875309-92-5

Basic information

• Product Name: (S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpho lino acetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoate
• Synonyms: (S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpho lino acetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoate;(alphaS)-alpha-[[2-(4-Morpholinyl)acetyl]amino]benzenebutanoyl-L-leucyl-L-phenylalanine phenylmethyl ester;TYLHGIYRTFHMRN-AFEGWXKPSA-N
• CAS NO: 875309-92-5
• Molecular Formula: C₃₈H₄₈N₄O₆
• Molecular Weight: 656.81092
• Mol File: 875309-92-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpho lino acetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpho lino acetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoate(875309-92-5)
• EPA Substance Registry System: (S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpho lino acetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoate(875309-92-5)

Safety Data

• Hazardous Substances Data: 875309-92-5(Hazardous Substances Data)

Usage

General Description

(S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoate is a complex chemical compound with multiple functional groups. It is a benzyl ester that contains a long chain of amide and carboxylic acid functional groups, as well as a morpholino group. The compound also contains phenyl and methyl groups. This chemical may have potential applications in the pharmaceutical industry, particularly in the development of new drugs or therapeutic agents, due to its complex structure and potential biological activity.

Upstream product

• 868540-15-2 (S)-benzyl 2-((S)-2-((S)-2-(tert-butoxycarbonylamino)-4-phenylbutanamido)-4-methylpentanamido)-3-phenylpropanoate 
• 70637-28-4 (S)-benzyl 2-((S)-2-amino-4-methylpentanamido)-3-phenylpropanoate TFA salt 
• 140834-91-9 (S)-benzyl 2-((S)-2-(tert-butoxycarbonylamino)-4-methylpentanamido)-3-phenylpropanoate 
• 2462-32-0 L-phenylalanine benzyl ester hydrochloride 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 3235-69-6 morpholin-4-ylacetic acid 
• 875309-83-4 C₂HF₃O₂*C₃₂H₃₉N₃O₄ 

Downstream Products

• 868540-17-4 carfilzomib 
• 868540-16-3 (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid 

Relevant articles and documents

Development of Novel Epoxyketone-Based Proteasome Inhibitors as a Strategy to Overcome Cancer Resistance to Carfilzomib and Bortezomib

Over the past 15 years, proteasome inhibitors (PIs), namely bortezomib, carfilzomib (Cfz) and ixazomib, have significantly improved the overall survival and quality-of-life for multiple myeloma (MM) patients. However, a significant portion of MM patients do not respond to PI therapies. Drug resistance is present either de novo or acquired after prolonged therapy through mechanisms that remain poorly defined. The lack of a clear understanding of clinical PI resistance has hampered the development of next-generation PI drugs to treat MM patients who no longer respond to currently available therapies. Here, we designed and synthesized novel epoxyketone-based PIs by structural modifications at the P1′ site. We show that a Cfz analog, 9, harboring a hydroxyl substituent at its P1′ position was highly cytotoxic against cancer cell lines displaying de novo or acquired resistance to Cfz. These results suggest that peptide epoxyketones incorporating P1′-targeting moieties may have the potential to bypass resistance mechanisms associated with Cfz and to provide additional clinical options for patients resistant to Cfz.

Compounds for enzyme inhibition

Peptide-based compounds including heteroatom-containing, three-membered rings efficiently and selectively inhibit specific activities of N-terminal nucleophile (Ntn) hydrolases. The activities of those Ntn having multiple activities can be differentially inhibited by the compounds described. For example, the chymotrypsin-like activity of the 20S proteasome may be selectively inhibited with the inventive compounds. The peptide-based compounds include at least three peptide units, an epoxide or aziridine, and functionalization at the N-terminus. Among other therapeutic utilities, the peptide-based compounds are expected to display anti-inflammatory properties and inhibition of cell proliferation.