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Keywords = polyether macrodiolides

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4 pages, 355 KB  
Proceeding Paper
Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl Moieties
by Ilgam Gaisin and Ilgiz Islamov
Chem. Proc. 2024, 16(1), 30; https://doi.org/10.3390/ecsoc-28-20111 - 12 Dec 2024
Viewed by 1049
Abstract
Macrocycles represent an important class of compounds that are widespread in nature. Of particular interest to researchers are aromatic macrocyclic compounds, which, due to their rigid structure and unique physicochemical properties, can find application in many areas of science, industry and medicine. Previously, [...] Read more.
Macrocycles represent an important class of compounds that are widespread in nature. Of particular interest to researchers are aromatic macrocyclic compounds, which, due to their rigid structure and unique physicochemical properties, can find application in many areas of science, industry and medicine. Previously, we synthesized polyether aromatic macrodiolides, which showed intriguing antitumor properties. In the work, Peyrottes S. and co-authors showed that the introduction of biphenyl or naphthyl rings, as well as triple bonds, into the structure of the compounds they synthesized, not only helps to reduce the molecular flexibility of the molecule, but also increases the bioavailability after oral administration of the corresponding neutral prodrugs. Studies in mice have shown that the presence of two aromatic groups is well tolerated and has resulted in compounds with valuable properties in vitro and in vivo. Based on these results, in continuation of our research on the synthesis of biologically active macrodiolides, in the framework of this work, new aromatic macrocycles were synthesized, the structure of which, along with the 1Z,5Z-diene fragment, contains phenyl or naphthyl rings. The target polyester macrodiolides were obtained by Hf-catalyzed intermolecular cyclocondensation of 1,14-tetradeca-5Z,9Z-dienedioic acid with diols synthesized from dihydroxybenzenes and naphthalenediols. Full article
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3 pages, 328 KB  
Proceeding Paper
Synthesis of New Unsaturated Polyether Macrodiolides Based on (7Z,11Z)-Octadeca-7,11-Diene-1,18-Dioic Acid
by Ilgiz Islamov, Ilgam Gaisin and Usein Dzhemilev
Chem. Proc. 2023, 14(1), 70; https://doi.org/10.3390/ecsoc-27-16047 - 15 Nov 2023
Viewed by 918
Abstract
Stereoselective synthesis of (7Z,11Z)-octadeca-7,11-diene-1,18-dioic acid was carried out using a homo-cyclomagnesiation reaction of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2H-pyran. After Steglisch esterification of the synthesized acid and polyester acetylenes in the presence of DCC and DMAP, the corresponding diesters were synthesized in [...] Read more.
Stereoselective synthesis of (7Z,11Z)-octadeca-7,11-diene-1,18-dioic acid was carried out using a homo-cyclomagnesiation reaction of 2-(nona-7,8-dien-1-yloxy)tetrahydro-2H-pyran. After Steglisch esterification of the synthesized acid and polyester acetylenes in the presence of DCC and DMAP, the corresponding diesters were synthesized in good yields (67–75%). Based on symmetric diesters with terminal triple bonds, polyether macrodiolides containing conjugated triple bonds and pharmacophoric cis,cis-1,5-diene fragments in their structure were synthesized for the first time. Full article
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4 pages, 342 KB  
Proceeding Paper
Synthesis of Aromatic Macrodiolides and Study of Their Antitumor Activity In Vitro
by Ilgam Gaisin, Ilgiz Islamov, Lilya U. Dzhemileva and Usein Dzhemilev
Chem. Proc. 2023, 14(1), 59; https://doi.org/10.3390/ecsoc-27-16102 - 15 Nov 2023
Viewed by 900
Abstract
Based on (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid, previously undescribed polyether aromatic macrodiolides were synthesized in good yields (53–67%). The cytotoxicity of the resulting macrocyclic compounds in vitro against tumor Jurkat cells, K562 cells, conditionally normal Hek293 cell lines and normal fibroblasts was [...] Read more.
Based on (5Z,9Z)-tetradeca-5,9-diene-1,14-dioic acid, previously undescribed polyether aromatic macrodiolides were synthesized in good yields (53–67%). The cytotoxicity of the resulting macrocyclic compounds in vitro against tumor Jurkat cells, K562 cells, conditionally normal Hek293 cell lines and normal fibroblasts was the assessment carried out. The ability of the most active macrodiolide to induce apoptosis toward Jurkat cells and influence the cell cycle was studied. Full article
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4 pages, 391 KB  
Proceeding Paper
Stereoselective Synthesis and Cytotoxic Activity of Aromatic Polyether Macrodiolides Containing 1Z,5Z-Diene Moiety
by Ilgiz Islamov, Adelya Yusupova, Lilya U. Dzhemileva and Usein Dzhemilev
Chem. Proc. 2022, 8(1), 58; https://doi.org/10.3390/ecsoc-25-11763 - 15 Nov 2021
Viewed by 1247
Abstract
The synthesis of previously undescribed aromatic polyether macrodiolides containing a 1Z,5Z-diene moiety was carried out in 56–72% yields and with >98% stereoselectivity. It has been shown that the synthesized macrodiolides exhibit higher cytotoxic activity in vitro against a number [...] Read more.
The synthesis of previously undescribed aromatic polyether macrodiolides containing a 1Z,5Z-diene moiety was carried out in 56–72% yields and with >98% stereoselectivity. It has been shown that the synthesized macrodiolides exhibit higher cytotoxic activity in vitro against a number of tumor cell lines (Jurkat, K562 and U937). Full article
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