85416-75-7

Usage

Uses

Used in Pharmaceutical Industry:
(4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one is used as a precursor in the synthesis of various pharmaceutical compounds, particularly those targeting the phosphodiesterase IV (PDE4) enzyme. Its unique structure allows for the development of potent PDE4 inhibitors, which have potential applications in treating inflammatory and autoimmune diseases, as well as depression.
Used in Research and Development:
In the field of medicinal chemistry, (4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one serves as a valuable research tool for studying the structure-activity relationships of PDE4 inhibitors. This knowledge can be applied to design and optimize new drugs with improved efficacy, safety, and pharmacokinetic profiles.
Used in Drug Delivery Systems:
Similar to gallotannin, (4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one can be incorporated into drug delivery systems to enhance its bioavailability, targeting, and therapeutic efficacy. This may involve the use of nanoparticles, liposomes, or other carriers to improve the compound's pharmacokinetics and reduce potential side effects.

Biological Activity

More active enantiomer of the PDE4 inhibitor rolipram (4-(3-(Cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one ); 2-10-fold more potent than the S-(+) enantiomer ((4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one ). Also available as part of the Phosphodiesterase Inhibitor Tocriset? .

Upstream product

• 137-43-9 Cyclopentyl bromide 
• 132683-32-0 (R)-4-(3-hydroxy-4-methoxyphenyl)pyrrolidin-2-one 
• 146426-63-3 (+/-)-1-Benzyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one 
• 613-70-7 2-methoxyphenyl acetate 
• 66037-04-5 1-acetoxy-5-bromo-2-methoxybenzene 
• 191610-55-6 (4R,5S)-1-tert-butoxycarbonyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-5-hydroxymethylpyrrolidin-2-one 
• 63909-29-5 (E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene 
• 141332-74-3 2-(cyclopentyloxy)-1-methoxy-4-(2-nitrovinyl)benzene 
• 108-59-8 malonic acid dimethyl ester 
• 133332-34-0 (E)-3-(3-cyclopentyloxy-4-methoxyphenyl)acrylaldehyde 
• 191610-56-7 (2S,3R)-1-tert-butoxycarbonyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-oxopyrrolidine-2-carboxylic acid 
• 145548-98-7 (3S,7R,7aR)-7-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 145548-99-8 (4R,5R)-4-(3-Cyclopentyloxy-4-methoxy-phenyl)-5-hydroxy-pyrrolidin-2-one 

Downstream Products

• 900796-18-1 (R)-4-(3-Cyclopentyloxy-4-methoxy-phenyl)-1-(3-nitro-phenyl)-pyrrolidin-2-one 
• 1295626-70-8 (R)-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-methylpyrrolidin-2-one 
• 686712-10-7 4-[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxopyrrolidin-1-yl]benzenesulfonamide 
• 132683-32-0 (R)-4-(3-hydroxy-4-methoxyphenyl)pyrrolidin-2-one 

Relevant academic research and scientific papers

Polysulfonate supported chiral diamine-nickel catalysts: Synthesis and applications

A series of chiral polysulfonate cyclohexyldiamine-Ni(II) catalysts were prepared via sulfur (VI) fluoride exchange click-reactions. The catalysts exhibited good catalytic activity and enantioselectivity in the Michael addition of malonates to nitroalkene

Synthesis method of flurolipram

The invention discloses a synthesis method of flurolipram, which comprises the following steps: carrying out catalytic reaction on a compound represented by formula 1 and an alcohol compound represented by formula II by using an N-heterocyclic carbene catalyst to generate an intermediate represented by formula 3.1 and/or 3.2, and carrying out a series of reactions on the intermediate represented by formula 3.1 and/or 3.2 to finally obtain flurolipram.The method is simple to operate, and the substrate is easy to prepare; reaction conditions are mild, and high yield and high stereoselectivity are achieved.

Enantioselective conjugate addition of an α,α-dithioacetonitrile with nitroalkenes using chiral bis(imidazoline)-Pd complexes

The enantioselective conjugate addition reaction of an α,α-dithioacetonitrile with nitroalkenes was catalysed by chiral bis(imidazoline)-palladium pincer-type complexes. The reaction was applicable to various nitroalkenes to afford products in good yield with high enantioselectivity. The obtained products can be converted to γ-lactam and biologically active rolipram.

