119357-91-4

Basic information

• Product Name: (S)-Methyl 2-amino-3-(naphthalen-1-yl)propanoate
• Synonyms: (S)-Methyl 2-amino-3-(naphthalen-1-yl)propanoate
• CAS NO: 119357-91-4
• Molecular Formula: C14H15NO2
• Molecular Weight: 229.2744
• Mol File: 119357-91-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-Methyl 2-amino-3-(naphthalen-1-yl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Methyl 2-amino-3-(naphthalen-1-yl)propanoate(119357-91-4)
• EPA Substance Registry System: (S)-Methyl 2-amino-3-(naphthalen-1-yl)propanoate(119357-91-4)

Safety Data

• Hazardous Substances Data: 119357-91-4(Hazardous Substances Data)

Usage

Description

(S)-Methyl 2-amino-3-(naphthalen-1-yl)propanoate, commonly known as (S)-Naproxen methyl ester, is a chiral amino acid derivative with the molecular formula C14H15NO2. It is a chemical compound that serves as a crucial precursor in the synthesis of pharmaceutical drugs, particularly nonsteroidal anti-inflammatory drugs (NSAIDs). (S)-Methyl 2-amino-3-(naphthalen-1-yl)propanoate possesses anti-inflammatory, analgesic, and antipyretic properties, making it a valuable building block in the pharmaceutical industry for the development of various medicines.

Uses

Used in Pharmaceutical Industry:
(S)-Methyl 2-amino-3-(naphthalen-1-yl)propanoate is used as a precursor for the synthesis of nonsteroidal anti-inflammatory drugs (NSAIDs) for its anti-inflammatory, analgesic, and antipyretic properties. It plays a vital role in the development of medicines that help alleviate pain, reduce inflammation, and lower fever.
Used in Drug Development:
As an important chemical building block, (S)-Methyl 2-amino-3-(naphthalen-1-yl)propanoate is used in the pharmaceutical industry for the development of new drugs. Its unique structure and properties make it a valuable component in the creation of innovative pharmaceutical compounds with potential therapeutic applications.

Upstream product

• 67-56-1 methanol 
• 55447-00-2 (S)-2-tert-butoxycarbonylamino-3-naphthalen-1-yl-propionic acid 
• 78306-92-0 3-(1-naphthyl)-D-alanine 
• 55516-54-6 L-1-naphthylalanine 

Relevant articles and documents

An increase in side-group hydrophobicity largely improves the potency of ritonavir-like inhibitors of CYP3A4

Identification of structural determinants required for potent inhibition of drug-metabolizing cytochrome P450 3A4 (CYP3A4) could help develop safer drugs and more effective pharmacoenhancers. We utilize a rational inhibitor design to decipher structure-activity relationships in analogues of ritonavir, a highly potent CYP3A4 inhibitor marketed as pharmacoenhancer. Analysis of compounds with the R1 side-group as phenyl or naphthalene and R2 as indole or naphthalene in different stereo configuration showed that (i) analogues with the R2-naphthalene tend to bind tighter and inhibit CYP3A4 more potently than the R2-phenyl/indole containing counterparts; (ii) stereochemistry becomes a more important contributing factor, as the bulky side-groups limit the ability to optimize protein-ligand interactions; (iii) the relationship between the R1/R2 configuration and preferential binding to CYP3A4 is complex and depends on the side-group functionality/interplay and backbone spacing; and (iv) three inhibitors, 5a-b and 7d, were superior to ritonavir (IC50 of 0.055–0.085 μM vs. 0.130 μM, respectively).

CHIRAL FLUORINATING REAGENTS

This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.

N-benzoyl amino acids as LFA-1/ICAM inhibitors 1: Amino acid structure-activity relationship

The association of ICAM-1 with LFA-1 plays a critical role in several autoimmune diseases. N-2-Bromobenzoyl L-tryptophan, compound 1, was identified as an inhibitor to the formation of the LFA-1/ICAM complex. The SAR of the amino acid indicates that the carboxylic acid is required for inhibition and that L-histidine is the most favored amino acid.