5987-73-5

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside is used as a therapeutic agent for targeting rho-GTPase cell proteins, which play a crucial role in various cellular processes. Its inhibitory activity makes it a promising candidate for the development of drugs aimed at treating conditions related to the dysregulation of these proteins.
Used in Research and Development:
In the field of research, 2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside serves as a valuable tool for studying the role of rho-GTPase cell proteins in cellular signaling pathways. Its ability to inhibit these proteins can help researchers gain a deeper understanding of their functions and potential therapeutic applications.
Used in Drug Design and Development:
The inhibitory activity of 2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside on rho-GTPase cell proteins also makes it a valuable compound in the design and development of new drugs. Its unique structure can be used as a starting point for the development of more potent and selective inhibitors, potentially leading to the creation of novel therapeutic agents for a range of diseases.

InChI:InChI=1/C16H17ClN4O7/c1-7(22)25-4-10-12(26-8(2)23)13(27-9(3)24)16(28-10)21-6-20-11-14(17)18-5-19-15(11)21/h5-6,10,12-13,16H,4H2,1-3H3

Upstream product

• 32865-86-4 6-chloro-9-trimethylsilylpurine 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 87-42-3 6-chloropurine 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 87-42-3 6-chloro-7H-purine 
• 7013-16-3 9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one 
• 15830-52-1 (2R,3R,4S,5R)-2-(acetoxymethyl)-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 10517-16-5 9β-D-arabinofuranosylhypoxanthyne 
• 28069-16-1 Acetic acid (2R,3R,4S,5R)-4-acetoxy-5-acetoxymethyl-2-(6-hydroxy-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 63248-71-5 C₁₆H₁₈N₄O₈ 
• 5536-17-4 arabinosyl adenine 
• 63248-71-5 2',3',5'-tri-O-acetyl-β-arahypoxanthine 
• 58-63-9 inosine 
• 108-24-7 acetic anhydride 

Downstream Products

• 31199-61-8 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(dimethylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 15981-63-2 2',3',5'-tri-O-acetylnebularine 
• 2004-06-0 6-Chloropurine riboside 
• 132089-80-6 6-(4-chlorophenylsulfanyl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 
• 83026-93-1 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-phenyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 279670-58-5 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(4-methoxyphenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 352025-57-1 6-{4-[(Tetrahydropyran-2-yl)oxy]phenyl}-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 2620-62-4 N,N-dimethyladenosine 
• 30747-21-8 N⁶-benzoyl-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)adenine 

Relevant academic research and scientific papers

C6 substitution of inosine using hexamethylphosphorous triamide in conjunction with carbon tetrahalide or N-halosuccinimide

Herein we report the facile conversion of 2',3',5'-tri-O- acetylinosine to three different nucleoside analogs via reaction of hexamethylphosphorous triamide and an organic halide. Acetyl-protected 6-bromopurine riboside, 6- chloropurine riboside and N6,N6-dimethyladenosine can each be prepared in good yield from 2',3',5'-tri-O-acetylinosine, HMPT and halide. The major product of the reaction is determined by the identity of the halide used and the reaction temperature. (C) 2000 Elsevier Science Ltd.

Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA

TEMPO spin labels protected with 2-nitrobenzyloxymethyl groups were attached to the amino residues of three different nucleo-sides: deoxycytidine, deoxyadenosine, and adenosine. The corresponding phosphoramidites could be incorporated by unmodified standa

Highly efficient chemical phosphorylation of 6-(4-phenylpiperazine-1-yl)-9-(β-D-ribofuranosyl)-9H-purine

Antimetabolites, which are metabolic antagonists used in the treatment of cancer and viral diseases by replacing metabolites, inhibit the action of metabolic enzymes and disrupt the pathways of synthesis of structural units necessary for the formation of

Crystal form, preparation method and purpose of triacetyl-3-hydroxyphenyl adenosine

The invention relates to a crystal form, a preparation method and a purpose of hyperlipemia-treating medicine of triacetyl-3-hydroxyphenyl adenosine. The crystal form of the triacetyl-3-hydroxyphenyl adenosine comprises a type I crystal and a type II crystal of 2',3',5'-tri-O-acetyl-N6-(3-hydroxyphenyl) adenosine with a blood-lipid regulating effect, wherein the type I crystal has an X-ray powder diffraction pattern as shown in Figure 1, and the type II crystal has an X-ray powder diffraction pattern as shown in Figure 4.

