(E)-5-(2-Bromovinyl)uracil

CAS: 69304-49-0

Ref. 3D-FB04394

Product Information

• Name: (E)-5-(2-Bromovinyl)uracil
• Synonyms: 2,4(1H,3H)-Pyrimidinedione, 5-(2-bromoethenyl)-, (E)-, 2,4(1H,3H)-Pyrimidinedione, 5-[(1E)-2-bromoethenyl]-, 5-[(1E)-2-Bromoethenyl]-2,4(1H,3H)-pyrimidinedione, 5-[(E)-2-bromoethenyl]pyrimidine-2,4(1H,3H)-dione

Description

(E)-5-(2-Bromovinyl)uracil is a drug that has been shown to be effective against leukemic cells. It is a prodrug of 5-bromouracil, which is an antimetabolite and cytotoxic agent. (E)-5-(2-Bromovinyl)uracil has also been shown to be active against solid tumours, such as metastatic colorectal cancer, and bacteria. The mechanism of action involves the irreversible inhibition of the enzyme thymidylate synthase, which catalyzes the conversion of deoxyuridine monophosphate (dUMP) to thymidine monophosphate (dTMP). The drug binds to the dinucleotide phosphate pocket in the enzyme's active site and blocks access by dUMP. This leads to DNA synthesis errors, causing cell death. As a prodrug, it has low toxicity profiles and does not cause bone marrow suppression like

• Brand: Biosynth

Chemical properties

• Molecular weight: 217.02 g/mol
• Formula: C₆H₅BrN₂O₂
• Purity: (¹H-Nmr) Min. 95 Area-%
• Color/Form: Off-white to pale orange solid.
• InChI: InChI=1S/C6H5BrN2O2/c7-2-1-4-3-8-6(11)9-5(4)10/h1-3H,(H2,8,9,10,11)/b2-1+
• InChI key: InChIKey=BLXGZIDBSXVMLU-OWOJBTEDSA-N
• SMILES: O=c1[nH]cc(/C=C/Br)c(=O)[nH]1