Cyclen is a macrocyclic polyamine compound with a unique ring structure as well as easy modification and strong coordination ability to a variety of cations. It is an intermediate for organic synthesis, especially a precursor compound for the synthesis of metal ion macrocyclic chelating agents. For example, Cycln is used in the synthesis of the contrast agent gadobutrol for cranial and spinal magnetic resonance imaging, which can accurately determine the exact location of tumors and other lesions. It has great potential in the field of medical research. The molecular structure of Cycln contains multiple nitrogen atoms that are capable of forming a large ring structure, thus classifying it as a macrocyclic compound. The four imines on the ring provide a variety of possibilities for the preparation of various N-substituted derivatives, which can be further expanded by appropriate modifications to expand their coordination ability and the functionality of the resulting complexes.Cycln and its derivatives have a strong coordination ability to metal ions, and can form stable complexes with a variety of metal ions. This coordination ability makes Cycln important for applications in coordination chemistry, drug design and other fields.
In conclusion, Cycln is a macrocyclic polyamine compound with unique structure and strong coordination ability, which has a wide range of applications in many fields.
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| Chemical Formula | C8H20N4 |
| Molecular Weight | 172.27 |
| Exact Mass | 172.17 |
| m/z | 172.17 (100.0%), 173.17 (8.7%), 173.17 (1.5%) |
| Elemental Analysis | C, 55.78; H, 11.70; N, 32.52 |
| Melting point | 110-113 °C (lit.) |
| Boiling point | 292.61°C (rough estimate) |
| Density | 1.0415 (rough estimate) |
| Storage conditions | Keep in dark place,Sealed in dry,Room Temperature |
| Solubility | Chloroform (Slightly), Methanol (Slightly) |
| Refractive index | 1.5872 (estimate) |
| Acidity Coefficient (pKa) | 10.53±0.20(Predicted) |
| Form | Crystalline Powder |
| Color | Almost white to slightly yellow |
| water solubility | almost transparency |
| stability | hygroscopic |
Cyclen and its derivatives are a class of macrocyclic polyamine compounds with a unique ring structure and multiple nitrogen atoms. These compounds have a wide range of applications in several fields due to their special coordination ability and ease of modification.
The following are some of the major application areas of Cycln:
Medical imaging and nuclear magnetic resonance (NMR) contrast agents
Cycln and its metal complexes can be used as contrast agents in NMR imaging to improve the contrast of images and help doctors observe tissue structures and lesions.
01
Drug delivery systems
Cycln can be designed as a carrier for drug molecules for drug delivery systems. By binding to drug molecules, the stability, selectivity, and bioavailability of drugs can be improved, thus enhancing drug efficacy.
02
Biosensors and fluorescence analysis
Cycln and its metal complexes have potential applications in biosensors and fluorescence analysis for detecting the presence and change in concentration of metal ions or for monitoring biomolecular interactions.
03
Fluorescent probes
Cycln and its derivatives can be used as fluorescent probes for studying intermolecular interactions, localization of biomolecules and concentration measurements.
04
Water treatment and environmental sciences
Cycln and its metal complexes also have applications in water treatment and environmental sciences, where they can be used for the removal and separation of metal ions.
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The main uses of Cycln are as follows:
Metal Ion Chelators
Cycln and its derivatives can form stable complexes with a wide range of metal ions, so they are used as metal ion chelators. This property gives them important applications in fields such as water treatment, metal recycling, separation science, catalyst carriers and sensor technology.
Biomedical Imaging
Some of Cycln's metal complexes, such as gadolinium complexes, are used as contrast agents in magnetic resonance imaging (MRI). These complexes can improve the contrast of images and help doctors diagnose diseases more accurately.
Drug delivery systems
Cycln derivatives can be used in drug delivery systems by binding to drug molecules to form complexes. This binding enhances the stability, solubility and bioavailability of the drug, thus enhancing drug efficacy.
Biosensors and Fluorescent Probes
Cycln derivatives can be used to design biosensors and fluorescent probes for the detection of biomolecules, ions or other analytes. These probes can change their fluorescent properties by binding to the target analyte, enabling highly sensitive and selective detection.
Ion-Selective Electrodes
Cycln derivatives can be used as carriers for ion-selective electrodes to achieve selective detection of specific ions. This has application value in electrochemical analysis and environmental monitoring.
Catalyst
Cycln derivatives can be used as catalysts or catalyst carriers to promote or accelerate reactions in chemical reactions. They have potential applications in organic synthesis, petrochemicals and other fields.
Cycln and its derivatives can also be used in the preparation of nanomaterials, supramolecular structures, etc., and show a wide range of applications in the fields of materials science, energy science, etc.
There are various synthesis pathways for Cyclen, and the following is a detailed overview of two of the main synthesis methods and their steps:
1. Stetter synthesis method
- Step-by-step overview:
(1)Starting material: di-p-toluenesulfonamide derivative of ethylenediamine diacetyl chloride with ethylenediamine.
(2)Ring closure: The ring closure reaction is carried out under highly dilute conditions (~0.001 mol/dm³).
(3)Reduction and deprotection: the target product is obtained after reduction and deprotection steps.
