35109-88-7

Basic information

• Product Name: 2-IODOADENOSINE
• Synonyms: 2-IODOADENOSINE;2-Iodo-D-adenosine;(2R,3R,4R,5R)-2-(6-AMINO-2-IODO-PURIN-9-YL)-5-(HYDROXYMETHYL)OXOLANE-3,4-DIOL(2-IODOADENOSINE);6-Amino-2-iodo-9-(beta-D-ribofuranosyl)purine;(2R,3R,4S,5R)-2-(6-aMino-2-iodo-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol;(4S,2R,3R,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS NO: 35109-88-7
• Molecular Formula: C₁₀H₁₂IN₅O₄
• Molecular Weight: 393.13785
• EINECS: 1592732-453-0
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Nucleosides;Oligonucleotide Synthesis;Specialty Synthesis;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 35109-88-7.mol
• Article Data: 23

Chemical Properties

• Melting Point: 202-203°C
• Boiling Point: 776.26 °C at 760 mmHg
• Flash Point: 423.267 °C
• Appearance: Off-white crystalline solid
• Density: 2.69 g/cm³
• Vapor Pressure: 2.32E-25mmHg at 25°C
• Refractive Index: 1.994
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO, Methanol, Water
• PKA: 13.05±0.70(Predicted)
• CAS DataBase Reference: 2-IODOADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IODOADENOSINE(35109-88-7)
• EPA Substance Registry System: 2-IODOADENOSINE(35109-88-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 35109-88-7(Hazardous Substances Data)

Usage

Description

2-Iodoadenosine is a chemical compound that is produced from the oxidation of uridine. It is used in the synthesis of peptides, which are important for biological processes like signal transduction and cell growth.

Chemical Properties

Off-White Crystalline Solid

Uses

An intermediate in the synthesis of isoguanosine (crotonoside or 2-hydroxyadenosine), a naturally occuring nucleoside analogue of guanosine. Isoguanosine is incorporated into mammalian but not bacterial nucleic acids, stimulates the accumulation of cyclic AMP in the brain, and is an inhibitor of IMP:pyrophosphorylase.

InChI:InChI=1/C10H12IN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1

Upstream product

• 94042-04-3 6-amino-2-iodo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 118-00-3 G 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 
• 2004-07-1 2-Amino-6-chloropurine riboside 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 10310-21-1 2-Amino-6-chloropurin 
• 3387-63-1 2-amino-6-chloro-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine 
• 403842-37-5 C₃₁H₂₂ClIN₄O₇ 
• 313477-85-9 2-iodo-6-chloro-9-(β-D-ribofuranosyl)purine 
• 5987-76-8 6-chloro-2-iodo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 

Downstream Products

• 124499-05-4 (2R,3R,4S,5R)-2-[6-Amino-2-(3-phenyl-propylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 504406-60-4 2-(allylbenzene)adenosine 
• 457060-99-0 8-bromo-2-iodoadenosine 
• 313348-27-5 regadenoson 
• 141018-25-9 (3aR,4R,6R,6aR)-(6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 56720-66-2 2-(benzylamino)adenosine 
• 124499-07-6 (2R,3R,4S,5R)-2-{6-Amino-2-[2-(4-methoxy-phenyl)-ethylamino]-purin-9-yl}-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 56720-67-3 CGS 21223 
• 53296-12-1 2-cyclohexylamino-adenosine 
• 124499-08-7 2-[[2''-(p-hydroxyphenyl)ethyl]amino]adenosine 

Relevant articles and documents

Palladium-catalyzed cross-coupling of 2-iodoadenosine with terminal alkynes: Synthesis and biological activities of 2-alkynyladenosines

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2-Substituted α,β-Methylene-ADP Derivatives: Potent Competitive Ecto-5′-nucleotidase (CD73) Inhibitors with Variable Binding Modes

CD73 inhibitors are promising drugs for the (immuno)therapy of cancer. Here, we present the synthesis, structure-activity relationships, and cocrystal structures of novel derivatives of the competitive CD73 inhibitor α,β-methylene-ADP (AOPCP) substituted in the 2-position. Small polar or lipophilic residues increased potency, 2-iodo- and 2-chloro-adenosine-5′-O-[(phosphonomethyl)phosphonic acid] (15, 16) being the most potent inhibitors with Ki values toward human CD73 of 3-6 nM. Subject to the size and nature of the 2-substituent, variable binding modes were observed by X-ray crystallography. Depending on the binding mode, large species differences were found, e.g., 2-piperazinyl-AOPCP (21) was >12-fold less potent against rat CD73 compared to human CD73. This study shows that high CD73 inhibitory potency can be achieved by simply introducing a small substituent into the 2-position of AOPCP without the necessity of additional bulky N6-substituents. Moreover, it provides valuable insights into the binding modes of competitive CD73 inhibitors, representing an excellent basis for drug development.

Synthesis, characterization and biological evaluation of purine nucleoside analogues

We present a convenient route for the synthesis of C6-amino-C5′-N-cyclopropyl carboxamido-C2-alkynylated purine nucleoside analogues 11a–g via Sonogashira coupling reaction. The nine step synthesis is easy to perform, employing commercially available reagents. Compound 9 is used as key intermediate for the synthesis of analogues 11a–g. Synthetic intermediates and final products are appropriately characterized by IR, 1H NMR, 13C NMR and Mass. The modified nucleoside analogues 11a–g is evaluated for in vitro anticancer activity against MDA-MB-231 and Caco-2 cell lines. Screening data reveals that compounds 11b and 11e displayed potent IC50 value of 7.9, 6.8 μg/mL respectively against MDA-MB-231 and of 7.5, 8.3 μg/mL respectively against Caco-2 than the standard drug doxorubicin, thus establishing the potential anti-cancer properties of these newer derivatives.