Pevonedistat

Base Information

• Chemical Name: Pevonedistat
• CAS No.: 905579-51-3
• Molecular Formula: C₂₁H₂₅N₅O₄S
• Molecular Weight: 443.527
• UNII: S3AZD8D215
• ChEMBL ID: CHEMBL1231160
• DSSTox Substance ID: DTXSID701022549
• Metabolomics Workbench ID: 152861
• NCI Thesaurus Code: C77906
• Nikkaji Number: J2.697.452F
• Wikidata: Q25100575
• Wikipedia: Pevonedistat
• Mol file: 905579-51-3.mol

Synonyms:((1S,2S,4R)-4-(4-((1S)-2,3-dihydro-1H-inden-1-ylamino)-7H-pyrrolo(2,3-d)pyrimidin-7-yl)-2-hydroxycyclopentyl)methyl sulfamate;((1S,2S,4R)-4-(4-((1S)-2,3-dihydro-1H-inden-1-ylamino)-7H-pyrrolo(2,3-d)pyrimidin-7-yl)-2-hydroxycyclopentyl)methyl sulphamate;4-(4-((1S)-2,3-dihydro-1H-inden-1-ylamino)-7H-pyrrolo(2,3-d)pyrimidin-7-yl)-2-hydroxycyclopentyl methyl sulfamidate;MLN-4924;MLN4924;pevonedistat

Chemical Property of Pevonedistat

Chemical Property:

• Appearance/Colour: White Solid
• Melting Point: 161-163 °C
• Boiling Point: 721.0±70.0 °C at 760 mmHg
• PKA: 9.35±0.70(Predicted)
• Flash Point: 389.9±35.7 °C
• PSA: 140.74000
• Density: 1.6±0.1 g/cm³
• LogP: 3.91690
• Storage Temp.: -20?C Freezer
• Solubility.: Soluble in DMSO (up to 10 mg/ml).
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 443.16272547
• Heavy Atom Count: 31
• Complexity: 734

Purity/Quality:

99% ^*data from raw suppliers

MLN4924 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=CC=CC=C2C1NC3=C4C=CN(C4=NC=N3)C5CC(C(C5)O)COS(=O)(=O)N
• Isomeric SMILES: C1CC2=CC=CC=C2[C@H]1NC3=C4C=CN(C4=NC=N3)[C@@H]5C[C@H]([C@H](C5)O)COS(=O)(=O)N
• Recent ClinicalTrials: Testing the Combination of Pevonedistat With Chemotherapy for Bile Duct Cancer of the Liver
• Recent EU Clinical Trials: Treatment of MDS/AML patients with an impending hematological relapse with azacitidine alone or in combination with pevonedistat - a randomized phase 2 trial
• Recent NIPH Clinical Trials: Phase II study of pevonedistat plus niraparib in patient with recurrent ovarian cancer
• Description: MLN4924 (905579-51-3) is a potent and selective NEDD8-activating enzyme (NAE) inhibitor.1?It disrupts cullin-RING ligase-mediated protein turnover leading to apoptosis in human tumor cells. Suppresses the growth of human tumor xenografts in mice.2?Upregulates PD-L1 expression and enhances the efficacy of immune checkpoint blockade in glioblastoma.3?Modulates tumor microenvironment.4?Cell permeable.
• Uses: A potent and selective inhibitor of NAE. A potent and selective inhibitor of NAE. An inhibitor of NEDD8-activating enzyme as a new approach to treat cancer. The ubiquitin-proteasome pathway mediates the destruction of unwanted proteins. Potent NAE inhibitor; NEDD8 E1 Activating Enzyme Inhibitor.

Technology Process of Pevonedistat

There total 44 articles about Pevonedistat 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%

(1S,2S,4R)-2-{[(Aminosulfonyl)oxy]methyl}-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl acetate → ((1S,2S,4R)-4-(4-(((S)-2,3-dihydro-1H-inden-1-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxycyclopentyl)-methyl sulfamate (905579-51-3)

Guidance literature:

With methanol; ammonia; at 20 ℃; for 120h;

Reference yield: 90.0%

sulfamic acid 2-tert-butoxy-4-[4-(indan-1-ylamino)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclopentylmethyl ester (1281922-83-5) → ((1S,2S,4R)-4-(4-(((S)-2,3-dihydro-1H-inden-1-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxycyclopentyl)-methyl sulfamate (905579-51-3)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 2h;

Reference yield: 90.0%

sulfamic acid 2-tert-butoxy-4-[4-(indan-1-ylamino)pyrrolo-[2,3-d]pyrimidin-7-yl]cyclopentylmethyl ester → MLN4924 (905579-51-3)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 2h;

DOI:10.1021/jo2001897

upstream raw materials:

isocyanate de chlorosulfonyle

(1S,2S,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(hydroxymethyl)-cyclopentanol

6-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-4-one

6-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-4-ol