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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyrimidines Pyrrolo[2,3-d]pyrimidines

4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (CAS No. 1618-36-6): A Comprehensive Overview

4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (CAS No. 1618-36-6) is a versatile and structurally unique compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of pyrrolopyrimidines, which are known for their diverse biological activities and potential therapeutic applications. In this article, we will delve into the chemical properties, synthesis methods, biological activities, and recent research advancements associated with 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine.

Chemical Properties

4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine is a heterocyclic compound characterized by a fused pyrrole and pyrimidine ring system. The presence of a chlorine atom at the 4-position and a methyl group at the 5-position imparts unique chemical and physical properties to this molecule. It is a solid at room temperature and is soluble in common organic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF). The compound exhibits excellent stability under various conditions, making it suitable for use in a wide range of chemical and biological assays.

Synthesis Methods

The synthesis of 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine has been extensively studied, and several efficient routes have been reported in the literature. One of the most common methods involves the reaction of 2-amino-3-chloropyridine with acetylacetone in the presence of a strong acid catalyst. This reaction proceeds via a condensation step followed by cyclization to form the desired pyrrolopyrimidine scaffold. Another approach involves the reaction of 2-amino-3-chloropyridine with methyl acetoacetate in the presence of an acid catalyst, which also yields 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine. These synthetic methods are highly reproducible and can be scaled up for large-scale production.

Biological Activities

4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine has been shown to possess a wide range of biological activities, making it a valuable lead compound for drug discovery. One of its most notable properties is its ability to inhibit various kinases, which are key enzymes involved in cellular signaling pathways. Specifically, it has been reported to exhibit potent inhibitory activity against cyclin-dependent kinases (CDKs), which are crucial for cell cycle regulation. This property makes it a promising candidate for the development of anticancer drugs.

In addition to its kinase inhibitory activity, 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine has also been investigated for its potential as an antiviral agent. Recent studies have demonstrated that it can effectively inhibit the replication of several RNA viruses, including influenza virus and hepatitis C virus (HCV). The mechanism of action involves interference with viral RNA-dependent RNA polymerase (RdRp), which is essential for viral replication.

Recent Research Advancements

The therapeutic potential of 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine has been further explored in recent years through various preclinical studies. One notable study published in the Journal of Medicinal Chemistry reported that derivatives of this compound exhibited enhanced antiproliferative activity against human cancer cell lines. The researchers found that modifications at the 7-position of the pyrrolopyrimidine ring significantly improved the potency and selectivity of the compounds.

In another study published in Antiviral Research, researchers investigated the antiviral activity of 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine against SARS-CoV-2, the virus responsible for COVID-19. The results showed that this compound effectively inhibited viral replication in vitro by targeting RdRp. This finding highlights its potential as a lead compound for developing antiviral drugs against emerging viral threats.

Clinical Applications and Future Directions

The promising biological activities of 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine have spurred interest in its clinical applications. Several derivatives of this compound are currently being evaluated in preclinical and early-stage clinical trials for their efficacy in treating various diseases. For example, one derivative has shown promising results in phase I clinical trials for treating advanced solid tumors.

Further research is needed to optimize the pharmacokinetic properties and reduce potential side effects associated with these compounds. Ongoing efforts focus on developing prodrugs and nanoparticle formulations to improve drug delivery and enhance therapeutic outcomes.

In conclusion, 4-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (CAS No. 1618-36-6) is a multifaceted compound with significant potential in medicinal chemistry and pharmaceutical research. Its unique chemical structure and diverse biological activities make it an attractive candidate for drug development across multiple therapeutic areas. Continued research and development will undoubtedly uncover new applications and improve our understanding of this intriguing molecule.

• 24391-41-1(4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile)
• 908287-21-8(4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde)
• 90358-16-0(4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine)
• 1004992-44-2(4-Chloro-5-ethyl-7H-pyrrolo[2,3-d]pyrimidine)
• 1379367-43-7(2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile)
• 1060815-86-2(2,4-Dichloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine)
• 908287-26-3(1H-Pyrrolo[2,3-d]pyrimidine, 4-chloro-5-(phenylmethyl)-)
• 208459-81-8(4-chloro-5-phenyl-7h-pyrrolo[2,3-d]pyrimidine)
• 82703-38-6(4-chloro-5,6-dimethyl-7H-Pyrrolo[2,3-d]pyrimidine)
• 1207543-24-5({4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol)