19255-48-2

Usage

Uses

Used in Pharmaceutical Industry:
9-(2-Chloro-ethyl)-9H-purin-6-ylamine is used as an intermediate in the synthesis of various pharmaceutical compounds for [application reason]. Its unique chemical structure allows it to be a versatile building block in the development of new drugs targeting different therapeutic areas.
Used in Chemical Research:
In the field of chemical research, 9-(2-Chloro-ethyl)-9H-purin-6-ylamine is used as a research compound for [application reason]. It aids scientists in understanding the interactions and reactions of purine derivatives, which can lead to the discovery of novel chemical reactions and applications.
Used in Organic Synthesis:
9-(2-Chloro-ethyl)-9H-purin-6-ylamine is used as a key component in organic synthesis for [application reason]. Its chloro-ethyl group provides a reactive handle for further functionalization, making it a valuable precursor in the creation of complex organic molecules with potential applications in various industries.

InChI:InChI=1/C7H8ClN5/c8-1-2-13-4-12-5-6(9)10-3-11-7(5)13/h3-4H,1-2H2,(H2,9,10,11)

Upstream product

• 40428-86-2 sodium adeninate 
• 107-04-0 1-Bromo-2-chloroethane 
• 66224-66-6 adenine 
• 96-49-1 [1,3]-dioxolan-2-one 
• 107-06-2 1,2-dichloro-ethane 
• 707-99-3 9-(2-hydroxyethyl)adenine 
• 2524-64-3 chlorophosphoric acid diphenyl ester 

Downstream Products

• 20245-85-6 9-vinyladenine 
• 167780-54-3 9-(2'-chloroethyl)-N⁶-bis(phenoxy)phosphinyladenine 
• 186342-07-4 9-N-(2'-chloroethyl)-6-N-dimethoxytrityladenine 
• 59209-78-8 (adenylethyl)cobalamine 
• 662165-08-4 N⁹-(N²'-diphenylphosphino-N²'-n-propylaminoethyl)adenine 
• 662165-07-3 N⁹-(N^2'-diphenylphosphinoaminoethyl)adenine 
• 199522-02-6 [9-(2-Chloro-ethyl)-9H-purin-6-yl]-(9-phenyl-9H-xanthen-9-yl)-amine 
• 199522-03-7 (9-Phenyl-9H-xanthen-9-yl)-(9-vinyl-9H-purin-6-yl)-amine 
• 186342-08-5 9-N-vinyl-6-N-dimethoxytrityladenine 

Relevant academic research and scientific papers

Synthesis of adenine derivatives containing an amino alcohol fragment

The alkylation of adenine and N(6)-substituted adenine derivatives by 1,2-dihaloethanes and the production of 9-(2-haloethyl)derivatives of adenine were studied. In the reaction of the derivatives with amino alcohols a series of adenine derivat

Photochemical reactivity of 9-vinyladenine with diethyl fumarate

The photochemical reaction between 9-vinyladenine (2) and diethyl fumarate (4) gave an unusual photoadduct, epimers 4 and 5, probably derived from attack of the vinyl group on N-3 and reaction of diethyl fumarate on N-9 and N-6.

Synthesis, cyclopolymerization and cyclo-copolymerization of 9-(2-Diallylaminoethyl)adenine and Its Hydrochloride Salt

We report herein the synthesis and characterization of 9-(2- diallylaminoethyl) adenine. We evaluated two different synthetic routes starting with adenine where the optimal route was achieved through coupling of 9-(2-chloroethyl)adenine with diallylamine.

Crystal of 5-( (2-(6-amino)-9H-purin-9-yl) ethyl) amino) pentan-1-o1

The present invention provides a new crystal form of 5-((2-(6-amino)-9H-purin-9-yl)ethyl)amino)pentan-1-ol, which has a relatively better effect in selectively inhibiting adenylate cyclase 1 and is capable of preparing a medicament for treating neuropathi

Novel multi-target compounds in the quest for new chemotherapies against Alzheimer's disease: An experimental and theoretical study

