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4-Methoxyindole is an organic compound with an indole structure, in which the 4-position is substituted by a methoxy group. It is a white to light yellow solid, insoluble in water and soluble in organic solvents. It can be soluble in organic solvents such as ethanol, ether, acetone, but not in water. This makes it have certain application value in organic synthesis or drug manufacturing. The molecular structure contains an indole ring and a methoxy group. The indole ring is the core structure of the compound, while the methoxy group is located at position 4. Has certain chemical stability and can react with acids, bases, oxidants, etc. under certain conditions. For example, under acidic conditions, the compound may undergo hydrolysis reactions, releasing methanol and indole. In addition, due to its indole ring structure, it may have certain biological activity and can interact with specific enzymes or proteins in living organisms.
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Chemical Formula |
C9H9NO |
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Exact Mass |
147 |
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Molecular Weight |
147 |
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m/z |
147 (100.0%), 148 (9.7%) |
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Elemental Analysis |
C, 73.45; H, 6.16; N, 9.52; O, 10.87 |
as a pharmaceutical intermediate
GABA Analogs: 4-Methoxyindole has been utilized in the synthesis of gamma-aminobutyric acid (GABA) analogs. GABA is a major inhibitory neurotransmitter in the central nervous system, and its analogs are often explored for their potential in treating neurological disorders such as epilepsy, anxiety, and insomnia.
Sodium-Dependent Glucose Co-Transporter 2 (SGLT2) Inhibitors: These inhibitors are crucial in the management of hyperglycemia in diabetes. By blocking the SGLT2 protein, they prevent the reabsorption of glucose in the kidneys, leading to increased glucose excretion and lower blood sugar levels. The role in the synthesis of SGLT2 inhibitors highlights its importance in the development of antidiabetic medications.
Anticancer Agents: The compound has also been employed in the synthesis of anticancer agents. Its unique chemical structure allows for the design of molecules that can target specific cancer pathways, potentially leading to the development of more effective and targeted cancer therapies.
Integrase Strand-Transfer Inhibitors (INSTIs): INSTIs are a class of antiretroviral drugs used in the treatment of HIV. They work by inhibiting the integrase enzyme, which is essential for the integration of the viral DNA into the host cell's genome. The involvement in the synthesis of INSTIs underscores its contribution to the fight against HIV/AIDS.
Inhibitors of Proliferation of Colon Cancer Cells: Specific derivatives have shown promise in inhibiting the proliferation of colon cancer cells. This application highlights the compound's potential in the development of novel anticancer drugs targeting colorectal cancer.
HIV-1 Integrase Inhibitors: Beyond INSTIs, it has also been used in the synthesis of other HIV-1 integrase inhibitors. These inhibitors play a critical role in the antiretroviral therapy regimen, helping to suppress viral replication and improve patient outcomes.
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in organic synthesis
Synthesis of Caged Auxins
Caged Compounds
One of the notable applications is in the synthesis of caged auxins. Caged compounds are designed to release their active components upon exposure to a specific stimulus, such as light. In the case of caged auxins, these compounds are engineered to release the plant hormone auxin when illuminated.
Mechanism of Action
The caging group is typically attached to the auxin molecule in such a way that it blocks its biological activity. Upon light exposure, the caging group undergoes a photochemical reaction, leading to the release of free auxin. This controlled release mechanism allows researchers to precisely manipulate auxin levels in plant tissues.
Research Applications
Caged auxins are invaluable tools in plant biology research. They enable scientists to study auxin-responsive gene expression and auxin-related physiological responses with high spatial and temporal resolution. By selectively illuminating specific plant tissues or cells, researchers can investigate how auxin signaling pathways regulate plant growth, development, and responses to environmental stimuli.
Synthesis of Other Complex Molecules
Diversity of Applications
Beyond caged auxins, it has been utilized in the synthesis of numerous other complex molecules. Its indole core is a common structural motif found in many natural products and bioactive compounds, making it an ideal starting point for the construction of these molecules.
Functional Group Transformations
The methoxy group on the indole ring can be easily modified or transformed into other functional groups, allowing for the synthesis of a diverse range of indole derivatives. This versatility further enhances the utility in organic synthesis.
The use of 4-Methoxyindole in organic synthesis highlights its importance in chemical research. Its ability to serve as a key intermediate in the preparation of complex molecules has contributed to advancements in various fields, including medicinal chemistry, materials science, and plant biology. By leveraging the unique properties, researchers can design and synthesize novel compounds with tailored functions and properties, paving the way for new discoveries and innovations.
Synthesis method
A synthesis route involves dissolving indole in an appropriate amount of methanol and adding an alkaline catalyst. The selection of catalysts can be adjusted according to actual needs, and commonly used catalysts include alkali metal hydroxides or alkali metal carbonates.
