3-Deazaadenosine

Base Information

• Chemical Name: 3-Deazaadenosine
• CAS No.: 6736-58-9
• Molecular Formula: C11H14 N4 O4
• Molecular Weight: 266.257
• Hs Code.: 29419090
• UNII: 037V4520IY
• DSSTox Substance ID: DTXSID2040941
• Nikkaji Number: J15.731G
• Wikidata: Q27073728
• Pharos Ligand ID: QBUSGG3H8PKK
• Metabolomics Workbench ID: 148988
• ChEMBL ID: CHEMBL202701
• Mol file: 6736-58-9.mol

Synonyms:3-deazaadenosine;3-deazaadenosine hydrochloride

Chemical Property of 3-Deazaadenosine

Chemical Property:

• Vapor Pressure: 1.25E-18mmHg at 25°C
• Melting Point: 228-229°C
• Boiling Point: 665.7ºC at 760 mmHg
• PKA: 13.24±0.70(Predicted)
• Flash Point: 356.4ºC
• PSA: 126.65000
• Density: 1.9g/cm3
• LogP: -0.79380
• Storage Temp.: 2-8°C
• Solubility.: H2O: 10 mg/mL with heating to 60 °C
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 266.10150494
• Heavy Atom Count: 19
• Complexity: 334

Purity/Quality:

98%, ^*data from raw suppliers

3-Deazaadenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=C(C2=C1N(C=N2)C3C(C(C(O3)CO)O)O)N
• Isomeric SMILES: C1=CN=C(C2=C1N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
• Description: 3-Deazaadenosine (3-DZA) is an inhibitor of SAH (Sadenosylhomocysteine) hydrolase (Ki = 3.9 μM). It has antiinflammatory properties, inhibiting leukocyte adhesion and chemotaxis, lymphocyte-mediated cytolysis, phagocytosis, degranulation, and NF-κB signaling. 3-DZA also has anti-viral and anti-bacterial activities.
• Uses: Possesses antiviral activity. It is an inhibitor of leukocyte adhesion to TNF-treated endothelial cells Possesses antiviral activity. It is an inhibitor of leukocyte adhesion to TNF-treated endothelial cells.

Technology Process of 3-Deazaadenosine

There total 3 articles about 3-Deazaadenosine 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: 73.0%

7-methylinosine (33763-06-3) + 4-amino-1H-imidazo<4,5-c>pyridine hydrochloride (4261-05-6) → 7-methyl-1,7-dihydro-purin-6-one (1006-08-2) + 3-deazaadenosine (6736-58-9)

Guidance literature:

With phosphate buffer; purine nucleoside phosphorylase; In water; at 25 ℃; for 48h; pH 7.0-7.4;

DOI:10.1021/jo00280a046

Reference yield: 65.0%

4-amino-1H-imidazo<4,5-c>pyridine hydrochloride (4261-05-6) + C11H15N5O5*HI (81100-62-1) → 3-deazaadenosine (6736-58-9) + 7-methylguanine (578-76-7)

Guidance literature:

With purine nucleoside phosphorylase; In water; at 25 ℃; for 48h; pH 7.0-7.4;

DOI:10.1021/jo00280a046

Reference yield: 53.0%

7-methylguanosine (22164-16-5) + 4-amino-1H-imidazo<4,5-c>pyridine hydrochloride (4261-05-6) → 3-deazaadenosine (6736-58-9) + 7-methylguanine (578-76-7)

Guidance literature:

With phosphate buffer; purine nucleoside phosphorylase; In water; at 25 ℃; for 48h; pH 7.0-7.4;

DOI:10.1021/jo00280a046

upstream raw materials:

7-methylinosine

4-amino-1H-imidazo<4,5-c>pyridine hydrochloride

7-methylguanosine

C₁₁H₁₅N₅O₅*HI

Downstream raw materials:

4-{[2-(4-nitrophenyl)ethoxycarbonyl]amino}-N¹-(β-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridine

N-benzoyl-1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-amine

2'-deoxy-N⁶-benzoyl-3-deazaadenosine

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-N⁶-benzoyl-3-deazaadenosine