259214-37-4

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 4-[(7-methoxy-2-phenyl-4-quinolinyl)oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4R)-
• CAS NO: 259214-37-4
• Molecular Formula: C26H28N2O6
• Molecular Weight: 464.518
• Mol File: 259214-37-4.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[(7-methoxy-2-phenyl-4-quinolinyl)oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[(7-methoxy-2-phenyl-4-quinolinyl)oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4R)-(259214-37-4)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 4-[(7-methoxy-2-phenyl-4-quinolinyl)oxy]-, 1-(1,1-dimethylethyl) ester, (2S,4R)-(259214-37-4)

Safety Data

• Hazardous Substances Data: 259214-37-4(Hazardous Substances Data)

Upstream product

• 536-90-3 m-Anisidine 
• 189816-05-5 4-chloro-7-methoxy-2-phenylquinoline 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 855239-80-4 N-(2-acetyl-5-methoxyphenyl)benzamide 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 20430-72-2 7-methoxy-2-phenylquinolin-4-ol 
• 259214-70-5 (2S,4R)-4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 

Downstream Products

• 445305-87-3 (2S,4R)-2-((1R,2S)-1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 445305-88-4 (2S,4R)-2-((1S,2R)-1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 681809-20-1 C₄₂H₄₆N₄O₈S 
• 681809-26-7 C₃₉H₄₆N₄O₈S 
• 1010453-33-4 (2S,4R)-tert-butyl 2-(1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamoyl)-4-(7-methoxy-2-phenylquinolin-4-yloxy)pyrrolidine-1-carboxylate 
• 1051391-41-3 (2S,4R)-2-{(1R,2S)-1-[2-(8-methoxycarbonyl-octanoylamino)-benzenesulfonylaminocarbonyl]-2-vinyl-cyclopropylcarbamoyl}-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 852022-11-8 C₃₀H₃₅N₅O₆S 
• 793661-43-5 1-{[4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester 

Relevant articles and documents

Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More-Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420

An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high yields. By adapting this methodology, a convergent synthesis of a complex target of HCV NS3/4a protease inhibitor BI 201420 was accomplished.

Hepatitis C Virus Inhibitors

Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Discovery of novel, potent and bioavailable proline-urea based macrocyclic HCV NS3/4A protease inhibitors

A novel series of P3-truncated macrocyclic HCV NS3/4A protease inhibitors containing a P2 proline-urea or carbamate scaffold was synthesized. Very potent inhibitors were obtained through the optimization of the macrocycle size, urea and proline substitution, and bioisosteric replacement of the P1 carboxylic acid moiety. Variation of the lipophilicity by introduction of small lipophilic substituents resulted in improved PK profiles, ultimately leading to compound 13Bh, an extremely potent (Ki = 0.1 nM, EC50 = 4.5 nM) and selective (CC50 (Huh-7 cells) > 50 μM) inhibitor, displaying an excellent PK profile in rats characterized by an oral bioavailability of 54% and a high liver exposure after oral administration.