2620-62-4

Basic information

• Product Name: N6,N6-DIMETHYLADENOSINE
• Synonyms: N,N-Dimethyl-9-β-D-ribofuranosyl-9H-purine-6-amine;N6,N6-DIMETHYLADENOS;6-DiMethylaMino-9-(β-D-ribofuranosyl)purine;6-DIMETHYLAMINOPURINE-9-RIBOSIDE;N6,N6-DIMETHYLADENOSINE;6-(Dimethylamino)purine ribonucleoside;6-(Dimethylamino)purine riboside;6-Dimethyladenosine
• CAS NO: 2620-62-4
• Molecular Formula: C₁₂H₁₇N₅O₄
• Molecular Weight: 295.29
• EINECS: 220-057-7
• Product Categories: Bases & Related Reagents;Nucleotides;Pyridines, Pyrimidines, Purines and Pteredines;Nucleotides and Nucleosides;Nucleic acids
• Mol File: 2620-62-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 184-185°C
• Boiling Point: 607.3 °C at 760 mmHg
• Flash Point: 321.1 °C
• Appearance: White Powder
• Density: 1.71 g/cm³
• Vapor Pressure: 1.33E-15mmHg at 25°C
• Refractive Index: 1.757
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly, Heated), DMSO, Methanol (Sparingly), Water (Slightly, Son
• PKA: 13.11±0.70(Predicted)
• CAS DataBase Reference: N6,N6-DIMETHYLADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: N6,N6-DIMETHYLADENOSINE(2620-62-4)
• EPA Substance Registry System: N6,N6-DIMETHYLADENOSINE(2620-62-4)

Safety Data

• Hazardous Substances Data: 2620-62-4(Hazardous Substances Data)

Usage

Description

N6,N6-DIMETHYLADENOSINE, also known as 6-Dimethylaminopurine-9-riboside (CAS# 2620-62-4), is a methyladenosine compound characterized by the presence of two methyl groups attached to the N6 position of the adenine nucleobase. It is a white powder and is primarily used in organic synthesis.

Uses

1. Used in Organic Synthesis:
N6,N6-DIMETHYLADENOSINE is used as a key compound in organic synthesis for the development of various chemical products and materials. Its unique structure and properties make it a valuable building block in the synthesis of complex organic molecules.
2. Used in Pharmaceutical Industry:
N6,N6-DIMETHYLADENOSINE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties allow it to be a versatile component in the development of new drugs and therapeutic agents.
3. Used in Research and Development:
N6,N6-DIMETHYLADENOSINE is used as a research tool in the study of adenosine-related biological processes and pathways. Its unique structure provides insights into the role of methylation in the regulation of gene expression and cellular function.
4. Used in Chemical Analysis:
N6,N6-DIMETHYLADENOSINE is used as a reference compound in various analytical techniques, such as chromatography and mass spectrometry, to help identify and quantify similar compounds in complex mixtures.

InChI:InChI=1/C12H17N5O4/c1-16(2)10-7-11(14-4-13-10)17(5-15-7)12-9(20)8(19)6(3-18)21-12/h4-6,8-9,12,18-20H,3H2,1-2H3/t6-,8-,9-,12-/m1/s1

Upstream product

• 31199-61-8 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(dimethylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 124-40-3 dimethyl amine 
• 3510-73-4 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 52940-78-0 N⁶,N⁶,S-trimethyl-2-thio-isoguanosine 
• 506-59-2 N,N-dimethylammonium chloride 
• 2004-06-0 6-Chloropurine riboside 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 17287-03-5 trimethylsulphonium hydroxide 
• 58-61-7 adenosine 
• 158782-62-8 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-(1,2,4-triazol-4-yl)purine 
• 163632-54-0 9-(β-D-ribofuranosyl)-6-(1,2,4-triazol-4-yl)purine 
• 105499-44-3 2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride 
• 5991-01-5 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride 
• 938-55-6 6-(dimethylamino)purine 

