3181-38-2

Basic information

• Product Name: 2',3',5'-TRIACETYLINOSINE
• Synonyms: INOSINE 2',3',5'-TRIACETATE;ACETICACID3,4-DIACETOXY-5-(6-HO-PURIN-9-YL)-TETR;2,3,5-TRIACETYLINOS;2',3',5'-Tri-O-acetyl-D-inosine;2,3,5-TRIACETYLINOSINE CRYSTALLINE;(2R,3S,4R,5R)-2-(ACETOXYMETHYL)-5-(6-OXO-1H-PURIN-9(6H)-YL)TETRAHYDROFURAN-3,4-DIYL DIACETATE;2'',3'',5''-TRI-O-ACETYL-INOSIN;2'-O,3'-O,5'-O-Triacetyl-6-hydroxy-6-deaminoadenosine
• CAS NO: 3181-38-2
• Molecular Formula: C₁₆H₁₈N₄O₈
• Molecular Weight: 394.34
• EINECS: 221-669-7
• Product Categories: Pharmaceutical Raw Materials;Bases & Related Reagents;Nucleotides
• Mol File: 3181-38-2.mol
• Article Data: 33

Chemical Properties

• Melting Point: 234-236°C
• Boiling Point: 620.7 °C at 760 mmHg
• Flash Point: 329.2 °C
• Appearance: White crystalline solid
• Density: 1.63 g/cm³
• Vapor Pressure: 1.12E-23mmHg at 25°C
• Refractive Index: 1.727
• Storage Temp.: −20°C
• Solubility: Methanol (Sparingly), Water (Sparingly)
• PKA: 2.96±0.20(Predicted)
• Stability: Freezer
• CAS DataBase Reference: 2',3',5'-TRIACETYLINOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',5'-TRIACETYLINOSINE(3181-38-2)
• EPA Substance Registry System: 2',3',5'-TRIACETYLINOSINE(3181-38-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 3181-38-2(Hazardous Substances Data)

Usage

Description

2',3',5'-Tri-O-acetylinosine has been shown to inhibit the growth of cancer cells, and is also an efficient method for bond cleavage and radiation protection. 2',3',5'-Tri-O-acetylinosine has been shown to bind to pyridinium ions, and it has been used in the synthesis of tetrapeptides with hydroxyl groups or alkylation.

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 3181-38-2 differently. You can refer to the following data:
1. 2',3',5'-Tri-O-acetylinosine is an intermediate used for the synthesis of 6-substituted purine ribosides
2. An intermediate used for the synthesis of 6-substituted purine ribosides.

InChI:InChI=1/C16H18N4O8/c1-6(21)10(24)11-15(26,7(2)22)16(27,8(3)23)14(28-11)20-5-19-9-12(20)17-4-18-13(9)25/h4-5,10-11,14,24,26-27H,1-3H3,(H,17,18,25)/t10?,11-,14-,15-,16+/m1/s1

Upstream product

• 13035-61-5 1,2,3,5-tetraacetylribose 
• 123-56-8 Succinimide 
• 1441063-52-0 2′,3′,5′-tri-O-acetyl-1-[(E)-2-(methoxycarbonyl)vinyl]inosine 
• 112-55-0 1-dodecylthiol 
• 2466-76-4 N-Acetylimidazole 
• 58-63-9 Inosine 
• 7387-57-7 triacetyladenosine 
• 108-24-7 acetic anhydride 
• 58-63-9 inosine 
• 127218-16-0 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{2-bromo-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester 
• 127211-14-7 2-Bromo-6-[2-(4-nitro-phenyl)-ethoxy]-9-trimethylsilanyl-9H-purine 
• 127244-78-4 2-bromo-6-(4-nitrophenylethoxy)purine 
• 87781-93-9 2-bromo-1,9-dihydro-6H-purin-6-one 
• 863033-41-4 2',3',5'-tri-O-acetyl-1-(2,4-dinitrobenzenesulfonyl)inosine 

