purvalanol A

Base Information

• Chemical Name: purvalanol A
• CAS No.: 212844-53-6
• Molecular Formula: C₁₉H₂₅ClN₆O
• Molecular Weight: 388.9
• Hs Code.: 2933990090
• UNII: YP483E75C4
• DSSTox Substance ID: DTXSID30175553
• Nikkaji Number: J1.593.835H
• Wikidata: Q27464217
• Pharos Ligand ID: UFBLF59FBDP2
• Metabolomics Workbench ID: 52465
• ChEMBL ID: CHEMBL23327
• Mol file: 212844-53-6.mol

Synonyms:6-((3-chloro)anilino)-2-(isopropyl-2-hydroxyethylamino)-9-isopropylpurine;purvalanol A

Chemical Property of purvalanol A

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 8.68E-15mmHg at 25°C
• Refractive Index: 1.654
• Boiling Point: 590.5 °C at 760 mmHg
• PKA: 14.51±0.10(Predicted)
• Flash Point: 310.9 °C
• PSA: 87.89000
• Density: 1.33 g/cm³
• LogP: 4.37900
• Storage Temp.: −20°C
• Solubility.: methylene chloride: 50 mg/mL, clear, colorless
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 388.1778371
• Heavy Atom Count: 27
• Complexity: 468

Purity/Quality:

99% ^*data from raw suppliers

Purvalanol A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C(CO)NC1=NC(=C2C(=N1)N(C=N2)C(C)C)NC3=CC(=CC=C3)Cl
• Isomeric SMILES: CC(C)[C@H](CO)NC1=NC(=C2C(=N1)N(C=N2)C(C)C)NC3=CC(=CC=C3)Cl
• Description: Purvalanol A (212844-53-6) is a cyclin-dependent kinase inhibitor. IC50s= 4, 70, 35, 75 and 850 nM for cdc2/cyclin B, cdk2/cyclin A, cdk2/cyclin E, cdk5/p35 and cdk4/cyclin D1 and respectively.1?Reversibly arrests synchronized cells in G1 and G2 phase.2?Induces ER stress-mediated apoptosis and autophagy in colon cancer cells.3?Suppresses Src-mediated transformation by inhibiting both CDKs and c-Src.4?In cells transformed with MYC, purvalanol A rapidly down-regulates survivin expression and induces MYC-dependent apoptosis.5?Cell permeable.
• Uses: Purvalanol A acts as a potent, cell-permeable CDK inhibitor used in the treatment of cell proliferative disorders. Anti-cancer.

Technology Process of purvalanol A

There total 6 articles about purvalanol A 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: 86.0%

(R)-2-amino-3-methylbutanol (4276-09-9,473-75-6) + 2-(benzylsulfonyl)-6-(3-chlorophenylamino)-9-isopropylpurine (851370-53-1) → purvalanol A (212844-53-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 160 ℃; for 24h; Parr bomb;

DOI:10.1002/ejoc.200400748

Reference yield: 65.0%

(R)-2-amino-3-methylbutanol (4276-09-9,473-75-6) + (2-chloro-9-isopropyl-9H-purin-6-yl)(3-chlorophenyl)amine (190654-78-5) → (+/-)-Purvalanol A (220792-00-7,212844-53-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 150 ℃; for 12h;

DOI:10.1021/ol800353s

Reference yield:

6-chloro-2-phenylmethylsulfanylpurine (51998-91-5) → purvalanol A (212844-53-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / Ph₃P; DIAD / tetrahydrofuran / -50 - 20 °C

2: 98 percent / HCl / butan-1-ol / 24 h / 120 °C

3: 99 percent / MgSO₄; m-CPBA / CH₂Cl₂

4: 86 percent / EtN(iPr)2 / butan-1-ol / 24 h / 160 °C / Parr bomb

With hydrogenchloride; di-isopropyl azodicarboxylate; magnesium sulfate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; butan-1-ol;

DOI:10.1002/ejoc.200400748

upstream raw materials:

(R)-2-amino-3-methylbutanol

2-(benzylsulfonyl)-6-(3-chlorophenylamino)-9-isopropylpurine

6-chloro-2-phenylmethylsulfanylpurine

1,7-Dihydro-2-[(phenylmethyl)thio]-6H-purin-6-one

Refernces

• 1、 Taddei, David,Slawin, Alexandra M. Z.,Woollins, J. Derek. "2-(Benzylsulfanyl)-6-chloro-9-isopropylpurine, a valuable intermediate in the synthesis of diaminopurine cyclin dependent kinase inhibitors". . p. 939 - 947. Retrieved 2007/10/03.