79999-39-6

Basic information

• Product Name: 2-CHLORO-6-AMINO-9-(2',3',5'-TRI-O-ACETYL-?-D-RIBOFURANOSYL)PURINE
• Synonyms: 2-Chloro-adenosine 2',3',5'-Triacetate;2',3',5'-Tri-O-Acetyl-2-chloroadenosine;2-CHLORO-6-AMINO-9-(2',3',5'-TRI-O-ACETYL-?-D-RIBOFURANOSYL)PURINE;6-amino-2-chloro-9-(2’,3’,5’-tri-O-acetyl--D-ribofuranosyl)purine
• CAS NO: 79999-39-6
• Molecular Formula: C₁₆H₁₈ClN₅O₇
• Molecular Weight: 427.79642
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 79999-39-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 67-75°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-CHLORO-6-AMINO-9-(2',3',5'-TRI-O-ACETYL-?-D-RIBOFURANOSYL)PURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-6-AMINO-9-(2',3',5'-TRI-O-ACETYL-?-D-RIBOFURANOSYL)PURINE(79999-39-6)
• EPA Substance Registry System: 2-CHLORO-6-AMINO-9-(2',3',5'-TRI-O-ACETYL-?-D-RIBOFURANOSYL)PURINE(79999-39-6)

Safety Data

• Hazardous Substances Data: 79999-39-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

2-Chloro-6-amino-9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)purine (cas# 79999-39-6) is a compound useful in organic synthesis.

Upstream product

• 65024-85-3 1-β-D-ribofuranosyl-1H-benzotriazole 
• 1839-18-5 2-chloroadenine 
• 108-24-7 acetic anhydride 
• 146-77-0 2-Chloroadenosine 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 3056-18-6 (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 118-00-3 G 
• 58-61-7 adenosine 
• 79999-37-4 2',3',5'-tri-O-acetyl-1-N-acetyloxyinosine 
• 5383-06-2 N¹-hydroxyinosine 
• 79999-38-5 2',3',5'-tri-O-acetyl-1-hydroxyinosine 

Downstream Products

• 4291-63-8 2-chloro-2'-deoxyadenosine 
• 146-77-0 2-Chloroadenosine 
• 1403611-81-3 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-amino-2-chloro-8-cyclohexyl-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 920974-75-0 (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-chloro-6-(cyclohexylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 
• 81102-46-7 2,6-diamino-8-bromo-9-(2'-O-tosyl-β-D-ribufuranosyl)-purine 
• 81102-44-5 9-(β-D-ribofuranosyl)-2,6-diamino-8-bromopurine 
• 4546-70-7 2-amino-2'-deoxyadenosine 
• 144348-08-3 (2R,3R,4S,5R)-2-(6-Amino-2-{N'-[1-cyclohexyl-meth-(Z)-ylidene]-hydrazino}-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 15763-11-8 2-hydrazinoadenosine 

Relevant articles and documents

Discovery of novel purine nucleoside derivatives as phosphodiesterase 2 (PDE2) inhibitors: Structure-based virtual screening, optimization and biological evaluation

Phosphodiesterase 2 (PDE2) has received much attention for the potential treatment of the central nervous system (CNS) disorders and pulmonary hypertension. Herein, we identified that clofarabine (4), an FDA-approved drug, displayed potential PDE2 inhibitory activity (IC50 = 3.12 ± 0.67 μM) by structure-based virtual screening and bioassay. Considering the potential therapeutic benefit of PDE2, a series of purine nucleoside derivatives based on the structure and binding mode of 4 were designed, synthesized and evaluated, which led to the discovery of the best compound 14e with a significant improvement of inhibitory potency (IC50 = 0.32 ± 0.04 μM). Further molecular docking and molecular dynamic (MD) simulations studies revealed that 5′-benzyl group of 14e could interact with the unique hydrophobic pocket of PDE2 by forming extra van der Waals interactions with hydrophobic residues such as Leu770, Thr768, Thr805 and Leu809, which might contribute to its enhancement of PDE2 inhibition. These potential compounds reported in this article and the valuable structure-activity relationships (SARs) might bring significant instruction for further development of potent PDE2 inhibitors.

Pd-catalysed amidation of 2,6-dihalopurine nucleosides. Replacement of iodine at 0 °c

Pd-catalysed reactions of 2-Cl, 2-Br and 2-I derivatives of a 6-chloropurine nucleoside with benzamide have been compared, using Pd 2dba3, Xantphos and Cs2CO3 in toluene, between 20 and 80 °C. The reactivity order was 2-I > 2-Br > 6-Cl ? 2-Cl. The 2-I substituent could be replaced even at 0 °C, under conditions disclosed here for the first time. On the other hand, the replacement of the chlorine atom at position 2 (2-Cl) required 110 °C.

Synthesis and Characterization of Iodinated Adenosine Derivatives as Selective A1 and A2 Receptor Imaging Agents

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