147907-38-8

Basic information

• Product Name: L-Alanine, N-[chloro(4-methoxyphenoxy)phosphinyl]-, methyl ester
• CAS NO: 147907-38-8
• Molecular Formula: C11H15ClNO5P
• Molecular Weight: 307.671
• Mol File: 147907-38-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: L-Alanine, N-[chloro(4-methoxyphenoxy)phosphinyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, N-[chloro(4-methoxyphenoxy)phosphinyl]-, methyl ester(147907-38-8)
• EPA Substance Registry System: L-Alanine, N-[chloro(4-methoxyphenoxy)phosphinyl]-, methyl ester(147907-38-8)

Safety Data

• Hazardous Substances Data: 147907-38-8(Hazardous Substances Data)

Usage

Description

L-Alanine, N-[chloro(4-methoxyphenoxy)phosphinyl]-, methyl ester is a chemical compound derived from alanine, a non-essential amino acid. It is a methyl ester derivative of a phosphinic acid, which contains a chlorine atom and a 4-methoxyphenoxy group. This versatile compound has potential applications in various scientific and industrial fields, including pharmaceuticals, biochemistry, and organic synthesis.

Uses

Used in Pharmaceutical Industry:
L-Alanine, N-[chloro(4-methoxyphenoxy)phosphinyl]-, methyl ester is used as a building block in drug design and development. Its unique structure allows it to be incorporated into the synthesis of more complex organic molecules with specific properties and functions, which can be used for the treatment of various diseases and conditions.
Used in Biochemistry Research:
L-Alanine, N-[chloro(4-methoxyphenoxy)phosphinyl]-, methyl ester is used as a research tool in the study of biochemical pathways and mechanisms. Its ability to interact with other molecules and enzymes can provide valuable insights into the underlying processes of various biological systems.
Used in Organic Synthesis:
L-Alanine, N-[chloro(4-methoxyphenoxy)phosphinyl]-, methyl ester is used as a versatile building block in organic synthesis. Its unique functional groups and reactivity make it a valuable component in the synthesis of a wide range of organic compounds with diverse applications.

Upstream product

• 150-76-5 4-methoxy-phenol 
• 20464-68-0 4-methoxyphenyl phosphorodichloridate 
• 2491-20-5 L-alanine methyl ester hydrochloride 

Downstream Products

• 946511-37-1 5'-O-[[[(1S)-2-methoxy-1-methyl-2-oxoethyl]amino](4-methoxyphenoxy)phosphinyl]-2'-C-methylcytidine 
• 149560-32-7 3'-azidothymidine 5'-[p-methoxyphenyl methoxyalaninyl phosphate] 
• 217178-61-5 2',3'-didehydro-2',3'-dideoxythymidine 5'-(4-methoxyphenyl (methoxyalaninyl)phosphate) 

Relevant articles and documents

Synthesis and biological evaluation of aryl phosphoramidate prodrugs of fosfoxacin and its derivatives

Aryl phosphoramidate prodrugs of fosfoxacin derivatives 15a-b and 8a-b were synthesized and investigated for their ability to target bacteria. No growth inhibition was observed neither for Mycobacterium smegmatis nor for Escherichia coli on solid medium,

Phosphoramidate and phosphate prodrugs of (-)-β-D-(2R,4R)-dioxolane- thymine: Synthesis, anti-HIV activity and stability studies

A series of phosphoramidate and phosphate prodrugs of DOT were synthesized via dichlorophosphate or H-phosphonate chemistry and evaluated for their anti-HIV activity against LAI M184V mutants in PBM cells as well as for their cytotoxicity. The antiviral and cytotoxic profiles of the prodrugs were compared with that of the parent compound (DOT), and it was found that four aryl phosphoramidates 5, 18, 20, and 26 showed a significant enhancement (8- to 12-fold) in anti-HIV activity without cytotoxicity. Chemical stability of these prodrugs was evaluated in phosphate buffer at pH values of biological relevance (i.e., pH 2.0 and 7.4). Enzymatic hydrolysis was also studied in esterase or lipase in buffer solution. Chemical stability studies indicate that the phosphoramidates have good chemical stability at pH 2.0 and at pH 7.4 phosphate buffer. Phosphoramidate prodrugs were hydrolyzed in vitro by esterase or lipase and found to be better substrates for lipases than for esterases. 1,3-Diol cyclic phosphates showed potent anti-HIV activity without increasing the cytotoxicity compared with that of DOT and have good chemical and enzymatic stability. Long-chain lipid phosphates, although showed potent anti-HIV activity, exhibited increased cytotoxicity.

Intracellular delivery of bioactive AZT nucleotides by aryl phosphate derivatives of AZT

Novel aryl phosphate derivatives of the anti-HIV nucleoside analogue AZT have been prepared by phosphorochloridate chemistry. These materials were designed to act as membrane-soluble prodrugs of the bioactive free nucleotides. In vitro evaluation revealed the compounds to have a pronounced, selective anti-HIV activity in CEM cells; the magnitude of the biological effect varied considerably depending on the nature of the phosphate blocking group. Moreover, several of the compounds retain marked antiviral activity in TK- (thymidine kinase-deficient) mutant CEM cells in which AZT was virtually inactive. These data strongly support the hypothesis that the AZT phosphate derivatives exert their biological effects via intracellular release of AZT nucleotide forms and suggest that the potential of nucleoside drugs in antiviral chemotherapy may be enhanced by suitable nucleotide delivery strategies.