Synthesis and Evaluations of "1,4-Triazolyl Combretacoumarins" and Desmethoxy Analogues.

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ID: 58110
2019
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Abstract
have been prepared by linking the trimethoxyarene unit of combretastatin A4 with coumarins, a 1,2,3-triazole. For this, 4-azidocoumarins were accessed by a sequential two-step, one-pot reaction of 4-hydroxycoumarins with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), followed by reaction with NaN. In the reaction with BOP, a coumarin-derived phosphonium ion intermediate seems to form, leading to an -(benzotriazolyl)coumarin derivative. For the CuAAC reaction of azidocoumarins with 5-ethynyl-1,2,3-trimethoxybenzene, catalytic [(MeCN)Cu]PF in CHCl/MeOH with 2,6-lutidine, at 50 °C, was suitable. The 4-azidocoumarins were less reactive as compared to PhN and the NBO coefficients of the azido groups were compared by DFT analysis. Compound solubility was a problem in biological assays. On the basis of the biological and solubility data of one 1,4-triazolyl combretacoumarin, four analogues lacking one or two methoxy groups were synthesized. Reactivity differences among the phenylacetylenes were noted and the NBO coefficients of the alkynes were compared by DFT analysis. In antiproliferative assays, 1-phenyl-4-(3,4,5-trimethoxyphenyl)-1-1,2,3-triazole showed activity in CEM and MDA-MB-231 cell lines, possibly by apoptosis. The desmethoxy 6-bromo-4-(4-(4-methoxyphenyl)-1-1,2,3-triazol-1-yl)-2-chromen-2-one also showed cytotoxicity against the two cell lines, but this did not appear to be consistent with apoptosis. The antiviral activity of the compounds was unremarkable.
Reference Key
khandaker2019synthesiseuropean Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Khandaker, Tashrique A;Hess, Jessica D;Aguilera, Renato;Andrei, Graciela;Snoeck, Robert;Schols, Dominique;Pradhan, Padmanava;Lakshman, Mahesh K;
Journal european journal of organic chemistry
Year 2019
DOI
10.1002/ejoc.201900569
URL
Keywords
Triazole cuaac copper coumarin alkyne combretastatin

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