C8H7N + CH4O +alkaline catalyst → C9H9NO + H2O.
Prepare the required reagents: indole, methanol, sodium hydroxide or potassium hydroxide, water.
Prepare experimental equipment: beaker, magnetic stirrer, hot bath, dropper or syringe.
Put the required amount of indole into a beaker.
Add an appropriate amount of methanol to fully dissolve indole in methanol.
In another beaker, add an appropriate amount of water and the required alkaline catalyst (such as sodium hydroxide or potassium hydroxide).
Add the catalyst solution to the methanol solution dissolved with indole.
Heat the mixture to an appropriate temperature to promote the reaction.
Keep the mixture stirred in a hot bath and closely observe the progress of the reaction.
When the reaction reaches the desired level, stop heating and let the mixture cool to room temperature.
Separate the generated product from the reaction mixture through filtration or extraction methods.
Purify the isolated 4methoxyindole, such as through column chromatography, recrystallization, and other methods.
Dry the purified 4methoxyindole to remove any remaining methanol and other impurities.
The research on indole compounds can be traced back to the mid-19th century, when chemists began to have a strong interest in natural dyes and alkaloids. In 1836, German chemist Runge isolated indole from coal tar, but it was not until 1866 that Baeyer determined its structure. In this context, scientists began to systematically study various indole derivatives, laying the foundation for the discovery of 4-methoxyindole.
The first separation of 4-methoxyindole can be traced back to the late 19th century. In 1890, German chemists Erdmann and Volk isolated a new indole compound from the essential oil of a certain Asteraceae plant while studying indole derivatives derived from plants. Through elemental analysis and melting point determination, they preliminarily determined that this is a methoxy substituted indole, but at that time, the exact position of the methoxy group could not be determined. This discovery was published in the Journal of the German Chemical Society, marking the official entry of 4-methoxyindole into the field of scientists' vision.
At the beginning of the 20th century, with the development of organic structure theory and advances in spectroscopic technology, scientists began to work on determining the precise structure of 4-methoxyindole. In 1905, British chemist Perkin confirmed for the first time through systematic degradation experiments and synthetic verification that the methoxy group was located at position 4 of the indole ring. His method involved oxidizing 4-methoxyindole to the known indigo carmine acid, and then inferring the position of the methoxy group in the original structure through analysis of methylation sites.
The application of X-ray crystal diffraction technology provides decisive evidence for the structural confirmation of 4-methoxyindole. In the 1950s, Robertson et al. first obtained the single crystal structure of 4-methoxyindole, directly confirming Perkin's structural hypothesis. At the same time, the emergence of nuclear magnetic resonance technology has enabled scientists to study the structural characteristics of 4-methoxyindole in solution. In 1958, Jackman and Wiley first reported the proton NMR spectrum of 4-methoxyindole, further verifying its structure.
The early methods for synthesizing 4-methoxyindole mainly relied on the degradation of natural products and simple chemical modifications. In 1912, Fischer reported a method for synthesizing 4-methoxyindole through direct methoxylation of indole, but the yield was low and the selectivity was poor. In the 1920s, with the development of organic synthesis methodology, Reisset and Madinavetia respectively developed routes for synthesizing 4-methoxyindole through cyclization of phenylhydrazine derivatives, significantly improving synthesis efficiency.
Modern synthetic chemistry provides more efficient and selective methods for the preparation of 4-methoxyindole. In the 1970s, the application of cross coupling reactions made the synthesis of 4-substituted indoles more convenient. In 1995, Buchwald and Hartwig reported palladium catalyzed 4-methoxylation of indole, which is still a commonly used method for preparing 4-methoxyindole in the laboratory. After entering the 21st century, transition metal catalyzed C-H activation reactions provided a more atomically efficient pathway for the synthesis of 4-methoxyindole.
4-methoxyindole is widely distributed in nature, but its content is usually low. In addition to its initial discovery in Asteraceae plants, subsequent studies have detected the presence of 4-methoxyindole in various plants such as Brassicaceae and Fabaceae. It is particularly noteworthy that certain marine organisms such as sponges and corals also contain 4-methoxyindole derivatives, which opens up new research directions for marine natural product chemistry.
In terms of biosynthetic pathways, studies have shown that 4-methoxyindole in plants is mainly produced through the tryptophan metabolic pathway. In the 1990s, scientists identified specific cytochrome P450 enzymes responsible for 4-methoxylation of the indole ring in several plants. These findings not only explain the biosynthetic mechanism of 4-methoxyindole, but also lay the foundation for the production of such compounds using synthetic biology methods.
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