43003-87-8

Usage

Uses

3-Ethyl-adenine has been identified in urine of cigarette smokers

InChI:InChI=1/C7H9N5/c1-2-12-4-11-6(8)5-7(12)10-3-9-5/h3-4H,2,8H2,1H3

Upstream product

• 75018-20-1 1,4,7,8-tetrahydro-4-iminothiazolo<2,3-b>purine 
• 75-03-6 ethyl iodide 
• 73-24-5 7H-purin-6-ylamine 
• 3647-48-1 2-mercaptoadenine 

Downstream Products

• 107293-06-1 9-benzyl-3-ethyladenine hydrobromide 
• 107293-05-0 7-benzyl-3-ethyladenine hydrobromide 

Relevant academic research and scientific papers

Heterocyclic Ambident Nucleophiles. III* The Alkylation of Sodium Adenide

The alkylation of sodium adenide in HCONMe2 (30 deg) with various alkylating agents was analysed by 1H n.m.r. spectroscopy.Widely varying N3:N7:N9 alkylation patterns were observed, depending on the alkylating agent.These patterns are interpreted in terms of the electrostatic, thermodynamic and steric factors involved in the different SN2 transition states appropriate to each alkylating agent.Hydrogen bonding association between the 6-amino group and certain carbonyl containing alkylating agents is proposed to explain the enhancedN7-alkylation in some cases.Support for this latter proposal was obtain from a comparison of the adenine alkylation results with the corresponding alkylation patterns of 6-pivaloylamino- and 6-chloro-purine.

Dihydrothiazolopurines

Reaction of 1,2-dibromoethane with 2-mercaptoadenine gave both 4-amino-7,8-dihydrothiazolopurine (2) and the isomeric 3,6,7,9-tetrahydro-9-iminothiazolopurine (3).These tricyclic structures were identified by Raney nickel reduction to the corresponding 3- and 1-ethyladenines.

Isolation and identification of products from alkylation of nucleic acids: ethyl- and isopropyl purines

Ethylation and isopropylation of guanine in alkaline solution, or of adenine in formic acid, by alkyl methanesulphonates gave the following products: 1, N2, 3, O6, 7 and 9 alkylguanines; 1, 3, 7 and 9 alkyladenines. The products were identified from their characteristic UV absorption spectra, by comparison with either known ethyladenines or with the corresponding known methyladenines, and were also characterized by mass spectrometry. Their chromatographic properties on paper, TLC and various columns were determined. DNA was alkylated in neutral solution with 14C labelled alkyl methanesulphonates and the ratios of the alkylpurines formed were obtained, and compared for alkylation by methyl, ethyl and isopropyl methanesulphonates and by N methyl N nitrosourea. The extents of alkylation at O 6 of guanine relative to those at N 7 of guanine varied with the reactivity of the methylating agents according to the predictions of Swain & Scott relating nucleophilicity of the groups alkylated with the substrate constants of the alkylating agents. The relative extents of alkylation at N 3 of adenine did not allow this correlation.