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An applicable strategy of chemical labeling of morphine (M) and 6‐acetyl morphine (6‐AM) using diazonium salts is described. M or 6‐AM was coupled with aryl diazoinum salts to give morphine azo dyes. The coupling of the diazotized 4,4′‐diaminostilbene with M or 6‐AM in ratio 1:2 gave stilbene‐based azo dyes containing two M or 6‐AM units, respectively. Diazotization of 5‐(p‐aminophenyl)‐10,15,20‐triphenylporphyrin and subsequent azo coupling of the diazoniun salt with M and with 6‐AM was our route to get highly fluorescent morphine dyes. The resulting dyes can exist in two possible tautomeric structures, azo and hydrazone, stabilized to a significant extent by intramolecular H‐bonding. It was shown that these dyes exists predominantly or exclusively in their hydrazone form. This conclusion is drawn from the lack of a distinct band in the 380–420 nm region of the absorption spectra (a region in which the long wavelength absorption band for the azo‐form is observed), together with results of NMR studies in deuterated DMSO. The tautomeric properties of the compounds were judged by density functional calculations at the B3LYP/6‐31G* and B3LYP/6‐31G** levels. The analysis of spiked compounds in human urine samples was studied by capillary electrophoresis (CE) with UV‐fluorescence photo‐diode array detectors. J. Heterocyclic Chem., (2010).
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