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Enantiodivergent Synthesis of (R)- and (S)-Rolipram
Preclinical Research, Novartis Pharma Ltd, CH-4002 Basel, Switzerland
* Author to whom correspondence should be addressed.
Received: 2 November 1997; Accepted: 23 February 1998 / Published: 10 March 1998
Abstract: Both enantiomers of rolipram (1) have been prepared in large quantity from a common intermediate rac-3-(3’-cyclopentyloxy-4’-methoxy)phenyl-4-nitro butyric acid (6), which was resolved by way of the two readily separable diastereoisomeric amides obtained with (S)-(-)-phenylethylamine. Reduction of the nitro group and intramolecular transamidation gave (R)-(-)-1 and (S)-(+)-1, respectively. CD spectra of both enantiomers of rolipram are reported and discussed. Both enantiomers of rolipram presented the same potency of inhibitory activity against recombinant cyclic-AMP-selective phosphodiesterase (PDE4) subtypes.
Keywords: Rolipram; phosphodiesterase; circular dichroism (CD) spectra; enantiodivergent synthesis
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Demnitz, J.; LaVecchia, L.; Bacher, E.; Keller, T.H.; Müller, T.; Schürch, F.; Weber, H.-P.; Pombo-Villar, E. Enantiodivergent Synthesis of (R)- and (S)-Rolipram. Molecules 1998, 3, 107-119.
Demnitz J, LaVecchia L, Bacher E, Keller TH, Müller T, Schürch F, Weber H-P, Pombo-Villar E. Enantiodivergent Synthesis of (R)- and (S)-Rolipram. Molecules. 1998; 3(3):107-119.
Demnitz, Joachim; LaVecchia, Luigi; Bacher, Edmond; Keller, Thomas H.; Müller, Thomas; Schürch, Friedrich; Weber, Hans-Peter; Pombo-Villar, Esteban. 1998. "Enantiodivergent Synthesis of (R)- and (S)-Rolipram." Molecules 3, no. 3: 107-119.