Rodney W. Stevens

Novel imidazole compounds as a new series of potent, orally active inhibitors of 5-lipoxygenase

Replacement of the dihydroquinolinone pharmacophore of Zenecas ZD2138 by ionizable imidazolylphenyl moiety has lead to the discovery of a novel series of potent and orally active 5-lipoxygenase (5-LO) inhibitors. The synthesis and structure-activity relationship (SAR) of this series of compounds are described herein.

Synthesis of 2-acylindole-3-acetic acids: a novel base-mediated indole synthesis

An efficient and expedient synthetic route to 2-acylindole-3-acetic acids is described. This work first demonstrates a one-pot room-temperature indole ring construction via the in situ generation of indoline intermediate.

Efficient and practical synthesis of both enantiomers of 3-phenylcyclopentanol derivatives

An efficient, multigram scale synthesis of the respective optical isomers of 3-(substituted-phenyl) cyclopentanols was achieved by a lipase-catalyzed transesterification (kinetic resolution) in organic medium. This enzymatic reaction proceeded with great efficiency as measured by chemical yield and enantioselectivity. The racemic cis-alcohol 3 was successfully resolved to yield (1R,3S)-acetate 7 and the corresponding (1S,3R)-alcohol 3. The utility of this procedure was demonstrated by the practical syntheses of the biologically active compounds. The (1R,3S)-acetate 7 and the (1S,3R)-alcohol 3 were converted into orally active 5-lipoxygenase inhibitors, respectively, without loss of optical purity.