660448-79-3

Upstream product

• 214957-87-6 N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 501-53-1 benzyl chloroformate 
• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 214957-88-7 2-{[(benzyloxy)carbonyl]amino}-5-hydroxybenzoic acid 

Downstream Products

• 660448-80-6 2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamide 
• 660449-17-2 ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]prop-2-enoate 
• 660449-03-6 6-hydroxy-4-(4-methylphenyl)-2-(2-methylpropyl)quinoline-3-carbonitrile 
• 660449-04-7 tert-butyl {[6-hydroxy-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-3-yl]methyl}carbamate 
• 660449-16-1 3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl trifluoromethanesulfonate 
• 660449-70-7 (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)(3-fluorophenyl)methanone 
• 660449-59-2 (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)(3-methylphenyl)methanone 
• 660449-55-8 (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)(4-fluorophenyl)methanone 
• 1330529-96-8 (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}phenyl)(4-methylphenyl)methanone 
• 660449-05-8 methyl {[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]oxy}acetate 
• 660449-06-9 {[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]oxy}acetic acid 

Relevant academic research and scientific papers

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.