Downstream Products

• 110422-67-8 O^2'_,O3'-((R)-benzylidene)-N⁶,N⁶-dimethyl-adenosine 
• 19083-21-7 2',3'-O-isopropylidene-N₆,N₆'-dimethyladenosine 
• 128636-80-6 3',5'-Di-O-trityl-N⁶,N⁶-dimethyladenosine 
• 128612-08-8 2',5'-Di-O-trityl-N⁶,N⁶-dimethyladenosine 
• 19083-21-7 2',3'-O-Isopropylidene-N⁶,N⁶-dimethyladenosine 
• 74397-36-7 N⁶,N⁶-Dimethyl-5'-O-trityladenosine 
• 70230-66-9 2',3',5'-tri-O-benzyl-N,N-dimethyladenosine 
• 70230-70-5 N⁶,N⁶-dimethyladenosine tribenzoate 
• 57881-34-2 5'-O-monomethoxytrityl-N₆,N₆-dimethyladenosine 
• 661471-89-2 5'-O-(4,4'-dimethoxytrityl)-N⁶,N⁶-dimethyladenosine 
• 661471-90-5 5'-O-(4,4'-dimethoxytrityl)-N⁶,N⁶-dimethyl-2'-O-[[(triisopropylsilyl)oxy]methyl]adenosine 
• 219648-29-0 5'-O-monomethoxytrityl-2'-O-t-butyldimethylsilyl-N₆,N₆-dimethyladenosine 
• 101007-89-0 Phosphoric acid (2R,3R,4R,5R)-2-[(2-chloro-phenoxy)-methoxy-phosphoryloxymethyl]-5-(6-dimethylamino-purin-9-yl)-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester methyl ester 
• 101007-85-6 C₃₅H₄₃ClN₇O₁₅P 

Relevant articles and documents

Adenosine N1-oxide analogues as inhibitors of orthopox virus replication

Several new types of adenosine N1-oxide (ANO) derivatives including N1-alkoxy and N6-alkyl as well as the analogues with a trihydroxycyclopentane ring in place of the ribose residue were synthesized and their antiviral properties were evaluated in Vero and LLC-MK2 cell cultures infected with vaccinia, mousepox, monkeypox, cowpox, and different isolates of smallpox viruses. The antiviral activity of ANO and its derivatives significantly depended on the virus type and cell cultures. Mousepox and monkeypox viruses were the most sensitive to these compounds, while vaccinia and cowpox viruses were inhibited at the concentrations 1-1.5 orders of magnitude higher. The toxicity of the synthesized compounds was much lower than that of ANO. Modifications of the ANO N6-position did not offer any advantages over the parent compound. The synthesized N1-oxide derivatives of noraristeromycin retained the activity comparable with noraristeromycin and displayed a decreased toxicity. No direct correlation between antiviral activity and stability of the compounds was found.

6-Iodopurine as a Versatile Building Block for RNA Purine Architecture Modifications

Natural modified bases in RNA were found to be indispensable for basic biological processes. In addition, artificial RNA modifications have been a versatile toolbox for the study of RNA interference, structure, and dynamics. Here, we present a chemical method for the facile synthesis of RNA containing C6-modified purine. 6-Iodopurine, as a postsynthetic building block with high reactivity, was used for metal-free construction of C-N, C-O, and C-S bonds under mild conditions and C-C bond formation by Suzuki-Miyaura cross-coupling. Our strategy provides a convenient approach for the synthesis of various RNA modifications, especially for oligonucleotides containing specific structures.

Nucleotide Analog ARL67156 as a Lead Structure for the Development of CD39 and Dual CD39/CD73 Ectonucleotidase Inhibitors

Nucleoside triphosphate diphosphohydrolase1 (NTPDase1, CD39) inhibitors have potential as novel drugs for the (immuno)therapy of cancer. They increase the extracellular concentration of immunostimulatory ATP and reduce the formation of AMP, which can be further hydrolyzed by ecto-5’-nucleotidase (CD73) to immunosuppressive, cancer-promoting adenosine. In the present study, we synthesized analogs and derivatives of the standard CD39 inhibitor ARL67156, a nucleotide analog which displays a competitive mechanism of inhibition. Structure-activity relationships were analyzed at the human enzyme with respect to substituents in the N6- and C8-position of the adenine core, and modifications of the triphosph(on)ate chain. Capillary electrophoresis coupled to laser-induced fluorescence detection employing a fluorescent-labeled ATP derivative was employed to determine the compounds’ potency. Selected inhibitors were additionally evaluated in an orthogonal, malachite green assay versus the natural substrate ATP. The most potent CD39 inhibitors of the present series were ARL67156 and its derivatives 31 and 33 with Ki values of around 1 μM. Selectivity studies showed that all three nucleotide analogs additionally blocked CD73 acting as dual-target inhibitors. Docking studies provided plausible binding modes to both targets. The present study provides a full characterization of the frequently applied CD39 inhibitor ARL67156, presents structure-activity relationships, and provides a basis for future optimization towards selective CD39 and dual CD39/CD73 inhibitors.

OLIGONUCLEOTIDE

The present invention provides an oligonucleotide having improved affinity for AGO2, and the like. The oligonucleotide has a nucleotide residue or a nucleoside residue represented by formula (I) {wherein X1 is an oxygen atom or the like, R1 is formula (IIA) (wherein R5A is halogen or the like, and R6A is a hydrogen atom or the like) or formula (IVA) (wherein Y3A is a nitrogen atom or the like, and Y4A is CH or the like), or the like, R2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R3 is a hydrogen atom or the like} at the 5′ end thereof, and the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3.