220284-76-4

Basic information

• Product Name: Benzoic acid, 3-[4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-oxo-1-pyrrolidinyl]-5-(phenyl methoxy)-, methyl ester
• CAS NO: 220284-76-4
• Molecular Formula: C31H33NO6
• Molecular Weight: 515.606
• Mol File: 220284-76-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 3-[4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-oxo-1-pyrrolidinyl]-5-(phenyl methoxy)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3-[4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-oxo-1-pyrrolidinyl]-5-(phenyl methoxy)-, methyl ester(220284-76-4)
• EPA Substance Registry System: Benzoic acid, 3-[4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-oxo-1-pyrrolidinyl]-5-(phenyl methoxy)-, methyl ester(220284-76-4)

Safety Data

• Hazardous Substances Data: 220284-76-4(Hazardous Substances Data)

Upstream product

• 61413-54-5 Rolipram 

Downstream Products

• 220573-60-4 methyl 5-[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]-3-(3-methoxybenzyloxy)-benzoate 
• 220573-56-8 3-[4-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxo-pyrrolidin-1-yl]-5-(3-methoxybenzyloxy)-benzoic acid 
• 220573-59-1 3-[4-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-oxo-pyrrolidin-1-yl]-5-hydroxy-benzoic acid methyl ester 

Relevant articles and documents

Synthesis and structure - Activity relationship of N-arylrolipram derivatives as inhibitors of PDE4 isozymes

Structure activity studies of N-phenylrolipram derivatives have led to the identification of highly potent PDE4 inhibitors. The potential of these inhibitors for cellular activity was routinely assessed in an assay of fMLP induced oxidative burst in human eosinophils. Since first generation PDE4 inhibitors have been plagued with a number of unwanted side effects, parallel structure activity studies for competition with the [3H]-rolipram binding site in rat brain were performed. In this fashion 5-[4-(3-cyclopentyloxy-4-methoxyphenyl) -2-oxo-pyrrolidin-1-y1]-3-(3-methoxybenzyloxy)benzoic acid N′,N′-dimethylhydrazide (22) was identified as a potent inhibitor of PDE4 which exhibits >1000 fold selectivity versus PDE3, and is a nanomolar inhibitor in all the cellular assays tested. Studies on the stereoselectivity of PDE4 inhibition of this class of rolipram based compounds revealed, that for example (S)-11 is a more potent inhibitor than (R)-11. This effect can also be observed in primary human cells where the (S)-enantiomer is about 10 fold more potent than the corresponding (R)-enantiomer.

N-arylrolipram derivatives as potent and selective PDE4 inhibitors

Derivatization of rolipram led to the identification of 3-[4-(3- cyclopentyloxy-4-methoxypbenyl)-2-oxo-pyrrolidin-1-yl]-5-(3- methoxybenzyloxy)-benzoic acid N',N'-dimethylhydrazide (4), a potent and selective inhibitor of PDE4, which inhibits the activation of human leukocytes with pIC50 values in the range of 7.3 - 7.8, and blocks antigen induced eosinophilia in Brown Norway rats at a dose of 1 mg/kg (i.t.).