Marizomib

Base Information

• Chemical Name: Marizomib
• CAS No.: 437742-34-2
• Deprecated CAS: 855517-10-1
• Molecular Formula: C15H20ClNO4
• Molecular Weight: 313.781
• European Community (EC) Number: 854-165-6
• UNII: 703P9YDP7F
• ChEMBL ID: CHEMBL371405
• DSSTox Substance ID: DTXSID00904019
• Metabolomics Workbench ID: 56886
• NCI Thesaurus Code: C64634
• Nikkaji Number: J1.875.185B
• Pharos Ligand ID: 4HCJNGAWDPQ1
• Wikidata: Q7404722
• Wikipedia: Salinosporamide_A
• Mol file: 437742-34-2.mol

Synonyms:homosalinosporamide A;marizomib;NPI 0052;NPI-0052;salinosporamide A

Chemical Property of Marizomib

Chemical Property:

• Boiling Point: 547.0±50.0 °C(Predicted)
• PKA: 13.10±0.20(Predicted)
• PSA: 79.12000
• Density: 1.348±0.06 g/cm3(Predicted)
• LogP: 1.40870
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 313.1080858
• Heavy Atom Count: 21
• Complexity: 508

Purity/Quality:

98%,99%, ^*data from raw suppliers

Salinosporamide A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C(C(=O)NC1(C(=O)O2)C(C3CCCC=C3)O)CCCl
• Isomeric SMILES: C[C@]12[C@H](C(=O)N[C@]1(C(=O)O2)[C@H]([C@H]3CCCC=C3)O)CCCl
• Recent ClinicalTrials: A Phase III Trial of With Marizomib in Patients With Newly Diagnosed Glioblastoma
• Recent EU Clinical Trials: A phase III trial of marizomib in combination with standard temozolomide-based radiochemotherapy versus standard temozolomide-based radiochemotherapy alone in patients with newly diagnosed glioblastoma - MIRAGE
• Uses: Marizomib has been used as a proteasome inhibitor:to study its effects on glioblastoma cell linesto analyze its effects on the aging of killifish brainto test its effect on protein kinase B (PKB/AKT) levels in multiple myeloma cells

Technology Process of Marizomib

There total 200 articles about Marizomib 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: 95.0%

NPI-2062 (872360-17-3) → NPI-2076 (872360-18-4) + salinosporamide A (437742-34-2)

Guidance literature:

With sodium tetrahydroborate; In 1,2-dimethoxyethane; water; at -78 ℃; for 0.233333h; Cooling with acetone-dry ice;

Reference yield: 85.0%

NPI-2062 (872360-17-3) → salinosporamide A (437742-34-2)

Guidance literature:

With glucose dehydrogenase; D-glucose; In phosphate buffer; dimethyl sulfoxide; at 37 - 39 ℃; for 0.666667h; pH=6.9;

DOI:10.1016/j.tetlet.2007.02.017

Reference yield: 84.0%

(1S,2R,5R)-2-(2-chloroethyl)-5-{(S)-[(S)-cyclohex-2-enyl](triethylsilyloxy)methyl}-1-methyl-7-oxa-4-aza-bicyclo[3.2.0]heptane-3,6-dione (1064062-25-4) → salinosporamide A (437742-34-2)

Guidance literature:

With pyridine; pyridine hydrofluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol8016066

upstream raw materials:

(2R,3S,4R)-2-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-3-hydroxy-4-(2-hydroxy-ethyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid

NPI-2077

NPI-2062

NPI-2076

Downstream raw materials:

C₁₆H₂₀N₂O₄S

C₁₅H₂₂ClNO₅

Refernces

• 1、 Manam, Rama Rao,Macherla, Venkat R.,Potts, Barbara C.M.. "Stereoselective enzymatic reduction of keto-salinosporamide to (-)-salinosporamide A (NPI-0052)". . p. 2537 - 2540. Retrieved 2007.
• 2、 Gholami, Hadi,Kulshrestha, Aman,Favor, Olivia K.,Staples, Richard J.,Borhan, Babak. "Total Synthesis of (?)-Salinosporamide A via a Late Stage C?H Insertion". . p. 10110 - 10113. Retrieved 2019/04/25.