Danoprevir

Base Information

• Chemical Name: Danoprevir
• CAS No.: 850876-88-9
• Deprecated CAS: 1001913-18-3,916881-67-9,1225266-12-5
• Molecular Formula: C35H46FN5O9S
• Molecular Weight: 731.83
• UNII: 911Z9PCQ5F
• ChEMBL ID: CHEMBL258734
• Metabolomics Workbench ID: 144538
• NCI Thesaurus Code: C171872
• Nikkaji Number: J2.939.361C
• Wikidata: Q27271364
• Wikipedia: Danoprevir
• Mol file: 850876-88-9.mol

Synonyms:danoprevir;ITMN 191;ITMN-191;ITMN191;R 7227;R-7227;R7227 cpd;RG 7227;RG-7227;RG7227

Chemical Property of Danoprevir

Chemical Property:

• PSA: 188.90000
• Density: 1.378 g/cm³
• LogP: 5.21150
• Storage Temp.: -20°C Freezer
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 731.30002740
• Heavy Atom Count: 51
• Complexity: 1530

Purity/Quality:

98% min ^*data from raw suppliers

Danoprevir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCCCCC=CC2CC2(NC(=O)C3CC(CN3C1=O)OC(=O)N4CC5=C(C4)C(=CC=C5)F)C(=O)NS(=O)(=O)C6CC6
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H]1CCCCC/C=C\[C@@H]2C[C@]2(NC(=O)[C@@H]3C[C@H](CN3C1=O)OC(=O)N4CC5=C(C4)C(=CC=C5)F)C(=O)NS(=O)(=O)C6CC6
• Recent ClinicalTrials: Efficacy and Safety of Danoprevir/r + PR 12week Triple Therapy in Treatment Naive Non-Cirrhotic G1 CHC China III
• Recent EU Clinical Trials: A Randomized, Open-Label, Multicenter Study of the Safety, Efficacy, and Tolerability of Combination Treatment of Setrobuvir, Danoprevir, Ritonavir, and Copegus? with or without Mericitabine in Treatment Na?ve HCV Genotype 1?Infected Patients
• Description: Danoprevir is an orally bioavailable inhibitor of hepatitis C virus (HCV) nonstructural protein 3/4A (NS3/4A; IC50 = 1 nM), a serine protease essential for HCV replication. It is selective for NS3/4A over a panel of 53 proteases at a concentration of 10 μM. Danoprevir inhibits replication of the HCV genotypes 1a, 1b, 4, 5, and 6 (IC50s = 0.2-0.4 nM) as well as 2b and 3a (IC50s = 1.6 and 3.5 nM, respectively) in vitro. It also reduces the number of HCV genotype 1b replicons in Huh-7 cells (EC50 = 1.8 nM).
• Uses: Danoprevir is a selective and potent inhibitor of Hepatitis C virus.

Technology Process of Danoprevir

There total 3 articles about Danoprevir 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:

cyclopropanesulphonamide (154350-29-5) + C32H39FN4O7 (924307-72-2) → Danoprevir (850876-88-9)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 62 ℃; for 17h;

Reference yield:

cyclopropanesulphonamide (154350-29-5) + 6-[[(tert-butoxy)carbonyl]amino]-2-[[(4-fluoro-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-hexadecahydro-5,16-dioxo-(2R,6S,12Z,13aS,14aR,16aS)-cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid (924304-75-6) → Danoprevir (850876-88-9)

Guidance literature:

6-[[(tert-butoxy)carbonyl]amino]-2-[[(4-fluoro-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-hexadecahydro-5,16-dioxo-(2R,6S,12Z,13aS,14aR,16aS)-cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid; With acetic anhydride; sodium carbonate; In tetrahydrofuran; at 45 ℃; for 8.5h;

cyclopropanesulphonamide; With potassium carbonate; In tetrahydrofuran; at 62 ℃; for 17h;

Reference yield:

→ Danoprevir (850876-88-9)

Guidance literature:

upstream raw materials:

cyclopropanesulphonamide

C₃₂H₃₉FN₄O₇

6-[[(tert-butoxy)carbonyl]amino]-2-[[(4-fluoro-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-hexadecahydro-5,16-dioxo-(2R,6S,12Z,13aS,14aR,16aS)-cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid

Refernces

• 1、 -. "Process for the preparation of a macrocycle". Page/Page column 20-21. . Retrieved 2009/07/10.
• 2、 -. "MACROCYCLIC CARBOXYLIC ACIDS AND ACYLSULFONAMIDES AS INHIBITORS OF HCV REPLICATION". Page/Page column 178. . Retrieved 2008/06/13.