Downstream Products

• 33763-06-3 7-methylinosine 
• 2140-73-0 1-methylinosine 
• 5746-29-2 6-methoxypurine riboside 
• 106990-21-0 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxylic acid-(toluene-4-sulfonylamide) 
• 99824-67-6 2',3',5'-tri-O-acetyl-6-O-[(2,4,6-triisopropylphenyl)sulfonyl]inosine 
• 61444-45-9 2',3',5'-tri-O-acetyl-β-xanthosine 
• 659746-56-2 2',3',5'-tri-O-acetyl-1-[(benzyloxy)methyl]inosine 
• 51549-18-9 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(benzylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 70230-70-5 N⁶,N⁶-dimethyladenosine tribenzoate 
• 70230-67-0 2',3',5'-tri-O-benzyl-N,N,3-trimethyladenosine iodide 
• 70230-71-6 2',3',5'-tri-O-benzoyl-N,N,3-trimethyladenosine iodide 
• 70230-68-1 5-(Methylamino)-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 70230-66-9 2',3',5'-tri-O-benzyl-N,N-dimethyladenosine 
• 4542-23-8 N-<9-(β-ribofuranosyl)-9H-purin-6-yl>-L-aspartic acid 

Relevant articles and documents

Synthesis of isotopically labelled versions of adenosine agonist GR79236

Versions of adenosine receptor agonist GR79236, labelled either with carbon-14 at C-8 of the purine ring or with tritium in the cyclopentyl ring, were prepared in overall yields of 64% and 25% respectively. A mass labelled [M + 4] version containing carbon-13, nitrogen-15, and deuterium was also prepared in 3% yield.

SAICAR Synthesis method

A method of synthesizing SAICAR of the present invention is carried out at 5 - amino -1 - ((). 2R. 3R. 4S. 5R-3, 4 -dihydroxy -5 - (hydroxymethyl) tetrahydrofuran -2 -yl) -1H- Imidazol -4 - formamide is the starting material and is sequentially subjected to 5 - amino -1 - ((). 3aR. 4R. 6R. 6aR) -6 - (Hydroxymethyl) -2, 2 -dimethyltetrahydrofuran [3,4 -]d] [1, 3] Diox -4 - group) -1H-imidazole -4 -carboxamide. 5 - Amino -1 - (()3aR. 4R. 6R. 6aR) -6 - (Hydroxymethyl) -2, 2 -dimethyltetrahydrofuran [3,4 -]d] [1, 3] Diox -4 - group) -1H- Imidazole -4 - carboxylic acid, dibenzyl (5 - amino -1 -) (()3aR. 4R. 6R. 6aR) -6 - (Hydroxymethyl) -2, 2 -dimethyltetrahydrofuran [3,4 -]d] [1, 3] Diox -4 - group) -1H- Imidazol -4 - carbonyl) . LOf - aspartic acid and the like to obtain a finished product purity of up to 99.6%, impurities 0.4%, diastereomeric excess (de) values 97.3% and a yield 16.9%.

Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water

A convenient selective synthesis of 2′,3′-di-O-acetyl-nucleotide-5′-phosphates, 2′,3′-di-O-acetyl-nucleotide-5′-triphosphates and 2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their incorporation into protometabolism.

The isoprenoid derivative N6-benzyladenosine CM223 exerts antitumor effects in glioma patient-derived primary cells through the mevalonate pathway

Background and Purpose: N6-Isopentenyladenosine (i6A) is a modified nucleoside exerting in vitro and in vivo antiproliferative effects. We previously demonstrated that the actions of i6A correlate with the expression and activity of farnesyl pyrophosphate synthase (FPPS), a key enzyme involved in the mevalonate (MVA) pathway, which is aberrant in brain cancer. To develop new anti-glioma strategies, we tested related compounds exhibiting greater activity than i6A. Experimental Approach: We designed and synthesized i6A derivatives characterized by the introduction of diverse chemical moieties in the N6 position of adenosine and tested for their efficacy in U87 cells and in primary glioma cultures, derived from patients. NMR-based structural analysis, molecular docking calculations and siRNA mediated knockdown were used to clarify the molecular basis of their action, targeting FPPS protein. Key Results: CM223, the i6A derivative including a benzyl moiety in N6 position of adenine, showed marked activity in selectively targeting glioma cells, but not normal human astrocytes. This was due to induction of intrinsic pathways of apoptosis and inhibition of proliferation, along with blockade of FPPS-dependent protein prenylation, which counteracted oncogenic signalling mediated by EGF receptors. Conclusion and Implications: The biological effects together with structural data on interaction of CM223 with FPPS, provided additional evidence for the correlation of the i6A/CM223 antitumor activity with FPPS modulation. Because the MVA pathway is an important promising target, CM223 and its derivatives should be considered interesting active molecules in antiglioma research.