1458219-01-6

Basic information

• Product Name: 7-((3-chlorobenzyl)oxy)-3,4-dihydroquinolin-2(1H)-one
• Synonyms: 7-((3-chlorobenzyl)oxy)-3,4-dihydroquinolin-2(1H)-one
• CAS NO: 1458219-01-6
• Molecular Weight: 287.746
• Mol File: 1458219-01-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 7-((3-chlorobenzyl)oxy)-3,4-dihydroquinolin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-((3-chlorobenzyl)oxy)-3,4-dihydroquinolin-2(1H)-one(1458219-01-6)
• EPA Substance Registry System: 7-((3-chlorobenzyl)oxy)-3,4-dihydroquinolin-2(1H)-one(1458219-01-6)

Safety Data

• Hazardous Substances Data: 1458219-01-6(Hazardous Substances Data)

Upstream product

• 22246-18-0 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone 
• 766-80-3 1-bromomethyl-3-chlorobenzene 

Relevant articles and documents

Neuroprotective effects of benzyloxy substituted small molecule monoamine oxidase B inhibitors in Parkinson's disease

The benzyloxy substituted small molecules are well-known highly potent monoamine oxidase B inhibitors, but their therapeutic potential against Parkinson's disease have not been investigated in detail. In this paper, a series of representative benzyloxy substituted derivatives were synthesized and evaluated for MAO-A/B inhibition. In addition, their neuroprotective effects were investigated in 6-OHDA- and rotenone-treated PC12 cells. It was observed that most of the compounds exhibited a marked increase in survival of PC12 cells which treated with the neurotoxins. Among them, 13 exhibited remarkable and balanced neuroprotective potency. The protective effects of 13 against neurotoxins-induced apoptosis were confirmed with flow cytometry and staining methods. Furthermore, 13 also showed good BBB permeability and low toxicity according to in vitro BBB prediction and in vivo acute toxicity test. The results indicated that 13 is an effective and promising candidate to be further developed as disease-modifying drug for Parkinson's disease therapy.

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.