A tyrosinase-directed therapeutic approach for malignant melanoma therapy uses the depigmenting phenolic agents such as 4-hydroxyanisole (4-HA) to form cytotoxic o-quinones. However, renal and hepatic toxicity was reported as side effects in a recent 4-HA clinical trial. In search of
Tyrosinase hydroxylates 3-hydroxyanisole in the 4-position. The reaction product accumulates in the reaction medium with a lag time (tau) which diminishes with increasing concentrations of enzyme and lengthens with increasing concentrations of substrate, thus fulfilling all the predictions of the
The Journal of organic chemistry, 73(6), 2408-2411 (2008-02-26)
The m-methoxy group is normally electron-withdrawing (EW), sigma(m) = +0.12, sigma(m+) = +0.05. The strong EW activity of a phenoxyl radical's O* atom causes the m-methoxy group to become electron-donating (ED), sigma(m)(+) = -0.14. In valence bond terms, this can
[reaction: see text] A short synthesis of (+/-)-10-norparvulenone and (+/-)-O-methylasparvenone was developed starting from commercially available m-methoxyphenol, hinging on a xanthate-mediated addition-cyclization sequence for the construction of the alpha-tetralone subunit.
The Lewis acid catalyzed condensation of 3-methoxyphenol with octanal produced the C(4) symmetric calix[4]resorcinarene 2, in high yield. Of the numerous stereo- and regioisomers possible, the rccc isomer with C(4) symmetry was the only product isolated (as a racemate). The
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