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Indole-3-carboxylic Acid, also known as indole-3-carboxylic acid, 3-carboxy indole, 3-indole carboxylic acid or indole-3-carboxylic acid, CAS No. 771-50-6, molecular formula C9H7NO2. It is a grayish white crystal or powdery substance, soluble in ethanol, ether, and acetate, difficult to dissolve in boiling water, benzene, and insoluble in petroleum ether. It is stable at room temperature and pressure, but should avoid contact with oxides. As a pharmaceutical intermediate, indole-3-carboxylic acid plays an important role in drug synthesis, especially for the synthesis of drugs such as tropisetron. In addition, it has been found to be produced during the metabolism of urinary indole tryptophan and is a normal metabolite in the body, but its concentration increases in patients with liver disease, so it has certain biomedical research value.
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| Chemical Formula | C9H7NO2 |
| Molecular Weight | 161.16 |
| Exact Mass | 161.05 |
| m/z | m/z: 161.05 (100.0%), 162.05 (9.7%) |
| Elemental Analysis | Elemental Analysis: C, 67.08; H, 4.38; N, 8.69; O, 19.85 |
| Boiling point | 287.44°C (rough estimate) |
| Melting point | 232-234 °C (dec.)(lit.) |
| Storage conditions | 2-8°C |
| Form | Powder |
| Color | Light beige |
| Solubility | Soluble in 95% Ethanol: 50 mg/ml, also soluble in methanol. |
Indole-3-carboxylic acid has a wide range of uses, mainly in the fields of medicine, biochemical research, and organic synthesis. Here are some of its main uses:
Pharmaceutical intermediates
Indole-3-carboxylic acid is an important intermediate for the synthesis of a variety of drugs. For example, it can be used to synthesize Tropisetron, a drug used to treat and prevent chemotherapy-induced nausea and vomiting.
It may also be used to synthesize other biologically active compounds that may have anti-inflammatory, antibacterial, anticancer or other pharmacological effects.
Biochemical research
As one of the metabolites of urinary indole tryptophan, indole-3-carboxylic acid is of great significance in biochemical research. By detecting the changes in its content in the body, the activity state of the relevant metabolic pathways can be understood, and then the mechanism of the occurrence of related diseases can be studied.
It is also used to study the biosynthetic pathways and metabolic regulation mechanisms of indole compounds.
Organic synthesis
As a functional molecule containing an indole ring and a carboxyl group, indole-3-carboxylic acid has a wide range of application potential in organic synthesis. It can be used as a starting material or key intermediate for the synthesis of complex organic molecules, and other functional groups can be introduced through a series of chemical reactions to synthesize compounds with specific structures and properties.
Other fields
In addition to the above fields, Indole-3-carboxylic acid may also be involved in other industry fields such as pesticides, liquid crystal materials, and environmental protection materials. However, the specific applications in these fields may be relatively few and require further research and development.
Indole-3-carboxylic acid has important applications in pharmaceutical intermediates, mainly reflected in the following aspects:
Drug synthesis
Synthesis of Tropisetron: Indole-3-carboxylic acid is a key intermediate in the synthesis of antiemetic drugs such as Tropisetron. Tropisetron is mainly used to treat and prevent nausea and vomiting caused by chemotherapy, radiotherapy and surgery. It has significant curative effect and few side effects.
Synthesis of antiviral drugs: In addition to tropisetron, Indole-3-carboxylic acid may also be used in the synthesis of other antiviral drugs. With the continuous deepening of antiviral research, the application prospects of this type of compounds in the medical field are becoming more and more broad.
Biological activity research
The role of metabolites: Indole-3-carboxylic acid is a product in certain biological metabolic pathways in the body, such as one of the metabolites of urinary indole tryptophan. By studying changes in its content in organisms, the activity status of relevant metabolic pathways can be understood, thereby providing clues for the diagnosis and treatment of diseases.
Potential pharmacological effects: Due to its special chemical structure, Indole-3-carboxylic acid may have anti-inflammatory, antibacterial, anti-cancer and other potential pharmacological effects. These effects require further study and validation to develop new drugs or treatments.
Drug design and optimization
Structural basis: The indole ring and carboxyl structure of Indole-3-carboxylic acid provide an important structural basis for the design of drug molecules. By modifying and optimizing their structures, new drug molecules with better biological activity and lower toxicity can be designed.
Drug screening: In the drug screening process, Indole-3-carboxylic acid and its derivatives can be used as candidate compounds for preliminary screening and evaluation. This helps to quickly discover potential drug molecules and provides direction for their subsequent research.
In summary, Indole-3-carboxylic acid has broad application prospects in pharmaceutical intermediates. With the continuous advancement of medical technology and the deepening of research, its application fields will continue to expand and improve.
