215232-00-1

Basic information

• Product Name: α-Methyl OMuralide
• Synonyms: α-Methyl OMuralide;(-)-7-MethyloMuralide;(1R,5S)-1-[(1S)-1-Hydroxy-2-Methylpropyl]-4,4-diMethyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• CAS NO: 215232-00-1
• Molecular Formula: C11H17NO4
• Molecular Weight: 227.25698
• Product Categories: Aliphatics;Chiral Reagents;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 215232-00-1.mol

Chemical Properties

• Melting Point: 181-183 °C
• Boiling Point: 428.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.228±0.06 g/cm3(Predicted)
• PKA: 13.33±0.20(Predicted)
• CAS DataBase Reference: α-Methyl OMuralide(CAS DataBase Reference)
• NIST Chemistry Reference: α-Methyl OMuralide(215232-00-1)
• EPA Substance Registry System: α-Methyl OMuralide(215232-00-1)

Safety Data

• Hazardous Substances Data: 215232-00-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
α-Methyl OMuralide is used as a therapeutic agent for targeting proteasome function in cancer cells. Its irreversible inhibition of proteasomes can lead to the accumulation of damaged or misfolded proteins, ultimately causing cell death in cancerous cells. This makes it a promising candidate for the development of novel cancer treatments.
Used in Research Applications:
α-Methyl OMuralide is used as a research tool for studying the role of proteasomes in cellular processes. Its selective and irreversible inhibition of proteasome function allows researchers to investigate the effects of proteasome inhibition on various cellular pathways and mechanisms, contributing to a better understanding of cellular biology and the development of targeted therapies.
Used in Drug Development:
α-Methyl OMuralide is used as a lead compound in the development of new drugs targeting proteasomes. Its potent and selective inhibition of proteasome function makes it an attractive starting point for the design and synthesis of new molecules with improved properties, such as better bioavailability, reduced toxicity, and enhanced efficacy.

Upstream product

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• 87421-21-4 (2S,3S)-3-hydroxyleucine methyl ester 
• 148906-20-1 (4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester 
• 148843-19-0 (4R,5S)-4-Formyl-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 148843-18-9 (4S,5S)-4-Hydroxymethyl-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 220805-64-1 methyl (4S,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylate 
• 220805-65-2 (2R,3S)-2,3-dihydroxy-4-methylpentanoic acid methyl ester 
• 512184-28-0 (4R,5S)-5-Isopropyl-2-oxo-2λ⁴-[1,3,2]dioxathiolane-4-carboxylic acid methyl ester 
• 512184-25-7 (2S,3S)-2-azido-3-hydroxy-4-methylpentanoic acid methyl ester 
• 512184-24-6 (4R,5S)-5-Isopropyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid methyl ester 
• 512184-27-9 (2S,3S)-2-((S)-1-Benzoyloxy-2-methyl-propyl)-3-hydroxy-4,4-dimethyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 512184-26-8 (4S,5S)-4-((S)-2-Ethoxycarbonyl-1-hydroxy-2-methyl-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 215232-03-4 (1S,7S,7aS)-7-Hydroxy-7a-hydroxymethyl-1-isopropyl-6,6-dimethyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 

Relevant articles and documents

A short, stereocontrolled, and practical synthesis of α-methylomuralide, a potent inhibitor of proteasome function

An efficient and practical synthesis of α-methylomuralide (3), a selective inhibitor of proteasomes, has been developed as outlined in Scheme 1. Among the advantages of this route of synthesis over previously described approaches are (1) ease of scale-up

An efficient total synthesis of a new and highly active analog of lactacystin

An expeditious total synthesis of the stable and potent proteasome inhibitor 3 is described.