194809-23-9

Basic information

• Product Name: L-Glutamic acid, N-[4-amino-3-(trifluoromethyl)benzoyl]-4-fluoro-, bis(1-methylethyl) ester, (4R)-
• CAS NO: 194809-23-9
• Molecular Formula: C19H24F4N2O5
• Molecular Weight: 436.404
• Mol File: 194809-23-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: L-Glutamic acid, N-[4-amino-3-(trifluoromethyl)benzoyl]-4-fluoro-, bis(1-methylethyl) ester, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid, N-[4-amino-3-(trifluoromethyl)benzoyl]-4-fluoro-, bis(1-methylethyl) ester, (4R)-(194809-23-9)
• EPA Substance Registry System: L-Glutamic acid, N-[4-amino-3-(trifluoromethyl)benzoyl]-4-fluoro-, bis(1-methylethyl) ester, (4R)-(194809-23-9)

Safety Data

• Hazardous Substances Data: 194809-23-9(Hazardous Substances Data)

Upstream product

• 400-76-0 4-amino-3-(trifluoromethyl)benzoic acid 

Downstream Products

• 194809-24-0 (2S,4R)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-amino]-3-trifluoromethyl-benzoylamino}-4-fluoro-pentanedioic acid diisopropyl ester 

Relevant articles and documents

Synthesis and evaluation of novel fluorinated methotrexate derivatives for application to rheumatoid arthritis treatment

In ongoing search for new antifolate drugs useful against rheumatoid arthritis (RA) led us to prepare new methotrexate (MTX) derivatives containing enantiomerically pure L-erythro- or L-threo-γ-fluoroglutamic acid. The derivatives in which the phenyl ring was replaced by a 3'- substituted phenyl or methylthiophene ring showed potent immunosuppressive activities, including in vitro inhibition of mitogen responses of both T and B cells and in vivo inhibition of antibody production in mice. These compounds also exhibited inhibitory activity in adjuvant arthritis in rats. Their toxicity was lower than that of MTX, which was probably due to the strong electronegativity of fluorine, which increases the acidity of the γ- carboxyl group and thereby decreases polyglutamylation in normal cells. These results revealed the potential of the fluorinated MTX derivatives as candidate drugs for the treatment of RA.