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5-Chloroindole-2-carboxylic acid is a chemical substance, CAS 10517-21-2, The molecular formula is C9H6ClNO2. It presents almost white to pale yellow powder crystals, with high thermal stability and relatively low solubility. Almost insoluble in water at room temperature, but soluble in organic solvents such as sodium hydroxide solution, potassium hydroxide solution, ethanol, acetone, benzene, dichloromethane, etc. It can be used as various synthetic intermediates and pharmaceutical intermediates, mainly for laboratory research and development processes and pharmaceutical chemical production processes. It also plays an important role in the laboratory research and development process. Due to its unique chemical properties and reactivity, it can be used as a commonly used reagent and catalyst in laboratories to participate in the research and exploration of various chemical reactions.

|
Chemical Formula |
C9H6ClNO2 |
|
Exact Mass |
195 |
|
Molecular Weight |
196 |
|
m/z |
195 (100.0%), 197 (32.0%), 196 (9.7%), 198 (3.1%) |
|
Elemental Analysis |
C, 55.26; H, 3.09; Cl, 18.12; N, 7.16; O, 16.36 |


5-Chloroindole-2-carboxylic acid is an important organic compound with the chemical formula C9H6ClNO2, molecular weight 195.6024, and CAS number 10517-21-2. This compound has a wide range of applications in multiple fields, and the following is a detailed explanation of its uses:
This compound has a wide range of applications in the pharmaceutical field, especially in drug synthesis and biological activity research. Its unique chemical structure makes it an important intermediate for various drug molecules. For example, it can be used to synthesize compounds with anti-inflammatory, anti-tumor, and antibacterial activities. In terms of anti-inflammatory drugs, amide derivatives with anti-inflammatory activity can be generated by reacting with different amine compounds. These derivatives exert anti-inflammatory effects by inhibiting the release of inflammatory mediators. In the research of anti-tumor drugs, its structural modification can generate various compounds with potential anti-tumor activity. For example, by combining it with different heterocyclic compounds, molecules with inhibitory effects on tumor cell proliferation and inducing tumor cell apoptosis can be synthesized. These compounds exert anti-tumor effects by interfering with the signaling pathways of tumor cells or inhibiting the activity of key enzymes.

Application in the field of medicine

In addition, it has also shown potential in the development of antibacterial drugs. By combining it with different antibacterial groups, compounds with broad-spectrum antibacterial activity can be synthesized. These compounds exert antibacterial effects by disrupting bacterial cell walls or inhibiting bacterial protein synthesis. For example, the combination of this compound with β - lactam antibiotics can enhance its antibacterial effect and expand its antibacterial spectrum. In terms of biological activity research, it and its derivatives also exhibit various biological activities. For example, certain derivatives have antioxidant and neuroprotective effects and can be used to treat neurodegenerative diseases. In addition, it can also serve as a fluorescent probe for biological imaging and detection, helping researchers better understand the molecular mechanisms within living organisms.
The unique chemical structure of this compound makes it a key intermediate for various highly efficient pesticide molecules. In terms of insecticides, it can react with different organic phosphorus compounds or amino acid ester compounds to generate derivatives with strong insecticidal activity. These derivatives exert insecticidal effects by inhibiting the nervous system function of pests. For example, the combination of this substance with organic phosphorus compounds can generate organic phosphorus insecticides with high insecticidal activity, which are widely used in the control of agricultural pests. In the development of herbicides, it has also shown great potential.

Application in the field of pesticides

By combining it with different phenoxycarboxylic acid compounds, compounds with broad-spectrum herbicidal activity can be synthesized. These compounds inhibit the growth and reproduction of weeds by interfering with their growth hormone metabolism. For example, its combination with 2,4-dichlorophenoxyacetic acid can generate herbicides with efficient weed control activity, which are widely used for weed control in farmland. In addition, it can also be used to develop new types of fungicides. By combining it with different heterocyclic compounds, compounds with broad-spectrum bactericidal activity can be synthesized.
What is the anti-tumor mechanism of the derivatives produced by this compound?
5-Chloroindole-2-carboxylic acid derivatives play an important role in the development of anti-tumor drugs, and their anti-tumor mechanisms are diverse. The following is a detailed introduction to the anti-tumor mechanisms of some major indole derivatives:
Indolecarboxylic acid compounds
These compounds have inhibitory effects on cyclin dependent kinase 4 (CDK4). CDK4 plays a central role in the cell cycle regulatory network and is closely related to tumorigenesis. It is often overexpressed in tumor cells. Indolecarboxylic acid compounds, as CDK4 inhibitors, can prevent cell division and achieve anti-tumor effects. Pharmacological experiments show that these compounds have excellent CDK4 inhibitory activity and can be used to prepare drugs for preventing or treating diseases related to CDK4 inhibitors, such as melanoma, liver cancer, gastric cancer, non-small cell lung cancer, prostate cancer, thyroid cancer, colorectal cancer, pancreatic cancer cancer, ovarian cancer, breast cancer cancer, esophageal cancer, gastrointestinal cancer, etc.
Indole-3-methanol and its derivatives
Indole-3-carbinol, a natural component in brassica vegetables, can induce cell cycle arrest in human breast cancer cells. Its derivatives, such as indole-3-methanol, whose hydrogen on the nitrogen atom is replaced by alkoxy or whose carbon chain length is increased, can significantly enhance the inhibitory effect on human breast cancer cells. In addition, the derivatives of hydrogen substituted by benzyl at position 1 also greatly enhanced the inhibitory effect on human breast cancer MCF-7 and MDA-MB-231 cells.
Indole alkaloids
Changchun alkaloids: extracted from the flowers of the Apocynaceae family, belonging to the indole alkaloids. They achieve cytotoxicity by binding to microtubule proteins, inhibiting microtubule polymerization, preventing split cells from forming spindles and stopping division in the middle stage, thereby exerting anti-tumor effects.Marine indole alkaloids, such as topsentin and bromatopcentin, have strong physiological activity, especially anti-tumor activity. Its anti-tumor mechanism may involve multiple pathways, such as interfering with the cell cycle, inducing cell apoptosis, etc.
Monoterpenoid indole alkaloids
Camptothecin and 10 hydroxycamptothecin are extracted from the fruit of the deciduous tree Camptothecin in the family Gongtong. They can selectively act on the S phase of the cell cycle, inhibit the activity of type I topoisomerase, thereby interfering with DNA replication and inhibiting tumor cell mitosis. In addition, 10 hydroxycamptothecin can induce apoptosis in various tumor cells.
Indolezidine alkaloids
This type of alkaloid, such as coumarin, has a wide range of anti-tumor activities. Its anti-tumor mechanism may involve inhibiting mannosidase and mannosidase, leading to lysosomal storage disease and changes in glycoprotein synthesis, thereby causing neurological dysfunction. In addition, coumarin can stimulate lymphocyte proliferation, enhance the function of T lymphocytes stimulated by antigens, activate the natural anti-tumor immune system, and thus enhance the body's immune capacity.
Indoquinoline ketone
Banlangen ketone B: It has strong killing effect on human liver cancer cells and ovarian cancer cells in vitro, and its inhibitory effect is in a gradient relationship with concentration. At the same time, it also has the ability to induce differentiation, reduce the expression of telomerase activity, and reverse the transformation of tumor cells into normal cells.Wu Zhu Yin: One of the main active ingredients extracted from Wu Zhu Yin, it has significant cytotoxicity against various human tumor cells. Its anti-tumor mechanism may involve multiple pathways such as interfering with the cell cycle and inducing cell apoptosis.
Application and Mechanism Study of 5-Chloroindole-2-carboxylic Acid in the Field of Information Molecular Precursors
Information molecules (such as quorum sensing signaling molecules, neurotransmitters, hormones, etc.) play a critical regulatory role in biological systems, and their synthesis and degradation processes directly affect intercellular communication, group behavior, and disease development. 5-Chloroindole-2-carboxylic acid (CAS number 10517-21-2), as a chlorine containing indole derivative, has shown significant value in the synthesis of information molecule precursors, signal transduction interference, and the development of novel drugs due to its unique chemical structure (chlorine atom replacing the hydrogen at position 5 of the indole ring, carboxylic acid group located at position 2) and reactivity.
Mechanism of acting as a signal molecule antagonist or degrader
5-Chloroindole-2-carboxylic acid and its derivatives can competitively bind to signal molecule receptors through structural simulations, blocking signal transduction
AHL signal antagonism: Compounds such as thiolactones and cyclic azahemiatals, due to their structural similarity to AHLs, can competitively bind to LasR receptors and inhibit the expression of QS regulated toxic factors in Pseudomonas aeruginosa. 5-Chloroindole-2-carboxamide derivatives may interfere with AHLs LasR interactions through a similar mechanism.
AI-2 signal interference: 4,5-dihydroxy-2,3-pentanedione (DPD) is the active form of AI-2, and its homologs can competitively bind to LuxP receptors, inhibiting AI-2 mediated biofilm formation. 5-Chloroindole compounds may generate AI-2 antagonists by modifying the DPD structure.

Degradation of signal molecules

The enzymatic degradation of signaling molecules is an important mechanism for regulating QS. 5-Chloroindole-2-carboxylic acid may promote the degradation of signaling molecules through the following pathways:
Induced degradation enzyme expression: Some lactic acid bacteria can secrete AHL lactonase (AiiA) to hydrolyze the lactone ring of AHLs. 5-Chloroindole compounds may act as inducers to activate the expression of degradation enzyme genes in bacteria and enhance the ability to clear signaling molecules.
Chemical environment changes: The acidity of 5-chloroindole-2-carboxylic acid may lower local pH, promote hydrolysis of AHLs lactone rings (pH dependent degradation), and accelerate signal molecule inactivation.
Future research directions
Structural optimization
Screening highly active derivatives through computer-aided design (CADD) to improve selectivity towards specific signaling molecules or receptors.
Deepening the mechanism of action
Using techniques such as cryo electron microscopy and surface plasmon resonance (SPR) to analyze its binding mode with signal molecules or receptors.
Preclinical studies
Conduct pharmacokinetic (PK) and pharmacodynamic (PD) studies to evaluate their efficacy and safety in animal models.
Multi target regulation
Exploring its combination strategy with antibiotics and immune modulators to enhance the therapeutic effect on complex infections or diseases.
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