707-99-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(6-Aminopurin-9-yl)ethanol is used as a chemical intermediate for the synthesis of aryloxyalkyl derivatives of adenine. These derivatives exhibit significant antiviral activity, making them valuable in the development of new antiviral drugs and therapies. 2-(6-Aminopurin-9-yl)ethanol's role in the synthesis of these derivatives is essential for creating molecules that can effectively target and inhibit viral replication, thus offering potential treatments for a range of viral infections.

InChI:InChI=1/C7H9N5O/c8-6-5-7(10-3-9-6)12(1-2-13)4-11-5/h3-4,13H,1-2H2,(H2,8,9,10)

Upstream product

• 96-49-1 [1,3]-dioxolan-2-one 
• 66224-66-6 adenine 
• 1670-62-8 6-Chloro-9-(β-hydroxyethylamino)purine 
• 6623-88-7 5-amino-6-chloro-4-(2'-hydroxyethylamino)pyrimidine 
• 624-76-0 Iodoethanol 
• 15571-48-9 bis(isopropoxy) magnesium 
• 43047-77-4 8-bromo-9-(2-hydroxyethyl)-9H-adenine 
• 109153-46-0 N⁶-(2-methylpropionyl)adenine 
• 192130-43-1 9-(2-chloroethyl)-6-isobutyrylaminopurine 
• 101967-22-0 9-(2-hydroxyethyl)-8-hydrazinoadenine 

Downstream Products

• 167780-55-4 9-(2'-chloroethyl)-N⁶-bis(4-tolyl)phoshinyladenine 
• 19255-48-2 9-(2-chloroethyl)adenine 
• 167780-54-3 9-(2'-chloroethyl)-N⁶-bis(phenoxy)phosphinyladenine 
• 123156-00-3 N-[9-(2-Bromo-ethyl)-9H-purin-6-yl]-benzamide 
• 123156-01-4 9-(2-diethoxyphosphonylethyl)-N⁶-benzoyladenine 
• 106941-25-7 Adefovir 
• 1192066-30-0 9-(O-p-toluensulfonyl-2-hydroxyethyl)adenine 
• 142340-99-6 adefovir dipivoxyl 
• 116384-53-3 [[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester 
• 68217-74-3 9‐(2‐bromoethyl)‐9H‐purin‐6‐amine 
• 55343-28-7 9-(2-Hydroxyethyl)-N⁶-benzoyladenine 

Relevant academic research and scientific papers

6-Isobutyrylaminopurine: A convenient building block for the synthesis of carbocyclic adenosine analogs

Readily available 6-isobutyrylaminopurine can replace either a primary or secondary OH group under Mitsunobu conditions and provide an efficient synthesis of carbocyclic analogs of adenosine. X-ray data indicates that only the desired N9-substituted derivatives of adenine are formed.

Supramolecular copolymer micelles based on the complementary multiple hydrogen bonds of nucleobases for drug delivery

Novel supramolecular copolymer micelles with stimuli-responsive abilities were successfully prepared through the complementary multiple hydrogen bonds of nucleobases and then applied for rapid intracellular release of drugs. First, both adenine-terminated poly(-caprolactone) (PCL-A) and uracil-terminated poly(ethylene glycol) (PEG-U) were synthesized. The supramolecular amphiphilic block copolymers (PCL-A:U-PEG) were formed based on multiple hydrogen bonding interactions between PCL-A and PEG-U. The micelles self-assembled from PCL-A:U-PEG were sufficiently stable in water but prone to fast aggregation in acidic condition due to the dynamic and sensitive nature of noncovalent interactions. The low cytotoxicity of supramolecular copolymer micelles was confirmed by MTT assay against NIH/3T3 normal cells. As a hydrophobic anticancer model drug, doxorubicin (DOX) was encapsulated into these supramolecular copolymer micelles. In vitro release studies demonstrated that the release of DOX from micelles was significantly faster at mildly acid pH of 5.0 compared to physiological pH. MTT assay against HeLa cancer cells showed DOX-loaded micelles had high anticancer efficacy. Hence, these supramolecular copolymer micelles based on the complementary multiple hydrogen bonds of nucleobases are very promising candidates for rapid controlled release of drugs.

Synthesis and assembly behavior of heteronucleobase-functionalized poly(ε-caprolactone)

The heteronucleobase (adenine and uracil)-functionalized poly(ε-caprolactone) (A-PCL-U) possessing supramolecular structure has been successfully synthesized through the combination of ringopening polymerization and Michael addition reaction. Attachment of multiple hydrogen-bonding units to chain ends of PCL results in phase separation and substantial increase in the viscosity. The association constant (Ka) between adenine and uracil groups of A-PCL-U calculated from NMR measurement is 18.9 M-1. XRD and DSC analyses indicate that the crystalline structure of the A-PCL-U is changed to some extent due to phase segregation as compared to the PCL homopolymer. The AFM micrograph demonstrates that phase segregation is formed from the hard nucleobase chain ends and the soft poly(ε-caprolactone) chains of the supramolecular complex.

