| Identification | More | [Name]
6-O-Benzylguanine | [CAS]
19916-73-5 | [Synonyms]
2-Amino-6-(benzyloxy)purine
2-amino-6-(phenylmethoxy)-9h-purine
6-BENZYLOXY-9H-PURIN-2-AMINE
6-BENZYLOXY GUANINE
6-O-BENZYLGUANINE
O6-BENZYLGUANINE
4 6-Benzyloxyguanine
6-BENZYLOXY GUANINE2-AMINO-6-BENZYLOXYPURINE
O(sup 6)benzylguanidine
2-Amino-6-(benzyloxy)-9H-purine
6-(Benzyloxy)-1H-purin-2-amine | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C12H11N5O | [MDL Number]
MFCD00269931 | [Molecular Weight]
241.25 | [MOL File]
19916-73-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow Solid | [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 | [Usage]
An irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. Assists in the protection against carcinogenic and therapeutic alkylating agents. | [Detection Methods]
HPLC | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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. | [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 |
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