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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxylic acids and derivatives Indolecarboxylic acids

Methyl 1-methyl-1H-indole-5-carboxylate (CAS No. 128742-76-7): An Overview of Its Structure, Properties, and Applications

Methyl 1-methyl-1H-indole-5-carboxylate (CAS No. 128742-76-7) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique indole scaffold, has been the subject of numerous studies due to its potential therapeutic applications and intriguing chemical properties.

The molecular structure of Methyl 1-methyl-1H-indole-5-carboxylate is composed of an indole ring with a methyl group at the 1-position and a carboxylate ester at the 5-position. The indole core is a fundamental building block in many biologically active molecules, including natural products and synthetic drugs. The presence of the methyl and ester groups imparts specific functionalities that can influence the compound's reactivity and biological activity.

Recent advancements in computational chemistry have provided valuable insights into the electronic structure and conformational behavior of Methyl 1-methyl-1H-indole-5-carboxylate. Quantum mechanical calculations have revealed that the compound exhibits a planar geometry, which is crucial for its interactions with biological targets. The planarity of the indole ring enhances the compound's ability to form π-stacking interactions, a common feature in many protein-ligand complexes.

In terms of physical properties, Methyl 1-methyl-1H-indole-5-carboxylate is a solid at room temperature with a melting point of approximately 90°C. It is soluble in common organic solvents such as methanol, ethanol, and dimethyl sulfoxide (DMSO), making it amenable to various synthetic transformations and biological assays. The solubility profile of this compound is particularly advantageous for its use in high-throughput screening (HTS) platforms, where rapid and efficient testing of large compound libraries is essential.

The biological activity of Methyl 1-methyl-1H-indole-5-carboxylate has been extensively studied in recent years. One notable area of research involves its potential as an inhibitor of specific enzymes involved in various disease pathways. For instance, studies have shown that this compound can selectively inhibit certain kinases, which are key regulators of cellular signaling pathways implicated in cancer and inflammatory diseases. The mechanism of action involves the binding of the indole scaffold to the active site of the target enzyme, thereby disrupting its catalytic activity.

Furthermore, Methyl 1-methyl-1H-indole-5-carboxylate has demonstrated promising antiproliferative effects against various cancer cell lines. In vitro experiments have revealed that it can induce cell cycle arrest and apoptosis in cancer cells, suggesting its potential as a lead compound for the development of novel anticancer agents. These findings have spurred further investigations into optimizing the structure of this compound to enhance its potency and selectivity.

In addition to its direct biological effects, Methyl 1-methyl-1H-indole-5-carboxylate serves as a valuable intermediate in the synthesis of more complex molecules. Its reactivity with various functional groups allows for the introduction of additional substituents that can modulate its biological activity. For example, derivatization at the carboxylate ester position can yield compounds with enhanced pharmacokinetic properties or improved target specificity.

The safety profile of Methyl 1-methyl-1H-indole-5-carboxylate has also been evaluated in preclinical studies. Toxicity assessments have shown that it exhibits low cytotoxicity towards normal cells, indicating a favorable therapeutic window for potential drug development. However, further studies are needed to fully understand its long-term safety and potential side effects.

In conclusion, Methyl 1-methyl-1H-indole-5-carboxylate (CAS No. 128742-76-7) is a multifaceted compound with significant potential in medicinal chemistry and pharmaceutical research. Its unique structural features, coupled with its promising biological activity and synthetic versatility, make it an attractive candidate for further exploration and development as a therapeutic agent.

• 89369-38-0(9H-Carbazole-4-carboxylic acid, 9-methyl-, methyl ester)
• 1204-32-6(methyl 1-methyl-1H-indole-6-carboxylate)
• 89374-80-1(9H-Carbazole-2-carboxylic acid, 9-methyl-, ethyl ester)
• 89369-37-9(9H-Carbazole-3-carboxylic acid, 9-methyl-, ethyl ester)
• 89369-35-7(9H-Carbazole-3-carboxylic acid, 9-methyl-, methyl ester)
• 89374-79-8(9-Methyl-9H-carbazole-3-carboxylic acid)
• 186129-25-9(1-methyl-1H-indole-5-carboxylic acid)
• 56153-34-5(Ethyl 1-methylquinolin-1-ium-6-carboxylate)
• 88330-42-1(1H-Indole-5,6-dicarboxylic acid, 1-methyl-, dimethyl ester)
• 88129-39-9(9H-Carbazole-2,3-dicarboxylic acid, 9-methyl-, dimethyl ester)