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6-Chlorouracil is an important derivative of pyrimidine heterocyclic compounds. Its appearance is a white to off-white crystalline powder. Its structure can be regarded as the uracil parent nucleus having a chlorine atom substituted at the sixth carbon atom. This key modification significantly enhances its activity as a biological electronic equivalent, enabling it to competitively integrate into the nucleotide metabolic pathway, thereby effectively interfering with the biological synthesis of RNA and DNA. Based on this core mechanism, this compound is widely used in the field of medicinal chemistry as a key pharmacophore framework for constructing anti-tumor and anti-viral drugs. For example, it is an important precursor intermediate for synthesizing important chemotherapy drugs such as 5-fluorouracil. At the same time, it is also a multifunctional building block used in organic synthesis for constructing more complex heterocyclic molecules (such as purine analogues), and it demonstrates indispensable fundamental value in pharmaceutical research, biochemical research, and fine chemical fields.
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Chemical Formula |
C4H3ClN2O2 |
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Exact Mass |
146 |
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Molecular Weight |
147 |
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m/z |
146 (100.0%), 148 (32.0%), 147 (4.3%), 149 (1.4%) |
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Elemental Analysis |
C, 32.79; H, 2.06; Cl, 24.19; N, 19.12; O, 21.84 |
Chemical synthesis intermediates
6-Chlorouracil can also serve as a key intermediate in organic synthesis. It can undergo substitution, addition, elimination and other reactions with other compounds to generate organic compounds with specific structures and functions. These compounds may possess unique physical and chemical properties and have potential applications in fields such as materials science and dye industry. It can also be used for the modification and derivatization of bioactive molecules. By introducing this compound as a structural unit, the chemical properties of bioactive molecules can be altered, thereby endowing them with new biological activity or enhancing their stability and solubility. This modification and derivatization technology is of great significance for developing new drugs and improving drug efficacy. It can also serve as a starting material for synthesizing other pyrimidine compounds.
Scientific research
This compound can serve as a probe molecule for studying the structure and function of nucleic acids such as DNA and RNA. By introducing it into nucleic acid molecules, its effects on nucleic acid stability, replication, transcription, and other processes can be observed, thereby revealing the structural characteristics and functional mechanisms of nucleic acids. Meanwhile, it can also be used to study the interaction between proteins and nucleic acids, helping scientists understand how proteins recognize and bind to specific nucleic acid sequences. It can serve as a substrate or inhibitor for enzymatic reactions, used to study the catalytic mechanism and activity of specific enzymes. By observing its conversion under enzymatic action, the structural characteristics and catalytic mechanism of the enzyme can be inferred.
Scientific research
It can serve as a model molecule for drug screening, used to evaluate the biological activity and efficacy of new drugs. By interacting with specific receptors or enzymes, it is possible to determine whether a new drug has potential therapeutic effects. In gene editing technology, it can serve as a specific base analogue for introducing specific gene mutations or modifications. This technology can be used in fields such as studying gene function and constructing disease models. By observing the distribution and changes of this substance in genetic material, the transmission and expression patterns of genetic information can be revealed, providing important experimental evidence for genetic research.
Other applications
These new materials may have excellent conductivity, magnetism, optical properties, or mechanical properties, and have broad application prospects in fields such as electronics, optoelectronics, and magnetic materials. It can also be used in the dye industry. By introducing this structural unit, dye molecules with specific colors and properties can be synthesized. These dyes may have excellent dyeing performance, light resistance, wash resistance, etc., and are suitable for dyeing and printing in fields such as textiles, leather, and paper. In the field of environmental science, it can also serve as an indicator molecule for environmental pollutants. By detecting its content and distribution in the environment, the degree and source of environmental pollution can be evaluated, providing scientific basis for environmental protection and pollution control.
What are the side effects
Regarding the side effects of 6-Chlorouracil, although there is relatively little information directly related to its side effects in human applications, it can be inferred and analyzed from its chemical properties and application fields. The following is a summary of possible side effects of the substance:
Potential biological effects
Cytotoxicity
As a chemical synthesis intermediate, this compound may have certain cytotoxicity. In living organisms, it may interfere with DNA replication and transcription processes, leading to cell damage or death.
