39824-26-5

Usage

Uses

Used in Organic Synthesis:
6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a valuable building block for the creation of complex molecules, particularly in the pharmaceutical and chemical industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine is used as a key component in the development of new drugs. Its purine-based structure makes it a potential candidate for the treatment of various diseases, including cancer and viral infections, by targeting specific enzymes or receptors involved in these conditions.
Used in Chemical Research:
6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine is also utilized in chemical research to study the properties and reactivity of purine derivatives. This can lead to a better understanding of the mechanisms of action of various biologically active molecules and the development of more effective drugs and therapies.

InChI:InChI=1/C13H15ClN4O4/c1-13(2)21-8-6(3-19)20-12(9(8)22-13)18-5-17-7-10(14)15-4-16-11(7)18/h4-6,8-9,12,19H,3H2,1-2H3

Upstream product

• 2004-06-0 6-Chloropurine riboside 
• 67-64-1 acetone 
• 77-76-9 2,2-dimethoxy-propane 
• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 
• 2140-11-6 2',3'-O-isopropylideneinosine 
• 362-75-4 2',3'-isopropylidene adenosine 
• 58-61-7 adenosine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 

Downstream Products

• 5843-59-4 6-chloropurine riboside 5'-monophosphate 
• 176747-07-2 Phosphoric acid (3aR,4R,6R,6aR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 2-hydroxy-phenyl ester 
• 3249-96-5 ((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl benzoate 
• 53-83-8 6-thioinosine 5'-monophosphate 
• 213554-28-0 ((3aR,4R,6R,6aR)-2,2-dimethyl-6-(6-(phenylamino)-9H-purin-9-yl)tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 19083-21-7 2',3'-O-isopropylidene-N₆,N₆'-dimethyladenosine 
• 1134156-49-2 4-((((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)methyl)benzonitrile 
• 1325711-87-2 C₂₂H₂₆N₆O₅ 
• 1325711-74-7 3,4-dihydroxy-5-[6-(4-hydroxybenzylamino)purin-9-yl]tetrahydrofuran-2-carboxylic acid ethylamide 
• 1325711-77-0 C₂₁H₂₂N₆O₄ 
• 1325711-88-3 C₂₁H₂₃N₉O₄ 
• 1325711-75-8 2-[6-(4-methoxybenzylamino)purin-9-yl]-5-(1H-tetrazol-5-yl)tetrahydrofuran-3,4-diol 

Relevant academic research and scientific papers

O6-(4-nitrophenyl)inosine and -guanosine as chromogenic substrates for adenosine deaminase

O6-(4-Nitrophenyl)inosine (1a), O6-(4-nitrophenyl)guanosine (1c) and O6-(4-methylumbelliferonyl)inosine (2) were obtained by reaction of 6-chloro-9-(β-D-ribofuranosyl)purine (3a) or 2-amino-6-chloro-9-(β-D-ribofuranosyl)purine (3c) with sodium salts of 4-nitrophenol or 4-methylumbelliferone in N,N-dimethylformamide. Similarly, 6-chloro-9-(β-D-2,3-isopropylideneribofuranosyl)purine (3b) was transformed to 2',3'-O-isopropylidene-O6-(4-nitrophenyl)inosine (1b). Deprotection of 1b with CF3COOH gave compound 1a and O6-(4-nitrophenyl)hypoxanthine (4). Compounds 1a and 1c are substrates for adenosine deaminase releasing 4-nitrophenol which is readily detected visually or spectrophotometrically. Rate and extent of hydrolysis of 1a are significantly increased in the presence of purine nucleoside phosphorylase but xanthine oxidase has no influence. A potential fluorogenic analogue 2 is not a substrate for adenosine deaminase.

Development of fluorescence polarization-based competition assay for nicotinamide N-methyltransferase

Methylation-mediated pathways play important roles in the progression of various diseases. Thus, targeting methyltransferases has proven to be a promising strategy for developing novel therapies. Nicotinamide N-methyltransferase (NNMT) is a major metaboli

Approaches to Isozyme-Specific Inhibitors. 17. Attachment of a Selectivity-Inducing Substituent to a Multisubstrate Adduct. Implications for Facilitated Design of Potent, Isozyme-Selective Inhibitors

The synthesis is described of a methyl-C5' adduct of L-methionine and β,γ-imido-ATP bearing a 6-S-n-Bu group in place of the 6-NH2 group of the parent adduct.The latter is a potent multisubstrate inhibitor in a model system consisting of the M-2 and M-T isozymes of rat methionine adenosyltransferase.When attached to ATP, the 6-S-n-Bu group induces selectivity for M-T inhibition by elevating affinity for the ATP site of M-T but not of M-2.In the above adduct it exerted a similar effect, expressed by selectivity and increased inhibitory potency toward M-T.This affords a second illustration of the ability of this approach to generate, relatively readily, a potent inhibitor with moderate isozyme selectivity.An overview is given of extensive evidence from the present series of studies that moderate (ca. 10-fold) isozyme selectivity is often exhibited by substrate derivatives bearing a single short substituent at a variety of atoms.This, together with features of another feasible approach to isozyme-selective inhibitor design, suggests an approach that has potential to facilitate the design of potent inhibitors that are both isozyme-selective and selective for a given metabolic conversion.It comprises (1) evaluation of the above type of substrate derivatives as inhibitors of a chemotherapeutically significant set of isozymes (target and nontarget), (2) attempted derivation of a potent multisubstrate adduct inhibitor of the isozymes, (3) attachment to such an adduct of one or more selectivity-inducing substituents revealed in the first step, and, if desired, (4) systematic modification of substituents with a view to obtaining enhanced potency and/or isozyme-selectivity.