The lack of any effective therapy along with the aging world population anticipates a growth of the worldwide incidence of Alzheimer's disease (AD) to more than 100 million cases by 2050. Accumulation of extracellular amyloid-β (Aβ) plaques, intracellular tangles in the brain, and formation of reactive oxygen species (ROS) are the major hallmarks of the disease. In the amyloidogenic process, a β-secretase, known as BACE 1, plays a fundamental role in the production of Aβ fragments, and therefore, inhibition of such enzymes represents a major strategy for the rational design of anti-AD drugs. In this work, a series of four multi-target compounds (1–4), inspired by previously described ionophoric polyphenols, have been synthesized and studied. These compounds have been designed to target important aspects of AD, including BACE 1 enzymatic activity, Aβ aggregation, toxic concentrations of Cu2+ metal ions and/or ROS production. Two other compounds (5 and 6), previously reported by some of us as antimalarial agents, have also been studied because of their potential as multi-target species against AD. Interestingly, compounds 3 and 5 showed moderate to good ability to inhibit BACE 1 enzymatic activity in a FRET assay, with IC50′s in the low micromolar range (4.4 ± 0.3 and 1.7 ± 0.3 μM, respectively), comparable to other multi-target species, and showing that the observed activity was in part due to a competitive binding of the compounds at the active site of the enzyme. Theoretical docking calculations overall agreed with FRET assay results, displaying the strongest binding affinities for 3 and 5 at the active site of the enzyme. In addition, all compounds selectively interacted with Cu2+ metal ions forming 2:1 complexes, inhibited the production of Aβ-Cu2+ catalyzed hydroxyl radicals up to a ～100% extent, and scavenged AAPH-induced peroxyl radical species comparably to resveratrol, a compound used as reference in this work. Our results also show good anti-amyloidogenic ability: compounds 1–6 inhibited both the Cu2+-induced and self-induced Aβ(1–40) fibril aggregation to an extent that ranged from 31% to 77%, while they disaggregated pre-formed Aβ(1–40) mature fibrils up to a 37% and a 69% extent in absence and presence of Cu2+, respectively. Cytotoxicity was additionally studied in Tetrahymena thermophila and HEK293 cells, and compared to that of resveratrol, showing that compounds 1–6 display lower toxicity than that of resveratrol, a well-known non-toxic polyphenol.

Two simple protocols for the preparation of diallylaminoethyl-substituted nucleic bases: A comparison

The syntheses of pyrimidine and purine nucleic bases substituted with diallylaminoethyl groups are reported following two different protocols. A comparison is made between the yield, expense, and difficulty of each route.

Synthesis and coordination chemistry of aminophosphine derivatives of adenine

Two aminophosphine derivatives of adenine N9-(N2′-diphenylphosphinoaminoethyl)adenine L1 and N9-(N2′-diphenylphosphino-N2′-n-pro pylaminoethyl)adenine L2 were synthesized. Oxidation of L1 and L2 with

Syntheses and coordination chemistry of aminomethylphosphine derivatives of adenine

Two aminomethylphosphane derivatives of adenine 9-(2-{bis[(diphenylphosphanyl)methyl]amino}ethyl)adenine (La) and 9-(3-{bis[(diphenylphosphanyl)methyl]amino}propyl)adenine (Lb) were synthesised. Oxidation of La and Lb with H2O2, elemental sulfur or elemental selenium led to the corresponding oxidized products 4a/b-6a/b. Both La and Lb behave as didentate ligands towards late transition metals. Reaction of La or Lb with [MX2(cod)] (M = Pd, Pt; X = Cl, Me) gave chelate complexes 7a/b-10a/b. Reaction of La or Lb with [AuCl(tht)] of [{RuCl(μ-Cl)(p-MeC6H4iPr)}2] gave the didentate bridging complexes 11a/b and 12a. All compounds have been fully characterised by microanalysis, IR, 1H and 31P{1H} NMR spectroscopy, and EI/CI/FAB mass spectrometry. 1H{31P} NMR and 1H-13C correlation experiments were used to confirm the spectral assignments where necessary. Two compounds were structurally characterised by X-ray crystallographic analysis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

A novel class of 4'-aza analogues of 2',3'-dideoxynucleosides as potential anti-HIV drugs

The 1,3 dipolar cycloaddition approach represents the most valuable strategy for the preparation of isoxazolidine nucleosides. The latter posses more conformational degrees of freedom than the corresponding dideoxyribosides. Side reactions due to the presence of formaldehyde in the reaction media can be avoided by proper derivatization of the vinyl- nucleobase.