Chloro-IB-MECA

Base Information

• Chemical Name: Chloro-IB-MECA
• CAS No.: 163042-96-4
• Molecular Formula: C18H18ClIN6O4
• Molecular Weight: 544.736
• Hs Code.: 2934999090
• European Community (EC) Number: 634-077-2
• UNII: Z07JR07J6C
• DSSTox Substance ID: DTXSID80167504
• Nikkaji Number: J626.443C
• Wikidata: Q27076097
• NCI Thesaurus Code: C79826
• Pharos Ligand ID: VH8X4CVMP3A8
• Metabolomics Workbench ID: 153783
• ChEMBL ID: CHEMBL431733
• Mol file: 163042-96-4.mol

Synonyms:2-chloro-N(6)-(3-iodobenzyl)-9-(5-(methylcarbamoyl)-beta-D-ribofuranosyl)adenine;2-chloro-N(6)-(3-iodobenzyl)adenosine-5'-N-methyluronamide;2-chloro-N6-(3-iodobenzyl)adenosine-5'-N-methylcarboxamide;2-Cl-IB-MECA;C-IBzA-MU;CF102 compound

Chemical Property of Chloro-IB-MECA

Chemical Property:

• Melting Point: 209 °C
• Refractive Index: 1.814
• PKA: 12.68±0.70(Predicted)
• PSA: 134.42000
• Density: 2.041 g/cm³
• LogP: 1.52550
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: >20mg/mL
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 544.01228
• Heavy Atom Count: 30
• Complexity: 623

Purity/Quality:

97% ^*data from raw suppliers

2-Cl-IB-MECA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=C(N=C32)Cl)NCC4=CC(=CC=C4)I)O)O
• Isomeric SMILES: CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)Cl)NCC4=CC(=CC=C4)I)O)O
• Recent ClinicalTrials: Namodenoson in the Treatment of Advanced Hepatocellular Carcinoma in Patients With Child-Pugh Class B7 Cirrhosis
• Recent EU Clinical Trials: A Phase 2B Randomized, Double-Blind, Placebo-Controlled Study of the Efficacy and Safety of Namodenoson in the Treatment of Non-Alcoholic Steatohepatitis (NASH)
• Uses: 2-Cl-IB-MECA acts as an A3 adenosine receptor-selective nucleoside.

Technology Process of Chloro-IB-MECA

There total 12 articles about Chloro-IB-MECA which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.7%

2-chloro-N6-(3-iodobenzyl)-9-<5-(methylcarbamoyl)-2,3-di-O-benzoyl-β-D-ribofuranosyl>adenine (163042-90-8) → 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide (163042-96-4)

Guidance literature:

With ammonia; for 16h; Ambient temperature;

DOI:10.1021/jm00047a018

Reference yield: 31.8%

((3aR,4R,6R,6aR)-6-(2-chloro-6-(3-iodobenzylamino)9H-purine-9-yl) 2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (1000980-71-1) + methylamine (74-89-5) → 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide (163042-96-4)

Guidance literature:

((3aR,4R,6R,6aR)-6-(2-chloro-6-(3-iodobenzylamino)9H-purine-9-yl) 2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol; With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In water; acetonitrile; at 20 ℃; for 4h;

With thionyl chloride; In ethanol; at 0 - 20 ℃; for 12h; Inert atmosphere;

methylamine; In tetrahydrofuran; at 20 ℃; for 12h;

Reference yield:

2,6 dichloropurine (5451-40-1) → 1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide (163042-96-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / Et₃N / ethanol / 120 h / Ambient temperature

2: ammonium sulfate / 5 h / Heating

3: 33 percent / TMSOTf / 1,2-dichloro-ethane / 62 h / Heating

4: 68.7 percent / methanolic NH₃ / 16 h / Ambient temperature

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; ammonia; triethylamine; In ethanol; 1,2-dichloro-ethane;

DOI:10.1021/jm00047a018

upstream raw materials:

2-chloro-N⁶-(3-iodobenzyl)-9-<5-(methylcarbamoyl)-2,3-di-O-benzoyl-β-D-ribofuranosyl>adenine

3-iodobenzylamine hydrochloride

2,6 dichloropurine

2-chloro-N-⁶-(3-iodobenzyl)adenine