69359-47-3

Basic information

• Product Name: 8-ethyladenosine
• Synonyms: 8-ethyladenosine
• CAS NO: 69359-47-3
• Molecular Formula: C12H17N5O4
• Molecular Weight: 0
• Mol File: 69359-47-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 676.8°C at 760 mmHg
• Flash Point: 363.1°C
• Appearance: /
• Density: 1.85g/cm³
• Vapor Pressure: 3.06E-19mmHg at 25°C
• Refractive Index: 1.813
• CAS DataBase Reference: 8-ethyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-ethyladenosine(69359-47-3)
• EPA Substance Registry System: 8-ethyladenosine(69359-47-3)

Safety Data

• Hazardous Substances Data: 69359-47-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H17N5O4/c1-2-6-16-7-10(13)14-4-15-11(7)17(6)12-9(20)8(19)5(3-18)21-12/h4-5,8-9,12,18-20H,2-3H2,1H3,(H2,13,14,15)/t5-,8-,9-,12-/m1/s1

Upstream product

• 101904-36-3 8-ethyl-2',3'-O-isopropylideneadenosine 
• 97-93-8 triethylaluminum 
• 2946-39-6 8-bromoadenosine 
• 597-64-8 tetraethyltin 
• 60091-08-9 8-bromo-2',3',5'-(triOTMS)adenosine 
• 101904-35-2 5'-O-acetyl-2',3'-O-isopropylidene-8-(α-ethoxycarbonylethyl)adenosine 
• 69359-30-4 5'-O-acetyl-8-ethoxycarbonylmethyl-2',3'-O-isopropylideneadenosine 
• 69359-29-1 5'-O-acetyl-2',3'-O-isopropylidene-8-methylsulfonyladenosine 
• 872025-37-1 2',3',5'-tris-(O-acetyl)-8-ethyladenosine 

Relevant articles and documents

New insights into the design of inhibitors of human S-adenosylmethionine decarboxylase: studies of adenine C8 substitution in structural analogues of S-adenosylmethionine

S-Adenosylmethionine decarboxylase (AdoMetDC) is a critical enzyme in the polyamine biosynthetic pathway and depends on a pyruvoyl group for the decarboxylation process. The crystal structures of the enzyme with various inhibitors at the active site have shown that the adenine base of the ligands adopts an unusual syn conformation when bound to the enzyme. To determine whether compounds that favor the syn conformation in solution would be more potent AdoMetDC inhibitors, several series of AdoMet substrate analogues with a variety of substituents at the 8-position of adenine were synthesized and analyzed for their ability to inhibit hAdoMetDC. The biochemical analysis indicated that an 8-methyl substituent resulted in more potent inhibitors, yet most other 8-substitutions provided no benefit over the parent compound. To understand these results, we used computational modeling and X-ray crystallography to study C8-substituted adenine analogues bound in the active site.

INHIBITORS OF S-ADENOSYL-L-METHIONINE DECARBOXYLASE

Novel mechanism-based inhibitors of S-adenosyl-L-methionine decarboxylase are provided. These compounds of formula (1) inhibit the life cycle of trypanosomes, and are useful to treat subjects infected with African trypanosomes. The invention includes pharmaceutical compositions and methods of using the compounds of formula (1).

Antiviral Activity of C-Alkylated Purine Nucleosides Obtained by Cross-Coupling with Tetraalkyltin Reagents

2-, 6-, And 8-alkylated (methyl, ethyl, and vinyl) adenosine analogues were synthesized by a palladium-catalyzed cross-coupling of a tetraalkyltin with the halogenated purine nucleosides.The synthesis of the 8-substituted analogues was accomplished using a transient protection procedure.The 6-alkylated-9-β-D-ribofuranosylpurines as well as 2-ethyladenosine were cytotoxic at relatively low concentrations (0.8-10 μg/mL). 8-Methyladenosine was a potent and selective inhibitor of vaccinia virus, whereas 8-ethyl- and 8-vinyladenosine were specifically inhibitory to respiratory syncytial virus. 8-Vinyladenosine displayed particular activity against herpes simplex virus (type 1).