Synthesis of β-Substituted γ-Aminobutyric Acid Derivatives through Enantioselective Photoredox Catalysis

β-Substituted chiral γ-aminobutyric acids feature important biological activities and are valuable intermediates for the synthesis of pharmaceuticals. Herein, an efficient catalytic enantioselective approach for the synthesis of β-substituted γ-aminobutyr

Highly Enantioselective Synthesis of Chiral γ-Lactams by Rh-Catalyzed Asymmetric Hydrogenation

A Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system has been identified for the straightforward asymmetric synthesis of chiral γ-lactams. A variety of NH free α,β-unsaturated lactams bearing a β-aryl or β-alkyl substituent were smoothly hydrogenated to

Efficient synthesis of (?)-(R)- and (+)-(S)-rolipram

A novel, efficient and protecting group free enantioselective synthetic approach of (?)-(R)-1 and (+)-(S)-rolipram 2 is described employing the organocatalyzed asymmetric Michael addition, Henry condensation, Wittig olefination and reductive lactamization

A synthetic γ-amino butyric acid kind of chiral the method for preparing the compound of

The invention discloses a method for synthesizing a gamma-aminobutyric acid chiral compound. The method comprises the following steps of: adding nitroolefin and malonate to a solvent in the presence of a catalyst A and an additive; carrying out conjugate

Identification and in vivo evaluation of a fluorine-18 rolipram analogue, [18F]MNI-617, as a radioligand for PDE4 imaging in mammalian brain

Phosphodiesterase (PDE) 4 is the most prevalent PDE in the central nervous system (CNS) and catalyzes hydrolysis of intracellular cAMP, a secondary messenger. By therapeutic inhibition of PDE4, intracellular cAMP levels can be stabilized, and the symptoms of psychiatric and neurodegenerative disorders including depression, memory loss and Parkinson's disease can be ameliorated. Radiotracers targeting PDE4 can be used to study PDE4 density and function, and evaluate new PDE4 therapeutics, in vivo in a non-invasive way, as has been shown using the carbon-11 labeled PDE4 inhibitor R-(-)-rolipram. Herein we describe a small series of rolipram analogs that contain fluoro- or iodo-substituents that could be used as fluorine-18 PET or iodine-123 SPECT PDE4 radiotracers. This series was evaluated with an in vitro binding assay and a 4-(fluoromethyl) derivative of rolipram, MNI-617, was identified, with a five-fold increase in affinity for PDE4 (Kd = 0.26 nM) over R-(-)-rolipram (Kd = 1.6 nM). A deutero-analogue d2-[18F]MNI-617 was radiolabeled and produced in 23% yield with high (>5 Ci/μmol) specific activity and evaluated in non-human primate, where it rapidly entered the brain, with SUVs between 4 and 5, and with a distribution pattern consistent with that of PDE4.

METHOD FOR PREPARING (R)-ROLIPRAM PRECURSOR BY CATALYTIC ENANTIOSELECTIVE MICAHEL REACTION AND METHOD FOR PREPARING (R)-ROLPTRAM USING THE (R)-ROLIPRAM PRECURSOR

According to the present invention, a method for preparing chiral (R)-rolipram precursors includes a step of enabling an asymmetric Michael reaction of 3-(cyclo pentoxy)-4-methoxyphenyl nitro and malonate in the presence of a soluble chiral catalyst. Accordingly, the present invention can synthesize chiral (R)-rolipram precursors at low costs by using an organic catalyst not including transition metals with high optical selectivity and reactivity in the presence of water, aqueous solution, or a mixed solution of an organic solvent which are not harmful to the human body and do not cause environmental pollution.COPYRIGHT KIPO 2015

Multistep continuous-flow synthesis of (R)- and (S)-rolipram using heterogeneous catalysts

Chemical manufacturing is conducted using either batch systems or continuous-flow systems. Flow systems have several advantages over batch systems, particularly in terms of productivity, heat and mixing efficiency, safety, and reproducibility. However, fo