892-48-8

Basic information

• Product Name: 5'-CHLORO-5'-DEOXYADENOSINE
• Synonyms: 5'-CHLORO-5'-DEOXYADENOSINE;5-CHLORO-5-DEOXYADENOSINE HYDRATE;5'-CHLORO-5'-DEOXYADENOSINE MONOHYDRATE;5’-chloro-5’-deoxy-adenosin;5'-CHLORO-5'-DEOXY-D-ADENOSINE;5'-Deoxy-5'-chloroadenosine;5'-Cl-5'-deoxyadenosine;Adenosine,5'-chloro-5'-deoxy-
• CAS NO: 892-48-8
• Molecular Formula: C₁₀H₁₂ClN₅O₃
• Molecular Weight: 285.69
• Mol File: 892-48-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: 187 °C (exothermic decomp onset @144.5 C)(lit.)
• Boiling Point: 645.6 °C at 760 mmHg
• Flash Point: 344.2 °C
• Appearance: /
• Density: 2.03g/cm³
• Vapor Pressure: 1.5E-17mmHg at 25°C
• Refractive Index: 1.87
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Water (Slightly, Heated)
• PKA: 13.03±0.70(Predicted)
• CAS DataBase Reference: 5'-CHLORO-5'-DEOXYADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-CHLORO-5'-DEOXYADENOSINE(892-48-8)
• EPA Substance Registry System: 5'-CHLORO-5'-DEOXYADENOSINE(892-48-8)

Safety Data

• WGK Germany: 3
• RTECS: AU7357200
• Hazardous Substances Data: 892-48-8(Hazardous Substances Data)

Usage

Uses

5''-Deoxy-5''-chloroadenosine is an intermediate in the synthesis of 5''-Deoxy-5''-(methylthio)adenosine (D242600), a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways.

InChI:InChI=1/C10H12ClN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)

Upstream product

• 58-61-7 adenosine 
• 2004-06-0 6-Chloropurine riboside 
• 142031-35-4 adinosine 
• 24514-56-5 9-((3aR,4R,6S,6aS)-6-(chloromethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine 
• 69260-62-4 5'-chloro-5'-deoxy-2',3'-O-sulphinyladenosine hydrochloride 
• 662131-88-6 5'-chloro-5'-deoxy-2',3'-O-sulfinyladenosine 

Downstream Products

• 5135-37-5 5'-S-phenyl-5'-thioadenosine 
• 153920-20-8 5'-S-(4-Chlorophenyl)-5'-thioadenosine 
• 2457-80-9 5'-Deoxy-5'-methylthioadenosine 
• 21017-05-0 5'-chloro-5'-deoxyinosine 
• 79146-35-3 5'-deoxy-5'-(2-phenylethylthio)adenosine 
• 35899-54-8 5'-Isobutylthioadenosine 
• 58-61-7 adenosine 
• 737-76-8 5'-azido-5'-deoxyadenosine 
• 1401415-27-7 5'-azido-2',3'-bis-O-tert-butyldiphenylsilyl-5'-deoxyadenosine 
• 485-80-3 S-adenosyl-L-methionine 
• 5135-39-7 5’-deoxy-5’-(benzylthio)adenosine 
• 35899-53-7 S-Adenosyl-L-cysteine 
• 4754-39-6 5'-deoxyadenosine 
• 83332-24-5 [(2S,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-[3-(2-hydroxy-phenyl)-3-methyl-butyl]-methyl-sulfonium 

Relevant articles and documents

Synthesis and characterization of Se-adenosyl-L-selenohomocysteine selenoxide

Selenium is an essential micronutrient in humans due to the important roles of the selenocysteine-containing selenoproteins. Organoselenium metabolites are generally found to be substrates for the biochemical pathways of their sulfur analogs, and the redox chemistry of selenomethionine and some other metabolites have been previously reported. We now report the first synthesis and characterization of Se-adenosylselenohomocysteine selenoxide (SeAHO) prepared via hydrogen peroxide oxidation of Se-adenosylselenohomocysteine. The selenoxide SeAHO, in contrast to its corresponding sulfoxide S-adenosylhomocysteine (SAHO), can form hydrate, has an electrostatic interaction between the α-amino acid moiety and the highly polar selenoxide functional group, and readily oxidizes glutathione (GSH) and cysteine thiols.

Transformation of adenosine into N3,3' and N3,5' cycloadenosines via the reactions with sulfuryl chloride and thionyl chloride

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Potent SARS-CoV-2 mRNA Cap Methyltransferase Inhibitors by Bioisosteric Replacement of Methionine in SAM Cosubstrate

Viral mRNA cap methyltransferases (MTases) are emerging targets for the development of broad-spectrum antiviral agents. In this work, we designed potential SARS-CoV-2 MTase Nsp14 and Nsp16 inhibitors by using bioisosteric substitution of the sulfonium and amino acid substructures of the cosubstrate S-adenosylmethionine (SAM), which serves as the methyl donor in the enzymatic reaction. The synthetically accessible target structures were prioritized using molecular docking. Testing of the inhibitory activity of the synthesized compounds showed nanomolar to submicromolar IC50 values for five compounds. To evaluate selectivity, enzymatic inhibition of the human glycine N-methyltransferase involved in cellular SAM/SAH ratio regulation was also determined, which indicated that the discovered compounds are nonselective inhibitors of the studied MTases with slight selectivity for Nsp16. No cytotoxic effects were observed; however, this is most likely a result of the poor cell permeability of all evaluated compounds.

5'-Deoxidation-5'-isopropyl-substituted-amino nucleoside compound and preparing method and application thereof

The invention discloses a 5'-deoxidation-5'-isopropyl-substituted-amino nucleoside compound shown in a formula 7, a preparing method of the compound shown in the formula 7 and application of the compound shown in the formula 7 to preparing a 5'-deoxidation-5'-polysubstitution amino nucleoside compound 1 as a midbody. The formula is defined in the description.

Purine compound containing bicyclic group, and preparation method thereof

The invention provides a purine compound containing a bicyclic group which is shown as a formula (I) and a formula (II) and a pharmaceutically acceptable salt, and a preparation method thereof. The compound is an inhibitor of histone methyltransferase DOT1L, and can be used for treating diseases caused by the abnormity of enzyme activity, such as tumor.