1310822-76-4Relevant academic research and scientific papers
Synthesis of diverse 3-azido-5-(azidomethyl)benzene derivatives via formal C-H azidation and functional group-selective transformations
Nishiyama, Yoshitake,Misawa, Yoshihiro,Hazama, Yuki,Oya, Kazuhiro,Yoshida, Suguru,Hosoya, Takamitsu
, p. 1053 - 1072 (2019/07/31)
3-Azido-5-(azidomethyl)benzene derivatives are useful compounds for preparing diverse bistriazole compounds and photoaffinity probes for target identification of bioactive compounds. To more easily synthesize a diverse range of diazido compounds, a facile
Formal C-H-azidation-based shortcut to diazido building blocks for the versatile preparation of photoaffinity labeling probes
Yoshida, Suguru,Misawa, Yoshihiro,Hosoya, Takamitsu
supporting information, p. 3991 - 3995 (2014/07/08)
Short synthetic routes to diazido building blocks with different connectable groups were established on the basis of the sequential iridium-catalyzed C-H borylation and copper-catalyzed azidation of 1,3-disubstituted benzenes, followed by diverse azido-fr
Synthesis of trifunctional bis-azide photoaffinity probe
Klein, Larry L.,Petukhova, Valentina
, p. 2242 - 2245 (2013/07/25)
Methyl 3-azidomethyl-5-azido-benzoate (1b) and its corresponding hydroxymethyl reduction product (1a) have been utilized for the synthesis of valuable nonradioactive photoaffinity probes. Previous preparations of (1a) depend upon a nonselective monoactiva
Design, synthesis, docking, and biological evaluation of novel diazide-containing isoxazole- and pyrazole-based histone deacetylase probes
Neelarapu, Raghupathi,Holzle, Denise L.,Velaparthi, Subash,Bai, He,Brunsteiner, Michael,Blond, Sylvie Y.,Petukhov, Pavel A.
, p. 4350 - 4364 (2011/09/16)
The design, synthesis, docking, and biological evaluation of novel potent HDAC3 and HDAC8 isoxazole- and pyrazole-based diazide probes suitable for binding ensemble profiling with photoaffinity labeling (BEProFL) experiments in cells is described. Both the isoxazole- and pyrazole-based probes exhibit low nanomolar inhibitory activity against HDAC3 and HDAC8, respectively. The pyrazole-based probe 3f appears to be one of the most active HDAC8 inhibitors reported in the literature with an IC50 of 17 nM. Our docking studies suggest that unlike the isoxazole-based ligands the pyrazole-based ligands are flexible enough to occupy the second binding site of HDAC8. Probes/inhibitors 2b, 3a, 3c, and 3f exerted the antiproliferative and neuroprotective activities at micromolar concentrations through inhibition of nuclear HDACs, indicating that they are cell permeable and the presence of an azide or a diazide group does not interfere with the neuroprotection properties, or enhance cellular cytotoxicity, or affect cell permeability.
