Chlorinated phenyl azides as photolabeling reagents. Synthesis of an ortho,ortho'-dichlorinated arylazido PCP receptor ligand

Abstract

The enhanced photolabeling properties of chlorinated phenyl azides are demonstrated by the synthesis and photolysis of methyl 4-azido-2,3,5,6-tetrachlorobenzoate (3) and methyl 4-azido-3,5-dichlorobenzoate (4). Photolysis of azide 3 in 1 M diethylamine/cyclohexane as the trapping medium gave 34% NH-insertion product. Similar photolysis of azide 4 gave 35% NH insertion product. These results demonstrate that chlorinated phenyl azides are significantly better at undergoing NH insertion than nonhalogenated analogs and suggest that improvement of existing aryl azide-based photolabels might be achieved by introduction of chlorine atoms on either side of the azide group. As an application, 3-azido-2,4-dichloro-10,5-(iminomethano)-10,11-dihydro-5H- dibenzo[a,d]cycloheptene (19), an analog of the potent PCP receptor ligand IDDC (14), was synthesized and its affinity for the PCP receptor was determined to be 6.3 +/- 0.7 microM (IC50 against [3H]MK801).

Chemistry of Bifunctional Photoprobes. 1. Perfluoroaryl Azido Functionalized Phosphorus Hydrazides as Novel Photoreactive Heterobifunctional Chelating Agents: High Efficiency Nitrene Insertion on Model Solvents and Proteins

“…The solvent was removed, and the residue was distilled (100 °C/0.5 mmHg) using a Kügelrohr apparatus to give a yellow liquid (79%). The physical constants of the compound coincided well with the earlier report 14a…”

Synthesis and Characterization of 1,2,3-Triazole and Hydrazone Derivatives as Potent Antimicrobial Agent

“…The minimum inhibitory concentration (MIC) was determined by the conventional paper disc diffusion method [21] . Finally all the compounds were confirmed by mass spectrometry and elemental analysis, where all the results were in agreement with the proposed structure of the synthesized compounds.…”

Modification and bio‐testing of polyethylene films

“…Since then, many derivatives are the subject of extensive investigation because of their important biological and industrial applications as photoaffinity labeling agents [6][7], cross-linking reagents in photoresists [8], the formation of conducting polymers [9], and the light induced activation of polymer surfaces [10][11]. In the other hand, it is well known that sulfonamides are widely used for therapeutic and prophylatic purpose in humans and other animals and sometime as additives in animal feed [12].…”