Amenamevir

Base Information

• Chemical Name: Amenamevir
• CAS No.: 841301-32-4
• Molecular Formula: C₂₄H₂₆N₄O₅S
• Molecular Weight: 482.56
• UNII: 94X46KW4AE
• ChEMBL ID: CHEMBL4297592
• DSSTox Substance ID: DTXSID101027753
• Metabolomics Workbench ID: 144591
• NCI Thesaurus Code: C90782
• Nikkaji Number: J2.327.474D
• Wikidata: Q27271708
• Wikipedia: Amenamevir
• Mol file: 841301-32-4.mol

Synonyms:amenamevir;ASP2151

Chemical Property of Amenamevir

Chemical Property:

• PKA: 12.60±0.70(Predicted)
• PSA: 130.85000
• Density: 1.360±0.06 g/cm3(Predicted)
• LogP: 4.30370
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 482.16239112
• Heavy Atom Count: 34
• Complexity: 800

Purity/Quality:

97% ^*data from raw suppliers

Amenamevir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)N(CC(=O)NC2=CC=C(C=C2)C3=NOC=N3)C(=O)C4CCS(=O)(=O)CC4
• Recent ClinicalTrials: Drug-Drug Interaction Study: ASP2151 and Ciclosporin
• Recent NIPH Clinical Trials: A Study to Investigate the Effects of NPC-06 on the Pharmacokinetics of Amenamevir.
• Description: Amenamevir is an antiviral inhibitor of herpes simplex virus 1 (HSV-1) helicase-primase complex activity. It inhibits recombinant HSV-1 helicase with an IC50 value of 0.078 μM and recombinant HSV-1 primase when used at concentrations greater than or equal to 0.03 μM. Amenamevir inhibits replication of varicella-zoster virus (VZV), HSV-1, and HSV-2 in human embryonic fibroblast (HEF) cells (EC50s = 0.047, 0.036, and 0.028 μM, respectively) and is not cytotoxic to HEF cells with a 50% cytotoxic concentration (CC50) of greater than 30 μM. Amenamevir also inhibits replication of clinical VZV isolates in HEF cells (EC50s = 0.038-0.10 μM). In vivo, it increases survival of cutaneously HSV-1-infected mice in a zosteriform-spread model of progressive HSV-1 infection (ED50 = 1.9 mg/kg twice per day).
• Uses: Amenamevir is a helicase-primase inhibitor which has potent antiviral activity against HSVs with an EC50 of 14 ng/mL.

Technology Process of Amenamevir

There total 11 articles about Amenamevir 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: 91.0%

N-(2,6-dimethylphenyl)-N-(1,1-dioxohexahydropyran-4-formyl)glycine + 4-[1,2,4]oxadiazol-3-yl-phenylamine (59908-70-2) → N-(2-((4-(1,2,4-oxadiazol-3-yl)phenyl)amino)-2-oxoethyl)-N-(2,6-dimethylphenyl)tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide (841301-32-4)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; at 60 ℃; for 3h; Reagent/catalyst;

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-(4-isocyanophenyl)-1,2,4-oxadiazole + 2,6-dimethylaniline (87-62-7) + 1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid (64096-87-3) → N-(2-((4-(1,2,4-oxadiazol-3-yl)phenyl)amino)-2-oxoethyl)-N-(2,6-dimethylphenyl)tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide (841301-32-4)

Guidance literature:

In methanol; at 20 ℃; for 72h; Solvent;

Reference yield:

2,6-dimethylaniline (87-62-7) → N-(2-((4-(1,2,4-oxadiazol-3-yl)phenyl)amino)-2-oxoethyl)-N-(2,6-dimethylphenyl)tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide (841301-32-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetyl chloride / tetrahydrofuran / 3 h / 30 °C

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C

2.2: 3 h / 20 °C

3.1: sodium hydroxide; water / ethanol / 4 h / 20 °C

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / tetrahydrofuran / 3 h / 60 °C

With potassium tert-butylate; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; acetyl chloride; sodium hydroxide; In tetrahydrofuran; ethanol;

upstream raw materials:

4-[1,2,4]oxadiazol-3-yl-phenylamine

2,6-dimethylaniline

1,1-dioxo-hexahydro-1λ⁶-thiopyran-4-carboxylic acid

4-nitrobenzonitrile