1256490-52-4

Basic information

• Product Name: L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester
• Synonyms: L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester;Isopropyl (2S)-2-[[(2,3,4,5,6-pentafluorophenoxy)-phenoxy-phosphoryl]amino]propanoate;propan-2-yl (2S)-2-{[pentafluorophenoxy(phenoxy)phosphoryl]amino}propanoate;N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester
• CAS NO: 1256490-52-4
• Molecular Formula: C₁₈H₁₇F₅NO₅P
• Molecular Weight: 453.297057
• Mol File: 1256490-52-4.mol

Chemical Properties

• Boiling Point: 442.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.405±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -3.81±0.70(Predicted)
• CAS DataBase Reference: L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester(1256490-52-4)
• EPA Substance Registry System: L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester(1256490-52-4)

Safety Data

• Hazardous Substances Data: 1256490-52-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester is used as a research tool for studying the enzyme dipeptidyl peptidase-4 (DPP-4) and related enzymes. Its potent inhibitory activity against DPP-4 aids in understanding the enzyme's role in blood glucose regulation and the development of potential therapeutic agents.
Used in Drug Development for Diabetes Treatment:
L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester is used as a potential drug candidate for the treatment of diabetes. Its ability to inhibit DPP-4 may help in modulating blood glucose levels, offering a new approach to managing this metabolic disorder.
Used in Drug Development for Metabolic Disorders:
Beyond diabetes, L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester may also be used in the development of drugs for other metabolic disorders. Its inhibitory effect on DPP-4 could have implications for the treatment of conditions related to glucose metabolism and insulin sensitivity.
Used in Peptide Synthesis:
L-Alanine, N-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphinyl]-, 1-Methylethyl ester is used in peptide synthesis, where its unique structure and properties can be leveraged to create novel peptide-based therapeutics and diagnostic agents. Its presence in synthetic peptides may enhance their stability, bioavailability, or target specificity, contributing to the advancement of peptide-based drug discovery.

Upstream product

• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 770-12-7 O-phenyl phosphorodichloridate 
• 39613-92-8 alanine isopropyl ester hydrochloride 
• 39825-33-7 isopropyl L-alanine 
• 338-69-2 D-Alanine 
• 67-63-0 isopropyl alcohol 
• 261909-49-3 phenyl(isopropoxy-L-alaninyl) phosphorochloridate 
• 2263-53-8 sodium pentafluorophenolate 
• 17788-07-7 2,3,4,5,6-pentafluorophenyl dichlorophosphate 
• 108-95-2 phenol 

Downstream Products

• 1403250-92-9 C₂₂H₃₂N₅O₈P 
• 1403250-91-8 (2S)-isopropyl 2-(((((2R,3S,4R,5R)-4-amino-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 
• 1403574-71-9 C₂₂H₃₀N₇O₈P 
• 1605283-78-0 C₃₁H₄₄N₅O₉P 
• 1605283-80-4 C₃₁H₄₄N₅O₉P 
• 1605283-84-8 C₃₁H₄₂N₅O₁₀P 
• 1605283-86-0 C₂₆H₃₆N₇O₉P 
• 1605283-89-3 C₃₀H₄₂N₇O₁₀P 
• 1605283-90-6 C₂₆H₃₆N₇O₉P 
• 1605283-94-0 C₂₇H₃₅N₄O₁₀P 
• 1567899-65-3 C₂₃H₂₈N₃O₁₀P 
• 1610022-14-4 C₂₇H₃₄N₃O₁₁P 
• 1231747-08-2 (S)-2-{(S)-[(1R,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-4-(R)-fluoro-3-hydroxy-4-methyl-tetrahydrofuran-2-ylmethoxy]phenoxy-phosphorylamino}propionic acid isopropyl ester 

Relevant articles and documents

Design, synthesis and evaluation of 2′-acetylene-7-deaza-adenosine phosphoamidate derivatives as anti-EV71 and anti-EV-D68 agents

A series of phosphoamidate derivatives of nucleoside 2′-acetylene-7-deaza-adenosine (NITD008) were synthesized and evaluated for their in vitro antiviral activities against the enteroviruses EV71 and EV-D68. The phosphoamidate (15f) containing a hexyl est

CYCLOBUTYL PURINE DERIVATIVE OR SALT THEREOF

An object of the present invention is to provide a compound exhibiting an excellent drug efficacy as an anti-adenoviral agent, and an anti-adenoviral agent. The present invention provides a compound represented by General Formula [1] (in the formula, R1 represents a halogen atom, an amino group which may be substituted, a C1-6 alkoxy group which may be substituted, a hydroxyl group which may be protected, or the like; R2 represents a hydrogen atom or an amino protecting group; R3 represents a C1-20 alkoxy group which may be substituted, an aryloxy group which may be substituted, an amino group which may be substituted, or the like; R4 represents a C1-20 alkoxy group which may be substituted, an aryloxy group which may be substituted, an amino group which may be substituted, or the like); or a salt thereof.

Nucleotide derivative and pharmaceutical composition and application thereof

The invention discloses a nucleotide derivative and a pharmaceutical composition and application thereof, wherein the nucleotide derivative is as shown in a formula (I). The compound can be used for preparing anti-virus infection drugs.

