16754-80-6

Basic information

• Product Name: 6-Chloro-7-deazapurine-b-D-riboside
• Synonyms: 4-Chloro-7-(D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine;6-Chloro-7-deazapurine-b-D-riboside;6-Chloro-9-(D-ribofuranosyl)-7-deazapurine;6-Deamino-6-chlorotubercidin;NSC 101161;6-Chloro-7-deaza-9-(b-D-ribofuranosyl)purine;6-CHLORO-7-DEAZAPURINE-SS-D-RIBOSIDE;6-Chloro-7-deaza-9-(β-D-ribofuranosyl)purine
• CAS NO: 16754-80-6
• Molecular Formula: C₁₁H₁₂ClN₃O₄
• Molecular Weight: 285.686
• Product Categories: Bases & Related Reagents;Intermediates;Nucleotides;Carbohydrates & Derivatives
• Mol File: 16754-80-6.mol

Chemical Properties

• Melting Point: 160-162°C
• Boiling Point: 591.4°Cat760mmHg
• Flash Point: 311.5°C
• Appearance: /
• Density: 1.87g/cm³
• Vapor Pressure: 7.8E-15mmHg at 25°C
• Refractive Index: 1.786
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.39±0.70(Predicted)
• CAS DataBase Reference: 6-Chloro-7-deazapurine-b-D-riboside(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-7-deazapurine-b-D-riboside(16754-80-6)
• EPA Substance Registry System: 6-Chloro-7-deazapurine-b-D-riboside(16754-80-6)

Safety Data

• Hazardous Substances Data: 16754-80-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloro-7-deazapurine-b-D-riboside is used as an adenosine kinase inhibitor for its ability to inhibit the activity of adenosine kinase, an enzyme that plays a crucial role in the regulation of adenosine levels in the body. This inhibition can have potential therapeutic applications in various diseases and conditions, such as cancer, where adenosine signaling is known to promote tumor growth and immune evasion.
Additionally, due to its adenosine kinase inhibitory properties, 6-Chloro-7-deazapurine-b-D-riboside can be used in the development of novel drug delivery systems to enhance the efficacy and bioavailability of other therapeutic agents targeting adenosine-related pathways.

InChI:InChI=1/C11H12ClN3O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2

Upstream product

• 41028-66-4 1,5-anhydroribitol 
• 55726-00-6 (3R,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 1615680-91-5 6-chloro-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine 
• 217309-46-1 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 
• 29914-75-8 (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diyl dibenzoate 
• 1039752-77-6 4-chloro-7-[5-O-[(1,1-dimethylethyl)dimethysilyl]-2,3-O-(1-methylethylidene)-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 75921-20-9 5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose 
• 102690-94-8 2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride 
• 115479-39-5 4-chloro-7-<5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl>-7H-pyrrolo<2,3-d>pyrimidine 

Downstream Products

• 1039752-83-4 4-[(2-fluorobenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-85-6 4-[(2-bromobenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-84-5 4-[(2-chlorobenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-91-4 4-[(3-methylbenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-92-5 4-[(4-fluorobenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-94-7 4-[(4-bromobenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039753-01-9 4-[(4-tert-butylbenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-99-2 4-[(4-methylbenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-86-7 4-[(2-methylbenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-89-0 4-[(3-trifluoromethylbenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-88-9 4-[(3-nitrobenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039752-97-0 4-[(4-cyanobenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039753-07-5 4-[(3,4-dichlorobenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1039753-04-2 4-[(4-methoxybenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS

The present disclosure describes novel heterocyclic PRMT5 inhibitors and methods for preparing them. The pharmaceutical compositions comprising such PRMT5 inhibitors and methods of using them for treating cancer, infectious diseases, and other PRMT5 associated disorders are also described.

HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS

The present disclosure describes novel PRMT5 inhibitors and methods for preparing them. The pharmaceutical compositions comprising such PRMT5 inhibitors and methods of using them for treating cancer, infectious diseases, and other PRMT5 associated disorde

ADENOSINE ANALOG AND ITS USE IN REGULATING THE CIRCADIAN CLOCK

Provided are a kind of nucleoside analogue compounds, and compositions comprising these compounds and pentostatin, their use for modulating circadian rhythm, preferably, for shifting circadian phase, and methods for modulating circadian rhythm, preferably, for shifting circadian phase via these compounds or the compositions.

