An efficient synthesis of 1,3-thiazole drivatives is described via a three component reaction isothiocyanates, tetramethyl thiourea and ethyl bromopyruvate.

The catalyst-free multicomponent reaction of 1,2-diaminobenzene, dialkyl acetylenedicarboxylates, and ethyl bromopyruvate forms pyrrolo[1,2-a]quinoxaline derivatives in good yields. Ethylenediamine also reacts under similar conditions to produce new pyrrolo[1,2-a]pyrazine derivatives.

The enzyme, 2-keto-3-deoxy-6-phosphogluconic aldolase is inactivated by the substrate analog, bromopyruvate. Inactivation results from either an active site carboxyl group or a cysteine being alkylated by bromopyruvate. Treatment of enzyme inactivated by carboxylate ester formation with borohydride produces the secondary amine resulting from reduction of a Schiff’s base between the covalently f...

3-Bromopyruvate, an alkylating agent and a well-known inhibitor of energy metabolism, has been proposed as a specific anticancer agent. However, the chemopreventive effect of 3-bromopyruvate in lung tumorigenesis has not been tested. In this study, we investigated the chemopreventive activity of 3-bromopyruvate in a mouse lung tumor model. Benzo(a)pyrene was used to induce lung tumors, and 3-br...

N-Acetylneuraminic acid aldolase from Glostridium perfringens was irreversiblv inactivated by 1 mM-bromopyruvate with a half-life of 4.2min at pH 7.2 and 370C. The rate of inactivation was diminished in the presence of pyruvate but not with N-acetyl-D-mannosamine, indicating that the inhibitor acted at, or close to, the pyruvate-binding site. The apparent K, for bromopyruvate, calculated from t...

PURPOSE P-glycoprotein mediated efflux is one of the main mechanisms for multidrug resistance in cancers, and 3-Bromopyruvate acts as a promising multidrug resistance reversal compound in our study. To test the ability of 3-Bromopyruvate to overcome P-glycoprotein-mediated multidrug resistance and to explore its mechanisms of multidrug resistance reversal in MCF-7/ADR cells, we evaluate the in ...

Incubation with bromopyruvate did not cause appreciable inactivation of either supernatant or mitochondrial isozyme of aspartate aminotransferase from pig heart. In the presence of either L-cysteine sulfinate or L-aspartate, however, bromopyruvate rapidly inactivated both isozymes. Bromopyruvate also acted as a keto acid substrate in the conversion of the pyridoxamine form of both enzymes to th...

Pyruvate, phosphate dikinase was purified and crystallized from Bacteroides symbiosus. The function of histidyl and cysteinyl residues of the enzyme were investigated by chemical modification with diethylpyrocarbonate and bromopyruvate. Diethylpyrocarbonate rapidly inactivated the enzyme by combination with histidyl residues. The modified enzyme loses the ability to form phosphoryl enzyme and e...

Bromopyruvate inactivates the pyruvate dehydrogenase complex of Escherichia coli in a thiamine pyrophosphate (TPP)-dependent process. The catalytic activities of the individual enzyme components within the complex are not destroyed by bromopyruvate under similar conditions, but the activities of the pyruvate dehydrogenase and dihydrolipoyl dehydrogenase components are reduced in thiamine pyroph...

Anticancer drug efficacy might be leveraged by strategies to target certain biochemical adaptations of tumors. Here we show how depriving cancer cells of glutamine can enhance the anticancer properties of 3-bromopyruvate, a halogenated analog of pyruvic acid. Glutamine deprival potentiated 3-bromopyruvate chemotherapy by increasing the stability of the monocarboxylate transporter-1, an effect t...