28563-19-1

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 857, 1988 DOI: 10.1002/jhet.5570250330

InChI:InChI=1/C15H10ClNO2/c16-10-6-7-11-12(8-10)17-15(19)13(14(11)18)9-4-2-1-3-5-9/h1-8H,(H2,17,18,19)

Upstream product

• 147778-09-4 4-chloro-2-phenylacetylamino-benzoic acid methyl ester 
• 103-80-0 phenylacetyl chloride 
• 5900-58-3 2-amino-4-chloro-benzoic acid methyl ester 
• 243841-37-4 7-chloro-2-ethoxy-(4H)-3,1-benzoxazine-4-one 
• 101-97-3 Ethyl 2-phenylethanoate 

Downstream Products

• 150097-43-1 7-chloro-4-methoxycarbonylmethoxy-3-phenyl-2(1H)-quinolone 
• 150097-42-0 4-allyloxy-7-chloro-3-phenyl-2(1H)-quinolone 
• 150097-51-1 7-chloro-4-methylcarbonylmethoxy-3-phenyl-2(1H)-quinolone 
• 1027606-09-2 (7-Chloro-2-oxo-3-phenyl-1,2-dihydro-quinolin-4-yloxy)-acetaldehyde 
• 150097-44-2 4-carboxymethoxy-7-chloro-3-phenyl-2(1H)-quinolone 

Relevant academic research and scientific papers

An efficient route to 3-aryl-substituted quinolin-2-one and 1,8-naphthyridin-2-one derivatives of pharmaceutical interest

Reaction of arylacetic ester enolates with 2-alkoxy-4H-3,1-benzoxazin-4-ones offers a short and versatile synthetic route to 3-aryl-4-hydroxyquinolin-2(1H)-ones, through the cyclization of the β-ketoesters produced. Similar reactions of 4H-pyrido[2,3-d][1

Identification and initial structure-activity relationships of a novel non-peptide quinolone GnRH receptor antagonist

Screening of the Merck sample collection for non-peptide compounds with binding affinity for the rat GnRH receptor led to the identification of the substituted quinolone (1) as a lead compound in the search for a non-peptide GnRH receptor antagonist. Substantial improvements in potency (~300 fold) were achieved by addition of an alkyl amine at the 4-position, a 3,5-dimethylphenyl group at the 3-position and 6-nitro-7-chlorosubstitution of the 1H-quinolone core.