101622-51-9

Basic information

• Product Name: OLOMOUCINE
• Synonyms: 6-BENYLAMINO-2-(2-HYDROXYETHYLAMINO)-9-METHYLPURINE;6-BENZYLAMINO-2-(2-HYDROXYETHYLAMINO)-9-METHYLPURINE;2-[[9-METHYL-6[(PHENYLMETHYL)AMINO]-9H-PURIN-2-YL]AMINO]-ETHANOL;2-(2-HYDROXYETHYLAMINO)-6-BENZYLAMINO-9-METHYLPURINE;N2-[(2-HYDROXYETHYL)]-N6-BENZYLADENINE;OLOMOUCINE;OLOMOUCINE SYNTHETIC >95%;Olomoucine,highpurity
• CAS NO: 101622-51-9
• Molecular Formula: C₁₅H₁₈N₆O
• Molecular Weight: 298.34
• Product Categories: Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Inhibitors;Nucleotides;Protein Kinase;inhibitor
• Mol File: 101622-51-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 120-130 °C
• Boiling Point: 579.578 °C at 760 mmHg
• Flash Point: 304.318 °C
• Appearance: White to off-white/Solid
• Density: 1.36
• Vapor Pressure: 2.83E-14mmHg at 25°C
• Refractive Index: 1.69
• Storage Temp.: −20°C
• Solubility: DMSO, Methanol (Slightly)
• PKA: 14.55±0.10(Predicted)
• CAS DataBase Reference: OLOMOUCINE(CAS DataBase Reference)
• NIST Chemistry Reference: OLOMOUCINE(101622-51-9)
• EPA Substance Registry System: OLOMOUCINE(101622-51-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 101622-51-9(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white solid

Uses

Different sources of media describe the Uses of 101622-51-9 differently. You can refer to the following data:
1. A purine derivative which inhibits cyclin-dependent kinases and induces G1 arrest.
2. A purine derivative which inhibits cyclin-dependent kinases and induces G1 arrest

Biological Activity

Cyclin-dependent kinase inhibitor that competes for the ATP binding site of the kinase. Selectively inhibits cdc2/cyclin B (IC 50 = 7 μ M), cdk2/cyclin A (IC 50 = 7 μ M), cdk2/cyclin E (IC 50 = 7 μ M), cdk/p35 kinase (IC 50 = 3 μ M)? and ERK1/MAP kinase (IC 50 = 25 μ M). Arrests human fibroblasts in the G1 phase.

Biochem/physiol Actions

Olomoucine is a purine derivative which inhibits cyclin-dependent kinases and induces G arrest.

Enzyme inhibitor

This ATP site-competitive purine derivative (FW = 298.35 g/mol; CAS 101622-51-9), systematically named 6-benzylamino-2-[2-hydroxyethylamino]- 9-methylpurine, is a potent inhibitor of cyclin-dependent kinases, with an IC50 value of 7 μM for both cdk1 and cdk2 and an IC50 value of 3 μM for cdk5, arresting cells in G1. Olomoucine also inhibits cytokinin 7b-glucosyltransferase.

references

[1]. vesel j, havlicek l, strnad m, et al. inhibition of cyclin-dependent kinases by purine analogues. eur j biochem. 1994 sep 1;224(2):771-86.[2]. abraham rt, acquarone m, andersen a, et al. cellular effects of olomoucine, an inhibitor of cyclin-dependent kinases. biol cell. 1995;83(2-3):105-20.[3]. tian ds, xie mj, yu zy, et al. cell cycle inhibition attenuates microglia induced inflammatory response and alleviates neuronal cell death after spinal cord injury in rats. brain res. 2007 mar 2;1135(1):177-85.

InChI:InChI=1/C15H18N6O/c1-21-10-18-12-13(17-9-11-5-3-2-4-6-11)19-15(16-7-8-22)20-14(12)21/h2-6,10,22H,7-9H2,1H3,(H2,16,17,19,20)

Upstream product

• 100-46-9 benzylamine 
• 2382-10-7 2,6-dichloro-9-methyl-9H-purine 
• 5451-40-1 2,6 dichloropurine 
• 39639-47-9 N⁶-benzyl-2-chloroadenine 
• 158982-11-7 2-amino-6-benzylamino-9-purine 
• 5502-78-3 9-Methylguanine 
• 74-89-5 methylamine 
• 1979-96-0 4,6-dichloro-2-(methylthio)-5-nitropyrimidine 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 141-43-5 ethanolamine 
• 1651-29-2 6-chloro-2-fluoropurine 
• 74-88-4 methyl iodide 
• 101622-53-1 2-chloro-6-benzylamino-9-methylpurine 

Relevant articles and documents

Novel solid-phase preparation of 2,6,9-trisubstituted purines for combinatorial library generation

A novel procedure for the preparation of 2,6,9-trisubstituted purine libraries has been developed.

An efficient direct amination of cyclic amides and cyclic ureas

An efficient one-step amination of cyclic amides and ureas has been developed. Treatment of cyclic amides and cyclic ureas with BOP in the presence of DBU in various solvents led to the formation of cyclic amidines and cyclic guanidines in good to excellent yields. Concise syntheses of biologically intriguing kinetin and potent kinase inhibitor olomoucin were thus achieved in just one and two steps, respectively.

The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas

(Chemical Equation Presented) An efficient "one-step" synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas with benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), base, and nitrogen nucleophiles leads to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent yields. This method has also been used to prepare heteroaryl ethers and thioethers using phenol and thiophenol nucleophiles. Time course NMR and HPLC-MS studies have facilitated explicit characterization of the proposed intermediates (the phosphonium salt and HOBt adduct); the data reveal a stepwise reaction pathway.