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4-Nitroindole is an organic compound with CAS 4769-97-5 and molecular formula C8H6N2O2. A solid or crystalline substance with a light yellow to yellow brown color and a slight irritating odor. The molecular structure contains a nitro group (- NO2), a benzene ring, and a five membered nitrogen heterocycle. The presence of nitro groups gives the compound a significant electron withdrawing effect, affecting the electronic distribution and chemical reaction properties of the entire molecule. It has optical activity, that is, it has optical rotation. This means that it can have different optical configurations, one of which is right-handed and the other is left-handed. This optical rotation can be used to prepare chiral drugs or catalysts. There are obvious absorption peaks in the ultraviolet and visible light ranges. By measuring its spectral characteristics, the molecular structure and electronic distribution of the compound can be understood, which can be used for analysis, detection, and identification applications. It has bright colors and good solubility, and can be used to synthesize some dyes and pigments. For example, by reacting with certain acids, a series of dyes and pigments with different colors and properties can be obtained.
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Chemical Formula |
C8H6N2O2 |
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Exact Mass |
162 |
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Molecular Weight |
162 |
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m/z |
162 (100.0%), 163 (8.7%) |
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Elemental Analysis |
C, 59.26; H, 3.73; N, 17.28; O, 19.73 |
Protein synthesis and functional research
It can be used to study the synthesis and function of proteins. In terms of protein synthesis, it can serve as a fluorescent labeled amino acid analogue for synthesizing peptides. Due to its good photostability, it can be used for fluorescence detection and protein sequence analysis. In addition, by using amino acids labeled with 4Nitroindole, the interaction between proteins and the structure and function of proteins can also be studied.
Enzyme activity research and inhibitor design
Can be used for enzyme activity research and inhibitor design. Due to its electron withdrawing effect, it can serve as an inhibitor of enzyme active sites. By binding to the active site of an enzyme, it can inhibit its catalytic activity, which can be used to study the mechanism of enzyme action and inhibitor design. In addition, by using 4Nitroindole as a probe, the interaction and recognition mechanism between substrates and enzymes can also be studied.
Research on Cell Signal Transduction
Can be used for cell signal transduction research. In the process of cellular signal transduction, many signal transduction molecules need to interact with ATP or other small molecules. By using ATP analogues labeled with 4Nitroindole, the interaction between these signal transduction molecules and ATP can be studied. In addition, by using inhibitors labeled with 4Nitroindole, the regulatory mechanisms of signal transduction pathways and inhibitor design can also be studied.
Design and screening of anti-tumor drugs
It can be used for the design and screening of anti-tumor drugs. Due to its anti-tumor activity, it can be used to prepare anti-tumor drugs. Through high-throughput screening technology, 4Nitroindole analogues with anti-tumor activity can be discovered, and their mechanisms of action and structure-activity relationships can be further studied to develop new anti-tumor drugs. In addition, the proliferation and apoptosis mechanisms of tumor cells can also be studied by using 4Nitroindole labeled probes.
Neuroscience research
Can be used for neuroscience research. In the nervous system, many neurotransmitters and modulators need to interact with receptors. By using neurotransmitters or regulatory analogues labeled with 4Nitroindole, the interaction and recognition mechanisms between these molecules and receptors can be studied. In addition, by using Nitroindole labeled inhibitors, the regulatory mechanisms and inhibitor design of neurotransmitters and modulators can also be studied.
Applications in Biochemical Reagents
It can serve as a signaling molecule and probe for studying the signaling and regulatory mechanisms within living organisms. For example, it can bind to specific biomolecules such as proteins, enzymes, etc., thereby altering the activity or function of these molecules. By monitoring the interaction between the substance and biomolecules, we can gain a deeper understanding of the signaling pathways and regulatory mechanisms within the organism.
Specific examples:
When studying neurotransmitter receptors, they can act as ligands to bind to the receptors, thereby altering their activity. By monitoring the activity changes of receptors, we can understand the transmission and mechanism of neurotransmitters in organisms.
When studying enzyme catalyzed reactions, it can serve as a substrate or inhibitor, binding to enzymes and affecting their catalytic activity. By monitoring changes in enzyme activity, we can understand the structure and function of enzymes, as well as their regulatory mechanisms in organisms.
Used for biomarkers and imaging
It can also be used in biomarker and imaging technologies. By binding it to specific biomolecules, labeling and tracking of these molecules can be achieved. This helps to gain a deeper understanding of the distribution, dynamic changes, and functions of biomolecules.
