Pharmakon1600-01504183

Base Information

• Chemical Name: Pharmakon1600-01504183
• CAS No.: 70-00-8
• Molecular Formula: C10H11F3N2O5
• Molecular Weight: 296.203
• Hs Code.: 29349990
• NSC Number: 759595
• Wikidata: Q27167003
• Mol file: 70-00-8.mol

Synonyms:NCGC00166323-01;Spectrum_001560;SpecPlus_000960;Prestwick3_001056;Spectrum3_001653;Spectrum4_000617;Spectrum5_001542;?,?,?-Trifluorothymidine;BSPBio_001012;BSPBio_003405;KBioGR_001174;KBioSS_002040;MLS002154131;DivK1c_007056;SPECTRUM1504183;BPBio1_001114;CHEBI:95193;KBio1_002000;KBio2_002040;KBio2_004608;KBio2_007176;KBio3_002625;BRD5570;HMS1922F11;HMS2094O07;HMS2098C14;HMS2234P22;Pharmakon1600-01504183;BRD-5570;NSC759595;AKOS024458169;CCG-213276;NSC-759595;NCGC00178087-01;NCGC00178087-02;SMR001233438;SBI-0052661.P002;AB00514023;AB00053164_06;SR-05000001890;SR-05000001890-1;BRD-A64485570-001-03-7;Q27167003

Chemical Property of Pharmakon1600-01504183

Chemical Property:

• Appearance/Colour: Almost white crystalline power
• Melting Point: 190-193 °C(lit.)
• Refractive Index: 50 ° (C=1, H2O)
• PKA: pKa 7.85 (Uncertain)
• PSA: 104.55000
• Density: 1.646 g/cm³
• LogP: -0.80390
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Water (up to 14 mg/ml)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 296.06200594
• Heavy Atom Count: 20
• Complexity: 464

Purity/Quality:

98%, ^*data from raw suppliers

5-Trifluorothymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)C(F)(F)F)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](OC1N2C=C(C(=O)NC2=O)C(F)(F)F)CO)O
• Description: Trifluridine (trifluorothymidine, TFT), a fluorinated pyrimidine nucleoside, is an anti-herpesvirus agent and an antitumor antimetabolite agent. It is an analog of thymidine which inhibits thymidylate synthase possesses antiviral and anticancer activity. After phosphorylation by thymidine kinase, it is incorporated into DNA where it induces DNA-damage and interferes with repair enzymes. Enhances frame shift insertion and deletion in CRISPR genome editing in pluripotent stem cells.
• Uses: Trifluridine is used as anti-herpesvirus antiviral agent in ophthalmie preparations.
• Indications: Trifluridine (Viroptic) is a fluorinated pyrimidine nucleoside that has in vitro activity against HSV-1 and HSV- 2, vaccinia, and to a lesser extent, some adenoviruses. Activation of trifluridine requires its conversion to the 5 monophosphate form by cellular enzymes.Trifluridine monophosphate inhibits the conversion of deoxyuridine monophosphate (dUMP) to deoxythymidine monophosphate (dTMP) by thymidylate synthetase. In addition, it competes with deoxythymidine triphosphate (dTTP) for incorporation by both viral and cellular DNA polymerases. Trifluridine-resistant mutants have been found to have alterations in thymidylate synthetase specificity.

Technology Process of Pharmakon1600-01504183

There total 29 articles about Pharmakon1600-01504183 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: 97.0%

C24H17Cl2F3N2O7 → 2'-deoxy-5-trifluoromethyluridine (70-00-8)

Guidance literature:

With methanol; sodium methylate; at 4 - 6 ℃; for 3.5h;

DOI:10.1021/op025555o

Reference yield: 95.0%

5-trifluoromethyl-2′-deoxyuridine-3′,5′-diacetate (65499-42-5) → 2'-deoxy-5-trifluoromethyluridine (70-00-8)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

DOI:10.1016/j.bmcl.2008.08.090

Reference yield: 94.8%

2'-deoxyuridine (951-78-0,63844-76-8) + Langlois reagent (2926-29-6) → 2'-deoxy-5-trifluoromethyluridine (70-00-8)

Guidance literature:

With tert.-butylhydroperoxide; In water; at -3 - 60 ℃; for 2h; Temperature; Inert atmosphere;

upstream raw materials:

1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-erythro-pentofuranosyl>-5-trifluoromethyluracil

Hexanoic acid (2R,3S,5R)-5-(2,4-dioxo-5-trifluoromethyl-3,4-dihydro-2H-pyrimidin-1-yl)-2-hexanoyloxymethyl-tetrahydro-furan-3-yl ester

5-(trifluoromethyl)-3',5'-di-O-trityl-2'-deoxyuridine

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

Downstream raw materials:

(2R,3S,5R)-5-(2,4-dioxo-5-(trifluoromethyl)-3,4-dihydropyrimidin-1(2H)-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl-4-methylbenzoate

1-((2R,4S,5R)-5-Benzyloxymethoxymethyl-4-hydroxy-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

1-((2R,4S,5R)-4-Benzyloxymethoxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

1-((2R,4S,5R)-4-Benzyloxymethoxy-5-benzyloxymethoxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

Refernces

• 1、 -. "METHOD FOR PREPARING TRIFLURIDINE". Paragraph 0074-0077. . Retrieved 2021/09/26.
• 2、 -. "Fluridine crystal form B and preparation method thereof". Paragraph 0028-0057. . Retrieved 2020/06/02.