7780-10-1

Usage

Structural Composition

A purine derivative with an amino group at the 2-position and a phenyl group at the 8-position

Pharmacological Properties

Anti-inflammatory: Studied for its potential to reduce inflammation.
Anticancer: Investigated for its possible role in cancer treatment.

Application

Used in research and experimental studies to explore its biological effects and potential therapeutic uses.

Upstream product

• 14091-60-2 2,6-diamino-5-benzamido-4-pyrimidone 
• 592517-93-6 6-benzyloxy-4-N-benzoyl-2,4-diamino-5-nitrosopyrimidine 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 108732-34-9 benzoic acid isobutoxycarbonyl ester 
• 592518-02-0 2-amino-6-benzyloxy-8-phenylpurine 
• 79953-03-0 8-phenylguanosine 
• 55-21-0 benzamide 
• 156006-89-2 6-chloro-8-phenyl-7⁽⁹⁾H-purin-2-ylamine 

Relevant academic research and scientific papers

IKK-β as target to 2-amino-8-substituted guanine derivatives, application and its preparation method

The invention discloses a 2-amino-8-substituted guanine derivative with IKK-beta as a target spot, as well as an application and a preparation method thereof. The inhibition ratio of the inhibitory activity, to A549 cells, of the compounds is increased along with the increase of concentrations of drugs; however, the compounds basically have no inhibition effect on cell strains b16-f10, H460 and U251, and the selective inhibition effect is specifically significant when the compounds are taken as specific anti-tumor medicines.

Concerning the hydrolytic stability of 8-aryl-2′-deoxyguanosine nucleoside adducts: Implications for abasic site formation at physiological pH

(Chemical Equation Presented) Direct addition of aryl radical species to the C8-site of 2′-deoxyguanosine (dG) affords C 8-aryl-dG adducts that are produced by carcinogenic arylhydrazines, polycyclic aromatic hydrocarbons (PAHs), and

Efficient syntheses of C8-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA

(Chemical Equation Presented) The synthesis of the C8-aryl adducts of adenine and guanine formed by reaction of the radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BP) and dibenzo[def,p]chrysene (DBC), with DNA is reported. The synthetic approach involves in the key step direct reaction of a PAH aldehyde with a di- or triamine precursor of a purine. The method is operationally simple, affords good yields of adducts, and is broad in its scope. The C 8-aryl adducts of adenine and guanine derived from BP (6-BP-8-Ade and 6-BP-8-Gua) and DBC (10-DBC-8-Ade and 10-DBC-8-Gua) were synthesized in good yields by this method. Analogous C8-aryl adenine and guanine derivatives of other PAHs (anthracene, benz[a]anthracene, and chrysene) were also readily prepared via this approach. This method of synthesis is superior to the only method mat is currently available. It entails direct reaction of short-lived PAH radical cations (generated electrochemically or chemically) with 2′-deoxyribonucleosides or the corresponding purine bases. It provides the adducts in low yields accompanied by complex mixtures of secondary products. An alternative synthesis that involves Pd-catalyzed Suzuki-Miyaura coupling of arylboronic acids with 8-bromopurine nucleosides was also investigated. Although the C8-purine adducts of PAHs, such as naphthalene, phenanthrene, pyrene, and chrysene, could be prepared by this method, analogous adducts of carcinogenic PAHs and other structurally related PAHs, e.g., anthracene, benz[a]anthracene, benzo[a]pyrene, and dibenzo[def,p]chrysene, could not be obtained. This difference was shown to be a consequence of the facility of competing hydrolytic deboronation of the corresponding arylboronic acids.

An improved procedure for the preparation of 8-substituted guanines

The preparation of 8-substituted guanines using a new phosphorus(III)-mediated cyclisation of 4-acylamino-5-nitrosopyrimidines as the key step is described.

Reactions of Benzenediazonium Ions with Guanine and Its Derivatives

Guanine reacts with several benzenediazonium ions rapidly in aqueous solution at pH 10.5 to form 8-(arylazo)guanines in good yield.The reaction of guanine with 4-bromobenzenediazonium ion forms ε-guanine about 50-fold more rapidly than the reaction of adenine with this ion to yield 6-purine under these experimental conditions.Guanosine reacts much more slowly than guanine with the benzenediazonium ions in aqueous solution at pH 8.5 or 10.5 to give 8-arylguanosines.The structures of these products were established by their spectroscopic properties and by their quantitative conversion to 8-arylguanines. 5'-Guanylic acid also reacts quite slowly with the benzenediazonium ions in aqueous solution at pH 10.5.Only the compounds with strong electron-withdrawing groups yield N-2 triazenes at ambient temperature.No 8-aryl or 8-arylazo compounds are formed with 5'-guanylic acid at this temperature.However, 4-bromo- and 4-sulfobenzenediazonium ions react with 5'-guanylic acid at higher temperatures to yield the 8-aryl-5'-guanylic acids in low yield.The structures of these products were proven by hydrolysis to 8-arylguanines.The 8-arylguanosines and the 8-aryl-5'-guanylic acids are formed via free-radical phenylation reactions.The factors governing the reactivity of the adenines and the guanines are discussed.