Specific examples:
In cell imaging, it can bind to specific cellular components such as cell membrane, nucleus, etc., to achieve labeling and imaging of cells. This helps to observe changes in the morphology, structure, and function of cells.
In proteomics research, it can be used as a labeling reagent to bind to specific proteins and label their positions. Qualitative and quantitative analysis of proteins can be achieved through techniques such as mass spectrometry analysis.
It can also participate in various biochemical reactions and synthesis processes. It can act as a reactant, catalyst, or intermediate, participating in various metabolic pathways and synthesis processes within living organisms.
Specific examples:
In drug synthesis, it can serve as an important intermediate and participate in the synthesis and modification process of drugs. By introducing nitro groups, the activity and selectivity of drugs can be altered, leading to the development of new drugs with better efficacy and lower side effects.
In the metabolic pathways within living organisms, it can participate in the synthesis and transformation of certain metabolites. For example, it can act as a substrate or inhibitor for certain enzymes, affecting the generation and accumulation of metabolites.
Used for biological detection and diagnosis
It can also be used in the field of biological detection and diagnosis. By binding to specific biomolecules and generating specific signals (such as fluorescence, color changes, etc.), detection and diagnosis of biomolecules can be achieved.
Specific examples:
In disease diagnosis, it can serve as a diagnostic reagent that binds to specific pathogens (such as bacteria, viruses, etc.) and generates specific signals. By monitoring changes in signals, rapid detection and diagnosis of pathogens can be achieved.
In environmental monitoring, it can be used as an indicator to monitor pollutants and harmful substances in the environment. By combining with these substances and generating specific signals, environmental quality assessment and monitoring can be achieved.
Specific application cases in biochemical research
Case 1: Study on the function and regulatory mechanism of neurotransmitter receptors
In the field of neuroscience, it can act as a ligand to bind with neurotransmitter receptors, thereby altering their activity. By monitoring the activity changes of receptors, we can understand the transmission and mechanism of neurotransmitters in organisms. For example, researchers can use it as a probe to study the functions and regulatory mechanisms of neurotransmitter receptors such as dopamine receptors and serotonin receptors. This helps to gain a deeper understanding of the structure and function of the nervous system, as well as its mechanisms of action in diseases.
Case 2: Developing new drugs and treatment methods
In the field of drug development, it can be used as an important intermediate or raw material to participate in the synthesis and modification process of drugs. By introducing nitro groups, the activity and selectivity of drugs can be altered, leading to the development of new drugs with better efficacy and lower side effects. For example, researchers can use it as a raw material to synthesize new drugs with anti-tumor, anti-inflammatory and other activities. These new drugs have broad application prospects in fields such as cancer treatment and inflammatory disease treatment.
Case 3: Monitoring Environmental Pollution and Ecological Changes
In the field of environmental monitoring, it can be used as an indicator to monitor pollutants and harmful substances in the environment. By combining with these substances and generating specific signals (such as fluorescence, color changes, etc.), environmental quality assessment and monitoring can be achieved. For example, researchers can use it as a fluorescent probe to monitor the content and distribution of harmful substances such as heavy metal ions and organic pollutants in water bodies. This helps to timely detect and solve environmental pollution problems, protect the ecological environment and human health.
Method 1 is to use ortho nitroaniline as the raw material, generate diazonium salts by co heating with formaldehyde and concentrated hydrochloric acid, and then hydrolyze with alkali to obtain 4-nitroindole. The following are the specific steps of this method and its corresponding chemical equations:
Step 1: Synthesize diazonium salts
(1) Add o-nitroaniline (1.0g, 6.9mmol) and formaldehyde (3.2g, 34mmol) to a dry 250ml three necked bottle. This step involves a nucleophilic addition reaction between the amino group of o-nitroaniline and the aldehyde group of formaldehyde to generate diazonium salts.
(2) Cool to 0 ° C and add 10ml of water containing 3.4g (40mmol) of concentrated hydrochloric acid while stirring. Concentrated hydrochloric acid serves as a catalyst and proton source here, providing the necessary protons for the synthesis of diazonium salts.
NH2C6H4NO2 + HCHO + 2HCl → N-CH=N-CH2-C6H4-NO2 + H2O
Step 2: Hydrolysis of diazonium salts
(1) Cool the reaction mixture to 0 ° C with 10% NaOH (20ml) and stir for 30 minutes. This step utilizes the hydrolysis of alkali to convert diazonium salts into the target product.
(2) Extract with ethyl acetate, wash with saturated salt water, and dry with anhydrous sodium sulfate. These steps are common extraction and drying operations used to purify the target product.