2,4,7-SUBSTITUTED-7-DEAZA-2'-DEOXY-2'-FLUOROARABINOSYL NUCLEOSIDE AND NUCLEOTIDE PRO-DRUGS AND USES THEREOF

The present disclosure is concerned with 2,4,7-substituted-7-deaza-2'-deoxy-2'- fluoroarabinosyl nucleoside and nucleotide prodrugs that are capable of inhibiting viral infections and methods of treating viral infections such as, for example, human immunodeficiency virus (HIV), human papillomavirus (HPV), herpes simplex virus (HSV), human cytomegalovirus (HCMV), chicken pox, infectious mononucleosis, mumps, measles, rubella, shingles, ebola, viral gastroenteritis, viral hepatitis, viral meningitis, human metapneumovirus, human parainfluenza virus type 1, parainfluenza virus type 2, parainfluenza virus type 3, respiratory syncytial virus, viral pneumonia, Chikungunya virus (CHIKV), Venezuelan equine encephalitis (VEEV), dengue (DENV), influenza, West Nile virus (WNV), zika (ZIKV), 229E, NL63, OC43, HKU1, Middle East respiratory syndrome coronavirus (MERS-CoV), severe acute respiratory syndrome coronavirus (SARS-CoV), and severe acute respiratory syndrome coronavirus disease 2019 (SARS-CoV-2), using these compounds. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Preparation method for phosphamide compound used for synthesis chiral drug

The invention provides a preparation method for a phosphamide compound used for synthesis of a chiral drug. According to the invention, a compound II with high yield and high purity can be prepared byadopting a NaHCO3 aqueous solution with a specific pH value and a specific volume-to-mass ratio as a solvent for pulping and controlling a temperature and a stirring speed during pulping. By adoptionof a reaction system provided by the invention, an organic solvent is not needed; the discharge of a large amount of an organic solvent waste liquid is reduced; and the process is environmentally-friendly, green and pollution-free.

2'-SUBSTITUTED-N6-SUBSTITUTED PURINE NUCLEOTIDES FOR RNA VIRUS TREATMENT

The use of described compounds or pharmaceutically acceptable salts or compositions thereof for the treatment of a host infected with an RNA virus other than HCV, or other disorder more fully described herein.

Antiviral nucleoside phosphoramidate and pharmaceutical composition and applications thereof

The invention provides an antiviral nucleoside phosphoramidate and a pharmaceutical composition and applications thereof. The nucleoside phosphoramidate compound is prepared by connecting nucleoside with phosphate through phosphorus-oxygen bonds. The structural formulas of the nucleoside phosphoramidate compound are represented by a, a1, a2, b, b1, and b2. The invention also discloses stereoisomers, pharmaceutically acceptable salts, hydrates, solvates, or crystals of the nucleoside phosphoramidate compound. The anti-hepatitis C activity of the provided novel nucleoside phosphoramidate is obviously better than that of sofosbuvir used in clinic. On the saccharide ring, the fluorine atoms are replaced by chlorine atoms, and the cytotoxicity of measure cell lines is prominently reduced. By systematically modifying and optimizing the basic groups, saccharide rings, and prodrugs, the anti-hepatitis C activity of partial synthesized compounds is 2 to 10 times higher than that of sofosbuvir. At the same time, the key parts of metabolism are optimized, the metabolism stability and chemical stability of synthesized compounds in plasma are better, compared with those of sofosbuvir.

A rope non-cloth Wei preparation of intermediate

The invention discloses a preparation method of a sofosbuvir intermediate, which comprises the following step: in an anhydrous non-protonic solvent, carrying out dynamic kinetic resolution on a compound disclosed as Formula (II) under the action of an organic alkali and/or inorganic alkali to prepare a compound disclosed as Formula (I), wherein the non-protonic solvent is one or more of ester solvent, ketone solvent and ether solvent, the organic alkali and/or inorganic alkali account/accounts for 0.1-10 wt% of the compound disclosed as Formula (II), the temperature of the dynamic kinetic resolution is 10-30 DEG C, and the time of the dynamic kinetic resolution is 5-10 hours. The preparation method has the advantages of high conversion rate, high product purity and low cost, and is environment-friendly.

Method for preparing sofosbuvir key intermediate

The invention relates to the technical field of medicinal chemistry, and in particular relates to a method for preparing a sofosbuvir key intermediate N-[(S)-(2,3,4,5,6-pentafluorophenyl) phenoxyl phosphoryl-L-alanine isopropyl ester. According to the novel method, on the basis of reaction principles, the influence of an addition sequence of L-alanine isopropyl ester hydrochloride and phenol to the reaction is studied firstly, dichlorophosphate pentafluorophenyl ester is adopted as an initial raw material which is reacted with the L-alanine isopropyl ester hydrochloride to obtain a compound III, and the compound III is further spliced with phenol, and thus a compound I can be prepared. By adopting the method, the problems of rigorous reaction conditions, high reaction equipment requirements and the like can be solved, and according to the method, the reaction condition is mild, the operation is simple and convenient, the product yield is high, the purity is good and the method is applicable to large-scale industrial production.

NUCLEOSIDE PHOSPHORAMIDATES USEFUL FOR THE TREATMENT OF VIRAL INFECTIONS AND PREPARATION THEREOF

The present invention relates to an industrially applicable process for the preparation of phosphoramidates useful for the treatment of viral infections, such as sofosbuvir, and to intermediates useful for the preparation thereof. Formula (I):