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4-Chloro-7-azaindole is an important nitrogen-containing aromatic heterocyclic compound. Its structure can be regarded as a carbon atom on the benzene ring of the indole molecule being replaced by a nitrogen atom, thereby forming a double-ring core skeleton of pyridine and pyrrole, and a chlorine atom is connected at the 4th position of this skeleton. This ingenious structural modification endows it with unique physical and chemical properties: it is a white to light yellow crystalline powder, and the coexistence of the electron-rich pyrrole ring and the electron-deficient pyridine ring in its molecule generates a significant intramolecular charge transfer effect, which also enables it to act as both a hydrogen bond donor and a hydrogen bond acceptor, greatly enhancing the molecular recognition and self-assembly capabilities. Therefore, this compound plays a crucial role in the fields of medicinal chemistry, materials science, and organic synthesis, especially being widely used as a key pharmacophore or advantageous structure for designing and synthesizing protein kinase inhibitors to develop new anti-cancer drugs; moreover, it is also a core synthetic building block for constructing organic light-emitting materials, coordination polymers, and complex alkaloid natural products, demonstrating extremely high application value and broad research prospects.
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C.F |
C7H5ClN2 |
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E.M |
152 |
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M.W |
153 |
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m/z |
152 (100.0%), 154 (32.0%), 153 (7.6%), 155 (2.4%) |
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E.A |
C, 55.10; H, 3.30; Cl, 23.23; N, 18.36 |
Application in the pharmaceutical field
4-chloro-7-azaindole, with the chemical formula C7H5ClN2, is an important organic and pharmaceutical intermediate. It usually appears as a white or off white powder with certain chemical and thermal stability. In pharmaceutical and chemical synthesis processes, it is often used as a starting material or intermediate to participate in various chemical reactions and generate biologically active compounds.
1. Synthesis of antibacterial drugs
It can also be used for synthesizing antibacterial drugs. Antibacterials are important tools for the treatment of infectious diseases, and their derivatives can achieve the purpose of treating infectious diseases by inhibiting the growth and reproduction of bacteria. These types of drugs usually have broad-spectrum antibacterial activity and can target multiple bacteria for bactericidal or bacteriostatic effects.
In the development process of antibacterial drugs, as an intermediate, it can participate in various chemical reactions to generate compounds with different antibacterial activities. Through screening and optimization, new antibacterial drugs with high efficiency, low toxicity, and broad-spectrum antibacterial activity can be obtained.
2. Synthesis of antiviral drugs
In addition to anti-tumor and antibacterial drugs, it can also be used for synthesizing antiviral drugs. Viral diseases are a major public health issue worldwide, and antiviral drugs are an important means of treating viral diseases. Its derivatives can achieve the goal of treating viral diseases by interfering with the replication and infection process of viruses.
In the development process of antiviral drugs, as starting materials or intermediates, they can participate in various chemical reactions to generate compounds with antiviral activity. These compounds have shown significant antiviral effects in both in vitro and in vivo experiments, and are expected to become important candidate compounds for novel antiviral drugs.
In biochemical reagents
4-chloro-7-azaindole, as an important biochemical reagent, has wide application value in life science research. Its unique chemical structure and biological activity make it an important tool for studying complex biochemical processes in organisms, exploring new drug development, and understanding the metabolic mechanisms of organisms.
As a biomaterial for life science related research
It was first used as a biomaterial in the field of biochemistry. Biomaterials refer to materials that interact with biological systems and are used for diagnosis, treatment, or improvement of biological functions. Due to its unique chemical properties, it can simulate or affect certain biochemical processes within living organisms, making it a valuable tool for studying biological functions, metabolism, and disease mechanisms.
In life science research, it is often used in cell culture experiments. Cells are the fundamental structural and functional units of living organisms, and studying their behavior and characteristics is crucial for understanding the overall function of living organisms. It can serve as a regulator of cell proliferation, helping scientists study the mechanisms of cell proliferation, cell cycle regulation, and apoptosis by affecting the growth and division processes of cells.
In addition, it can also be used to study signal transduction processes within living organisms. Signal transduction is an important way of transmitting information between and within cells in living organisms, involving various biomolecules and complex biochemical reactions. It can affect the activity of signal transduction pathways by binding to receptors or enzymes in the body, thus revealing the mechanism and regulation of signal transduction in the body.
Not only is it used as a biological material for life science research, but it has also become an important compound in drug discovery research due to its unique biological activity. Drug discovery is a complex and lengthy process that involves a deep understanding of disease mechanisms in living organisms, identification of potential drug targets, and screening and optimization of candidate drugs.
It can be used as a useful intermediate in the process of drug discovery to synthesize compounds with specific pharmacological activities. By modifying and altering its chemical structure, a series of derivatives with different biological activities can be generated, which can be further screened and optimized as candidate drugs.
For example, it can be used to synthesize 7-azaindole derivatives, which exhibit good biological activities in anti-tumor, anti-inflammatory, antibacterial and other aspects. By studying their pharmacological mechanisms, we can gain a deeper understanding of the potential and application prospects of these compounds in the treatment of related diseases.
In addition, it can also be used for synthesizing cytokinin analogs. Cytokinins are important hormones that regulate cell proliferation and differentiation in organisms, playing a crucial role in maintaining normal growth and development. By synthesizing cytokinin analogs, their functions and mechanisms of action in vivo can be studied, providing important evidence for the development of new therapeutic methods and drugs.
