189232-42-6

Basic information

• Product Name: BOHEMINE
• Synonyms: 3-((6-(benzylaMino)-9-isopropyl-9H-purin-2-yl)aMino)propan-1-ol;3-{[6-(Benzylamino)-9-Isopropyl-9H-Purin-2-Yl]Amino}-1-Propanol;1-Propanol,3-[[9-(1-methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-
• CAS NO: 189232-42-6
• Molecular Formula: C₁₈H₂₄N₆O
• Molecular Weight: 340.429
• Product Categories: Inhibitors
• Mol File: 189232-42-6.mol

Chemical Properties

• Melting Point: 101-103 °C
• Boiling Point: 589.4±60.0 °C(Predicted)
• Appearance: /powder
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: −20°C
• Solubility: chloroform: 50 mg/mL, soluble
• PKA: 14.94±0.10(Predicted)
• CAS DataBase Reference: BOHEMINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOHEMINE(189232-42-6)
• EPA Substance Registry System: BOHEMINE(189232-42-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 189232-42-6(Hazardous Substances Data)

Usage

Biological Activity

a highly conserved array of mechanisms regulating cyclin-dependent kinases (cdk), which govern the timing of cell cycle progression and division, has developed in eukaryotes. cdk inhibitors have been shown to play an key regulatory role in cell proliferation, differentiation, senescence, as well as programmed death.

in vitro

bohemine was applied to cultures of mouse hybridoma cells in order to evaluate its capacity of cell growth and the production of monoclonal antibody. results showed that addition of bohemine at concentrations in the range of 1-10 μm led to a short-term arrest of growth and monoclonal antibody production. such short-term suppression of cell functions was followed by a significant temporary increase of specific growth rate and specific production rate. in semicontinuous cultures, the steady-state viable cell density values showed a certain stimulation of cell growth in the presence of bohemine at micromolar concentrations, and growth inhibition at 10 and 30 μm [1].

in vivo

in mice, bohemine was found to be rapidly and completely metabolized and disappeared from circulation during the first 60 min following i.v. administration. moreover, the metabolites were eliminated by the hepatobiliary tract and also by renal excretion [2].

IC 50

1 μm for cyclin-dependent kinase

references

[1] franek f,strnad m,havlícek l,siglerová v,fismolová i,eckschlager t. diverse effects of the cyclin-dependent kinase inhibitor bohemine: concentration- and time-dependent suppression or stimulation of hybridoma culture. cytotechnology.2001 jul;36(1-3):117-23. [2] chmela z,vesel j,lemr k,rypka m,hanus j,havlícek l,krystof v,michnová l,fuksová k,lukes j. in vivo metabolism of 2,6,9-trisubstituted purine-derived cyclin-dependent kinase inhibitor bohemine in mice: glucosidation as the principal metabolic route. drug metab dispos.2001 mar;29(3):326-34.

Upstream product

• 67-63-0 isopropyl alcohol 
• 156-87-6 propan-1-ol-3-amine 
• 203436-45-7 2,6-dichloro-9-isopropyl-9H-purine 
• 5451-40-1 2,6 dichloropurine 
• 1175562-42-1 C₂₉H₄₆N₆O₃Si 
• 186692-41-1 2-chloro-6-phenylmethylamino-9-iso-propylpurine 
• 479486-07-2 6-chloro-2-iodo-purine-9-carboxylic acid tert-butyl ester 
• 10310-21-1 2-Amino-6-chloropurin 

Downstream Products

• 1269437-89-9 bis[2-(3-hydroxypropylamino)-6-benzylamino-9-isopropylpurino]-(cyclobutan-1,1-dicarboxylato)-platinum(ll) complex 

Relevant articles and documents

Microwave-assisted solid-phase synthesis (MASS) of 2,6,9-trisubstituted purines

In an attempt to discover a high-throughput method for the synthesis of 2,6,9-trisubstituted purines, it was found that microwave irradiation was beneficial in accelerating the nucleophilic displacement of halogens by amines at the C-2 position of the purine nucleus. A method for microwave-assisted solid-phase synthesis (MASS) of 2,6,9-trisubstituted purines is presented.

Adamantane-substituted purines and their β-cyclodextrin complexes: Synthesis and biological activity

Cyclin-dependent kinases (CDKs) play an important role in the cell-division cycle. Synthetic inhibitors of CDKs are based on 2,6,9-trisubstituted purines and are developed as potential anticancer drugs; however, they have low solubility in water. In this

Facile and efficient access to 2,6,9-tri-substituted purines through sequential N9, N2 Mitsunobu reactions

A facile, efficient and mild synthesis of 2,6,9-tri-substituted purines is presented, starting from commercially available 2-amino-6-chloropurine, which employs sequential N9 then N2 Mitsunobu reactions as key steps. Importantly, our synthetic approach to

Cyclin dependent kinase inhibitor

The present invention is based on the method of treating a patient suffering from leukemia comprising administering a therapeutically effective amount of the compound 2-([(3-hydroxypropyl)amino]-6-benzylamino)-9-isopropylpurine or a pharmaceutically accep