Next Article in Journal
Evaluation of Effect of Microwave Irradiation on Syntheses and Reactions of Some New 3-Acyl-methylchromones
Previous Article in Journal
A New Convenient Synthesis of 5-Acyl-1,2,3,4-tetrahydropyrimidine-2-thiones/ones
Open AccessArticle

Enantiodivergent Synthesis of (R)- and (S)-Rolipram

Preclinical Research, Novartis Pharma Ltd, CH-4002 Basel, Switzerland
*
Author to whom correspondence should be addressed.
Molecules 1998, 3(3), 107-119; https://doi.org/10.3390/30300107
Received: 2 November 1997 / Accepted: 23 February 1998 / Published: 10 March 1998
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. View Full-Text
Keywords: Rolipram; phosphodiesterase; circular dichroism (CD) spectra; enantiodivergent synthesis Rolipram; phosphodiesterase; circular dichroism (CD) spectra; enantiodivergent synthesis
Show Figures

Figure 1

MDPI and ACS Style

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. https://doi.org/10.3390/30300107

AMA Style

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. https://doi.org/10.3390/30300107

Chicago/Turabian Style

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. https://doi.org/10.3390/30300107

Find Other Styles

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Search more from Scilit
 
Search
Back to TopTop