Sorivudine

Base Information

• Chemical Name: Sorivudine
• CAS No.: 77181-69-2
• Deprecated CAS: 80434-16-8
• Molecular Formula: C₁₁H₁₃BrN₂O₆
• Molecular Weight: 349.138
• UNII: C7VOZ162LV
• ChEMBL ID: CHEMBL70046
• Metabolomics Workbench ID: 153064
• NCI Thesaurus Code: C1460
• Nikkaji Number: J242.999C
• Wikidata: Q905418
• Wikipedia: Sorivudine
• Mol file: 77181-69-2.mol

Synonyms:(E)-1-beta-D-arabinofuranosyl-5-(2-bromoethenyl)-2,4(1H,3H)-pyrimidinedione,;1-beta-D-arabinofuranosyl-5-(2-bromovinyl)uracil;1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil;5-(2-bromovinyl)-1-beta-D-arabinofuranosyluracil;bravavir;BV-ara-U;BV-araU;sorivudine

Chemical Property of Sorivudine

Chemical Property:

• Melting Point: 182° (Sakata, 1980); mp 195-200° (dec) (Machida, Sakata, 1983)
• PKA: 8.37±0.10(Predicted)
• PSA: 124.78000
• Density: 1.979g/cm³
• LogP: -1.48630
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 347.99570
• Heavy Atom Count: 20
• Complexity: 480

Purity/Quality:

97% ^*data from raw suppliers

Sorivudine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)C=CBr
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O)/C=C/Br
• Recent ClinicalTrials: Comparison of Brovavir Versus Acyclovir in the Treatment of Herpes in HIV-Infected Patients
• Description: Sorivudine is an orally-active antiviral nucleoside analog. It has potent and selective activity against herpes simplex virus type-1 (HSV-1) and varicella-zoster virus (VZV). In a cutaneous model infection of mice with HSV-1, oral administration of sorivudine at dose of 20 mg/kg resulted in a significant increase in the survival rate. Five percent sorivudine cream is also useful in the topical treatment of cutaneous HSV-1 infection, including immunocompromised patients. It has been suggested that its antiviral activity may be mediated by inhibition of DNA synthesis in virus infected cells.Since the metabolite of sorivudine inhibits the enzyme for pyrimidine catabolism, caution should be taken not to use sorivudine in combination with fluorouracil drugs in order to avoid hematological disorders.
• Uses: Sorivudine is an antimetabolite drug and can be used to synthesize antiviral compounds as well as compounds that can treat diseases of viral etiol. Antiviral.

Technology Process of Sorivudine

There total 5 articles about Sorivudine 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: 21.8%

3-(1-(β-D-arabinofuranosyl)uracil-5-yl)-acrylic acid (95119-95-2) → BVaraU (77181-69-2,134528-32-8,80434-16-8)

Guidance literature:

3-(1-(β-D-arabinofuranosyl)uracil-5-yl)-acrylic acid; With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20 ℃; for 5.5h;

Reference yield:

1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-(E)-2-(bromovinyl)uracil (87877-27-8) → BVaraU (77181-69-2,134528-32-8,80434-16-8)

Guidance literature:

With ammonia; In methanol;

DOI:10.1016/S0040-4039(00)93411-7

Reference yield:

1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-(Z)-<2-(trimethylsilyl)vinyl>uracil (132054-88-7) → BVaraU (77181-69-2,134528-32-8,80434-16-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / C₅H₅N*HBr₃ / CH₂Cl₂ / 0.25 h / 0 deg C to r.t.

2: NH₃ / methanol

With ammonia; pyridinium hydrobromide perbromide; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)93411-7

upstream raw materials:

Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[5-((Z)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester

1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-(E)-2-(bromovinyl)uracil

1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-(Z)-<2-(trimethylsilyl)vinyl>uracil

3-(1-(β-D-arabinofuranosyl)uracil-5-yl)-acrylic acid

Downstream raw materials:

1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)-5(E)-(2-bromovinyl)uracil

5-((Z)-2-Bromo-vinyl)-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione