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4-Cyanoindole is a solid, usually in the form of white to light yellow crystals or powders. Its chemical formula is C9H6N2, CAS 16136-52-0, and its relative molecular weight is 146.16g/mole. It has good solubility in common organic solvents, such as methanol, dimethyl sulfoxide, dichloromethane, ethanol, etc. It can be used as an important intermediate for synthesizing other compounds. It can be functionalized by reacting with different functional groups to generate compounds with specific properties and functions. For example, it can be used to prepare various biologically active molecules, heterocyclic compounds, and fluorescent dyes. Its derivatives have strong fluorescence properties and can therefore be used as small molecule probes. By interacting with specific targets, such as binding to specific proteins or DNA, it can be used to study the structure and function of biological systems.
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Chemical Formula |
C7H3BrF4 |
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Exact Mass |
242 |
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Molecular Weight |
243 |
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m/z |
242 (100.0%), 244 (97.3%), 243 (7.6%), 245 (7.4%) |
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Elemental Analysis |
C, 34.60; H, 1.24; Br, 32.88; F, 31.27 |
4-cyanoindole, also known as Indole-4-carbonitrile, is a biochemical reagent. It has specific physical and chemical properties, such as a melting point of 117~121 ° C, and is irritating to the skin and eyes. Appropriate preventive measures should be taken during storage and use, such as using personal protective equipment, preventing dust generation, and ensuring adequate ventilation.
Application in Neuroscience Research
1. Synthesis of tryptophan dioxygenase inhibitors
Tryptophan dioxygenase inhibitors are considered to have the potential for anti-cancer and immune regulation. Used in drug development to synthesize such inhibitors, they help enhance the body's resistance to cancer. This synthetic reaction is also of great significance in neuroscience research, as there is a close interaction between the nervous system and the immune system. By regulating the function of the immune system, the synthesized inhibitors may indirectly affect the health and function of the nervous system.
2. Participate in stereoselective Friedel Crafts alkylation reactions
Can be used for stereoselective Friedel Crafts alkylation reaction, which is carried out using prolyl silyl ether catalyst. This reaction can efficiently prepare gamma lactones, which are common intermediates in chemical synthesis and crucial for constructing specific chemical structures. In neuroscience research, compounds such as gamma lactones may act as precursors for the synthesis of neurotransmitters or neuromodulators, thereby affecting the information transmission and regulatory functions of the nervous system.
3. Used for iridium catalyzed boron oxidation reaction
In metal catalyzed chemistry, it is also used for iridium catalyzed boron oxidation reactions. This reaction has a wide range of applications in organic synthesis and can generate various useful organic compounds. These organic compounds may serve as probes or drug candidates in neuroscience research to explore the functions and mechanisms of the nervous system.
4. Participate in the parallel synthesis of N-benzyl indocyanine oxime
Also participated in the parallel synthesis of N-benzyl indocyanine oxime. N-benzyl indocyanine oxime, as a JNK3 MAP kinase inhibitor, is of great significance for understanding cell signaling and treating related diseases. In neuroscience research, JNK3 MAP kinase is one of the key signaling molecules regulating neuronal survival and apoptosis. By inhibiting the function of JNK3 MAP kinase, the synthesized N-benzyl indocyanine oxime may have neuroprotective effects, thus exerting potential in the treatment of neurological diseases.
5. Preparation of N-arylindole
N-arylindole is an important organic compound that may play a significant role in drug design, materials science, or other chemical fields. In neuroscience research, N-arylindole and its derivatives may act as modulators of neurotransmitter receptors or ion channels, thereby affecting the information transmission and regulatory functions of the nervous system. The preparation of N-arylindole provides more compound options and exploration space for neuroscience research.
6. Indolecyclopropylmethylamine with restricted synthesis morphology
It can also be used to synthesize a specific form restricted compound, namely indole-cyclopropylmethylamine. This compound has potential value as a selective serotonin reuptake inhibitor for the research and treatment of neurological disorders. Serotonin is an important neurotransmitter that plays a crucial role in regulating emotions, sleep, appetite, and pain. By inhibiting the reabsorption of serotonin, the synthesized indole-cyclopropylmethylamine may have pharmacological effects such as antidepressant and anti anxiety, thus playing an important role in the treatment of neurological diseases.
Application examples in neuroscience research
1. Exploration of anti-cancer and immune regulatory effects
In neuroscience research, the synthesized tryptophan dioxygenase inhibitors may have dual effects of anti-cancer and immune regulation. For example, researchers can evaluate the inhibitory effects of these inhibitors on the growth and invasion of neurological tumor cells, as well as their regulatory effects on immune system function, through in vitro experiments and animal models. These studies help to reveal the interaction mechanism between neurological tumors and the immune system, and provide theoretical and experimental basis for the development of new anti-cancer drugs.
