IB-Meca

Base Information

• Chemical Name: IB-Meca
• CAS No.: 152918-18-8
• Deprecated CAS: 215462-30-9
• Molecular Formula: C18H19 I N6 O4
• Molecular Weight: 510.291
• Hs Code.: 2934999090
• European Community (EC) Number: 814-882-7
• UNII: 30679UMI0N
• DSSTox Substance ID: DTXSID50165158
• Nikkaji Number: J584.717F
• Wikidata: Q27088384
• NCI Thesaurus Code: C166615
• Pharos Ligand ID: 3X9RXHN1BTAH
• Metabolomics Workbench ID: 66342
• ChEMBL ID: CHEMBL119709
• Mol file: 152918-18-8.mol

Synonyms:3-IB-MECA;IB-MECA;N(6)-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine;N(6)-(3-iodobenzyl)adenosine-5'-N-methyluronamide;N(6)-IBAMU

Chemical Property of IB-Meca

Chemical Property:

• Refractive Index: 1.808
• Boiling Point: °Cat760mmHg
• PKA: 12.72±0.70(Predicted)
• Flash Point: °C
• PSA: 134.42000
• Density: 1.98g/cm³
• LogP: 0.87210
• Storage Temp.: 2-8°C
• Solubility.: hot ethanol: >10 mg/mL
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 510.05125
• Heavy Atom Count: 29
• Complexity: 589

Purity/Quality:

97% ^*data from raw suppliers

IB-MECA ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)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=CN=C32)NCC4=CC(=CC=C4)I)O)O
• Recent ClinicalTrials: Safety and Efficacy Study of CF101 to Treat Psoriasis
• Recent EU Clinical Trials: Piclidenoson for Treatment of COVID-19 - A Randomized, Double-Blind, Placebo-Controlled Pilot Trial
• Uses: IB-MECA has been used for intraocular pressure and corneal thickness measurements in rabbits.

Technology Process of IB-Meca

There total 15 articles about 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: 95.45%

3,4-bis(tert-butyldimethylsilyloxy)-5-(6-(3-iodobenzylamino)-9H-purin-9-yl)-N-methyl-tetrahydrofuran 2-carboxamide → N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide (152918-18-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

Reference yield: 72.0%

(2S,3S,4R,5R)-5-(6-{[Benzotriazol-1-yl-(3-iodo-phenyl)-methyl]-amino}-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide → N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide (152918-18-8)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; for 8h; Heating;

DOI:10.1002/jhet.5570370218

Reference yield:

IB-MECA acetonide (152918-48-4) → N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide (152918-18-8)

Guidance literature:

With hydrogenchloride; at 60 ℃; for 4h; Yield given;

DOI:10.1021/jm00031a014

upstream raw materials:

IB-MECA acetonide

m-iodobenzaldehyde

5'-N-methylcarboxamidoadenosine

3-iodobenzylamine hydrochloride

Downstream raw materials:

1-[2-chloro-6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide