3370-69-2

Basic information

• Product Name: 2,4 (1H, 3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-bromo-
• Synonyms: 2,4 (1H, 3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-bromo-;5-BroMoarabinouridine;1-(β-D-Arabino-furanosyl)-5-broMouracil;NSC 82222;1-beta-D-Arabinofuranosyl-5-bromouracil
• CAS NO: 3370-69-2
• Molecular Formula: C₉H₁₁BrN₂O₆
• Molecular Weight: 323.1
• Mol File: 3370-69-2.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.043g/cm³
• CAS DataBase Reference: 2,4 (1H, 3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4 (1H, 3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-bromo-(3370-69-2)
• EPA Substance Registry System: 2,4 (1H, 3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-bromo-(3370-69-2)

Safety Data

• Hazardous Substances Data: 3370-69-2(Hazardous Substances Data)

Usage

Uses

Used in Oncology:
2,4 (1H, 3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-bromois used as an antineoplastic agent for the treatment of various types of cancer, including leukemia and lymphoma. It is used for its ability to inhibit the synthesis of DNA and RNA in cancer cells, leading to their death.
Used in Antiviral Applications:
2,4 (1H, 3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-bromois used as a potential antiviral agent against herpes simplex virus due to its demonstrated antiviral activity. It may be developed into new antiviral agents to combat viral infections.

Upstream product

• 957-75-5 5-bromouridine 
• 35837-20-8 2',3'-anhydro-1-β-D-arabinofuranosyl-5-bromo-uracil 
• 3083-77-0 araU 

Downstream Products

• 17245-47-5 (3aS)-3c-hydroxy-2t-hydroxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-c]pyrimidine-6,8-dione 

Relevant articles and documents

Bromination at C-5 of pyrimidine and C-8 of purine nucleosides with 1,3-dibromo-5,5-dimethylhydantoin

Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5-dimethylhydantoin in aprotic solvents such as CH 2Cl2, CH3CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced the efficiency of bromination.

Anti-HCV nucleoside derivatives

The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

Synthesis, cytotoxic effect and antiviral activity of 1-(β-D- arabinofuranosyl)-5-bromo-N4-substituted cytosine and 1-(β-D- arabinofuranosyl)-5-bromo-4-methoxypyrimidin-2(1H)-one derivatives

A convenient and mild synthesis of 5-bromo-N4-substituted-1-(β-D- arabinofuranosyl)cytosine and 5-bromo-O4-methyl-1-(β-D- arabinofuranosyl)pyrimidin-2(1H)-one derivatives by selective oxyfunctionalization of the corresponding 4-thionucleosides with 3,3- dimethyldioxirane is reported. The cytotoxicity and the antiviral activity against parainfluenza 1 (Sendai virus) of all new synthesized products are also reported.

A mild and efficient methodology for the synthesis of 5-halogeno uracil nucleosides that occurs via a 5-halogeno-6-azido-5,6-dihydro intermediate

A mild and efficient methodology for the synthesis of 5-halogeno (iodo, bromo, or chloro) uracil nucleosides has been developed. 5-Halo-2'-deoxyuridines 4a-c (84-95%), 5-halouridines 7a-c (45-95%), and 5-haloarabinouridines 8a-c (65-95%) were synthesized in good to excellent yields by the reaction of 2'-deoxyuridine (2), uridine (5) and arabinouridine (6), respectively with iodine monochloride, or N-bromo (or chloro)succinimide, and sodium azide at 25-45°C. These C-5 halogenation reactions proceed via a 5-halo-6-azido-5,6-dihydro intermediate (3), from which HN3 is eliminated, to yield the 5-halogeno uracil nucleoside. The 5-halo-6-azido-5,6-dihydro intermediate products (10a, 10b) could be isolated from the reaction of 3',5'-di-O-acetyl-2'-deoxyuridine (9) with iodine monochloride or N-bromosuccinimide and sodium azide at 0°C. The isolation of 10a, 10b indicates that the C-5 halogenation reaction proceeds via a 5-halo-6-azido-5,6-dihydro intermediate.