Glycosylation of Pyrrolo[2,3- d]pyrimidines with 1- O-Acetyl-2,3,5-tri- O-benzoyl-β- d -ribofuranose: Substituents and Protecting Groups Effecting the Synthesis of 7-Deazapurine Ribonucleosides

Glycosylation of nonfunctionalized 6-chloro-7-deazapurine with commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose (45%) followed by amination and deprotection gave tubercidin in only two steps. Similar conditions applied for the synthe

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism

Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.

Groove modification of siRNA duplexes to elucidate siRNA-protein interactions using 7-bromo-7-deazaadenosine and 3-bromo-3-deazaadenosine as chemical probes

Elucidation of dynamic interactions between RNA and proteins is essential for understanding the biological processes regulated by RNA, such as RNA interference (RNAi). In this study, the logical chemical probes, comprising 7-bromo-7-deazaadenosine (Br7C7A) and 3-bromo-3-deazaadenosine (Br3C3A), to investigate small interfering RNA (siRNA)-RNAi related protein interactions, were developed. The bromo substituents of Br7C7A and Br3C3A are expected to be located in the major and the minor grooves, respectively, and to act as a steric hindrance in each groove when these chemical probes are incorporated into siRNAs. A comprehensive investigation using siRNAs containing these chemical probes revealed that (i) Br3C3A(s) at the 5′-end of the passenger strand enhanced their RNAi activity, and (ii) the direction of RISC assembly is determined by the interaction between Argonaute2, which is the main component of RISC, and siRNA in the minor groove near the 5′-end of the passenger strand. Utilization of these chemical probes enables the investigation of the dynamic interactions between RNA and proteins.

5'-SUBSTITUTED NUCLEOSIDE ANALOGS

The present invention relates to novel 5-substituted nucleoside compounds, pharmaceutical compositions comprising the compounds, and methods of using the compounds to treat cancer, more particularly for the treatment of cancer, in particular glioblastomas, melanoma, sarcomas, gastric cancer, pancreatic cancer, cholangiocarcinoma, bladder cancer, breast cancer, non-small cell lung cancer, leukemias including acute myeloid leukemia, and lymphomas.

Structure-activity relationships of 7-deaza-6-benzylthioinosine analogues as ligands of Toxoplasma gondii adenosine kinase

Several 7-deaza-6-benzylthioinosine analogues with varied substituents on aromatic ring were synthesized and evaluated against Toxoplasma gondii adenosine kinase (EC.2.7.1.20). Structure-activity relationships indicated that the nitrogen atom at the 7-position does not appear to be a critical structural requirement. Molecular modeling reveals that the 7-deazapurine motif provided flexibility to the 6-benzylthio group as a result of the absence of H-bonding between N7 and Thr140. This flexibility allowed better fitting of the 6-benzylthio group into the hydrophobic pocket of the enzyme at the 6-position. In general, single substitutions at the para or meta position enhanced binding. On the other hand, single substitutions at the ortho position led to the loss of binding affinity. The most potent compounds, 7-deaza-p-cyano-6- benzylthioinosine (IC50 = 5.3 μM) and 7-deaza-p-methoxy-6- benzylthioinosine (IC50 = 4.6 μM), were evaluated in cell culture to delineate their selective toxicity.

A facile and improved synthesis of tubercidin and certain related pyrrolo[2,3-d]pyrimidine nucleosides by the stereospecific sodium salt glycosylation procedure [1]

A simple synthesis of tubercidin, 7-deazaguanosine and 2'-deoxy-7-deazaguanosine has been accomplished using the sodium salt glycosylation procedure. Reaction of the sodium salt of 4-chloro- and 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine, 3 and 4, respectively, with 1-chloro-2,3-O-isopropylidene,5-O-(t-butyl)dimethylsilyl-α-D-ribofur nose gave the corresponding protected nucleosides 6 and 7 with β-anomeric configuration. Deprotection of 6 provided 8, which on heating with methanolic ammonia gave tubercidin in excellent yield. Functional group transformation of 7, followed by deisopropylidenation gave 2-aminotubercidin and 2-amino-7-β-ribofuranosylpyrrolo[2,3-d]pyrimidine-4(3H)-thione. Treatment of 7 with 1N sodium methoxide followed by exposure to aqueous trifluoroacetic acid, and ether cleavage furnished 7-deazaguanosine. 2'-Deoxy-7-deazaguanosine and 2'-deoxy-7-deaza-6-thioguanosine were also prepared by using similar sequence of reactions employing 4 and 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose.