4-Hydroxyindole CAS 2380-94-1

4-Hydroxyindole is an organic compound with the molecular formula C8H7NO. A solid powder with a grayish white to light yellow color, insoluble in water but soluble in organic solvents such as ether, chloroform, and methanol. In the molecular structure, a phenolic hydroxyl group replaces the hydrogen atom on the indole ring, giving the molecule some special properties. It has a low solubility in water and is almost insoluble in water, but it has a high solubility in organic solvents. It is easy to oxidize in the air, especially under alkaline conditions, and is more prone to oxidation reactions, generating dark substances. Therefore, it is necessary to avoid contact with air as much as possible during storage and use. There are two configurations, trans and cis, with the trans configuration being more stable. Under certain conditions, the cis configuration can be transformed into a trans configuration. Under ultraviolet light, it can emit strong fluorescence due to its conjugated double bonds and hydroxyl groups. In addition, structural identification and quantitative analysis can be carried out through methods such as infrared spectroscopy and nuclear magnetic resonance spectroscopy.

Alkaloids are a type of natural product with broad biological activity and unique pharmacological effects. 4-Hydroxyindole, as an important organic compound, has broad application value in the synthesis of alkaloids.

1. Vinblastine and vincristine:

Vincristine and Vinorelbine are widely used anti-tumor drugs in medicine, belonging to the alkaloids of Changchun flowers. They were constructed based on 4 Hydroxyindole as the basic structural unit, and various alkaloids with anticancer activity were obtained by chemical modification of their side chains.

The main mechanism of action of vinblastine and vincristine is to inhibit the polymerization of microtubule proteins, thereby interfering with cell division. They have certain therapeutic effects on cancers such as acute lymphoblastic leukemia, acute myeloid leukemia, and malignant lymphosarcoma. Due to their unique mechanism of action and excellent therapeutic effects, vinblastine and vincristine have become important drugs for clinical treatment of cancer.

2. Camptothecin alkaloids:

Camptothecin is an alkaloid with anticancer activity, originally isolated from the fruits of Chinese camptotheca trees. It is a topoisomerase inhibitor that can inhibit DNA helicase, causing DNA breakage and ultimately killing tumor cells.

The chemical structure of camptothecin is constructed based on 4 hydroxyindole as the basic structural unit, and various camptothecin derivatives have been obtained by modifying its side chains. Among them, Irinotecan is a water-soluble derivative of camptothecin, which has been widely used in clinical practice. Irinotecan has certain therapeutic effects on diseases such as colorectal cancer, ovarian cancer, and lung cancer, especially with significant therapeutic effects on colorectal cancer.

3. Other alkaloids:

In addition to vinblastine and camptothecin, it can also be used to synthesize other alkaloids with anticancer activity. For example, Etoposide is an anti-tumor drug that can inhibit DNA helicase and RNA polymerase, thereby killing tumor cells. Etoposide is constructed based on 4 Hydroxyindole as the basic structural unit, and various anticancer derivatives of Etoposide have been obtained by modifying its side chains.

In addition, it can also be used to synthesize other types of alkaloids, such as matrine, colchicine, etc. These alkaloids have a wide range of clinical applications, such as matrine which has certain therapeutic effects on liver disease, tumors, and cardiovascular diseases, and colchicine which is mainly used to treat gout. It has broad application value in the synthesis of alkaloids. By chemically modifying and modifying its side chains, various alkaloid derivatives with anticancer activity can be obtained. These alkaloid drugs have important clinical application value and play an important role in the treatment of diseases such as cancer, hepatitis, and gout.

4. As a synthetic intermediate: can be used as an intermediate for synthesizing other compounds. For example, 4-aminoindole can be obtained by reacting it with ammonia, which is an important intermediate in organic synthesis.

5. Synthesis of heterocyclic compounds: it can be used to synthesize heterocyclic compounds such as tryptophan, indole ketones, etc. These compounds have extensive applications in fields such as pharmaceuticals, pesticides, and materials.

The resorcinol method is a commonly used method for synthesizing 4-hydroxyindole. The following are the detailed steps and chemical equations of this method:

Step 1: Isomerization of resorcinol

Heat resorcinol to a molten state, then slowly add concentrated hydrochloric acid while stirring and heating. React at a temperature of approximately 70 ℃ for a period of time until resorcinol is completely dissolved. Then, pour the reaction mixture into ice water, adjust it to slightly acidic with a small amount of concentrated hydrochloric acid, and then extract with ether. Dry the extraction solution with anhydrous sodium sulfate, filter and recover ether to obtain 4-hydroxybenzoic acid.

Chemical equation:

C₆H₄(OH)₂ → HOOC-C₆H₄-COOH

Step 2: Catalytic hydrogenation

Dissolve 4-hydroxybenzoic acid in ethanol, add a certain amount of catalyst (such as palladium carbon), and carry out hydrogenation reaction at a certain temperature and pressure. After a period of reaction, filter the mixture, extract the filtrate with ether, dry the extract with anhydrous sodium sulfate, filter and recover ether to obtain 4-aminobenzoic acid.

Chemical equation:

HOOC-C₆H₄-COOH + 2H₂ → HOOC-C₆H₄-CH₂NH₂

Step 3: Cyclization reaction

Mix 4-aminobenzoic acid with ethyl bromopyruvate and undergo cyclization reaction at a certain temperature. After a period of reaction, filter the mixture, extract the filtrate with ether, dry the extract with anhydrous sodium sulfate, filter and recover ether to obtain product.

Chemical equation:

HOOC-C₆H₄-CH₂NH₂ + BrCH₂COOEt → H₂N-C₆H₄-CHBrCOOEt → C₈H₇NO+C₄H₈O₂ + HBr

The above are the detailed steps and chemical equations for the synthesis of 4-Hydroxyindole using resorcinol method. It should be noted that toxic or harmful raw materials and solvents should be avoided as much as possible during the synthesis process to reduce negative impacts on the environment and human health. Meanwhile, different synthesis methods and conditions can be selected and optimized according to actual needs to obtain high-quality products.

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