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
• General Description: Trifluridine (F3Thd) is a nucleoside analogue with notable antitumor properties, though its efficacy is limited by rapid degradation in plasma. To improve its stability and activity, various acyl derivatives were synthesized, with the 5'-O-hexanoyl compound demonstrating the highest antitumor potency, significantly outperforming the parent compound. These modifications, particularly at the 5'-O position, enhance resistance to enzymatic degradation, thereby maintaining higher plasma concentrations and improving therapeutic outcomes. However, excessive protection of the sugar moiety or N3-acylation reduces activity, indicating the importance of selective derivatization for optimal efficacy.

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:

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

O⁴-benzyl-2'-deoxy-5-(trifluoromethyl)uridine

N³-benzyl-2'-deoxy-5-(trifluoromethyl)uridine

3-(4-Fluoro-benzoyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

Refernces

Studies on antitumor agents. VI. Syntheses and antitumor activities of acyl derivatives of 2'-deoxy-5-trifluoromethyluridine.

10.1248/cpb.35.2090

The study investigates the synthesis and antitumor activities of various acyl derivatives of 2'-deoxy-5-trifluoromethyluridine (F3Thd) and 2'-deoxy-5-trifluoromethylcytidine. F3Thd, first synthesized in 1962, has significant biological activities but suffers from a short half-life in plasma due to rapid degradation by thymidine phosphorylase. To address this, acyl derivatives including 5'-O-acyl, 3',5'-di-O-acyl, N3-acyl, 3',5'-di-O-carbamoyl, and 3',5'-di-O-ethoxycarbonyl compounds were synthesized. These derivatives were tested for their antitumor effects against sarcoma 180 in mice through oral administration. The results showed that the 5'-O-hexanoyl compound of F3Thd exhibited the highest activity, with an ED50 value one-third that of F3Thd. Full protection of the sugar moiety with aroyl or carbamoyl groups significantly decreased activity. N3-benzoyl compounds were slightly more effective than F3Thd, but none surpassed the effective O-acyl compounds. The study highlights the potential of these acyl derivatives to enhance the antitumor activity of F3Thd by resisting degradation and maintaining higher plasma concentrations.