223568-69-2

Basic information

• Product Name: (3RS,4RS)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-fluoro-4-hydroxypentanoic acid, tert-butyl ester
• Synonyms: (3RS,4RS)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-fluoro-4-hydroxypentanoic acid, tert-butyl ester
• CAS NO: 223568-69-2
• Molecular Weight: 440.512
• Mol File: 223568-69-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3RS,4RS)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-fluoro-4-hydroxypentanoic acid, tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3RS,4RS)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-fluoro-4-hydroxypentanoic acid, tert-butyl ester(223568-69-2)
• EPA Substance Registry System: (3RS,4RS)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-fluoro-4-hydroxypentanoic acid, tert-butyl ester(223568-69-2)

Safety Data

• Hazardous Substances Data: 223568-69-2(Hazardous Substances Data)

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 161401-79-2 3-amino-4-hydroxy-5-fluoropentanoic acid,tert-butyl ester 
• 161401-79-2 (3RS,4RS)-3-amino-5-fluoro-4-hydroxypentanoic acid, tert-butyl ester 

Downstream Products

• 582316-00-5 3-(Cbz-Val-amido)-5-fluoro-4-oxo-pentanoic acid 
• 582317-91-7 3-(2-benzyloxycarbonylamino-3-methyl-butyrylamino)-5-fluoro-4-oxo-pentanoic acid tert-butyl ester 

Relevant articles and documents

MX1013, a dipeptide caspase inhibitor with potent in vivo antiapoptotic activity

1. Caspases play a critical role in apoptosis, and are considered to be key targets for the design of cytoprotective drugs. As part of our antiapoptotic drug-discovery effort, we have synthesized and characterized Z-VD-fmk, MX1013, as a potent, irreversible dipeptide caspase inhibitor. 2. MX1013 inhibits caspases 1, 3, 6, 7, 8, and 9, with IC50 values ranging from 5 to 20nM. MX1013 is selective for caspases, and is a poor inhibitor of noncaspase proteases, such as cathepsin B, calpain I, or Factor Xa (IC50 values > 10 μM). 3. In several cell culture models of apoptosis, including caspase 3 processing, PARP cleavage, and DNA fragmentation, MX1013 is more active than tetrapeptide- and tripeptide-based caspase inhibitors, and blocked apoptosis at concentrations as low as 0.5 μM. 4. MX1013 is more aqueous soluble than tripeptide-based caspase inhibitors such as Z-VAD-fmk. 5. At a dose of 1 mgkg-1 i.v., MX1013 prevented liver damage and the lethality caused by Fas death receptor activation in the anti-Fas mouse-liver apoptosis model, a widely used model of liver failure. 6. At a dose of 20 mgkg-1 (i.v. bolus) followed by i.v. infusion for 6 or 12 h, MX1013 reduced cortical damage by approximately 50% in a model of brain ischemia/reperfusion injury. 7. At a dose of 20 mgkg-1 (i.v. bolus) followed by i.v. infusion for 12 h, MX1013 reduced heart damage by approximately 50% in a model of acute myocardial infarction. 8. Based on these studies, we conclude that MX1013, a dipeptide pan-caspase inhibitor, has a good combination of in vitro and in vivo properties. It has the ability to protect cells from a variety of apoptotic insults, and is systemically active in three animal models of apoptosis, including brain ischemia.

(Substituted)acyl dipeptidyl inhibitors of the ICE/ced-3 family of cysteine proteases

This invention is directed to novel (substituted)acyl dipeptidyl ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as the use of such compositions in the treatment of pa