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.

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 °C and were applied in the C?H arylation of unactivated arenes using either rhodium or ruthenium catalysts. A broad range of heterocyclic systems of high interest for synthetic and medicinal chemistry was accessed in high yields. The developed C?H functionalization could not be achieved using reported reagents or methods, highlighting the unique reactivity of Indole- and Pyrrole-BX.

PROBE FOR IMAGING PARP-1 ACTIVITY

Provided are embodiments of a small molecule tracer for positron emission tomography (PET) imaging of the enzyme activity of PARP-1 that is responsible for DNA-damage sensing and critically involved in radiation therapy and some chemotherapy response mechanisms. These PARP-1 tracers are derivatives of nicotinamide adenine dinucleotide (NAD), which is the natural substrate for PARP-1. Provided are NAD derivatives that include a linker moiety to which may be attached a label moiety such as a PET detectable fluorine to generate a 6N-(triazo-PEG2-18F)-NAD. Especially advantageous for use in PET and MRI scanning detection systems is the attachment of a chelating agent that allows for the formation of a chelator-metal ion complex.

α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5′-Nucleotidase (CD73) Inhibitors

ecto-5′-Nucleotidase (eN, CD73) catalyzes the hydrolysis of extracellular AMP to adenosine. eN inhibitors have potential for use as cancer therapeutics. The eN inhibitor α,β-methylene-ADP (AOPCP, adenosine-5′-O-[(phosphonomethyl)phosphonic acid]) was used as a lead structure, and derivatives modified in various positions were prepared. Products were tested at rat recombinant eN. 6-(Ar)alkylamino substitution led to the largest improvement in potency. N6-Monosubstitution was superior to symmetrical N6,N6-disubstitution. The most potent inhibitors were N6-(4-chlorobenzyl)- (10l, PSB-12441, Ki 7.23 nM), N6-phenylethyl- (10h, PSB-12425, Ki 8.04 nM), and N6-benzyl-adenosine-5′-O-[(phosphonomethyl)phosphonic acid] (10g, PSB-12379, Ki 9.03 nM). Replacement of the 6-NH group in 10g by O (10q, PSB-12431) or S (10r, PSB-12553) yielded equally potent inhibitors (10q, 9.20 nM; 10r, 9.50 nM). Selected compounds investigated at the human enzyme did not show species differences; they displayed high selectivity versus other ecto-nucleotidases and ADP-activated P2Y receptors. Moreover, high metabolic stability was observed. These compounds represent the most potent eN inhibitors described to date.

Synthesis of nelarabine with pure β-anomer through late-stage C-H nitration/nitro-reduction

An efficient and pure β-anomer synthesis of the clinical drug nelarabine from the readily available vidarabine has been achieved for the first time. The C6 amino group of vidarabine was transformed to methoxy group by diazotization/chlorination followed by methoxylation using Na2CO3/MeOH system. The formation of C(2)-N bond was achieved via the highly selective C-H bond functionalization by reacting with 2,2,2-trifluoroacetic anhydride (TFAA) and tetrabutylammonium nitrate. The final product was obtained in total yield of 58.6% by 5 steps-synthesis from vidarabine after the reduction of nitro group to amino group. Moreover, the drug nelarabine could be obtained in 100 grams scale successfully and no chromatography was needed, which made this route more attractive for industrial application.

2-catalyzed directed N -Boc amidation of arenes "on water"

Rhodium(III) catalysis "on water" is effective for directed C-H amidation of arenes. The catalytic process is promoted by OH groups present on the hydrophobic water surface and is inefficient in all (most) common organic solvents investigated so far. In the presence of easily prepared tert-butyl 2,4-dinitrophenoxycarbamate, a new and stable nitrene source, the "on water" reaction can efficiently provide the desired N-Boc-aminated products with good functional group tolerance.