39824-26-5

Basic information

• Product Name: 6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine
• Synonyms: 6-CHLORO-9-BETA-D-(2,3-ISOPROPYLIDENE)RIBOFURANOSYLPURINE;6-CHLORO-9-[2,3-O-(ISOPROPYLIDENE)-BETA-D-RIBOFURONOSYL]-9H-PURINE;6-CHLOROPURINE-9-(2,3-ISOPROPYLIDENE-B-D-RIBOFURANOSIDE);6-CHLOROPURINE-9-(2,3-ISOPROPYLIDENE-BETA-D-RIBOFURANOSIDE);6-Chloropurine-9-(2,3-isopropylidene)-b-d-ribfuraniside;6-CHLORO-9-[2,3-O-(ISOPROPYLIDENE)-β-D-RIBOFURONOSYL]-9H-PURINE;6-Chloro-9-b-D-(2,3-isopropylidene)ribofuranosylpurine;6-CHLORO-9-[2.3-0-(ISOPROPYLIDENE)-BETA-D-RIBOFURONOSYL]-9H-PURINE
• CAS NO: 39824-26-5
• Molecular Formula: C₁₃H₁₅ClN₄O₄
• Molecular Weight: 326.74
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 39824-26-5.mol
• Article Data: 37

Chemical Properties

• Melting Point: 156-159°C
• Boiling Point: 527.786 °C at 760 mmHg
• Flash Point: 272.996 °C
• Appearance: pale yellow solid
• Density: 1.79 g/cm³
• Vapor Pressure: 5.73E-12mmHg at 25°C
• Refractive Index: 1.76
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Diethyl Ether (Slightly), Eth
• PKA: 14.14±0.10(Predicted)
• CAS DataBase Reference: 6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine(39824-26-5)
• EPA Substance Registry System: 6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine(39824-26-5)

Safety Data

• Hazardous Substances Data: 39824-26-5(Hazardous Substances Data)

Usage

Description

6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine, also known as 6-Chloropurine-9-(2,3-isopropylidene-β-D-ribofuranoside) with the CAS number 39824-26-5, is a pale yellow solid compound that is primarily used in organic synthesis. It is a derivative of purine, a key component in the structure of nucleic acids and ATP, and features a chloro group at the 6th position and an isopropylidene ribofuranosyl group at the 9th position.

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 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 2140-11-6 2',3'-O-isopropylideneinosine 
• 58-61-7 adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 

Downstream Products

• 5843-59-4 6-chloropurine riboside 5'-monophosphate 
• 86231-92-7 [6-Chloro-9-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-8-yl]-diphenyl-methanol 
• 86231-89-2 [6-Chloro-9-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-8-yl]-phenyl-methanol 
• 120355-42-2 (3AS,4S,6R,6AR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 
• 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 
• 249757-27-5 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)purine 
• 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 
• 249757-30-0 6-chloro-8-iodo-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)purine 
• 249757-31-1 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-phenylpurine 
• 249757-28-6 6-chloro-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 
• 249757-38-8 6-chloro-2-formyl-9-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)-8-(triisopropylsilyl)purine 

Relevant articles and documents

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.

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.

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.

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.