Brivudine

Base Information

• Chemical Name: Brivudine
• CAS No.: 69304-47-8
• Molecular Formula: C11H13BrN2O5
• Molecular Weight: 333.139
• Hs Code.: 29349990
• UNII: 2M3055079H
• DSSTox Substance ID: DTXSID0045755
• Nikkaji Number: J1.228.200A,J353.477D,J59.517I
• Wikipedia: Brivudine
• Wikidata: Q904107
• NCI Thesaurus Code: C67088
• Metabolomics Workbench ID: 147839
• ChEMBL ID: CHEMBL31634
• Mol file: 69304-47-8.mol

Synonyms:Uridine,5-(2-bromoethenyl)-2'-deoxy-, (E)-;(E)-5-(2-Bromovinyl)-2'-deoxyuridine;(E)-5-(2-Bromovinyl)deoxyuridine;(E)-5-O-(2-bromoethenyl)-2'-deoxyuridine;5-[(E)-2-Bromoethenyl]-2'-deoxyuridine;Bromovinyldeoxyuridine;Helpin;

Chemical Property of Brivudine

Chemical Property:

• Vapor Pressure: 4.56E-06mmHg at 25°C
• Melting Point: 165 °C
• Refractive Index: 1.6520 (estimate)
• Boiling Point: 382.9ºC at 760 mmHg
• PKA: 8.37±0.10(Predicted)
• Flash Point: 185.4ºC
• PSA: 104.55000
• Density: 1.857 g/cm³
• LogP: -0.45710
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water and methanol.
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 332.00078
• Heavy Atom Count: 19
• Complexity: 450

Purity/Quality:

99.5%min ^*data from raw suppliers

Brivudine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C=CBr)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)/C=C/Br)CO)O
• Recent ClinicalTrials: Effects of RP101 in Post-menopausal Women With Dry Eye Syndrome
• Recent EU Clinical Trials: A Phase II trial comparing Brivudin 0.1% ophthalmic solution with Aciclovir 3 % ophthalmic ointment in the treatment of patients with herpetic dendritic keratitis
• Description: (E)-5-(2-Bromovinyl)-2'-deoxyuridine is an thymidine analogue and acts as an anti-viral by inhibiting DNA plymerase.
• Uses: It is used as pharmaceutical intermediate. Brivudine is a nucloside analog which causes induction of neuronal differentiation in human reporter cell lines and adult stem cells. Anti-Herpes medication.

Technology Process of Brivudine

There total 24 articles about Brivudine 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: 95.0%

(E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid (74131-06-9) → (E)-5-(2-bromovinyl)-2'-deoxyuridine (69304-47-8)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; water; at 25 ℃; for 0.5h;

DOI:10.1016/j.bmc.2005.07.046

Reference yield: 94.0%

(E)-5-(2-bromovinyl)-2'-deoxy-3',5'-di-O-(p-toluoyl)uridine (73446-74-9) → (E)-5-(2-bromovinyl)-2'-deoxyuridine (69304-47-8)

Guidance literature:

With sodium methylate; In methanol; at 22 ℃; for 24h;

DOI:10.1039/P19810001665

Reference yield: 93.0%

E-5-(2-bromovinyl)-1-<2'-deoxy-3',5'-di-O-(p-chlorobenzoyl)>uridine → (E)-5-(2-bromovinyl)-2'-deoxyuridine (69304-47-8)

Guidance literature:

With sodium methylate; In methanol; for 6h; Ambient temperature;

DOI:10.1002/jhet.5570320135

upstream raw materials:

3',5'-Di-O-acetyl-(Z)-5-<2-(trimethylsilyl)ethenyl>-2'-deoxyuridine

5-(1-fluoro-2-bromoethyl)-3',5'-di-O-acetyl-2'-deoxyuridine

(E)-5-(2-bromovinyl)-2'-deoxy-3',5'-di-O-(p-toluoyl)uridine

(E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid

Downstream raw materials:

3',5'-di-O-acetyl-(E)-5-(2-bromovinyl)-2'-deoxyuridine

(E)-5-(2-bromovinyl)-2'-deoxyuridine 5'-monophosphate

5'-O-(N-t-butyloxycarbonyl-ε-aminocaproyl)-2'-deoxy-5-(E)-bromovinyluridine

Refernces

• 1、 Ardhapure, Ajaykumar V.,Sanghvi, Yogesh S.,Kapdi, Anant R.,García, Joaquín,Sanchez, Gregorio,Lozano, Pedro,Serrano, J. Luis. "Pd-imidate complexes as recyclable catalysts for the synthesis of C5-alkenylated pyrimidine nucleosides via Heck cross-coupling reaction". . p. 24558 - 24563. Retrieved 2015.
• 2、 Kandil, Sahar,Balzarini, Jan,Rat, Stephanie,Brancale, Andrea,Westwell, Andrew D.,McGuigan, Christopher. "ProTides of BVdU as potential anticancer agents upon efficient intracellular delivery of their activated metabolites". . p. 5618 - 5623. Retrieved 2016/11/29.