860354-59-2

Usage

Uses

Used in Organic Synthesis:
Methyl 5-bromo-3-ureidothiophene-2-carboxylate is used as a building block for the synthesis of various heterocyclic compounds due to its unique structure and reactivity.
Used in Pharmaceutical Research:
Methyl 5-bromo-3-ureidothiophene-2-carboxylate is used as a valuable tool in pharmaceutical research for its potential therapeutic applications.
Used in Chemical Synthesis:
Methyl 5-bromo-3-ureidothiophene-2-carboxylate is used as a versatile tool in chemical synthesis due to its bromine atom, which allows for further derivatization.
Further research is needed to fully explore the potential applications of methyl 5-bromo-3-ureidothiophene-2-carboxylate in various fields.

Upstream product

• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 860354-57-0 methyl 3-({[(trichloroacetyl)amino]carbonyl}amino)thiophene-2-carboxylate 
• 860354-58-1 methyl 5-bromo-3-({[(trichloroacetyl)amino]carbonyl}amino)thiophene-2-carboxylate 

Downstream Products

• 1311275-35-0 6-bromo-2,4-dichlorothieno[3,2-d]pyrimidine 

Relevant academic research and scientific papers

Synthesis and pharmacological characterization of the selective GluK1 radioligand (: S)-2-amino-3-(6-[3H]-2,4-dioxo-3,4-dihydrothieno[3,2- d] pyrimidin-1(2 H)-yl)propanoic acid ([3H]-NF608)

The kainic acid receptors belong to the class of ionotropic glutamate receptors and comprise five subunits named GluK1-5. Radioligands are essential tools for use in binding assays aimed at ligand-receptor structure-activity-relationship studies. Previous work has led to the synthesis of GluK1 radioligands [3H]-SYM2081, [3H]-UBP310 and [3H]-ATPA, however all strategies were work-intensive and thus not attractive. Herein, we report the synthesis of [3H]-NF608 and subsequent pharmacological evaluation at homomeric recombinant rat GluK1 receptors. Binding affinities of a series of standard GluK1 ligands were shown to be in line with previously reported affinities obtained by use of already reported radioligands.

2,4-Diaminothienopyrimidines as orally active antimalarial agents

A novel series of 2,4-diaminothienopyrimidines with potential as antimalarials was identified from whole-cell high-throughput screening of a SoftFocus ion channel library. Synthesis and structure-activity relationship studies identified compounds with potent antiplasmodial activity and low in vitro cytotoxicity. Several of these analogues exhibited in vivo activity in the Plasmodium berghei mouse model when administered orally. However, inhibition of the hERG potassium channel was identified as a liability for this series.

Discovery of checkpoint kinase inhibitor (S)-5-(3-fluorophenyl)-N- (piperidin-3-yl)-3-ureidothiophene-2-carboxamide (AZD7762) by structure-based design and optimization of thiophenecarboxamide ureas

Checkpoint kinases CHK1 and CHK2 are activated in response to DNA damage that results in cell cycle arrest, allowing sufficient time for DNA repair. Agents that lead to abrogation of such checkpoints have potential to increase the efficacy of such compounds as chemo- and radiotherapies. Thiophenecarboxamide ureas (TCUs) were identified as inhibitors of CHK1 by high throughput screening. A structure-based approach is described using crystal structures of JNK1 and CHK1 in complex with 1 and 2 and of the CHK1-3b complex. The ribose binding pocket of CHK1 was targeted to generate inhibitors with excellent cellular potency and selectivity over CDK1and IKKβ, key features lacking from the initial compounds. Optimization of 3b resulted in the identification of a regioisomeric 3-TCU lead 12a. Optimization of 12a led to the discovery of the clinical candidate 4 (AZD7762), which strongly potentiates the efficacy of a variety of DNA-damaging agents in preclinical models.

SUBSTITUTED HETEROCYCLES AND THE USES THEREOF

This invention relates to novel compounds having the structural formula (I) and to their pharmaceutical compositions and to their methods of use. These novel compounds provide a treatment or prophylaxis of cancer.