N(4)-Hydroxycytidine

Base Information

• Chemical Name: N(4)-Hydroxycytidine
• CAS No.: 3258-02-4
• Molecular Formula: C9H13 N3 O6
• Molecular Weight: 259.219
• European Community (EC) Number: 868-922-3
• UNII: C3D11PV2O4
• DSSTox Substance ID: DTXSID20186274
• Nikkaji Number: J900H
• Wikidata: Q83057523
• Metabolomics Workbench ID: 155595
• ChEMBL ID: CHEMBL2178720
• Mol file: 3258-02-4.mol

Synonyms:4-oxime uridine;Beta-D-N4-hydroxycytidine;EIDD-1931;N(4)-hydroxycytidine;N4-hydroxycytidine

Chemical Property of N(4)-Hydroxycytidine

Chemical Property:

• Vapor Pressure: 1.14E-15mmHg at 25°C
• Melting Point: 169-172 °C(Solv: methanol (67-56-1))
• Boiling Point: 576.1°Cat760mmHg
• PKA: 8.19±0.20(Predicted)
• Flash Point: 302.2°C
• PSA: 137.07000
• Density: 1.93g/cm³
• LogP: -2.27110
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Water (up to 15 mg/ml with warming).
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 259.08043514
• Heavy Atom Count: 18
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

EIDD1931 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)N=C1NO)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=CN(C(=O)N=C1NO)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Description: EIDD-1931 is a ribonucleoside analog with antiviral activity. It inhibits replication of severe acute respiratory syndrome coronavirus (SARS-CoV) in Vero 76 cells, Middle East respiratory syndrome coronavirus (MERS-CoV) in Calu-3 2B4 cells, and SARS-CoV-2 in Vero cells (IC50s =0.1, 0.15 and 0.3 μM, respectively). It also reduces viral titers of Venezuelan equine encephalitis virus (VEEV) TC-83 in infected Vero cells (EC50 = 0.426 μM) and wild-type and remdesivir-resistant strains of the model CoV mouse hepatitis virus (MHV) in infected DBT cells. EIDD-1931 (100 and 400 mg/kg twice per day) reduces lung viral titers in mouse models of respiratory syncytial virus (RSV) and H1N1 influenza A virus infection.
• Uses: EIDD 1931 is an orally bioavailable broad-spectrum antiviral that inhibits SARS-CoV-2 and other multiple endemic, epidemic and bat coronavirus and has the potential for seasonal and pandemic influenza treatment. A broad-spectrum ribonucleoside analog inhibitor of influenza and respiratory syncytial viruses.

Technology Process of N(4)-Hydroxycytidine

There total 29 articles about N(4)-Hydroxycytidine 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: 90.0%

[(2R,3R,4R)-3,4-diacetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate (82913-19-7) → 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxylamino)pyrimidin-2(1H)-one (3258-02-4)

Guidance literature:

With hydroxylamine; In isopropyl alcohol; at 20 ℃; for 18h;

DOI:10.1128/AAC.00766-18

Reference yield: 89.0%

CYTIDINE (65-46-3) → uridine 4-oxime (3258-02-4)

Guidance literature:

With cytidine deaminase; hydroxylamine; In water monomer; at 4 ℃; for 3h; Enzymatic reaction;

DOI:10.1021/jacs.1c11048

Reference yield: 88.8%

triacetyl-N4-hydroxycytidine → uridine 4-oxime (3258-02-4)

Guidance literature:

With ammonia; In methanol; at 20 ℃; Reagent/catalyst; Solvent;

upstream raw materials:

4-thiouridine

tribenzoyl uridine

1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-thiouracil

uridine

Downstream raw materials:

CYTIDINE

Refernces

• 1、 Purohit, Meena K.,Poduch, Ewa,Wei, Lianhu William,Crandall, Ian Edward,To, Terrence,Kain, Kevin C.,Pai, Emil F.,Kotra, Lakshmi P.. "Novel cytidine-based orotidine-5′-monophosphate decarboxylase inhibitors with an unusual twist". . p. 9988 - 9997. Retrieved 2012.
• 2、 -. "N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO". . . Retrieved 2021/08/13.
• 3、 -. "Preparation method of N4-hydroxycytidine". Paragraph 0018; 0047-0050. . Retrieved 2021/08/28.