126595-74-2

Usage

Uses

Used in Pharmaceutical Industry:
N7-(2-Hydroxyethyl)adenine is used as a DNA adduct for the study of ethylene oxide hydroxyethylnitrosourea interactions with DNA. This is important in understanding the mechanisms of DNA damage and repair, which can contribute to the development of new therapeutic strategies for various diseases.
Used in Antiviral Research:
N7-(2-Hydroxyethyl)adenine is used as a key component in the preparation of acyclic nucleosides and nucleotides, which have potential applications as antiviral agents. These compounds can help in the development of new drugs to combat viral infections by targeting specific viral processes or by enhancing the host's immune response.

Upstream product

• 624-76-0 Iodoethanol 
• 66224-66-6 adenine 
• 96-49-1 [1,3]-dioxolan-2-one 
• 73-24-5 7H-purin-6-ylamine 
• 550346-48-0 α-hydroperoxy-N-nitrosomorpholine 
• 958-09-8 2'-deoxy-D-adenosine 
• 4244-45-5 3-(6-aminopurin-9-yl)propionitrile 
• 374678-37-2 7-[(methoxycarbonyl)methyl]adenine 

Relevant academic research and scientific papers

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.

A adefovir dipivoxil isomer impurities and its preparation method and application

The invention discloses a adefovir dipivoxil isomer impurities 1 and its preparation method, it is in order to adenine and ethylenedioxy carbonate as the raw material by alkylation, condensation, hydrolysis, esterification and multi-step reaction synthesis adefovir dipivoxil isomer impurities 1, and by the MS and1 The conclusive evidence of the structure H NMR and the like. Adefovir dipivoxil isomer impurities 1 is different from literature reports of adefovir dipivoxil impurity, which belongs to the adefovir dipivoxil isomer, with similar structure [...] component, its physical and chemical properties may also [...] content is relatively similar, process step of removing the other impurities and relatively great difficulty, adefovir dipivoxil residual in the finished product the possibility of large also. Therefore adefovir dipivoxil and intermediate isomer impurities synthetic study for the quality control of the adefovir dipivoxil is of great significance.

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.

Products of the direct reaction of the diazonium ion of a metabolite of the carcinogen N -nitrosomorpholine with purines of nucleosides and dna

A number of putative purine nucleoside and nucleobase adducts of the diazonium ion derived from 3-hydroxy-N-nitrosomorpholine have been synthesized as dimethylacetals. These are converted, in most cases nearly quantitatively, to the aldehydes, or in two c

8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands

Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radio

IMPROVED SYNTHESIS FOR HYDROXYALKYLATED HETEROCYCLIC BASES

A hydroxyalkylated heterocyclic base is prepared by reacting a heterocyclic base with an alkylene carbonate in dimethylacetamide as a solvent, wherein the hydroxyalkylated heterocyclic base is isolated from the solvent using isopropanol or tert-butylmethylether.

Design, synthesis, and biological evaluation of novel nucleoside and nucleotide analogues as agents against DNA viruses and/or retroviruses

A novel strategy was developed for the synthesis of N7-purine acyclic nucleosides 9 and 14. The key step involved the reaction between [2-(p- methoxyphenyloxy)ethoxy]methyl chloride and N9-tritylated nucleobases 6 or 11 followed by concomitant self-detritylation. N7-Guanine acyclic nucleoside 9 exhibited antiviral activity, but was phosphorylated by both HSV and Vero cell thymidine kinases. Thus, it showed more potent cellular toxicity than acyclovir (2). N7-Adenine acyclic nucleoside 14 was found to be an excellent antiviral agent as well as a good inhibitor of calf mucosal adenosine deaminase. This inhibitory property allows for a greater expression of antiviral activity of antiviral agents, such as N9-adenine acyclic nucleoside 1 and ara-A (3). Compound 14 was phosphorylated neither by herpes simplex virus (HSV) thymidine kinase nor by Vero cell thymidine kinase, yet it enhanced the rate constant for the monophosphorylation of acyclovir (2) by HSV thymidine kinase. Consequently, the combination of acyclovir (2) and 14 exhibited greater antiviral activity than acyclovir alone. 7-[2(Phosphonomethoxy)ethyl] adenine (20) was also synthesized. The key step involved the reaction of 9-(2-cyanoethyl)adenine (15) with methyl iodoacetate in the presence of lithium 2,2,6,6-tetramethylpiperidine in THF. Unlike 9-[2- (phosphonomethoxy)ethyl] adenine (PMEA, 4), the N7-isomer 20 was not phosphorylated effectively by 5-phosphoribosyl 1-pyrophosphate synthetase (PRPP synthetase). Thus, it did not exhibit pronounced antiviral activity. Dinucleotide 5′-monophosphate 24 and its butenolide ester 25 were also synthesized. Compound 24 showed substrate activity toward PRPP synthetase and exhibited notable activity against DNA viruses. The antiviral activity of the ester derivative 25 was found to be higher than that of the parent molecule 24. Dinucleotide 5′-monophosphate 24 is suseptible to degradation by snake venom and spleen phosphodiesterases. However, its respective butenolide ester derivative 25 was completely resistant to snake venom and spleen enzymes. Butenolide ester derivatives 28 and 29 were also synthesized and exhibited notable anti-DNA virus and anti-retrovirus activity in vitro. Compounds 2, 4, 9, 14, 20, 24, 25, and 28 were also evaluated for their inhibitory effect on HSV-1-induced mortality in NMRI mice. N7-adenine acyclic nucleoside 14 [LD50 (intraperitoneal, ip) 950 mg/kg], nucleotide-containing butenolide 25 [LD50 (ip) 675 mg/kg], and butenolide 28 [LD50 (ip) 710 mg/kg] were found to be potent anti-HSV-1 agents in vivo. In addition, butenolide 28 efficiently decreased tumor formation induced by Moloney murine sarcoma virus (MSV) in NMRI mice while significantly increasing the survival time of MSV-infected mice.