1561139-31-8

Basic information

• Product Name: N-(2,4-difluorobenzyl)-1-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamide
• CAS NO: 1561139-31-8
• Molecular Weight: 330.291
• Mol File: 1561139-31-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-(2,4-difluorobenzyl)-1-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,4-difluorobenzyl)-1-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamide(1561139-31-8)
• EPA Substance Registry System: N-(2,4-difluorobenzyl)-1-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamide(1561139-31-8)

Safety Data

• Hazardous Substances Data: 1561139-31-8(Hazardous Substances Data)

Upstream product

• 72235-52-0 2,4-Difluoro-benzylamine 
• 16026-93-0 methyl 1-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate 
• 552-89-6 2-nitro-benzaldehyde 
• 65974-52-9 dimethyl 2-[(2-nitrophenyl)methylidene]malonate 

Relevant articles and documents

Bicyclic 1-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide-containing HIV-1 integrase inhibitors having high antiviral potency against cells harboring raltegravir-resistant integrase mutants

Integrase (IN) inhibitors are the newest class of antiretroviral agents developed for the treatment of HIV-1 infections. Merck's Raltegravir (RAL) (October 2007) and Gilead's Elvitegravir (EVG) (August 2012), which act as IN strand transfer inhibitors (INSTIs), were the first anti-IN drugs to be approved by the FDA. However, the virus develops resistance to both RAL and EVG, and there is extensive cross-resistance to these two drugs. New "2nd- generation" INSTIs are needed that will have greater efficacy against RAL- and EVG-resistant strains of IN. The FDA has recently approved the first second generation INSTI, GSK's Dolutegravir (DTG) (August 2013). Our current article describes the design, synthesis, and evaluation of a series of 1,8-dihydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides, 1,4-dihydroxy-2-oxo-1, 2-dihydro-1,8-naphthyridine-3-carboxamides, and 1-hydroxy-2-oxo-1,2-dihydro-1,8- naphthyridine-3-carboxamides. This resulted in the identification of noncytotoxic inhibitors that exhibited single digit nanomolar EC50 values against HIV-1 vectors harboring wild-type IN in cell-based assays. Importantly, some of these new inhibitors retain greater antiviral efficacy compared to that of RAL when tested against a panel of IN mutants that included Y143R, N155H, G140S/Q148H, G118R, and E138K/Q148K.