CEP-18770

Base Information

• Chemical Name: CEP-18770
• CAS No.: 847499-27-8
• Molecular Formula: C₂₁H₂₈BN₃O₅
• Molecular Weight: 413.281
• Hs Code.: 29333990
• Mol file: 847499-27-8.mol

Synonyms:CEP 18770;CEP-18770;

Chemical Property of CEP-18770

Chemical Property:

• Appearance/Colour: white powder
• PKA: 9.67±0.43(Predicted)
• PSA: 138.76000
• Density: 1.207
• LogP: 2.60570
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Delanzomib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Delanzomib is an orally bioavailable inhibitor of chymotrypsin-like proteasome activity (IC50 = 3.8 nM in isolated human erythrocytes) that only marginally inhibits tryptic and peptidyl glutamyl proteasome activity. Delanzomib pre-treatment (20 nM) in vitro inhibits IκBα degradation, NF-κB activation, and the expression of NF-κB-regulated genes, including IκBα, XIAP, TNF-α, IL-1β, ICAM-1, and VEGF. Delanzomib induces apoptosis in multiple myeloma cell lines and inhibits proliferation in a panel of human hematologic and solid tumor cell lines (IC50s = 5.6-34.2 nM). It reduces tumor weight in an RPMI 8226 human multiple myeloma mouse xenograft model when administered intravenously at doses ranging from 1.5-4 mg/kg twice daily and leads to complete tumor regression at a chronic oral dose of 13 mg/kg. Delanzomib reduces the serum level of circulating cytokines, prevents renal tissue damage, and increases lifespan in a mouse model of fatal lupus nephritis.
• Uses: Delanzomib is an orally active proteasome inhibitor. Delanzomib has been shown to down-modulate NF-κB, induce apoptosis, inhibit angiogenesis and M-CSF-RANKL-induced osteoclastogenesis.

Technology Process of CEP-18770

There total 8 articles about CEP-18770 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(2S,3R)-N-[(1R)-1-(1,3,6,2-dioxazaborocan-2-yl)-3-methylbutyl]-3-hydroxy-2-[(6-phenylpyridin-2-yl)formamido]butanamide → Delanzomib (847499-27-8)

Guidance literature:

With hydrogenchloride; In water;

Reference yield: 90.0%

6-(2S,3R)-N-[(1R)-1-(1,3,6,2-dioxazaborocan-2-yl)-3-methylbutyl]-3-hydroxy-2-[(6-phenylpyridin-2-yl)formamido]butanamide → Delanzomib (847499-27-8)

Guidance literature:

With hydrogenchloride; In water; 4-methyl-2-pentanone; Product distribution / selectivity;

Reference yield:

N-[(1S,2R)-1-[[[(1R)-1-1[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-hydroxypropyl]-6-phenyl-2-pyridinecarboxamide (847494-64-8) → Delanzomib (847499-27-8)

Guidance literature:

With hydrogenchloride; In methanol; hexane; at 20 ℃; for 16h;

DOI:10.1021/jm7010589

upstream raw materials:

N-[(1S,2R)-1-[[[(1R)-1-1[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-hydroxypropyl]-6-phenyl-2-pyridinecarboxamide

6-phenyl-pyridine-2-carboxylic acid

C₁₆H₁₆N₂O₄

6-phenyl-pyridine-2-carbonyl chloride

Refernces

• 1、 Roemmele, Renee C.,Christie, Michael A. "Development and scale-up of an optimized route to the peptide boronic acid, CEP-18770". . p. 422 - 426. Retrieved 2013/06/05.
• 2、 Dorsey, Bruce D.,Iqbal, Mohamed,Chatterjee, Sankar,Menta, Ernesto,Bernardini, Raffaella,Bernareggi, Alberto,Cassarà, Paolo G.,D'Arasmo, Germano,Ferretti, Edmondo,De Munari, Sergio,Oliva, Ambrogio,Pezzoni, Gabriella,Allievi, Cecilia,Strepponi, Ivan,Ruggeri, Bruce,Ator, Mark A.,Williams, Michael,Mallamo, John P.. "Discovery of a potent, selective, and orally active proteasome inhibitor for the treatment of cancer". . p. 1068 - 1072. Retrieved 2008/12/22.