2968-28-7

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-a-D-erythro-pentofuranosyl)-5-fluoro-
• Synonyms: Uracil,1-(2-deoxy-a-D-erythro-pentofuranosyl)-5-fluoro-(7CI,8CI); Uracil, 1-(2-deoxy-a-D-ribofuranosyl)-5-fluoro- (6CI); 2'-Deoxy-a-D-ribofuranosyl-5-fluorouracil; NSC 66259; a-5-Fluoro-2'-deoxyuridine
• CAS NO: 2968-28-7
• Molecular Formula: C₉H₁₁FN₂O₅
• Molecular Weight: 246.1924
• Mol File: 2968-28-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.64g/cm³
• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-a-D-erythro-pentofuranosyl)-5-fluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-a-D-erythro-pentofuranosyl)-5-fluoro-(2968-28-7)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-a-D-erythro-pentofuranosyl)-5-fluoro-(2968-28-7)

Safety Data

• Hazardous Substances Data: 2968-28-7(Hazardous Substances Data)

Usage

General Description

The chemical 2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-a-D-erythro-pentofuranosyl)-5-fluoro- is a nucleoside analog of cytidine that is used as an antiviral and antineoplastic agent. It works by inhibiting the replication of viral and cancerous cells by interfering with the synthesis of their genetic material. 2,4(1H,3H)-Pyrimidinedione,1-(2-deoxy-a-D-erythro-pentofuranosyl)-5-fluoro- is commonly used in the treatment of various types of cancer, including leukemia and lymphomas, as well as viral infections such as hepatitis B and C. It is administered intravenously or orally and can cause side effects such as bone marrow suppression, gastrointestinal disturbances, and liver toxicity. The chemical's molecular structure makes it a valuable tool for researchers in the field of medical chemistry and pharmacology.

Upstream product

• 40632-45-9 1-(3',5'-di-O-benzoyl-2'-deoxy-α-D-ribofuranosyl)-uracil 
• 110558-30-0 C₂₃H₁₇Cl₂FN₂O₇ 
• 77180-96-2 C₂₃H₁₉FN₂O₇ 
• 2907-25-7 1-(2-deoxy-3,5-di-O-p-toluyl-α-D-ribofuranosyl)-5-fluorouracil 

Downstream Products

• 88410-68-8 α-2'-deoxy-5-fluorouridine 5'-phosphate 

Relevant articles and documents

2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: Synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity

A convenient synthesis of 5-fluoro-2-thiouracil (11) is based on hydrolytic deamination of 5-fluoro-2-thiocytosine (9). Lewis acid-catalyzed condensation of di-TMS-5-fluoro-2-thiouracil (13) or di-TMS-2-thiouracil (14) with 2-deoxy-3,5-di-O-p-toluyl-D-ribofuranosyl chloride (15) led to mixtures of the β- and α-anomers of 3',5'-toluylated 2'-deoxy-5-fluoro-2-thiouridine (16 and 18) or 2'-deoxy-2-thiouridine (17 and 19), each of which was deblocked with MeOH-NH3 to give the desired free anomeric nucleoside pairs 1, 5 and 3, 7, respectively. These were selectively converted to the corresponding 5'-monophosphates 2, 6 and 4, 8, with the aid of the wheat shoot phosphotransferase system. Conformations of the nucleosides 1, 3, 5, 7 are deduced from 1H NMR spectra, and circular dichroism spectra for nucleotide anomeric pairs 2, 6 and 4, 8 are reported. Whereas β-2-thio-dUMP (4) was a good substrate (K(m) ? 10-5 M), β-5-fluoro-2-thio-dUMP (2) proved to be a potent competitive, slow-binding inhibitor (K(i) ? 10-8 M) of the purified enzymes from Ehrlich ascites carcinoma and L1210 cells. The α-anomer 6 was a weak inhibitor, with K(i) in the mM range, and its congener 8 hardly interacted with the enzyme. The β-anomer 1 exhibited antitumor activity in a mouse leukemic cell line L5178Y (IC50 ? 10-6 M), hence 40- 100-fold weaker than 5-fluoro-dUrd. Its α-anomer 5 was 10-fold less active, but exhibited at least 10-fold higher selectivity with respect to the tumor cells than the β-anomer 1.

Preparation, antibacterial effects and enzymatic degradation of 5-fluorouracil nucleosides

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