Synthesis and evaluation of adenosine derivatives as A1, A2A, A2B and A3 adenosine receptor ligands containing boron clusters as phenyl isosteres and selective A3 agonists

A series of adenosine and 2′-deoxyadenosine pairs modified with a 1,12-dicarba-closo-dodecaborane cluster or alternatively with a phenyl group at the same position was synthesized, and their affinity was determined at A1, A2A, A2B and A3 adenosine receptors (ARs). While AR affinity differences were noted, a general tendency to preferentially bind A3 AR over other ARs was observed for most tested ligands. In particular, 5′-ethylcarbamoyl-N6-(3-phenylpropyl)adenosine (18), N6-(3-phenylpropyl)-2-chloroadenosine (24) and N6-(3-phenylpropyl)adenosine (40) showed nanomolar A3 affinity (Ki 4.5, 6.4 and 7.5 nM, respectively). Among the boron cluster-containing compounds, the highest A3 affinity (Ki 206 nM) was for adenosine derivative 41 modified at C2. In the matched molecular pairs, analogs bearing boron clusters were found to show lower binding affinity for adenosine receptors than the corresponding phenyl analogs. Nevertheless, interestingly, several boron cluster modified adenosine ligands showed significantly higher A3 receptor selectivity than the corresponding phenyl analogs: 7 vs. 8, 15 vs. 16, 17 vs. 18.

COMPOUND USED AS AUTOPHAGY REGULATOR, AND PREPARATION METHOD THEREFOR AND USES THEREOF

It is related to compounds used as autophagy modulators and a method for preparing and using the same, specifically providing a compound of general formula (I), or pharmaceutically acceptable salts thereof, which is a type of autophagy modulators, particularly mammalian ATG8 homologues modulators.

Synthesis and biological evaluation of lipophilic nucleoside analogues as inhibitors of aminoacyl-tRNA synthetases

Emerging antibiotic resistance in pathogenic bacteria and reduction of compounds in the existing antibiotics discovery pipeline is the most critical concern for healthcare professionals. A potential solution aims to explore new or existing targets/compoun

COMPOUND WITH ANALGESIC EFFECT FOR USE IN PREVENTION AND TREATMENT OF PAIN

Compounds for use in prevention and/or treatment of pain are disclosed. The compounds are derived by conjugation of N6-(4-hydroxybenzyl)adenosine and analogous compounds with amino acids or peptides. In one embodiment of the invention, the compound is 5'-glycylcarbonyl-N6-(4-hydroxybenzyl)adenosine (I-a1). In another embodiment of the invention, the compound is 5'-deoxy-5'-(N'- glycylureido)-N6-(4-hydroxybenzyl)adenosine (I-d1). Also disclosed are methods of making and using the same.

Semisynthesis, characterization and evaluation of new adenosine derivatives as antiproliferative agents

We describe the semisynthesis and biological effects of adenosine derivatives, which were anticipated to function as agonists for the A3 receptor. Molecular docking was used to select candidate compounds. Fifteen nucleoside derivatives were obtained through nucleophilic substitutions of the N6-position of the nucleoside precursor 6-chloropurine riboside by amines of different origin. All compounds were purified by column chromatography and further characterized by spectroscopic and spectrometric techniques, showing moderate yield. These molecules were then evaluated for their antiproliferative activity in human gastric cancer cells expressing the A3 receptor. We found that the compounds obtained have antiproliferative activity and that new structural modifications can enhance their biological activity. The ADME (Absorption, Distribution, Metabolism and Excretion) properties of the most active compounds were also evaluated theoretically.

Synthesis and evaluation of analogs of 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (MDL 73811, or AbeAdo) – An inhibitor of S-adenosylmethionine decarboxylase with antitrypanosomal activity

We describe our efforts to improve the pharmacokinetic properties of a mechanism-based suicide inhibitor of the polyamine biosynthetic enzyme S-adenosylmethionine decarboxylase (AdoMetDC), essential for the survival of the eukaryotic parasite Trypanosoma brucei responsible for Human African Trypanosomiasis (HAT). The lead compound, 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (1, also known as MDL 73811, or AbeAdo), has curative efficacy at a low dosage in a hemolymphatic model of HAT but displayed no demonstrable effect in a mouse model of the CNS stage of HAT due to poor blood–brain barrier permeation. Therefore, we prepared and evaluated an extensive set of analogs with modifications in the aminobutenyl side chain, the 5′-amine, the ribose, and the purine fragments. Although we gained valuable structure–activity insights from this comprehensive dataset, we did not gain traction on improving the prospects for CNS penetration while retaining the potent antiparasitic activity and metabolic stability of the lead compound 1.

ANALOGS OF ADENOSINE MONOPHOSPHATE (AMP) AS INHIBITORS OF UBIQUITIN-LIKE MODIFIER-ACTIVATING ENZYME ATG7

Disclosed are analogs of adenosine monophosphate (AMP) as inhibitors of ubiquitin-like modifier-activing enzyme ATG7. The AMP analogs may be formulated as pharmaceutical compositions for treating diseases or disorders that depend on ATG7 activity and/or autophagy such as cell proliferative diseases and disorders.