Genetic toxicity
The structure of this substance is similar to uracil, and it may enter DNA or RNA molecules as an analog of uracil, causing base mismatches or changes in genetic information, thus possessing potential genetic toxicity.
Possible side effects in drug application
If the compound is used as a drug or drug precursor, its possible side effects include but are not limited to:
Digestive system reactions
Symptoms such as nausea, vomiting, and diarrhea may be caused by its stimulating effect on the digestive system.
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Neurological response
Headache, dizziness, fatigue and other neurological symptoms may be caused by the interference of the substance on the nervous system.
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Allergic reactions
Some patients may have allergic reactions to it, manifested as symptoms such as rash, itching, and difficulty breathing.
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Liver and kidney damage
Long term or excessive use may cause damage to liver and kidney function, leading to abnormal manifestations such as elevated transaminase levels and proteinuria.
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Other precautions
Patients with a history of genetic disease should use caution
For patients with a history of genetic disorders, the use of this substance may increase the risk of genetic mutations, so it should be used with caution.
Pregnant and lactating women are prohibited from using
Due to its potential genetic toxicity, pregnant and lactating women should avoid using this medication to prevent adverse effects on the fetus or infant.
Drug interactions
This compound may interact with other drugs, affecting their efficacy or increasing side effects. Therefore, it is recommended to consult a doctor before use to understand the risks of drug interactions.
In which countries or regions is uracil banned or restricted from use
Regarding the question of which countries or regions have banned or restricted the use of uracil, as uracil is an important component of nucleic acids, it is usually not banned or restricted as a separate chemical substance. However, in certain specific situations, such as the production and use of pesticide adjuvants or certain chemicals, restrictions or bans on uracil or its analogues may be involved.
The following are restrictions and prohibitions on the use of pesticide adjuvants or related chemicals in some countries or regions, which may involve substances similar or related to uracil, but please note that this information does not directly target uracil itself:
The United States
The Environmental Protection Agency (EPA) has classified and regulated the safety of pesticide additives earlier, and has issued a list of banned or restricted additives. These lists may contain substances with similar chemical structures or properties to uracil, but whether they specifically include uracil or its analogues needs to be confirmed by consulting the relevant lists.
EU
The European Commission has also released a list of banned additives in pesticide formulations and requires relevant countries to rectify them within a specified time frame. Similarly, these lists may contain substances related to uracil, but whether they specifically include uracil itself needs to be confirmed by consulting relevant regulations.
Other countries
such as Indonesia, Japan, Australia, and Canada, have also implemented restrictions on the use of pesticide additives in accordance with their respective pesticide management regulations. These regulations may involve substances similar to uracil, but the specific situation needs to be understood by consulting relevant national regulations.
What are the alternatives to uracil
As an important component of nucleic acids, has irreplaceable physiological functions in living organisms. However, in certain specific chemical synthesis, drug development, or experimental research, alternatives to uracil may be sought to meet specific needs. Here are some substances or methods that may serve as alternatives to uracil:
5-Fluorouracil
5-Fluorouracil is a commonly used anti-tumor drug with a structure similar to uracil. It can replace uracil in DNA, thereby blocking nucleic acid synthesis and achieving anti-tumor effects. Among antifungal drugs, 5-fluorouracil can also serve as a substitute for uracil, exerting antibacterial effects by interfering with fungal DNA synthesis.
Other halogenated uracil
In addition to 5-fluorouracil, other halogenated uracil may also be used as a substitute for uracil in certain specific situations. These halogenated uracils have a structure similar to uracil, but with different chemical properties and biological activities.
Azauracil
Nitrogen substituted uracil is a type of compound formed by replacing certain atoms in uracil with nitrogen atoms. These compounds may have different biological activities and chemical properties from uracil, making them substitutes for uracil in certain specific situations.
Qingxin
Qingxin is a plant growth regulator with a structure very similar to uracil. In plants, anthocyanins can replace uracil, causing metabolic abnormalities and regulating plant growth. Although anthocyanins are mainly used for plant growth regulation, they may also serve as a substitute for uracil in certain chemical synthesis or experimental studies.
