Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

Christoph W. Grathwol, Nathalie Wössner, Sören Swyter, Adam C. Smith, Enrico Tapavicza, Robert K. Hofstetter, Anja Bodtke, Manfred Jung and Andreas Link
Beilstein J. Org. Chem. 2019, 15, 2170–2183. https://doi.org/10.3762/bjoc.15.214

Supporting Information

The Supporting Information features experimental and analytical data for the synthesis of intermediates and compounds 4a, 4b, 2c–2h and 8a and 1H and 13C NMR spectra for all synthesized compounds. Procedures of photochemical experiments and their analysis are described. Detailed summaries of electronic structure calculations for two conformers (A and B) of each double bond isomer ((E)-2b and (Z)-2b), photocyclization and oxidation products 8a and 8b are given.

Supporting Information File 1: Experimental procedures, analytical data and quantum chemical calulations.
Format: PDF Size: 7.8 MB Download

Cite the Following Article

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors
Christoph W. Grathwol, Nathalie Wössner, Sören Swyter, Adam C. Smith, Enrico Tapavicza, Robert K. Hofstetter, Anja Bodtke, Manfred Jung and Andreas Link
Beilstein J. Org. Chem. 2019, 15, 2170–2183. https://doi.org/10.3762/bjoc.15.214

How to Cite

Grathwol, C. W.; Wössner, N.; Swyter, S.; Smith, A. C.; Tapavicza, E.; Hofstetter, R. K.; Bodtke, A.; Jung, M.; Link, A. Beilstein J. Org. Chem. 2019, 15, 2170–2183. doi:10.3762/bjoc.15.214

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 494.1 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Brals, J.; McGuire, T. M.; Watson, A. J. B. A Chemoselective Polarity-Mismatched Photocatalytic C(sp3 )-C(sp2 ) Cross-Coupling Enabled by Synergistic Boron Activation. Angewandte Chemie (International ed. in English) 2023, 62, e202310462. doi:10.1002/anie.202310462
  • Brals, J.; McGuire, T. M.; Watson, A. J. B. A Chemoselective Polarity‐Mismatched Photocatalytic C(sp3)−C(sp2) Cross‐Coupling Enabled by Synergistic Boron Activation**. Angewandte Chemie 2023, 135. doi:10.1002/ange.202310462
  • Franzke, Y. J.; Holzer, C.; Andersen, J. H.; Begušić, T.; Bruder, F.; Coriani, S.; Della Sala, F.; Fabiano, E.; Fedotov, D. A.; Fürst, S.; Gillhuber, S.; Grotjahn, R.; Kaupp, M.; Kehry, M.; Krstić, M.; Mack, F.; Majumdar, S.; Nguyen, B. D.; Parker, S. M.; Pauly, F.; Pausch, A.; Perlt, E.; Phun, G. S.; Rajabi, A.; Rappoport, D.; Samal, B.; Schrader, T.; Sharma, M.; Tapavicza, E.; Treß, R. S.; Voora, V.; Wodyński, A.; Yu, J. M.; Zerulla, B.; Furche, F.; Hättig, C.; Sierka, M.; Tew, D. P.; Weigend, F. TURBOMOLE: Today and Tomorrow. Journal of chemical theory and computation 2023, 19, 6859–6890. doi:10.1021/acs.jctc.3c00347
  • Orvoš, J.; Fischer, R.; Brachňaková, B.; Pavlik, J.; Moncoľ, J.; Šagátová, A.; Fronc, M.; Kožíšek, J.; Routaboul, L.; Bousseksou, A.; Šalitroš, I. Pyridyl-benzimidazole derivatives decorated with phenylazo substituents and their low-spin iron(ii) complexes: a study of the synthesis, structure and photoisomerization. New Journal of Chemistry 2023, 47, 1488–1497. doi:10.1039/d2nj04774h
  • Schulte, A. M.; Kolarski, D.; Sundaram, V.; Srivastava, A.; Tama, F.; Feringa, B. L.; Szymanski, W. Light-Control over Casein Kinase 1δ Activity with Photopharmacology: A Clear Case for Arylazopyrazole-Based Inhibitors. International journal of molecular sciences 2022, 23, 5326. doi:10.3390/ijms23105326
  • Laczi, D.; Johnstone, M. D.; Fleming, C. L. Photoresponsive Small Molecule Inhibitors for the Remote Control of Enzyme Activity. Chemistry, an Asian journal 2022, 17, e202200200. doi:10.1002/asia.202200200
  • Behnisch-Cornwell, S.; Grathwol, C. W.; Schulig, L.; Voigt, A.; Baecker, D.; Link, A.; Bednarski, P. J. Correlation Analysis of Protein Expression of 10 HDAC/Sirtuin Isoenzymes with Sensitivities of 23 Anticancer Drugs in 17 Cancer Cell Lines and Potentiation of Drug Activity by Co-Treatment with HDAC Inhibitors. Cancers 2021, 14, 187. doi:10.3390/cancers14010187
  • Tapavicza, E.; von Rudorff, G. F.; De Haan, D. O.; Contin, M.; George, C.; Riva, M.; von Lilienfeld, O. A. Elucidating an Atmospheric Brown Carbon Species-Toward Supplanting Chemical Intuition with Exhaustive Enumeration and Machine Learning. Environmental science & technology 2021, 55, 8447–8457. doi:10.1021/acs.est.1c00885
  • Schalk, O.; Tapavicza, E. ACS In Focus; American Chemical Society, 2020. doi:10.1021/acs.infocus.7e4009
  • Balasubramani, S. G.; Chen, G. P.; Coriani, S.; Diedenhofen, M.; Frank, M. S.; Franzke, Y. J.; Furche, F.; Grotjahn, R.; Harding, M. E.; Hättig, C.; Hellweg, A.; Helmich-Paris, B.; Holzer, C.; Huniar, U.; Kaupp, M.; Khah, A. M.; Khani, S. K.; Müller, T.; Mack, F.; Nguyen, B.; Parker, S. M.; Perlt, E.; Rappoport, D.; Reiter, K.; Roy, S.; Rückert, M.; Schmitz, G.; Sierka, M.; Tapavicza, E.; Tew, D. P.; van Wüllen, C.; Voora, V. K.; Weigend, F.; Wodyński, A.; Yu, J. M. TURBOMOLE: Modular program suite for ab initio quantum-chemical and condensed-matter simulations. The Journal of chemical physics 2020, 152, 184107. doi:10.1063/5.0004635
  • Grathwol, C. W.; Wössner, N.; Behnisch‐Cornwell, S.; Schulig, L.; Zhang, L.; Einsle, O.; Jung, M.; Link, A. Activation of Sirtuin 2 Inhibitors Employing Photoswitchable Geometry and Aqueous Solubility. ChemMedChem 2020, 15, 1480–1489. doi:10.1002/cmdc.202000148
  • Grathwol, C. W.; Chrysochos, N.; Elvers, B. J.; Link, A.; Schulzke, C. Crystal structure of benzo[h]quinoline-3-carbox­amide. Acta crystallographica. Section E, Crystallographic communications 2019, 75, 1828–1832. doi:10.1107/s2056989019014440
Other Beilstein-Institut Open Science Activities