An improved synthesis of adefovir and related analogues

An improved synthesis of the antiviral drug adefovir is presented. Problems associated with current routes to adefovir include capricious yields and a reliance on problematic reagents and solvents, such as magnesium tert-butoxide and DMF, to achieve high conversions to the target. A systematic study within our laboratory led to the identification of an iodide reagent which affords higher yields than previous approaches and allows for reactions to be conducted up to 10 g in scale under milder conditions. The use of a novel tetrabutylammonium salt of adenine facilitates alkylations in solvents other than DMF. Additionally, we have investigated how regioselectivity is affected by the substitution pattern of the nucleobase. Finally, this chemistry was successfully applied to the synthesis of several new adefovir analogues, highlighting the versatility of our approach.

Preparation method of adefovir dipivoxil crystals

The invention belongs to the technical field of drug preparation and in particular relates to a preparation method of adefovir dipivoxil crystals. The preparation method comprises the following steps: synthesizing diethyl phosphite; synthesizing diethyl (p-phenylsulfonyloxy)methylphosphonate; synthesizing 9-(2-hydroxyethyl) adenine; synthesizing 4,9-[2-(diethylphosphonomethoxy)ethyl]adenine; synthesizing adefovir; synthesizing adefovir dipivoxil. Compared with the prior art, the preparation method of the adefovir dipivoxil crystals, provided by the invention, takes acetonitrile as a water-soluble organic medium, and the difficulty that DMF (Dimethyl Formamide) is difficult to remove is overcome; ethyl acetate is used for replacing isopropyl acetate in a previous process, isopropyl ether is used for replacing ethyl ether and ethanol is used for replacing acetone; the preparation method is simple to operate; the obtained product has good purity and high yield; the industrialized production is easy to realize and the production cost is reduced.

Hg2+ detecting aggregation-induced emission type fluorescent sensor and production method and application thereof

The invention discloses an Hg2+ detecting aggregation-induced emission type fluorescent sensor and a production method and application thereof. The structural formula of the fluorescent sensor is as shown in specification. The fluorescent sensor is of aggregation-induced emission property and is nonluminous in solution, and its fluorescent light is enhanced in an aggregation state, accordingly, the fluorescent sensor can be applied to recognition of highly specific selectivity and anti-interference performance of Hg2+. Besides, the fluorescent sensor has high biocompatibility and cellular permeability, can target mitochondria in cells and light the Hg2+ in mitochondria by fluorescent light, and accordingly can realize detection of Hg2+ in the mitochondria.

Adefovir dipivoxil a hydrate and its preparation method (by machine translation)

Adefovir dipivoxil this invention relates to a method for preparing a hydrate thereof, with an aqueous acetone as the solvent, can be obtained by the freeze-drying of a water composition of adefovir dipivoxil freeze-dried powder. The method is simple and convenient to operate, can selectively obtain a hydrate, high product yield, purity is good, is very suitable for large-scale production. (by machine translation)

Ester prodrugs of acyclic nucleoside thiophosphonates compared to phosphonates: Synthesis, antiviral activity and decomposition study

9-[2-(Thiophosphonomethoxy)ethyl]adenine [S-PMEA, 8] and (R)-9-[2-(Thiophosphonomethoxy)propyl]adenine [S-PMPA, 9] are acyclic nucleoside thiophosphonates we described recently that display the same antiviral spectrum (DNA viruses) as approved and potent phosphonates PMEA and (R)-PMPA. Here, we describe the synthesis, antiviral activities in infected cell cultures and decomposition study of bis(pivaloyloxymethoxy)-S-PMEA [Bis-POM-S-PMEA, 13] and bis(isopropyloxymethylcarbonyl)-S-PMPA [Bis-POC-S-PMPA, 14] as orally bioavailable prodrugs of the S-PMEA 8 and S-PMPA 9, in comparison to the equivalent "non-thio" derivatives [Bis-POM-PMEA, 11] and [Bis-POC-PMPA, 12]. Compounds 11, 12, 13 and 14 were evaluated for their in vitro antiviral activity against HIV-1-, HIV-2-, HBV- and a broad panel of DNA viruses, and found to exhibit moderate to potent antiviral activity. In order to determine the decomposition pathway of the prodrugs 11, 12, 13 and 14 into parent compounds PMEA, PMPA, 8 and 9, kinetic data and decomposition pathways in several media are presented. As expected, bis-POM-S-PMEA 13 and bis-POC-S-PMPA 14 behaved as prodrugs of S-PMEA 8 and S-PMPA 9. However, thiophosphonates 8 and 9 were released very smoothly in cell extracts, in contrast to the release of PMEA and PMPA from "non-thio" prodrugs 11 and 12.

8-(2-Furyl)adenine derivatives as A2A adenosine receptor ligands

Selective adenosine receptor modulators are potential tools for numerous therapeutic applications, including cardiovascular, inflammatory, and neurodegenerative diseases. In this work, the synthesis and biological evaluation at the four human adenosine receptor subtypes of a series of 9-substituted 8-(2-furyl)adenine derivatives are reported. Results show that 8-(2-furyl)-9-methyladenine is endowed with high affinity at the A2A subtype. Further modification of this compound with introduction of arylacetyl or arylcarbamoyl groups in N6-position takes to different effects on the A2A affinity and in particular on the selectivity versus the other three adenosine receptor subtypes. A molecular modelling analysis at three different A2A receptor crystal structures provides an interpretation of the obtained biological results.

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.