Enantiodivergent synthesis of (R)- and (S)-rolipram

被引：37

作者：

Demnitz, J ^{[1
]}

LaVecchia, L ^{[1
]}

Bacher, E ^{[1
]}

Keller, TH ^{[1
]}

Muller, T ^{[1
]}

Schurch, F ^{[1
]}

Weber, HP ^{[1
]}

Pombo-Villar, E ^{[1
]}

机构：

[1] Novartis Pharma Ltd, Preclin Res, CH-4002 Basel, Switzerland

来源：

MOLECULES | 1998年 / 3卷 / 03期

关键词：

rolipram; phosphodiesterase; circular dichroism (CD) spectra; enantiodivergent synthesis;

D O I：

10.3390/30300107

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：107 / 119

页数：13

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