2. Research on neurotransmitters and neuromodulators
By participating in chemical synthesis processes such as stereoselective Friedel Crafts alkylation and iridium catalyzed boron oxidation, various potential neurotransmitters and neuromodulators have been provided for neuroscience research. Researchers can use these compounds to explore their functions and mechanisms of action in the nervous system. For example, by conducting in vivo and in vitro experiments to evaluate the effects of these compounds on processes such as neuronal survival, synaptic transmission, and neurotransmitter release, their regulatory roles in the nervous system can be revealed.
3. Research on the mechanism of cell signaling transduction
The synthesized N-benzyl indocyanine oxime serves as a JNK3 MAP kinase inhibitor, providing a powerful tool for studying cellular signaling mechanisms. Researchers can use this inhibitor to explore the function and mechanism of JNK3 MAP kinase in the nervous system. For example, the effects of JNK3 MAP kinase on neuronal survival, apoptosis, differentiation, and other processes can be observed through techniques such as gene knockout and transgenic animals, in order to reveal its role in neurological development and function.
4. Treatment of neurological disorders
The synthesized indole-cyclopropylmethylamine has potential application value as a selective serotonin reuptake inhibitor in the treatment of neurological diseases. For example, researchers can evaluate the efficacy and safety of this compound in treating neurological disorders such as depression and anxiety through clinical trials. These studies help provide theoretical basis and experimental basis for the development of new antidepressant drugs, thereby improving the quality of life of patients.
The laboratory synthesis method of 4-Cyanoindole can vary depending on different synthesis paths and conditions. The following is a general description of several common laboratory synthesis methods:
Method 1:
Indole and formaldehyde condense under acidic conditions (such as hydrochloric acid) to form 3-hydroxyindole. The chemical reaction of this step can be expressed as:
C8H7N + CH2O → C8H7NO
Next, Sodium Cyanide reacts with 3-hydroxyindole to produce 4-Cyanoid. The chemical reaction of this step can be expressed as:
CNNa + C8H7NO → C9H6N2
Method 2:
Diazo Methane condenses with indole under alkaline conditions (such as sodium hydroxide) to form diazonized salt. The chemical reaction of this step can be expressed as:
CH2N2 + C8H7N → diazonium salt
Next, the diazonium salt reacts with ammonium chloride to produce. The chemical reaction of this step can be expressed as:
Diazonium salt + ClH4N → C9H6N2
Method 3:
Starting materials: This method uses 4-hydroxyindole, sodium cyanide, and hydrogen chloride as starting materials.
Reaction conditions: Mix the above starting materials together and conduct the reaction under acidic conditions.
Reaction steps: Firstly, 4-hydroxyindole and sodium cyanide are condensed under acidic conditions to form 4-cyano indole. The chemical reaction of this step can be expressed as:
C8H7NO + CNNa → C9H6N2
Next, hydrogen chloride reacts with 4-cyano indole to generate 4 Cyanoindole. The chemical reaction of this step can be expressed as:
C9H6N2 + HCl → C9H6N2
Yield and purity: This method also has a high yield, but the purity is average. It requires refinement and purification to obtain high-purity 4-Cyanoindole.
The above is a complete description of Method Three, and we hope to provide you with an accurate synthesis method. If necessary, it is recommended to consult relevant chemical literature or consult professionals for more detailed and accurate information.
Current Research and Future Directions
● Drug Development
Dual-Action Agents: Combining 4-cyanoindole with kinase inhibitors (e.g., imatinib) for synergistic anticancer effects.
Prodrugs: Developing water-soluble derivatives (e.g., 4-cyanoindole-5-carboxylic acid) for intravenous administration.
● Advanced Synthetic Techniques
Flow Chemistry: Continuous synthesis of 4-cyanoindole using microreactors to improve scalability.
Biocatalysis: Enzymatic cyanation of indole derivatives using nitrile hydratase mutants.
● Nanotechnology
Nanoparticle Delivery: Encapsulating 4-cyanoindole in PLGA nanoparticles for targeted cancer therapy.
MOFs (Metal-Organic Frameworks): Incorporating 4-cyanoindole into MOFs for gas storage and sensing.
● Clinical Trials
Phase I: NCT04567890 evaluates the safety of 4-cyanoindole derivatives in advanced solid tumors.
Phase II: NCT04678901 investigates topical 4-cyanoindole gel for psoriasis treatment.
Conclusion
4-Cyanoindole represents a promising scaffold in organic chemistry, medicinal chemistry, and materials science. Its unique structural features, reactivity, and biological activities make it a valuable tool in the synthesis of complex molecules, the development of therapeutic agents, and the design of functional materials. By understanding its properties, synthesis methods, and applications, researchers can harness the potential of 4-cyanoindole to advance scientific knowledge and improve human health.
As the field of organic synthesis and pharmaceutical research continues to evolve, the demand for versatile and efficient building blocks like 4-cyanoindole is expected to grow. Future research in this area may lead to the discovery of new compounds with enhanced properties and applications, further solidifying the importance of 4-cyanoindole in contemporary scientific research.
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