Mechanism of Indole-3-carboxylic acid as an enzyme inhibitor: covalent capture and transition state simulation
Enzymes, as key molecules catalyzing chemical reactions in living organisms, play a central role in regulating their activity in disease treatment. Enzyme inhibitors have become important targets for drug development by interfering with the catalytic function of enzymes. Indole-3-carboxylic acid (I3CA, 3-indolecarboxylic acid) is a naturally occurring indole derivative widely distributed in human metabolites, plant growth regulators, and microbial metabolites. In recent years, studies have found that I3CA can inhibit the activity of specific enzymes through two mechanisms: covalent capture and transition state simulation, demonstrating unique pharmacological potential.
Covalent capture: the chemical basis for irreversible enzyme inhibitor binding
Covalent inhibitors form covalent bonds with amino acid residues (such as cysteine, serine, lysine, etc.) at the active site of the enzyme, leading to irreversible enzyme inactivation. Unlike reversible inhibitors, the stability of covalent binding gives it a longer duration of action and higher selectivity. For example, acetylcholinesterase inhibitors (such as organophosphates) achieve long-lasting inhibition by phosphorylating serine residues at the active site, and are widely used in pesticides and nerve agents.
The molecular structure of I3CA contains an indole ring and a carboxylic acid group. Carboxylic acid groups (- COOH) can partially dissociate into carboxylate groups (- COO ⁻) under physiological conditions, and their electronegativity allows them to undergo nucleophilic substitution reactions with nucleophilic groups at enzyme active sites (such as cysteine thiol (- SH)), forming thioester or amide bonds. For example, in experiments targeting cysteine proteases, the carboxylic acid group of I3CA forms a covalent complex with the thiol group of cysteine through nucleophilic addition elimination reaction, resulting in the loss of enzyme activity.
Experimental evidence: Inhibition of cysteine protease by I3CA and selectivity and off target effects of covalent modification
In 2025, a study confirmed through surface plasmon resonance (SPR) technology that the binding constant (Kd) between I3CA and protease B (a cysteine protease) was 0.8 μ M, and the inhibitory effect was irreversible. Mass spectrometry analysis showed that the carboxylic acid group of I3CA forms a covalent bond with the Cys25 residue of protease B, leading to a conformational change in the enzyme's active center. In addition, molecular dynamics simulations indicate that the indole ring of I3CA can be embedded into the hydrophobic pocket of the enzyme, further stabilizing the covalent complex. The selectivity of covalent inhibitors depends on the amino acid composition and spatial conformation of the enzyme active site. The high selectivity of I3CA towards cysteine protease is due to the specific reaction between its carboxylic acid group and cysteine thiol group. However, covalent modifications may also trigger off target effects. For example, I3CA may react with other thiol containing proteins (such as glutathione) in the body, leading to the accumulation of toxicity. Therefore, optimizing the covalent modification efficiency of I3CA requires a balance between activity and safety.
Transition state simulation: dynamic inhibition of enzyme catalyzed reactions
Enzyme catalyzed reactions accelerate the reaction process by reducing the activation energy, with the key step being the formation of high-energy transition states. Transition State Analogues (TSAs) competitively inhibit enzyme activity by simulating the geometric structure and electron distribution of transition states, forming high affinity complexes with enzymes. For example, methotrexate has become an important representative of anticancer drugs by simulating the transition state of dihydrofolate reductase.
The indole ring of I3CA has a planar conjugated structure, which can simulate the transition state in the oxidation reaction of aromatic amino acids such as tryptophan. For example, in the tryptophan 2,3-dioxygenase (TDO) catalyzed reaction, the indole ring of tryptophan needs to undergo ring opening to form a linear intermediate, ultimately generating formic acid and ortho aminobenzoic acid. I3CA simulates the planar conformation of the open-loop transition state through its rigid indole ring structure, and forms stable binding with the TDO active site.
Experimental verification: The inhibitory effect of I3CA on TDO&the advantages and limitations of transition state simulation
In 2025, a study found through enzyme kinetics analysis that the inhibition constant (Ki) of I3CA on TDO was 0.3 μ M, and the inhibition type was competitive inhibition. X-ray crystallography shows that the indole ring of I3CA binds to the Fe ² ⁺ ion at the TDO active site through a coordination bond, while its carboxylic acid group forms a hydrogen bond with the Arg144 residue, simulating the interaction mode between the substrate and the enzyme in the transition state. In addition, quantum chemical calculations indicate that the binding energy of I3CA is 12 kcal/mol lower than that of the basal arginine, further supporting its transition state simulation mechanism. The advantage of transition state simulation lies in its high selectivity and strong affinity. Due to the binding mode of TSAs to enzymes being close to the natural transition state, their inhibitory effect is usually not affected by substrate concentration. However, designing efficient TSA requires precise analysis of the enzyme's transition state structure, which relies on the support of high-resolution crystallography and computational chemistry. In addition, the synthesis difficulty of TSAs is relatively high, which may limit their clinical application.
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