874362-20-6

Basic information

• Product Name: L-Valine, N-[chloro(1-naphthalenyloxy)phosphinyl]-, phenylmethyl ester
• CAS NO: 874362-20-6
• Molecular Formula: C22H23ClNO4P
• Molecular Weight: 431.856
• Mol File: 874362-20-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: L-Valine, N-[chloro(1-naphthalenyloxy)phosphinyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Valine, N-[chloro(1-naphthalenyloxy)phosphinyl]-, phenylmethyl ester(874362-20-6)
• EPA Substance Registry System: L-Valine, N-[chloro(1-naphthalenyloxy)phosphinyl]-, phenylmethyl ester(874362-20-6)

Safety Data

• Hazardous Substances Data: 874362-20-6(Hazardous Substances Data)

Upstream product

• 90-15-3 α-naphthol 
• 31651-76-0 1-naphthyl dichlorophosphate 
• 21760-98-5 L-valine benzyl ester 

Relevant articles and documents

ProTides of BVdU as potential anticancer agents upon efficient intracellular delivery of their activated metabolites

Nucleosides represent a major chemotherapeutic class for treating cancer, however their limitations in terms of cellular uptake, nucleoside kinase-mediated activation and catabolism are well-documented. The monophosphate pro-nucleotides known as ProTides represents a powerful strategy for bypassing the dependence on active transport and nucleoside kinase-mediated activation. Herein, we report the structural tuning of BVdU ProTides. Forty six phosphoramidates were prepared and biologically evaluated against three different cancer cell lines; murine leukemia (L1210), human CD4+T-lymphocyte (CEM) and human cervical carcinoma (HeLa). Twenty-fold potency enhancement compared to BVdU was achieved against L1210 cells. Interestingly, a number of ProTides showed low micromolar activity against CEM and HeLa cells compared to the inactive parent BVdU. The ProTides showed poor, if any measurable toxicity to non-tumourigenic human lung fibroblast cell cultures. Separation of four pairs of the diastereoisomeric mixtures and comparison of their spectral properties, biological activities and enzymatic activation rate is reported.

Novel potential anticancer naphthyl phosphoramidates of BVdU: Separation of diastereoisomers and assignment of the absolute configuration of the phosphorus center

We have previously reported our SAR optimization of the anticancer agent thymectacin. Tuning of the parent ProTide structure initially involved the amino acid and, subsequently, the aromatic masking group on the phosphate moiety. Herein, derivatives beari