6-O-Benzylguanine Chemical Properties

Melting point:

193(dec.)

Boiling point:

459.3±55.0 °C(Predicted)

Density 

1.48±0.1 g/cm3(Predicted)

storage temp. 

room temp

solubility 

methanol: 20 mg/mL

form 

solid

pka

7.47±0.20(Predicted)

color 

Off-White to Light Yellow

InChI

InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)

InChIKey

KRWMERLEINMZFT-UHFFFAOYSA-N

SMILES

N1C2C(=NC(N)=NC=2OCC2=CC=CC=C2)NC=1

CAS DataBase Reference

19916-73-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

6-O-Benzylguanine Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

An irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. Assists in the protection against carcinogenic and therapeutic alkylating agents.

Uses

O6-Benzylguanine is an effective substrate and efficient inactivator of DNA alkyltransferase. O6-Benzylguanine is an inhibitor of MGMT. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

Biochem/physiol Actions

O6-Benzylguanine (O6BG) inhibits methylguanine methyltransferase (MGMT) by blocking the active site through benzyl group transfer. The use of O6BG with bis-chloroethylnitrosourea (BCNU) or carmustine is effective in treating solid tumors including lymphomas, melanomas and sarcoma.

Synthesis

GENERAL STEPS: Benzyl alcohol (37.5 g, 0.347 mol) was mixed with sodium hydroxide (2.96 g, 0.074 mol) and heated until the sodium hydroxide was completely dissolved. After the reaction mixture was cooled, 2-amino-6-chloropurine (6.00 g, 0.035 mol) was added and the reaction was stirred at 80-90 °C for 5 hours. After completion of the reaction, methyl tert-butyl ether (120 mL) was added to the reaction mixture and extracted twice with sodium hydroxide solution (70 mL). The alkaline aqueous layers were combined, washed with toluene and subsequently evaporated to remove the toluene. The solution was neutralized to pH 6-8 with 35% hydrochloric acid and the precipitated crystals were collected by filtration. The resulting crude product 2-amino-6-(benzyloxy)purine (7.60 g, 0.032 mol, 92% yield) was dried under reduced pressure.

References

[1] Patent: WO2003/84957, 2003, A1. Location in patent: Page/Page column 9-10
[2] Nucleosides and Nucleotides, 1999, vol. 18, # 10, p. 2219 - 2231
[3] Helvetica Chimica Acta, 2012, vol. 95, # 12, p. 2621 - 2634
[4] Tetrahedron, 2007, vol. 63, # 24, p. 5323 - 5327
[5] Synthetic Communications, 2003, vol. 33, # 6, p. 941 - 952

6-O-Benzylguanine(19916-73-5)Related Product Information

• EC 2.6.1.2
• 6-Aminocaproic acid
• 2-Aminopurine
• Benzyltrimethylammonium chloride
• Benzyl chloride
• 3-Aminophenol
• 6-Benzylaminopurine
• Glycine
• ALTRENOGEST
• Purine
• Guanine
• Acetaminophen
• Benzyltriethylammonium chloride
• 4-Methoxybenzylchloride
• Iminodibenzyl
• 6-Thioguanine
• Tris(hydroxymethyl)aminomethane
• 6-O-Methyl-guanine