Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl Moieties
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 medici...
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2024-12-01
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| author | Ilgam Gaisin Ilgiz Islamov |
| author_facet | Ilgam Gaisin Ilgiz Islamov |
| author_sort | Ilgam Gaisin |
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| description | 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. |
| format | Article |
| id | doaj-art-ed024fd71ae64c5eb70c356bd69aa417 |
| institution | Kabale University |
| issn | 2673-4583 |
| language | English |
| publishDate | 2024-12-01 |
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| series | Chemistry Proceedings |
| spelling | doaj-art-ed024fd71ae64c5eb70c356bd69aa4172025-08-20T03:26:21ZengMDPI AGChemistry Proceedings2673-45832024-12-011613010.3390/ecsoc-28-20111Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl MoietiesIlgam Gaisin0Ilgiz Islamov1Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, RussiaInstitute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, RussiaMacrocycles 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.https://www.mdpi.com/2673-4583/16/1/301,5-Dienoic compoundshomo-cyclomagnesiationpolyether macrodiolidesaromatic macrocycles |
| spellingShingle | Ilgam Gaisin Ilgiz Islamov Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl Moieties Chemistry Proceedings 1,5-Dienoic compounds homo-cyclomagnesiation polyether macrodiolides aromatic macrocycles |
| title | Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl Moieties |
| title_full | Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl Moieties |
| title_fullStr | Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl Moieties |
| title_full_unstemmed | Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl Moieties |
| title_short | Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl Moieties |
| title_sort | synthesis of new 1z 5z dienoic macrodiolides with benzenyl and naphthyl moieties |
| topic | 1,5-Dienoic compounds homo-cyclomagnesiation polyether macrodiolides aromatic macrocycles |
| url | https://www.mdpi.com/2673-4583/16/1/30 |
| work_keys_str_mv | AT ilgamgaisin synthesisofnew1z5zdienoicmacrodiolideswithbenzenylandnaphthylmoieties AT ilgizislamov synthesisofnew1z5zdienoicmacrodiolideswithbenzenylandnaphthylmoieties |