19916-73-5

Basic information

• Product Name: 6-O-Benzylguanine
• Synonyms: O(sup 6)benzylguanidine;2-Amino-6-(benzyloxy)-9H-purine;6-(Benzyloxy)-1H-purin-2-amine;O6-Benzylguanine ,98%;6-(benzyloxy)-7H-purin-2-aMine;6-(PhenylMethoxy)-9H-purin-2-aMine;NSC 637037;6-benzylguanine
• CAS NO: 19916-73-5
• Molecular Formula: C₁₂H₁₁N₅O
• Molecular Weight: 241.25
• EINECS: 1592732-453-0
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Alkylguanine-DNA alkyltransferase, mammalian DNA repair proteinApoptosis and Cell Cycle;DNA Repair Regulators;A to;DNA metabolism;Enzyme Inhibitors by Enzyme
• Mol File: 19916-73-5.mol
• Article Data: 26

Chemical Properties

• Melting Point: 193(dec.)
• Boiling Point: 621.4 °C at 760 mmHg
• Flash Point: 329.6 °C
• Appearance: /solid
• Density: 1.431 g/cm³
• Vapor Pressure: 2.3E-15mmHg at 25°C
• Refractive Index: 1.743
• Storage Temp.: -20°C Freezer
• Solubility: methanol: 20 mg/mL
• PKA: 7.47±0.20(Predicted)
• CAS DataBase Reference: 6-O-Benzylguanine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-Benzylguanine(19916-73-5)
• EPA Substance Registry System: 6-O-Benzylguanine(19916-73-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 19916-73-5(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Solid

Uses

Different sources of media describe the Uses of 19916-73-5 differently. You can refer to the following data:
1. An irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. Assists in the protection against carcinogenic and therapeutic alkylating agents.
2. 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.

InChI:InChI=1/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)

Upstream product

• 10310-21-1 2-Amino-6-chloropurin 
• 100-51-6 benzyl alcohol 
• 1340543-34-1 (6-(benzyloxy)-2-((((4-nitrobenzyl)oxy)carbonyl)amino)-9H-purin-9-yl)methyl pivalate 
• 1340543-35-2 (6-(benzyloxy)-2-(((1-(4-nitrophenyl)ethoxy)carbonyl)-amino)-9H-purin-9-yl)methyl pivalate 
• 1340543-31-8 4-nitrobenzyl (6-(benzyloxy)-9H-purin-2-yl)carbamate 
• 1340543-32-9 1-(4-nitrophenyl)ethyl (6-(benzyloxy)-9H-purin-2-yl)carbamate 
• 1340543-33-0 2-(4-nitrophenyl)propan-2-yl (6-(benzyloxy)-9H-purin-2-yl)carbamate 
• 619-73-8 4-nitrobenzyl chloride 
• 20194-18-7 sodium phenyl-methanolate 
• 3056-33-5 2,9-diacetylguanine 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 100199-49-3 2-Benzyloxy-5-(2'-p-toluenesulfonyl-oxyethyl)-2-oxo-1,3,2-dioxaphosphorinane 
• 612507-56-9 2-amino-6-benzyloxypurine methanolate 
• 34798-95-3 2-amino-N,N,N-trimethyl-9H-purine-6-ylammonium chloride 

Downstream Products

• 127089-49-0 6-Benzyloxy-9-(2-chloro-ethyl)-9H-purin-2-ylamine 
• 142613-45-4 9-(2-acetoxyethyl)-6-O-benzylguanine 
• 105797-65-7 Acetic acid 4-(2-amino-6-benzyloxy-purin-9-yl)-butyl ester 
• 105797-66-8 Acetic acid 4-(2-amino-6-benzyloxy-purin-7-yl)-butyl ester 
• 125331-02-4 2-amino-6-(benzyloxy)-9-<4-(diethylphosphono)butyl>purine 
• 100994-98-7 (+/-)-2-amino-6-(benzyloxy)-9-<<2-(benzyloxy)-1-propoxy>methyl>purine 
• 125331-17-1 2-amino-6-(benzyloxy)-9-<4,4-difluoro-4-(diethylphosphono)butyl>purine 
• 125331-05-7 2-amino-6-(benzyloxy)-9-<2-<<(diethylphosphono)methyl>thio>ethyl>purine 
• 123903-68-4 2-amino-6-(benzyloxy)-9-<<1,3(R)-bis(benzyloxy)-4-fluoro-2(R)-butoxy>methyl>purine 
• 123903-74-2 6-Benzyloxy-7-((1R,2R)-2-benzyloxy-1-benzyloxymethyl-3-fluoro-propoxymethyl)-7H-purin-2-ylamine 
• 132294-27-0 <1R-(1α,2β,3α)>-3-<2-amino-6-(phenylmethoxy)-9H-purin-9-yl>-1,2-cyclobutanedimethanol 1,2-dibenzoate ester 
• 132294-19-0 <1S-(1α,2β,3α)>-3-<2-amino-6-(phenylmethoxy)-9H-purin-9-yl>-1,2-cyclobutanedimethanol 1,2-dibenzoate ester 
• 126261-75-4 C₃₂H₂₉N₅O₅ 
• 124490-72-8 (1R,2R,4R)-2-(2-Amino-6-benzyloxy-purin-9-yl)-4-benzyloxymethyl-cyclobutanol 

Relevant articles and documents

Regioselective alkylation of guanine derivatives in the synthesis of peptide nucleic acid monomers

A method for the synthesis of 6-O-benzyl- and 6-O-benzyl-2-N-benzyloxycarbonyl-protected guanine derivatives starting from 2-amino-6-chloropurin is described. A regioselective alkylation of these N(9)-protected guanine derivatives gave the corresponding α-monomers of chiral peptide nucleic acids, the L-glutamic acid derivatives. It was shown that these compound do not inhibit (in the concentrations -1) the topoisomerase I activity.

Synthesis and biological evaluation of new HIV-1 protease inhibitors with purine bases as P2-ligands

Introducing purine bases to P2-ligands might enhance the potency of Human Immunodeficiency Virus-1 (HIV-1) protease inhibitory because of the carbonyl and NH groups promoting the formation of extensive H-bonding interactions. In this work, thirty-three compounds are synthesized and evaluated, among which inhibitors 16a, 16f and 16j containing N-2-(6-substituted-9H-purin-9-yl)acetamide as the P2-ligands along with 4-methoxylphenylsulfonamide as the P2′-ligand, display potent inhibitory effect on the activity of HIV-1 protease with IC50 43 nM, 42 nM and 68 nM in vitro, respectively.

Benzyl guanine derivative, an organic salt compound thereof, a medicine composition, and application thereof

The invention relates to the field of antitumor medicines and especially relates to a benzyl guanine derivative, an organic salt compound thereof, a medicine composition, and an application thereof. The benzyl guanine derivative is easy to prepare, has good druggability, can inhibit enzyme-catalysis activity of Pin 1 protein, can improve biosynthesis of mature microRNA at cellular and animal levels, and increases the types of antitumor medicines.