova, Lilya U. Dzhemileva, Usein Dzhemilev, The 25th International Electronic Conference on Synthetic Organic Chemistry, 2021, 58
Saumitra Sengupta, Goverdhan Mehta, “MacrocyclizationviaC–H functionalization: a new paradigm in macrocycle synthesis”, Org. Biomol. Chem., 18:10 (2020), 1851
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