147907-41-3

Basic information

• Product Name: L-Leucine, N-(chlorophenoxyphosphinyl)-, methyl ester
• CAS NO: 147907-41-3
• Molecular Formula: C13H19ClNO4P
• Molecular Weight: 319.725
• Mol File: 147907-41-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: L-Leucine, N-(chlorophenoxyphosphinyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Leucine, N-(chlorophenoxyphosphinyl)-, methyl ester(147907-41-3)
• EPA Substance Registry System: L-Leucine, N-(chlorophenoxyphosphinyl)-, methyl ester(147907-41-3)

Safety Data

• Hazardous Substances Data: 147907-41-3(Hazardous Substances Data)

Upstream product

• 2666-93-5 (S)-Leu-OMe 
• 770-12-7 O-phenyl phosphorodichloridate 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 61-90-5 L-leucine 
• 108-95-2 phenol 

Downstream Products

• 1240428-38-9 N-((phenoxy)((5-hydroxy-2-phenyl-4-oxo-4H-chromene-7-yl)oxy)phosphoryl)-L-leucine methyl ester 
• 1250829-97-0 (S)-2-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}-4-methylpentanoic acid methyl ester 

Relevant articles and documents

Phosphoramidate protides of five flavones and their antiproliferative activity against HepG2 and L-O2 cell lines

A series of flavone-7-phosphoramidate derivatives were synthesized and tested for their antiproliferative activity in vitro against human hepatoma cell line HepG2 and human normal hepatic cell line L-O2. Compound 8d, 16d and 17d, incorporating the amino acid alanine, exhibited high inhibitory activity on HepG2 cell line with IC50 values of 9.0 μmol/L, 5.5 μmol/L and 6.6 μmol/L. The introduction of acyl groups played a pivotal role in the selective inhibition toward human hepatoma HepG2 cells, except for compound 8a, 9a and 16b. Compound 8d, 16d and 17d could significantly induce G2/M arrest in HepG2 cells. Specially, Compound 16d could lead early apoptosis in HepG2 cells.

Discovery of a luoro-2′-β- C -methyluridine Nucleotide Prodrug (PSI-7977) for the treatment of hepatitis C virus

Hepatitis C virus (HCV) is a global health problem requiring novel approaches for effective treatment of this disease. The HCV NS5B polymerase has been demonstrated to be a viable target for the development of HCV therapies. β-d-2′-Deoxy-2′-α-fluoro-2′-β-C-methyl nucleosides are selective inhibitors of the HCV NS5B polymerase and have demonstrated potent activity in the clinic. Phosphoramidate prodrugs of the 5′-phosphate derivative of the β-d-2′-deoxy-2′-α- fluoro-2′-β-C-methyluridine nucleoside were prepared and showed significant potency in the HCV subgenomic replicon assay (1 μM) and produced high levels of triphosphate 6 in primary hepatocytes and in the livers of rats, dogs, and monkeys when administered in vivo. The single diastereomer 51 of diastereomeric mixture 14 was crystallized, and an X-ray structure was determined establishing the phosphoramidate stereochemistry as Sp, thus correlating for the first time the stereochemistry of a phosphoramidate prodrug with biological activity. 51 (PSI-7977) was selected as a clinical development candidate.

CHEMICAL COMPOUNDS

Phosphoramidate derivatives of nucleotides and their use in the treatment of cancer are described. The base moieties of, for example, each of deoxyuridine, cytarabine, gemcitabine and citidine may be substituted at the 5-position. The phosphoramidate moiety has attached to the P atom an aryl-O moiety and an α-amino acid moiety. The α-amino acid moiety may correspond to or be derived from either a naturally occurring or a non-naturally occurring amino acid.