2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid: A Comprehensive Product Introduction
2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (CAS 1211443-58-1) is a significant organic compound in the field of chemical research. This compound has attracted considerable attention due to its unique chemical structure and potential applications in various industries. In this article, we will delve into the details of this product, including its properties, uses, applications in different fields, and preparation methods.
Properties of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid
2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid is an off – white to light yellow crystalline powder. It has a specific molecular formula and molecular weight that are crucial for understanding its chemical behavior. The molecular formula of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid is C12H12ClN3O2, and its molecular weight is approximately 265.69 g/mol. This compound is sparingly soluble in water but shows better solubility in some organic solvents such as dimethyl sulfoxide (DMSO) and N,N – dimethylformamide (DMF). The solubility characteristics play an important role in its applications, especially in chemical synthesis and biological assays.
The melting point of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid is in the range of 200 – 205°C. This relatively high melting point indicates the strong intermolecular forces within the compound, which is related to its chemical structure, including the presence of multiple rings and polar functional groups. The stability of the compound at different temperatures and under various environmental conditions is also an important aspect. It is relatively stable under normal storage conditions, but it may decompose when exposed to strong acids, bases, or high – energy radiation.
Uses of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid
One of the primary uses of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid is in the field of medicinal chemistry. It serves as a key intermediate in the synthesis of various pharmaceutical compounds. Due to its unique structure, it can be modified and incorporated into more complex molecules to develop drugs with specific biological activities. For example, it can be used to synthesize kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways, and abnormal kinase activity is associated with many diseases, including cancer. By using 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid as a building block, researchers can design and synthesize novel kinase inhibitors that may have better efficacy and fewer side – effects.
In addition to medicinal chemistry, this compound is also used in the field of agrochemicals. It can be used as a starting material for the synthesis of pesticides and herbicides. The cyclopentyl and pyrrolopyrimidine moieties in its structure can be exploited to design molecules with specific biological activities against pests and weeds. For example, it can be used to develop compounds that target specific enzymes or receptors in pests, leading to their control or elimination.
Applications in Different Fields
Medical Field
In the medical field, the potential of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid is mainly explored in the development of anticancer drugs. As mentioned earlier, it can be used to synthesize kinase inhibitors. In pre – clinical studies, some of the derivatives synthesized from this compound have shown promising results in inhibiting the growth of cancer cells. For example, in in vitro cell culture experiments, these derivatives can block the activation of specific kinases involved in cancer cell proliferation, survival, and metastasis. In in vivo animal models, they can reduce the tumor size and improve the survival rate of the animals.
Moreover, 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid can also be used in the development of drugs for other diseases such as autoimmune diseases. Some kinases are involved in the regulation of the immune system, and by inhibiting these kinases, it may be possible to treat autoimmune diseases such as rheumatoid arthritis and multiple sclerosis. However, more research is needed to fully understand the potential of this compound in these areas and to develop effective drugs.
Agrochemical Field
In the agrochemical field, 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid can be used to develop pesticides with high selectivity and low toxicity. For example, it can be used to synthesize insecticides that target specific receptors in insects. By modifying the structure of the compound, researchers can design molecules that have a high affinity for these receptors, leading to the disruption of the insect’s nervous system and ultimately its death. This approach can reduce the impact on non – target organisms and the environment.
For herbicides, the compound can be used to develop molecules that inhibit specific enzymes in weeds. These enzymes are essential for the growth and development of weeds, and by inhibiting them, the weeds can be controlled. The advantage of using 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid as a starting material is that its structure can be easily modified to optimize the activity and selectivity of the herbicides.
Chemical Research Field
In chemical research, 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid is used as a model compound for studying the reactivity and mechanism of organic reactions. Its structure contains multiple functional groups and rings, which provide a rich platform for exploring different reaction pathways. For example, the chloro group can undergo substitution reactions, and the carboxylic acid group can be used for esterification and amide formation reactions. By studying these reactions, researchers can gain a better understanding of organic chemistry principles and develop new synthetic methods.
Preparation Methods of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid
There are several methods for the preparation of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid. One common method involves a multi – step synthesis starting from commercially available starting materials.
The first step usually involves the synthesis of the pyrrolopyrimidine core structure. This can be achieved by reacting appropriate precursors, such as pyrrole derivatives and pyrimidine derivatives, under specific reaction conditions. For example, a pyrrole compound with a suitable substituent can react with a pyrimidine compound in the presence of a base and a catalyst to form the pyrrolopyrimidine ring system. After the formation of the core structure, the cyclopentyl group can be introduced through a substitution reaction. This may involve the use of a cyclopentyl halide and a base to react with the appropriate position on the pyrrolopyrimidine ring.
The introduction of the chloro group and the carboxylic acid group also requires specific reaction steps. The chloro group can be introduced by using a chlorinating agent, such as thionyl chloride or phosphorus oxychloride, under appropriate reaction conditions. The carboxylic acid group can be formed by hydrolysis of an ester or a nitrile group that is previously introduced into the molecule. For example, if an ester group is present, it can be hydrolyzed in the presence of an acid or a base to form the carboxylic acid.
Another approach for the preparation of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid is through a one – pot synthesis method. This method aims to simplify the synthesis process by combining multiple reaction steps in a single reaction vessel. However, this method usually requires careful optimization of reaction conditions, such as the choice of solvents, catalysts, and reaction temperatures, to achieve high yields and selectivity.
Send InquiryReferences
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- Reference 3: Organic Reaction Mechanisms and Syntheses. [Online]. Available: https://example.com/ref3