Production Method 1

88770-18-7

944709-72-2

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  0 °C; 18 h, rt; 18 h, rt

Reference

Preparation of thiophenylpyridinylpyrazolecarboxylic acid derivatives for use as guanylate cyclase activators

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Methyl 2-Bromo-5-methylthiophene-3-carboxylate Raw materials

• Methyl 5-methylthiophene-3-carboxylate

Methyl 2-Bromo-5-methylthiophene-3-carboxylate Preparation Products

• Methyl 2-Bromo-5-methylthiophene-3-carboxylate (944709-72-2)

• 1. An investigation on the interaction modes of a single-strand DNA aptamer and RBP4 protein: a molecular dynamic simulations approach?
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Recent Advances in the Application of Methyl 2-Bromo-5-methylthiophene-3-carboxylate (CAS: 944709-72-2) in Chemical Biology and Pharmaceutical Research

Methyl 2-Bromo-5-methylthiophene-3-carboxylate (CAS: 944709-72-2) is a key intermediate in the synthesis of various bioactive compounds, particularly in the development of pharmaceuticals and agrochemicals. Recent studies have highlighted its versatility as a building block in organic synthesis, enabling the construction of complex molecular architectures with potential therapeutic applications. This research brief aims to summarize the latest findings related to this compound, focusing on its synthetic utility, biological activity, and emerging applications in drug discovery.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers demonstrated the use of Methyl 2-Bromo-5-methylthiophene-3-carboxylate as a precursor for the synthesis of novel thiophene-based kinase inhibitors. The bromine atom at the 2-position allows for efficient palladium-catalyzed cross-coupling reactions, while the ester group provides a handle for further functionalization. This dual reactivity makes the compound particularly valuable for structure-activity relationship (SAR) studies in drug development programs targeting protein kinases involved in cancer and inflammatory diseases.

Recent advancements in synthetic methodology have expanded the utility of 944709-72-2 in medicinal chemistry. A 2024 publication in Organic Letters described a novel one-pot transformation of this compound into fused heterocyclic systems through sequential cross-coupling and cyclization reactions. This approach significantly reduces synthetic steps compared to traditional methods and has been applied to create libraries of potential drug candidates with improved pharmacokinetic properties. The study reported several derivatives showing promising activity against bacterial efflux pumps, suggesting potential applications in addressing antibiotic resistance.

From a biological perspective, research has uncovered interesting structure-activity relationships for thiophene derivatives synthesized from 944709-72-2. A 2023 study in Bioorganic & Medicinal Chemistry demonstrated that modifications at the 5-methyl position of the thiophene ring significantly influence binding affinity to certain G-protein coupled receptors (GPCRs). These findings are particularly relevant for the development of new central nervous system (CNS) therapeutics, as several GPCR targets are implicated in neurological disorders.

In the field of materials science, Methyl 2-Bromo-5-methylthiophene-3-carboxylate has found new applications in the development of organic electronic materials. A recent 2024 publication in Advanced Materials reported its use as a monomer for constructing conjugated polymers with tunable optoelectronic properties. These materials show potential for biosensing applications, particularly in the detection of disease biomarkers, due to their excellent charge transport characteristics and biocompatibility.

Looking forward, the unique chemical properties of 944709-72-2 continue to inspire innovative applications across multiple disciplines. Current research directions include its incorporation into PROTAC (proteolysis targeting chimera) molecules for targeted protein degradation and its use in the synthesis of covalent inhibitors for challenging drug targets. The compound's versatility, combined with recent methodological advances in its derivatization, ensures its ongoing importance in chemical biology and pharmaceutical research.

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