It also plays an important role in the study of metabolic mechanisms in living organisms. Metabolism is the process of converting substances and energy within an organism, involving various biomolecules and complex biochemical reactions. Studying the metabolic mechanisms within living organisms is of great significance for understanding their normal physiological functions and the mechanisms of disease occurrence.
It can affect the rate and product distribution of metabolic reactions by binding with metabolic enzymes in the organism. By studying its metabolic processes in organisms, the activity of metabolic enzymes, substrate specificity, and the regulation of metabolic pathways can be revealed. These pieces of information are of great value for understanding the metabolic mechanisms in organisms, developing new metabolic regulatory drugs, and predicting the metabolic behavior of drugs in organisms.
Application in the study of cell signaling transduction
Cellular signal transduction is an important way of transmitting information between and within cells in organisms, involving various biomolecules and complex biochemical reactions. It also has important applications in the study of cell signaling.
4-chloro-7-azaindole can affect the activity of signaling pathways by binding to intracellular signaling molecules. By studying its mechanism of action in cellular signal transduction, the functions of signal molecules, the regulation of signal transduction pathways, and the important role of signal transduction in organisms can be revealed. These pieces of information are of great value for understanding the normal physiological functions and mechanisms of disease occurrence in organisms, developing new signal transduction regulatory drugs, and predicting the signal transduction effects of drugs in organisms.
In chemical reagents
4-Chloro-7-azaindole is an organic compound with various biological activities. Due to its unique chemical structure, it has been widely used in many fields.
1. Organic Chemistry:
In the field of organic chemistry, it is widely used to synthesize various types of organic compounds. It serves as a synthetic block and probe for studying organic chemical reaction mechanisms, molecular structures, and material properties. For example, various types of nitrogen heterocyclic compounds, amine compounds, and nitro compounds can be synthesized using 4-chloro-7 azaindole as a raw material, which can be used for further research and development.
2. Drug development field:
It is also widely used in the field of drug development. It serves as an important intermediate or raw material for the synthesis of anti-tumor drugs, antimalarial drugs, and antiviral drugs, providing important support and assistance for the development and research of new drugs. At the same time, it can also be used to study the structure and function of biological molecules, providing important tools for understanding life processes and disease mechanisms. Various types of drug intermediates and candidate drug molecules can be synthesized using 4-chloro-7 azaindole as a raw material, providing an important foundation for the discovery and development of new drugs.
3. Field of Materials Science:
In the field of materials science, it is also used to research and develop various polymer materials and nanomaterials. As a raw material for polymer materials such as synthetic rubber, plastics, and coatings, it can improve the performance and stability of these materials. At the same time, it can also be used to synthesize fluorescent materials and optoelectronic materials, providing new materials for research in the fields of optoelectronic devices and optoelectronic conversion. Various types of material molecules and polymer molecules can be synthesized using 4-chloro-7 azaindole as a raw material, providing an important foundation for studying the structure and properties of materials.
4. Biochemical field:
In the field of biochemistry, it is also used to study and analyze the structure and function of various biological molecules. It can be used to synthesize bioactive small molecule compounds and biological probes, providing important tools for studying the interactions and regulatory mechanisms of biological macromolecules. For example, various types of biological probes and inhibitor molecules can be synthesized using 4-chloro-7 azaindole as a raw material for studying biological processes such as protein, nucleic acid, and cell signal transduction.
A method for preparing 4-Chloro-7-azaindole in the laboratory:
Firstly, raw materials such as 7-azaindole, oxidant, sodium bisulfite, phosphorus oxychloride, and sodium hydroxide need to be prepared. Among them, 7-azaindole can be synthesized or extracted, and oxidants can be hydrogen peroxide, nitric acid, etc. Sodium bisulfite is a weak oxidant, phosphorus oxychloride is a common phosphorus oxidant, and sodium hydroxide is used for oxidative dehydrogenation reaction.
In this step, the oxidant undergoes an oxidation reaction with 7-azaindole to generate 7-azaindole nitrogen oxide. The specific chemical reaction equation is as follows:
C8H5N + HNO3 → C8H5NO
In this step, sodium bisulfite undergoes a reduction reaction with 7-azaindole nitrogen oxide to produce N-oxide-dihydro-7azaindole-2-sulfonic acid sodium. The specific chemical reaction equation is as follows:
C8H5NO + NaHSO3 → C8H5NO3Na
In this step, sodium N-oxide-dihydro-7azaindole-2-sulfonate reacts with phosphorus oxychloride to generate 4-chloro-7azaindole and other byproducts. The specific chemical reaction equation is as follows:
C8H5NO3Na + POCl3 → C8H4ClN + X
In this step, other by-products generated by the reaction are further treated by adding sodium hydroxide. The specific chemical reaction equation is as follows:
X + NaOH → Y + H2O
In this step, the organic solvent generated by the reaction is removed by a rotary evaporator, leaving behind the target product 4-chloro-7azaindole pharmaceutical intermediate.
Through the above steps, high-purity, high synthesis rate, and low-cost 4-chloro-7-azoindole pharmaceutical intermediates can be obtained. This intermediate can be used to synthesize various anti-tumor, antimalarial, and antiviral drugs, and has broad application prospects. In addition, the preparation method is easy to operate, safe and reliable, and suitable for industrial production.
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