144084-37-7

Basic information

• Product Name: 1H-Purin-2-amine, 6-[(4-fluorophenyl)methoxy]-
• CAS NO: 144084-37-7
• Molecular Formula: C12H10FN5O
• Molecular Weight: 259.243
• Mol File: 144084-37-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-Purin-2-amine, 6-[(4-fluorophenyl)methoxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Purin-2-amine, 6-[(4-fluorophenyl)methoxy]-(144084-37-7)
• EPA Substance Registry System: 1H-Purin-2-amine, 6-[(4-fluorophenyl)methoxy]-(144084-37-7)

Safety Data

• Hazardous Substances Data: 144084-37-7(Hazardous Substances Data)

Upstream product

• 459-56-3 4-fluorobenzylic alcohol 
• 10310-21-1 2-Amino-6-chloropurin 
• 3056-33-5 2,9-diacetylguanine 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 1333432-60-2 4-fluorobenzyl alcohol sodium salt 
• 34798-95-3 2-amino-N,N,N-trimethyl-9H-purine-6-ylammonium chloride 
• 10310-21-1 2-amino-6-chloropurine 

Downstream Products

• 351-66-6 1-[(phenylthio)methyl]-4-fluoro-benzene 
• 73-40-5 2-amino-6-hydroxypurine 

Relevant articles and documents

A convenient procedure for the synthesis of O6-benzylguanine derivatives by phase transfer catalysis

A convenient procedure by phase transfer catalysis has been developed for the synthesis of O6-BG (1) and its derivatives hydroxymethyl-BG (2a-c), halo-BG (3a-c, 4a-c, 5a-c, 6a-c), methoxy-BG (7), and methyl-BG (8). Compounds 2b, 2c, 4b, 4c, 5b, 5c, 6a, and 6c are new compounds.

COMPOSITIONS, METHODS, AND KITS FOR DETERMINING AN ALKYL TRANSFERASE

The present invention relates to novel compounds as well as to compositions, methods, and kits comprising the compounds for determining an alkyltransferase (ATase), in particular an alkylguanine-DNA alkyl transferase (AGT). In general, the novel compounds

Potentiation of the cytotoxicity of chloroethylnitrosourea by O6-arylmethylguanines

It was reported recently that monomeric O6-benzylguanine (1) acts as an alternative substrate for a DNA repair enzyme, O6-alkylguanine-DNA alkyltransferase (AGT), and that therefore pretreatment of cells with 1 induces depletion of AGT resulting in an enhanced cytotoxic response to alkylating antitumor agents. In order to study the interaction of O6-benzylguanine derivatives with AGT and to obtain greater AGT depletion, me synthesized the following O6-arylmethylguanine derivatives and related compounds: O6-(4-, 3- and 2-fluorobenzyl)guanines (2, 3, 4), O6-(4-,3- and 2-trifluoromethylbenzyl)guanines (5, 6, 7), O6-(4-, 3- and 2-pyridylmethyl)guanines (8, 9, 10), O6-(2- and 1-naphthylmethyl)guanines (11, 12), O6-biphenylmethylguanine (13), S and Se analogues of O6-benzylguanine (14, 15) and O6-phenylguanine (16). Ten of these are new compounds. All these compounds were tested for their potentiation of N'-[(4-amino-2-methyl-5-pyrimidinyl)methyl] (ACNU) cytotoxicity using HeLa S3 and C6-1 cells. Compounds 2, 3, 5, 8, 9, 11 and 13 were active, as was 1. Compounds 7 and 12, with a substituent at the a position of the benzyl group, and compound 10, the a-nitrogen analogue of 1, were almost completely devoid of potentiating activity. These results suggest that the a-position of the O6-benzyl group plays an important role in the interaction of O6-benzylguanines with AGT. Of the other compounds, 4 and 6 exhibited very weak activity and 14, 15 and 16 were inactive. Possible reasons for these differences in activity are discussed in relation to the biomimetic dealkylation rates of O6-benzylguanine derivatives and the chemical characteristics of their substituents.