660449-04-7

Basic information

• Product Name: Carbamic acid, [[6-hydroxy-4-(4-methylphenyl)-2-(2-methylpropyl)-3-quinolinyl]methyl]-, 1,1-dimethylethyl ester
• CAS NO: 660449-04-7
• Molecular Formula: C26H32N2O3
• Molecular Weight: 420.552
• Mol File: 660449-04-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [[6-hydroxy-4-(4-methylphenyl)-2-(2-methylpropyl)-3-quinolinyl]methyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [[6-hydroxy-4-(4-methylphenyl)-2-(2-methylpropyl)-3-quinolinyl]methyl]-, 1,1-dimethylethyl ester(660449-04-7)
• EPA Substance Registry System: Carbamic acid, [[6-hydroxy-4-(4-methylphenyl)-2-(2-methylpropyl)-3-quinolinyl]methyl]-, 1,1-dimethylethyl ester(660449-04-7)

Safety Data

• Hazardous Substances Data: 660449-04-7(Hazardous Substances Data)

Upstream product

• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 214957-87-6 N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide 
• 660448-80-6 2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamide 
• 660448-79-3 benzyl (4-{[tert-butyl(dimethyl)silyl]oxy}-2-{[methoxy(methyl)amino]carbonyl}phenyl)carbamate 
• 214957-88-7 2-{[(benzyloxy)carbonyl]amino}-5-hydroxybenzoic acid 
• 1330529-96-8 (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)(4-methylphenyl)methanone 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 5621-60-3 (2-amino-5-bromophenyl)-(4-methylphenyl)methanone 
• 64373-43-9 5-methyl-3-oxo-hexanenitrile 
• 556-24-1 methyl 3-methylbutanoate 
• 4692-98-2 5-bromoisatoic anhydride 
• 660449-03-6 6-hydroxy-4-(4-methylphenyl)-2-(2-methylpropyl)quinoline-3-carbonitrile 
• 660451-32-1 6-bromo-4-(4-methylphenyl)-2-(2-methylpropyl)quinoline-3-carbonitrile 

Downstream Products

• 660450-38-4 tert-butyl {[6-(cyanomethoxy)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl} carbamate 
• 660449-26-3 tert-butyl ({2-isobutyl-4-(4-methylphenyl)-6-[(2-methyl-1,3-thiazol-4-yl)methoxy]quinolin-3-yl}methyl)carbamate 
• 660449-16-1 3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl trifluoromethanesulfonate 
• 660451-99-0 tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate 
• 1262394-33-1 ethyl 3-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]propanoate 
• 660451-15-0 3-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]propanoic acid 
• 660452-01-7 6-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]hexanoic acid 
• 660449-17-2 ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]prop-2-enoate 
• 660452-00-6 tert-butyl {[6-(5-cyanopentyl)-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-3-yl]methyl}carbamate 
• 660449-06-9 {[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]oxy}acetic acid 
• 660449-07-0 tert-butyl ({6-[2-(methylamino)-2-oxoethoxy]-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-3-yl}methyl)carbamate 
• 660449-18-3 (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]prop-2-enoic acid 
• 660449-19-4 tert-butyl ({6-[(1E)-3-amino-3-oxoprop-1-en-1-yl]-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-3-yl}methyl)carbamate 
• 660450-71-5 tert-butyl {[6-(3-amino-3-oxopropyl)-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-3-yl]methyl}carbamate 

Relevant articles and documents

Discovery of potent, selective, and orally bioavailable quinoline-based dipeptidyl peptidase IV inhibitors targeting Lys554

Dipeptidyl peptidase IV (DPP-4) inhibition is a validated therapeutic option for type 2 diabetes, exhibiting multiple antidiabetic effects with little or no risk of hypoglycemia. In our studies involving non-covalent DPP-4 inhibitors, a novel series of quinoline-based inhibitors were designed based on the co-crystal structure of isoquinolone 2 in complex with DPP-4 to target the side chain of Lys554. Synthesis and evaluation of designed compounds revealed 1-[3-(aminomethyl)-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl] piperazine-2,5-dione (1) as a potent, selective, and orally active DPP-4 inhibitor (IC50 = 1.3 nM) with long-lasting ex vivo activity in dogs and excellent antihyperglycemic effects in rats. A docking study of compound 1 revealed a hydrogen-bonding interaction with the side chain of Lys554, suggesting this residue as a potential target site useful for enhancing DPP-4 inhibition.

FUSED HETEROCYCLIC COMPOUNDS

A compound represented by the formula wherein ring A is an optionally substituted 5- to 10-membered aromatic ring; R1 and R2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; X and Y are the same or different and each is a bond, -O-, -S-, -SO-, -SO?2#191- or -NR3- (R3 is a hydrogen atom or an optionally substituted hydrocarbon group); and L is a divalent hydrocarbon group, or a salt thereof shows a superior peptidase-inhibitory activity and is useful as a prophylactic or therapeutic agent of diabetes and the like.