- Characteristics:
(1)The required raw materials are not easily available.
(2)Carried out under highly dilute conditions, the reaction yield is not high.
(3)Not suitable for large quantity preparation and is rarely used nowadays.
2. Richman-Atkins synthesis method
- Summary of steps:
(1)Raw material preparation: using diethylenetriamine and diethanolamine via p-toluenesulfonylation, salt formation and ring closure respectively.
(2)Deprotection: via a deprotection step.
(3)Alkaline extraction: neutralization with sodium hydroxide to a strong base and extraction with chloroform to obtain cycln.
- Characteristics:
(1)High yield and large synthesis, it is one of the main ways to prepare cycln in the laboratory nowadays.
(2)There are more experimental steps, protection and deprotection consume large amount of reagents and are inconvenient to operate.
- Improved Richman-Atkins synthesis:
Tetraphenyltoluenesulfonyl-protected cycln was prepared by reacting 1,4,7,10-tetraphenyltoluenesulfonyl-1,4,7,10-tetraazadecane with 1,2-dibromoethane in the presence of an alkali metal carbonate using N,N-dimethylformamide as a solvent. This method eliminates the step of preparing p-toluenesulfonamide as a sodium salt.
Cyclen (chemical name: 1,4,7,10-tetraazacyclododecane) is an organic synthesis intermediate, especially in the field of medical imaging, its application as a contrast agent intermediate is particularly important. Contrast agent is a chemical substance used in medical imaging technology to improve the contrast of tissues or organs in the body, thereby helping doctors to observe and analyze more accurately. The unique structure and properties of cyclin make it an ideal intermediate for synthesizing high-performance contrast agents.
1. Structure and properties of cyclin
Cycln is a macrocyclic compound with four nitrogen atoms, and its molecular structure forms a stable twelve-membered ring. This structure gives cyclin unique coordination ability and chemical stability. The nitrogen atoms of cyclin can form stable complexes with metal ions, and these complexes have potential application value in medical imaging.
2. Basic principles of contrast agents
Contrast agents play a vital role in medical imaging technology. They help doctors observe and analyze more clearly by changing the contrast of tissues or organs in the body. The selection and performance of contrast agents depend on a variety of factors, including their chemical properties, biocompatibility, stability, and imaging effects.
In medical imaging technologies such as magnetic resonance imaging (MRI), X-ray computed tomography (CT), and ultrasound imaging, contrast agents are widely used to enhance the contrast of images. These contrast agents bind to specific tissues or organs in the body and change their imaging properties, thereby providing more detailed information.
3. The principle of cyclopentane as a contrast agent intermediate
The principle of cyclopentane as a contrast agent intermediate is mainly based on its unique coordination ability and chemical stability. The following is a detailed explanation:
The four nitrogen atoms of cyclopentane can form stable complexes with a variety of metal ions. These complexes have potential application value in medical imaging because they can bind to specific tissues or organs in the body and change their imaging properties.
For example, cyclopentane can form complexes with paramagnetic metal ions such as gadolinium ion (Gd³⁺). These complexes have significant imaging effects in MRI because they can shorten the T1 and T2 relaxation times of surrounding water molecules, thereby improving the contrast of images.
Biocompatibility and safety
As contrast agent intermediates, cyclopentane and its metal complexes need to have good biocompatibility and safety. The molecular structure of cyclopentane is stable and it is not easy to degrade or produce harmful substances in the body. In addition, cyclopentane and its metal complexes can also be quickly excreted through the kidneys, thereby reducing potential harm to the body.
Imaging effect and stability
As a contrast agent intermediate, the imaging effect and stability of cyclopentane are also key factors. The complexes formed by cyclopentane and metal ions have high relaxation rates and low toxicity, which makes them have excellent imaging effects in medical imaging technologies such as MRI. At the same time, these complexes are also highly stable in the body and are not easy to decompose or react with other substances, thereby ensuring the accuracy and reliability of imaging.
The application of cyclopentane as a contrast agent intermediate also involves its synthesis route and preparation process. Through reasonable synthesis routes and preparation processes, high-quality cyclopentane and its metal complexes can be efficiently prepared. The application effect of these compounds in medical imaging technology will be directly affected by their synthesis routes and preparation processes.
For example, a common method for synthesizing cyclopentane is to react appropriate raw materials under appropriate conditions through a one-pot reaction to obtain cyclopentane products. This synthesis method has the advantages of simple operation, high yield and easy industrialization.
When preparing cyclopentane metal complexes, it is necessary to select appropriate metal ions and reaction conditions. For example, when reacting with gadolinium ions, it is necessary to control factors such as reaction temperature, pH value and reaction time to obtain high-quality gadolinium-based contrast agents.
As a contrast agent intermediate, cyclopentane has broad application prospects in medical imaging technology. For example, in MRI, gadolinium-based contrast agents are widely used in imaging of tissues such as the brain and spinal cord. These contrast agents can significantly improve the contrast of images and help doctors observe and analyze lesions more accurately.
In addition, cyclopentane can also combine with other metal ions to form contrast agents with different imaging properties. These contrast agents also have potential application value in other medical imaging technologies such as CT and ultrasound imaging.
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