31383-66-1

Basic information

• Product Name: 1-[(2-Hydroxyethoxy)Methyl]adenine
• Synonyms: 1-[(2-Hydroxyethoxy)Methyl]adenine;2-((6-AMino-1H-purin-1-yl)Methoxy)ethanol;2-[(6-Amino-9H-purin-9-yl)methoxy]ethanol;AcycloA;9-[(2-hydroxyethoxy)methyl]adenine
• CAS NO: 31383-66-1
• Molecular Formula: C₈H₁₁N₅O₂
• Molecular Weight: 209.20524
• Mol File: 31383-66-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 496.1 °C at 760 mmHg
• Flash Point: 253.9 °C
• Appearance: /
• Density: 1.61 g/cm³
• Vapor Pressure: 1.16E-10mmHg at 25°C
• Refractive Index: 1.725
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 1-[(2-Hydroxyethoxy)Methyl]adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2-Hydroxyethoxy)Methyl]adenine(31383-66-1)
• EPA Substance Registry System: 1-[(2-Hydroxyethoxy)Methyl]adenine(31383-66-1)

Safety Data

• Hazardous Substances Data: 31383-66-1(Hazardous Substances Data)

Usage

General Description

1-[(2-Hydroxyethoxy)Methyl]adenine, also known as Penciclovir, is a synthetic chemical compound extensively used in antiviral medication. As an analog of guanosine, it closely replicates the structure of the natural nucleoside and interferes with DNA synthesis in viruses. It is particularly effective against the herpes simplex virus and varicella-zoster virus. The compound remains selectively active against these viruses by interacting with their specific viral DNA polymerases, thereby inhibiting their ability to replicate. Despite its effectiveness, it is noteworthy that this compound does not eliminate the virus from the body but, instead, reduces the severity and length of outbreaks.

InChI:InChI=1/C8H11N5O2/c9-7-6-8(11-3-10-7)13(4-12-6)5-15-2-1-14/h3-4,14H,1-2,5H2,(H2,9,10,11)

Upstream product

• 73484-26-1 2-<(6-chloro-9H-purin-9-yl)methoxy>ethanol 
• 81777-47-1 9-<(2-acetoxyethoxy)methyl>-6-chloropurine 
• 59277-84-8 2-benzoyloxy-1-(6-chloro-purin-9-ylmethoxy)-ethane 
• 66224-66-6 adenine 
• 4005-49-6 N-benzoyladenine 
• 87-42-3 6-chloropurine 
• 127277-98-9 2-<(adenin-9-yl)-methoxy>ethyl benzoate 
• 74-89-5 methylamine 
• 111392-47-3 Benzoic acid 2-(6-benzoylamino-purin-9-ylmethoxy)-ethyl ester 
• 69259-12-7 9-<(2-acethoxyethoxy)methyl>adenine 

Downstream Products

• 949891-67-2 2-[(adenine-9-yl)methoxy]-ethyl N-[(benzyloxy)carbonyl]-L-valinate 
• 123156-03-6 9-(2-bromoethoxymethyl)-N⁶-benzoyladenine 
• 201855-35-8 3-[1-(9-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethoxymethyl}-9H-purin-6-yl)-2,6-dioxo-piperidin-3-yl]-propionic acid 
• 201855-21-2 2-(9-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethoxymethyl}-9H-purin-6-yl)-isoindole-1,3-dione 
• 939794-99-7 9-{[({N-[2-(benzyloxy)benzoyl]sulfamoyl}-oxy)ethoxy]methyl}adenine 
• 201855-19-8 9-{{2-[(4,4'-dimethoxytrityl)oxy]etoxy}methyl}adenine 
• 72710-11-3 N6-benzoyl-9-<(2-hydroxyethoxy)methyl>adenine 
• 91897-95-9 9-<(2-hydroxyethoxy)methyl>hypoxanthine 

Relevant articles and documents

A direct method for the preparation of 2-hydroxyethoxymethyl derivatives of guanine, adenine, and cytosine

Alkylation of 2-chloro-6-iodopurine with iodomethyl [(trimethylsilyl)oxy]ethyl ether at -63°C and subsequent treatment of the 9-substituted chloroiodopurine with K2CO3 in aqueous dioxane at 25°C and then with NH3 under pressure at 150°C provided 9-[(2-hydroxyethoxy)methyl]guanine (1a), a potent antiviral agent against Herpes simplex virus type 1, in excellent yield. Its monophosphate (1g), which is enzymatically produced from 1a in the virus-infected cell, was also synthesized. 6-Chloropurine and 4-(methylthio)pyrimidin-2-one anions were similarly alkylated with iodomethyl [(trimethylsilyl)oxy]ethyl ether, and the products were transformed by treatment with methanolic NH3 at 110°C into 9-[(2-hydroxyethoxy)methyl]adenine and 1-[(2-hydroxyethoxy)methyl]cytosine respectively. The synthesis of these analogues, heretofore difficult to prepare by a simple procedure, has been conveniently accomplished.

Synthesis and in vitro stability of nucleoside 5′-phosphonate derivatives

Nucleoside derivatives are largely synthesized and tested to investigate their influence on platelet aggregation. It's well known that P2Y receptors play an important role in the regulation of platelet function and, as consequence, in controlling atherothrombotic events. The research of compounds that antagonize P2Y1 and, in particular, P2Y12 receptors is of great interest in the aim to obtain platelet aggregation inhibitors that are effective in the prevention and treatment of arterial thrombosis. In this study we present the synthesis and in vitro metabolic stability in human blood and rat liver homogenate of a new class of nucleoside derivatives, in particular 5′-phosphonate adenosine, inosine, guanosine and thioadenosine analogues also modified at the ribose moiety. On the basis of the results obtained we can hypothesize compounds 4 and 18 to have in vivo a relatively high stability.

PREVENTION AND TREATMENT OF CANCER AND OTHER DISEASES

Nucleoside chemical compounds, which interact with specific structures of deoxyribonucleic acid (DNA) or ribonucleic acid (RNA) are disclosed. The compounds interfere with the activities of telomerase and reverse transcriptase, and are useful as antivirals, antibacterials and anticancer agents. Methods of treating or preventing cancers in patients involving administration of a therapeutically effective amount of a composition having an inhibitor or antagonist of the reverse transcriptases (RTs) expressed in cells of the patients are also disclosed. Method of using nucleoside analogs and other inhibitors of RTs in conjunction with DNA damaging agents such as genotoxic agents or radiation or photodynamic therapy or combinations these for the treatment of various cancers are also disclosed.