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2005
Polyphenylalkene derivatives
Q 0740
A New Class of Acyclic 2-Alkyl-1,2-diaryl (E)-Olefins as Selective Cyclooxygena(COX-2) Inhibitors. — Reductive cross coupling of thioacetals (I) with carbonyl
01- 087 se-2
compounds (II) affords the corresponding thiomethyl olefinic intermediates with a
good (E)-selectivity. Oxidation of the intermediates yields the sulfones (III) as isomeric
mixtures. Fractional recrystallizations furnish exclusively the desired (E)-olefins (III).
Acyclic diaryl olefins possessing a transstilbenoid template show selective COX-2
inhibition when a p-methanesulfonylphenyl substituent is present at the C-2 position.
Also, the C-2 alkyl substituent chain length has influence on the COX-2 inhibitory potency and selectivity. The best combination of inhibitory potency and selectivity is
achieved with (IIId). — (UDDIN, M. J.; RAO, P. N. P.; RAHIM, M. A.; MCDONALD,
R.; KNAUS*, E. E.; Bioorg. Med. Chem. Lett. 14 (2004) 19, 4911-4914; Fac. Pharm.
Pharm. Sci., Univ. Alberta, Edmonton, Alberta T6G 2N8, Can.; Eng.) —
H. Hoennerscheid
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