214957-88-7

Basic information

• Product Name: Benzoic acid, 5-hydroxy-2-[[(phenylmethoxy)carbonyl]amino]-
• CAS NO: 214957-88-7
• Molecular Formula: C15H13NO5
• Molecular Weight: 287.272
• Mol File: 214957-88-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 5-hydroxy-2-[[(phenylmethoxy)carbonyl]amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 5-hydroxy-2-[[(phenylmethoxy)carbonyl]amino]-(214957-88-7)
• EPA Substance Registry System: Benzoic acid, 5-hydroxy-2-[[(phenylmethoxy)carbonyl]amino]-(214957-88-7)

Safety Data

• Hazardous Substances Data: 214957-88-7(Hazardous Substances Data)

Upstream product

• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 214957-87-6 N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide 
• 1335060-61-1 methyl 2-(benzyloxycarbonylamino)-5-methoxybenzoate 
• 23042-77-5 1-(2-amino-5-methoxy-phenyl)-ethanone 
• 1335060-63-3 4-(2-acetyl-4-methoxyphenylamino)butan-2-one 
• 1335060-62-2 benzyl 2-acetyl-4-methoxyphenylcarbamate 
• 214971-08-1 benzyl 4-methoxy-2-(methoxy(methyl)carbamoyl)phenylcarbamate 
• 1335060-71-3 allyl 3-(1-(tert-butyldiphenylsilyloxy)ethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate 
• 1335060-70-2 allyl 6-methoxy-4-methyl-2-(2-phenylethynyl)-3-(1-pivaloyloxyethyl)quinoline-1(2H)-carboxylate 
• 1335060-69-9 allyl 3-(1-acetoxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate 
• 1335060-67-7 allyl 3-(1-allyloxycarbonyloxyethyl)-6-methoxy-4-methyl-2-(2-phenylethynyl)quinoline-1(2H)-carboxylate 
• 1335060-66-6 3-(1-(tert-butyldiphenylsilyloxy)ethyl)-6-methoxy-4-methylquinoline 
• 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 
• 660451-57-0 tert-butyl {[4-(4-methylphenyl)-2-(2-methylpropyl)-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)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.