Resiquimod

Base Information

• Chemical Name: Resiquimod
• CAS No.: 144875-48-9
• Deprecated CAS: 171742-32-8,208711-44-8
• Molecular Formula: C17H22N4O2
• Molecular Weight: 314.387
• Hs Code.: 2933990090
• European Community (EC) Number: 842-607-0
• UNII: V3DMU7PVXF
• DSSTox Substance ID: DTXSID7040603
• Nikkaji Number: J754.943A
• Wikipedia: Resiquimod
• Wikidata: Q426054
• NCI Thesaurus Code: C63958
• Pharos Ligand ID: YB5L8547JU9F
• Metabolomics Workbench ID: 55467
• ChEMBL ID: CHEMBL383322
• Mol file: 144875-48-9.mol

Synonyms:R 848;R-848;R848 compound;resiquimod

Chemical Property of Resiquimod

Chemical Property:

• Vapor Pressure: 4.33E-13mmHg at 25°C
• Melting Point: 190-193°
• Boiling Point: 553.6°Cat760mmHg
• PKA: 14.63±0.29(Predicted)
• Flash Point: 288.6°C
• PSA: 86.19000
• Density: 1.28g/cm³
• LogP: 3.05530
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble10mg/mL, clear (warmed to 60 °C)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 314.17427596
• Heavy Atom Count: 23
• Complexity: 406

Purity/Quality:

98% ^*data from raw suppliers

Resiquimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOCC1=NC2=C(N1CC(C)(C)O)C3=CC=CC=C3N=C2N
• Recent ClinicalTrials: Dendritic Cell Vaccine for Patients With Brain Tumors
• Recent EU Clinical Trials: Clinical Trial Exit Interview Study in Cutaneous T-cell Lymphoma (CTCL) to Capture Meaningful Treatment Benefit from a Patient’s Perspective
• Description: Resiquimod (CAS 144875-48-9) is a Toll-like receptor 7/8 agonist.1 May be used as an immune adjuvant in cancer vaccines.2 Resiquimod-carrying synthetic vaccine particles augment the immune response to encapsulated antigen and exhibit strong local immune activation without inducing systemic cytokine release.3 Topical treatment of wild-type mice induces systemic autoimmune disease which may be used as a model of systemic Lupus erythematosus.4? It displayed potent antiviral activity (EC50 = 23.5 nM) in a murine norovirus replicon model.5
• Uses: Resiquimod is an imidazoquinoline derivative that acts as an immune response modifier. Resiquimod shows antitumor and antiviral activity and is used in the treatment of skin lesions such as herpes simplex virus. Resiquimod is a toll-like receptor 9 (TLR7) agonist. Resiquimod has been used in the stimulation of bone marrow-derived dendritic cells (BMDCs) stimulation( and B cells. It has also been used as a ligand for toll-like receptors (TLR7) in malignant melanoma cell line B16F10.

Technology Process of Resiquimod

There total 11 articles about Resiquimod 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:

2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide → resquimod (144875-48-9)

Guidance literature:

2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5N-oxide; With Trichloroacetyl isocyanate; In dichloromethane; at 0 - 20 ℃;

With sodium methylate; In methanol; at 20 ℃;

With hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium hydrogencarbonate; more than 3 stages;

Reference yield:

N-{2-chloro-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}-2-ethoxyacetamide (253120-65-9) → resquimod (144875-48-9)

Guidance literature:

With ammonia; In methanol; at 160 ℃; for 8h; Sealed tube; Autoclave;

Reference yield:

4-chloro-α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol (144876-01-7) → resquimod (144875-48-9)

Guidance literature:

With ammonia; In methanol; at 150 - 160 ℃; for 6h;

upstream raw materials:

4-chloro-α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

pyrographite

1-[(2-chloro-3-nitro-4-quinolinyl)amino]-2-methyl-2-propanol

Downstream raw materials:

triacetylglycerol

Refernces

• 1、 -. "LOCALLY ACTING TOLL-LIKE RECEPTOR 7 (TLR7) AND/OR TLR8 AGONIST IMMUNOTHERAPY COMPOUNDS AND THEIR USES". Paragraph 0031-0032; 00181; 00184-00187; 00195-00196. . Retrieved 2020/10/19.
• 2、 -. "METHOD FOR 1H-IMIDAZO[4,5-c]PYRIDINES AND ANALOGS THEREOF". Page/Page column 79-81. . Retrieved 2008/06/13.