92962-89-5

Basic information

• Product Name: 7-(benzyloxy)-3,4-dihydro-2(1H)-quinolinone
• Synonyms: 7-(benzyloxy)-3,4-dihydro-2(1H)-quinolinone
• CAS NO: 92962-89-5
• Molecular Weight: 253.301
• Mol File: 92962-89-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 7-(benzyloxy)-3,4-dihydro-2(1H)-quinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(benzyloxy)-3,4-dihydro-2(1H)-quinolinone(92962-89-5)
• EPA Substance Registry System: 7-(benzyloxy)-3,4-dihydro-2(1H)-quinolinone(92962-89-5)

Safety Data

• Hazardous Substances Data: 92962-89-5(Hazardous Substances Data)

Upstream product

• 22246-18-0 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 386273-52-5 7-(benzyloxy)quinolin-2(1H)-one 
• 852394-00-4 4-{4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl}-3-[1-(3-methoxy-propyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yloxymethyl]-5-oxo-piperazine-1-carboxylic acid tert-butyl ester 
• 777935-07-6 7-benzyloxy-1-(3-methoxypropyl)-3,4-dihydro-1H-quinolin-2-one 

Relevant articles and documents

A coumarin-labeled vinyl sulfone as tripeptidomimetic activity-based probe for cysteine cathepsins

A coumarin-tetrahydroquinoline hydride 8 was synthesized as a chemical tool for fluorescent labeling. The rigidified tricyclic coumarin structure was chosen for its suitable fluorescence properties. The connection of 8 with a vinyl sulfone building block was accomplished by convergent synthesis thereby leading to the coumarin-based, tripeptidomimetic activity-based probe 10, containing a Gly-Phe-Gly motif. Probe 10 was evaluated as inactivator of the therapeutically relevant human cysteine cathepsins S, L, K, and B: it showed particularly strong inactivation of cathepsin S. The detection of recombinant and native cathepsin S was demonstrated by applying 10 to in-gel fluorescence imaging. Tricycle light: A tripeptidomimetic, vinyl sulfone-type activity-based probe containing a rigid coumarin moiety fluorophore was prepared by convergent synthesis. The probe was evaluated as an inactivator of human cathepsins and, as exemplified with cathepsin S, it proved to be suitable for imaging in SDS-PAGE.

Inhibition of monoamine oxidase by 3,4-dihydro-2(1H)-quinolinone derivatives

In the present study, a series of 3,4-dihydro-2(1H)-quinolinone derivatives were synthesized and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The 3,4-dihydro-2(1H)-quinolinone derivatives are structurally related to a series of coumarin (1-benzopyran-2-one) derivatives which have been reported to act as MAO-B inhibitors. The results document that the quinolinones are highly potent and selective MAO-B inhibitors with most homologues exhibiting IC50 values in the nanomolar range. The most potent MAO-B inhibitor, 7-(3-bromobenzyloxy)-3,4-dihydro-2(1H)-quinolinone, exhibits an IC50 value of 2.9 nM with a 2750-fold selectivity for MAO-B over the MAO-A isoform. An analysis of the structure-activity relationships for MAO-B inhibition shows that substitution on the C7 position of the 3,4-dihydro-2(1H)-quinolinone scaffold leads to significantly more potent inhibition compared to substitution on C6. In this regard, a benzyloxy substituent on C7 is more favourable than phenylethoxy and phenylpropoxy substitution on this position. It may be concluded that C7-substituted 3,4-dihydro-2(1H)-quinolinones are promising leads for the therapy of Parkinson's disease.

PIPERAZINE DERIVATIVE RENIN INHIBITORS

Disclosed are piperazine derivatives, their manufacture and use as inhibitors of renin. Formula (I):