(3) Filter and concentrate to obtain a light yellow solid. The concentration step can remove solvents and other impurities to obtain crude products.
(4) Recrystallize with methanol to obtain light yellow crystals. Recrystallization is a purification method that utilizes the difference in solubility of the target product in different solvents to separate it.
(5) Analyze the purified product using high-performance liquid chromatography to obtain pure 4nitroindole. This is to further confirm the purity and structure of the product.
N-CH=N-CH2-C6H4-NO2 + 2NaOH → CH=CH-C6H4-NO2 + 2NaCl + 2H2O
Method 2 is to use acetophenone as the raw material, react with sodium nitrite and sulfuric acid to generate diazonium salts, and then hydrolyze with alkali to obtain 4nitroindole. The following are the specific steps of this method and its corresponding chemical equations:
Step 1: Synthesize diazonium salts
(1) Add acetophenone (1.0g, 6.9mmol) and sodium nitrite (1.2g, 17mmol) to a dry 50ml three necked bottle. This step involves a nucleophilic addition reaction between sodium nitrite and acetophenone to generate diazonium salts.
(2) Add 10ml of sulfuric acid and cool to 0 ° C. Sulfuric acid serves as a catalyst and proton source here, providing the necessary protons for the synthesis of diazonium salts.
(3) Add 10ml of water containing 3.6g (40mmol) of sodium hydroxide while stirring. Sodium hydroxide is used here as a base to regulate the pH value of the reaction system.
C6H5COCH3 + NaNO2 + H2SO4 → C6H5COCH2-N=N-COCH3 + NaHSO4 + H2O
Step 2: Hydrolysis of diazonium salts
(1) Stir the reaction mixture for 1 hour, then continue stirring at 30 ° C for 4 hours. This step utilizes the hydrolysis of alkali to convert diazonium salts into the target product 4nitroindole.
(2) Extract with ethyl acetate, wash with saturated salt water, and dry with anhydrous sodium sulfate. These steps are common extraction and drying operations used to purify the target product.
(3) Filter and concentrate to obtain a light yellow solid. The concentration step can remove solvents and other impurities to obtain crude products.
(4) Recrystallize with methanol to obtain light yellow crystals. Recrystallization is a purification method that utilizes the difference in solubility of the target product in different solvents to separate it.
(5) Analyze the purified product using high-performance liquid chromatography to obtain pure 4-nitroindole. This is to further confirm the purity and structure of the product.
C6H5COCH2-N=N-COCH3 + 2NaOH → C6H5COCH=CH-C6H4 + NO2 + 2NaCl + 2H2O
4-Nitroindole, also known by its CAS number 4769-97-5, is a chemical compound with the molecular formula C8H6N2O2. This yellow solid has a molecular weight of approximately 162.15 grams per mole. It is a member of the indole family, characterized by a bicyclic structure consisting of a six-membered benzene ring fused to a five-membered pyrrole ring, with a nitro group (-NO2) attached at the 4-position of the indole ring.
It exhibits several notable physical and chemical properties. It has a melting point range of 203-207°C and a boiling point of 362.6°C at 760 mmHg. The compound is relatively dense, with a density of 1.426 g/cm³, and has a flash point of 173.1°C. These properties make it a stable compound suitable for various chemical applications.
In terms of its uses, it is primarily employed as a biochemical reagent. It serves as a valuable biological material or organic compound in life science research. Specifically, it has been used in the synthesis of various compounds, including potential anticancer immunomodulators, protein kinase inhibitors, and anti-angiogenic agents. Additionally, it has been studied for its role in the management of hyperglycemia in diabetes.
The compound is also an important intermediate in the synthesis of other 4-indole derivatives and is used in the production of dyes and pharmaceuticals. Its versatility makes it a key compound in organic synthesis, where it can be further functionalized to produce a wide range of biologically active molecules.
When handling 4-nitroindole, proper safety precautions must be taken. The compound is classified as an irritant and can cause harm if not handled correctly. It should be stored in a cool, dry, and well-ventilated area, away from sources of ignition. Personal protective equipment, such as gloves and goggles, should be worn when working with this compound to avoid skin and eye contact.
It is a unique niche in organic synthesis, bridging pharmaceutical innovation and material science. Its reactivity, coupled with advancements in catalytic and green chemistry, positions it as a sustainable building block for next-generation therapeutics and technologies. As research into indole derivatives intensifies, 4-nitroindole will remain indispensable in the quest for novel bioactive molecules.
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