310404-47-8

Basic information

• Product Name: Benzenepropanoic acid,-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,(aR)-
• Synonyms: Benzenepropanoic acid,-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,(aR)-;Benzenepropanoic acid,α-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-, (αR)-;3-dioxo-2H-isoindol-2-yl)oxy]-;(R)-2-(1,3-Dioxoisoindolin-2-yloxy)-3-phenylpropanoic acid
• CAS NO: 310404-47-8
• Molecular Formula: C₁₇H₁₃NO₅
• Molecular Weight: 311.292
• Product Categories: API intermediates
• Mol File: 310404-47-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzenepropanoic acid,-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,(aR)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid,-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,(aR)-(310404-47-8)
• EPA Substance Registry System: Benzenepropanoic acid,-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,(aR)-(310404-47-8)

Safety Data

• Hazardous Substances Data: 310404-47-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzenepropanoic acid,-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,(aR)is used as a potential therapeutic agent for the treatment of pain and cancer. Its ability to inhibit the enzyme FAAH results in increased endocannabinoid levels, which may contribute to pain relief. Additionally, its capacity to induce apoptosis and inhibit cancer cell proliferation makes it a promising candidate for cancer therapy.
Used in Pain Management:
Benzenepropanoic acid,-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,(aR)is used as a pain-relief agent due to its ability to selectively inhibit the enzyme FAAH, leading to increased levels of endocannabinoids in the brain and other tissues. This mechanism may help in reducing pain and providing relief to patients suffering from various painful conditions.
Used in Cancer Therapy:
Benzenepropanoic acid,-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,(aR)is used as a potential anticancer agent, particularly for the treatment of solid malignancies. Its ability to induce apoptosis and inhibit the proliferation of cancer cells makes it a promising candidate for cancer therapy, offering a new approach to combat cancer and improve patient outcomes.

Upstream product

• 7622-23-3 L-α-hydroxyhydrocinnamic acid t-butyl ester 
• 7622-21-1 benzyl-(S)-(-)-2-hydroxy-3-phenylpropionate 
• 20312-36-1 L-3-phenyllactic acid 
• 63-91-2 L-phenylalanine 
• 380886-37-3 D-tert-butyl 2-phthalimid-N-oxy-3-phenylpropanoate 

Downstream Products

• 861445-49-0 [(S)-2-{(S)-2-[(R)-1-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethoxycarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 859838-39-4 (R)-2-{(R)-2-[(R)-2-((R)-2-{(R)-2-[(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-3-phenyl-propionylamino]-propionylaminooxy}-3-phenyl-propionylamino)-propionylaminooxy]-3-phenyl-propionylamino}-propionic acid tert-butyl ester 

Relevant articles and documents

α-Aminoxy Oligopeptides: Synthesis, Secondary Structure, and Cytotoxicity of a New Class of Anticancer Foldamers

α-Aminoxy peptides are peptidomimetic foldamers with high proteolytic and conformational stability. To gain an improved synthetic access to α-aminoxy oligopeptides we used a straightforward combination of solution- and solid-phase-supported methods and obtained oligomers that showed a remarkable anticancer activity against a panel of cancer cell lines. We solved the first X-ray crystal structure of an α-aminoxy peptide with multiple turns around the helical axis. The crystal structure revealed a right-handed 28-helical conformation with precisely two residues per turn and a helical pitch of 5.8 ?. By 2D ROESY experiments, molecular dynamics simulations, and CD spectroscopy we were able to identify the 28-helix as the predominant conformation in organic solvents. In aqueous solution, the α-aminoxy peptides exist in the 28-helical conformation at acidic pH, but exhibit remarkable changes in the secondary structure with increasing pH. The most cytotoxic α-aminoxy peptides have an increased propensity to take up a 28-helical conformation in the presence of a model membrane. This indicates a correlation between the 28-helical conformation and the membranolytic activity observed in mode of action studies, thereby providing novel insights in the folding properties and the biological activity of α-aminoxy peptides.

Structure-activity relationships of novel endomorphin-2 analogues with N-O turns induced by α-aminoxy acids

Endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2, EM-2) is a putative endogenous μ-opioid receptor ligand. To study the structure-activity relationship against its receptor, we introduced N-O turns into EM-2 and got the analogues with potent affinities for μ-opioid receptor. Our results indicated that N-O turn structures at the Pro2-aminoxy-Phe 3 position of EM-2 analogues played important roles for their affinities. These novel analogues with N-O turns provided a new approach to develop potent analgesics related to EM-2.

A cyclic hexapeptide comprising alternating α-aminoxy and α-amino acids is a selective chloride ion receptor

In nonpolar solvents, the cyclic hexapeptide 2, which comprises alternating D-α-amino and D-α-aminoxy acids, adopts a C3-symmetric conformation with alternating eight (N-O turns)- and seven (γ turns)-membered-ring hydrogen bonds. A series of anion-binding studies has suggested that 2 can function as an effective anion receptor that not only displays a high selectivity for chloride ions, but also the capability to extract chloride ions from aqueous solutions into organic phases.