Synthesis of Photoreactive 2‐Phenethylamine Derivatives – Synthesis of Adenosine Derivatives Enabling Functional Analysis of Adenosine Receptors by Photoaffinity Labeling

Abstract

Abstract2‐Phenylethylamine is well known as a substructure of many biologically active compounds, and the synthesis of its photoreactive derivatives to allow the analysis of biological functions is reported. This allowed us to synthesise ligands for adenosine receptors, which have many functional roles in biology and have been extensively studied for their many roles in maintaining homeostasis. Adenosine is one of the most common biochemical compounds, but photoaffinity labeling has not yet been used to study adenosine receptors. Synthetic methods for producing photoreactive adenosine derivatives that can be used with adenosine receptors were established for the photophores phenyl azide and benzophenone. The effect of the introduction of the photoreactive components was determined using an adenosine receptor assay.

The Life of Pi Star: Exploring the Exciting and Forbidden Worlds of the Benzophenone Photophore

“…The AlCl 3 -catalyzed Friedel–Crafts (F–C) acylation is probably the most widely used method for the generation of substituted BPs (Figure ). The use of trifluoromethanesulfonic acid as the catalyst was reported by Murai et al during the development of a phenethylamine photoprobe ( 371 ) . While classical F–C benzoylation with aluminum chloride at 90 °C for 7 h gave the corresponding BP only in 66% yield, the BP probe was synthesized at room temperature (4 h) in high yield (86%) by using benzoic anhydride in trifluoromethanesulfonic acid (TfOH).…”

Synthesis and biological evaluation of zinc chelating compounds as metallo-β-lactamase inhibitors

“…23 Quantitative conversion to the acid 1 was achieved by reaction with succinic anhydride. For the dipicolyl 1,2,3-triazolylmethylamine chelators (DPTA), the amine 6 was obtained by copperIJI)-mediated azide-alkyne cycloaddition (CuAAC) between tert-butyl 4-azidophenethylcarbamate (21), 24 and N-propargyl-diIJ2-picolyl)amine (22), 25 followed by deprotection with HCl. Preparation of the acid 2 from ethyl (4-bromophenyl)acetate (23) required conversion to the corresponding azide 24, 26 and subsequent CuAAC reaction with propargyl alcohol to afford the 1,2,3-triazole containing alcohol 25.…”

Synthesis and biological evaluation of indole-2-carboxamides bearing photoactivatable functionalities as novel allosteric modulators for the cannabinoid CB1 receptor

“…The benzophenone-substituted ethanamine 12 was synthesized using the methods depicted in Scheme 1 ( a ) with slight modification from a reported protocol in the purification process [46]. Briefly, Friedel-Crafts benzoylation of the commercially available N -phenethylacetamide 10 in nitrobenzene provided the benzophenone-substituted ethylenyl acetamide 11 and, subsequently was purified by chromatography upon complete removal of nitrobenzene through steam distillation.…”