1113-59-3 Usage
Chemical Properties
Off-white solid
Uses
Different sources of media describe the Uses of 1113-59-3 differently. You can refer to the following data:
1. Bromopyruvic Acid is a synthetic brominated derivative of pyruvic acid. Bromopyruvic Acid maybe a potential treatment for certain types of cancer as it has shown to be effective at eliminating aggress
ive liver tumors.
2. Bromopyruvic acid is used as an affinity label for cysteine residues and a potential anti-cancer agent. It is involved in the synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids and substituted pyranones. It plays a vital role as a cross-linker between nucleic acids and proteins. It is used as an anticancer agent for lung tumors.
3. 3-Bromopyruvic acid is an intermediate of the fungicide thiabendazole. It was also used in the synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids.
Preparation
Synthesis method of 3-bromopyruvic acid: add a little concentrated sulfuric acid and solvent dichloromethane to pyruvic acid in a reaction flask, add bromine dropwise for about 3.5h and stir, a white precipitate is produced, then continue to stir for 1h, dilute with cyclohexane and petroleum ether, then cool the reaction mixture to get crystals, filter, wash with petroleum ether and dry to get the finished product of 3-bromopyruvic acid.
Definition
ChEBI: 3-bromopyruvic acid is a 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is replaced by bromine. Synthetic brominated derivative and structural analog of pyruvic acid. Highly reactive alkylating agent. Anti-cancer drug It has a role as an alkylating agent and an antineoplastic agent. It is a 2-oxo monocarboxylic acid and an organobromine compound. It derives from a pyruvic acid. It is a conjugate acid of a 3-bromopyruvate.
General Description
Bromopyruvic acid is an affinity label for cysteine residues?. It acts as cross-linker between nucleic acids and proteins. Kinetics of inactivation of pancreatic ribonuclease A by bromopyruvic acid has been investigated.
Purification Methods
Dry it by azeotropic distillation (with toluene), and then recrystallise it from dry CHCl3. Dry for 48hours at 20o (0.5 torr) over P2O5. Store it at 0o. [Labandiniere et al. J Org Chem 52 157 1987, Beilstein 3 III 1167.]
Check Digit Verification of cas no
The CAS Registry Mumber 1113-59-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,1 and 3 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1113-59:
(6*1)+(5*1)+(4*1)+(3*3)+(2*5)+(1*9)=43
43 % 10 = 3
So 1113-59-3 is a valid CAS Registry Number.
InChI:InChI=1/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
1113-59-3Relevant articles and documents
Synthesis of Phosphoenolpyruvate and Its Use in Adenosine Triphosphate Cofactor Regeneration
Hirschbein, Bernard L.,Mazenod, Francois P.,Whitesides, George M.
, p. 3765 - 3766 (1982)
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Metal-mediated inhibition of escherichia coli methionine aminopeptidase: Structure-activity relationships and development of a novel scoring function for metal-ligand interactions
Schiffmann, Rolf,Neugebauer, Alexander,Klein, Christian D.
, p. 511 - 522 (2007/10/03)
We report the discovery of thiabendazole as a potent inhibitor (K 1 = 0.4 μM) of Escherichia coli methionine aminopeptidase (ecMetAP) and the synthesis and pharmacological evaluation of thiabendazole congeners with activity in the upper nanomolar range, Elucidation of the X-ray structure of ecMetAP in complex with thiabendazole and an unrelated inhibitor that was independently described by another group showed that that both compounds bind to an additional CoII ion at the entrance of the active site. This unexpected finding explains the inactivity of the compounds under in vivo conditions. It also allows us to discuss the structure-activity relationships of this series of compounds in a meaningful way, based upon docking runs with an auxiliary metal ion, We describe a new scoring function for the evaluation of metal-mediated inhibitor binding that, unlike the previously used scoring function implemented in the docking program, allows us to distinguish between active and inactive compounds, Finally, conclusions for the structure-based design of in vivo-active inhibitors of ecMetAP are drawn.
Kinetic study of the Ce(III)-, Mn(II)-, or ferroin-catalyzed Belousov-Zhabotinsky reaction with pyruvic acid
Lin, Hsing-Lien,Yu, Yueh-O,Jwo, Jing-Jer
, p. 408 - 418 (2007/10/03)
Ce(III)-, Mn(II)-, or ferroin (Fe(phen)32+)-catalyzed reaction of bromate ion and pyruvic acid (PA) or its dimer exhibits oscillatory behavior. Both the open-chain dimer (parapyruvic acid, γ-methyl-γ-hydroxyl-α-keto-glutaric acid, DP