Synthetic analogues
Through chemical synthesis methods, analogues with similar structures to uracil but different chemical properties and biological activities can be prepared. These analogues may serve as alternatives to uracil for specific chemical synthesis, drug development, or experimental research needs.
What compounds and drugs are similar to uracil
Uracil, as an organic compound, is a unique base of RNA and shares structural or functional similarities with various compounds and drugs. The following are compounds and drugs similar to uracil:
1.Compounds with similar structures
- Cytosine: Cytosine is another pyrimidine base that is structurally similar to uracil and is an important component of nucleic acids. Cytosine pairs with guanine in DNA, while uracil pairs with adenine in RNA.
- Thymine: Thymine is a DNA specific base that differs structurally from uracil, but can be converted from uracil through methylation. During DNA replication and transcription, thymine pairs with adenine.
- Other pyrimidine compounds, such as 5-fluorouracil, 6-chlorouracil, etc., are derivatives or analogues of uracil, structurally similar to uracil but with different chemical properties and biological activities.
2.Drugs with similar functions
- Fluorouracil (5-FU): Fluorouracil is an anti metabolic anti-cancer drug that can mimic uracil to enter cancer cells, interfere with DNA synthesis and replication, and thus exert anti-cancer effects. It is an important alternative to uracil in the field of anticancer drugs, widely used in the treatment of various solid tumors.
- Capecitabine: Capecitabine is an oral prodrug of fluorouracil that can be converted into fluorouracil in the body and has anti-cancer activity similar to fluorouracil. It is also a substitute for uracil in the field of anticancer drugs, used to treat various cancers.
- Other anti-tumor drugs, such as cytarabine and gemcitabine, although not structurally identical to uracil, belong to nucleoside analogues that can interfere with DNA or RNA synthesis, thereby exerting anti-tumor effects. They can also be seen to some extent as alternatives or analogues of uracil in the field of anti-tumor drugs.
In terms of its biological activity, 6-Chlorouracil is known for its potential as a pharmaceutical intermediate. It plays a crucial role in the synthesis of various drugs, particularly in the production of anti-diabetic medications such as alogliptin. Alogliptin is a dipeptidyl peptidase-4 (DPP-4) inhibitor used to treat type 2 diabetes by improving glycemic control. The incorporation in the synthesis process highlights its importance in the development of novel therapeutic agents.
Frequently Asked Questions
How many types of "tautomers" are there? Why is it more stable than uracil?
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There are 6 types of tautomers, and their overall stability is higher than that of uracil. The substitution of chlorine atoms at position 6 enhances the stability of various tautomers, which is in sharp contrast to the stability enhancing effect of 5-substituted compounds such as 5-chlorouracil - the stability enhancing effect of 5-substituted compounds is actually weaker.
What are the "obscure features" of its infrared spectrum? Why is it difficult to identify?
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Because it forms a tetramer unit cell in a solid state, single-molecule theoretical calculations cannot directly match experimental spectra. Researchers must use a tetramer model for density functional calculations (DFT) to accurately reproduce its infrared and Raman characteristic peaks, otherwise there will be significant errors.
Why does its melting point "split"? 290 ° C or 295 ° C?
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It doesn't really melt, it decomposes. The "melting point" of 290-295 ° C reported by different sources is actually the decomposition point (dec.), and TCI clearly indicates "295 ° C (dec.)", which means that the molecular structure begins to break down when heated to this temperature.
Why is it a neglected halogenated uracil? Who is more popular than 5-chlorouracil?
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Five substituted compounds (such as 5-fluorouracil) are the stars of anti-cancer research, with extensive coverage; And 6-chlorouracil has been neglected for decades. However, recent studies have found that 6-substituted compounds are actually more active in inhibiting thymidine phosphorylase and are being re examined.
Which key intermediate for the synthesis of "heavyweight drugs" is it?
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It is a key starting material for Alogliptin. Agiliptin is a DPP-4 inhibitor used to treat type 2 diabetes. In the synthetic route, 6-chlorouracil is first alkylated with 2- (bromomethyl) benzonitrile, and the final drug is obtained through multiple reactions.
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