1616491-41-8

Basic information

• Product Name: methyl 2-(3-(1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamido)propoxy)-6-hydroxybenzoate
• Synonyms: methyl 2-(3-(1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamido)propoxy)-6-hydroxybenzoate
• CAS NO: 1616491-41-8
• Molecular Weight: 549.512
• Mol File: 1616491-41-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 2-(3-(1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamido)propoxy)-6-hydroxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(3-(1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamido)propoxy)-6-hydroxybenzoate(1616491-41-8)
• EPA Substance Registry System: methyl 2-(3-(1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamido)propoxy)-6-hydroxybenzoate(1616491-41-8)

Safety Data

• Hazardous Substances Data: 1616491-41-8(Hazardous Substances Data)

Upstream product

• 1616491-55-4 ethyl 1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 709-46-6 2-fluoro-5-nitrobenzoyl chloride 
• 7304-32-7 2-fluoro-5-nitrobenzoic acid 
• 786641-60-9 methyl 2-(3-aminopropoxy)-6-hydroxybenzoate 
• 1616491-19-0 1-(4-fluorobenzyl)-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 692765-94-9 methyl 2-(3-((tert-butoxycarbonyl)amino)propoxy)-6-hydroxybenzoate 
• 2150-45-0 methyl 2,6-dihydroxybenzoate 

Relevant articles and documents

4-Quinolone-3-carboxylic acids as cell-permeable inhibitors of protein tyrosine phosphatase 1B

Protein tyrosine phosphatase 1B is a negative regulator in the insulin and leptin signaling pathways, and has emerged as an attractive target for the treatment of type 2 diabetes and obesity. However, the essential pharmacophore of charged phosphotyrosine or its mimetic confer low selectivity and poor cell permeability. Starting from our previously reported aryl diketoacid-based PTP1B inhibitors, a drug-like scaffold of 4-quinolone-3-carboxylic acid was introduced for the first time as a novel surrogate of phosphotyrosine. An optimal combination of hydrophobic groups installed at C-6, N-1 and C-3 positions of the quinolone motif afforded potent PTP1B inhibitors with low micromolar IC 50 values. These 4-quinolone-3-carboxylate based PTP1B inhibitors displayed a 2-10 fold selectivity over a panel of PTP's. Furthermore, the bidentate inhibitors of 4-quinolone-3-carboxylic acids conjugated with aryl diketoacid or salicylic acid were cell permeable and enhanced insulin signaling in CHO/hIR cells. The kinetic studies and molecular modeling suggest that the 4-quinolone-3-carboxylates act as competitive inhibitors by binding to the PTP1B active site in the WPD loop closed conformation. Taken together, our study shows that the 4-quinolone-3-carboxylic acid derivatives exhibit improved pharmacological properties over previously described PTB1B inhibitors and warrant further preclinical studies.