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Synthesis of Polyoxygenated 4,5-Diarylpyridazines with Antiproliferative and Antitubulin Activity via Inverse Electron-Demand Diels-Alder Reaction of 1,2,4,5- Tetrazine# Full article

Journal Current Organic Chemistry
ISSN: 1385-2728 , E-ISSN: 1875-5348
Output data Year: 2024, Volume: 28, Number: 20, Pages: 1613-1620 Pages count : 8 DOI: 10.2174/0113852728314401240613045216
Authors Adaeva Olga I. 1 , Demchuk Dmitry V. 1 , Dolotov Roman A. 1 , Kuptsova Tatiana S. 1 , Semenova Marina N. 2 , Semenov Victor V. 1
Affiliations
1 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russian Federation
2 N.K. Koltzov Institute of Developmental Biology, Russian Academy of Sciences, 26 Vavilov Street, 119334 Moscow, Russian Federation

Abstract: The synthesis of a series of multifunctionalized 4,5-diarylpyridazines via inverse electron-demand Diels-Alder reaction between highly oxygenated diarylacetylenes and unsubstituted 1,2,4,5-tetrazine was developed using polyalkoxybenzenes isolated from industrial essential oils as starting material. The reaction proceeded smoothly to afford combretastatin A-4 analogues with pyridazine linker in consistently high yield. In a phenotypic sea urchin embryo assay, diarylpyridazine with 3,4,5-trimethoxyphenyl and 3-amino- 4-methoxyphenyl aryl rings was identified as a potent antimitotic microtubule-destabilizing compound.
Cite: Adaeva O.I. , Demchuk D.V. , Dolotov R.A. , Kuptsova T.S. , Semenova M.N. , Semenov V.V.
Synthesis of Polyoxygenated 4,5-Diarylpyridazines with Antiproliferative and Antitubulin Activity via Inverse Electron-Demand Diels-Alder Reaction of 1,2,4,5- Tetrazine#
Current Organic Chemistry. 2024. V.28. N20. P.1613-1620. DOI: 10.2174/0113852728314401240613045216 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:001317392600007
Scopus: 2-s2.0-85203023829
OpenAlex: W4400323575
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