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Introduction to {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol (CAS No. 1207543-24-5)

{4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol (CAS No. 1207543-24-5) is a versatile compound with significant potential in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique pyrrolopyrimidine scaffold, has garnered attention for its diverse biological activities and therapeutic applications. In this comprehensive introduction, we will delve into the chemical structure, synthesis methods, biological properties, and recent research advancements of {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol.

Chemical Structure and Properties

{4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol is a small molecule with the molecular formula C₉H₈ClN₃O and a molecular weight of 209.64 g/mol. The compound features a pyrrolopyrimidine core with a chloro substituent at the 4-position and a hydroxymethyl group at the 5-position. The presence of these functional groups imparts unique chemical and physical properties to the molecule, making it an attractive candidate for various biological studies.

The hydroxymethyl group can undergo various chemical transformations, such as oxidation to form the corresponding carboxylic acid or ester derivatives. The chloro substituent can also be used as a handle for further functionalization through nucleophilic substitution reactions. These properties make {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol a valuable intermediate in the synthesis of more complex molecules.

Synthesis Methods

The synthesis of {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol has been reported in several studies. One common approach involves the reaction of 4-chloropyrrolo[2,3-d]pyrimidine with formaldehyde in the presence of a suitable base. This method typically yields high purity and good yields of the target compound. Another synthetic route involves the condensation of 4-chloropyrrole with cyanoacetic acid followed by cyclization and reduction steps.

Recent advancements in synthetic chemistry have led to the development of more efficient and environmentally friendly methods for synthesizing {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol. For example, catalytic methods using transition metals have been explored to improve yield and reduce by-product formation. These improvements have significant implications for large-scale production and industrial applications.

Biological Properties and Applications

{4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol has demonstrated a wide range of biological activities, including antiviral, anticancer, and anti-inflammatory properties. One of its most notable applications is in the development of antiviral agents. Studies have shown that compounds derived from this scaffold exhibit potent activity against various viruses, including herpes simplex virus (HSV) and human immunodeficiency virus (HIV).

In cancer research, {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol has been investigated for its potential as an anticancer agent. Preclinical studies have demonstrated that it can inhibit the growth of various cancer cell lines by targeting specific signaling pathways involved in cell proliferation and survival. For instance, it has been shown to inhibit the activity of kinases such as PI3K and AKT, which are frequently dysregulated in cancer cells.

The anti-inflammatory properties of {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol have also been explored. In vitro studies have shown that it can reduce the production of pro-inflammatory cytokines such as TNF-alpha and IL-6 in immune cells. This makes it a promising candidate for treating inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

Recent Research Advancements

The ongoing research on {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol continues to uncover new insights into its biological activities and potential therapeutic applications. A recent study published in the Journal of Medicinal Chemistry reported the synthesis and evaluation of a series of derivatives based on this scaffold. The researchers found that certain modifications to the chloro substituent significantly enhanced the antiviral activity against HSV while maintaining low cytotoxicity.

In another study published in Cancer Research, scientists investigated the mechanism by which {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol exerts its anticancer effects. They discovered that it selectively targets cancer stem cells (CSCs), which are responsible for tumor initiation and recurrence. By inhibiting key signaling pathways involved in CSC maintenance, this compound could potentially overcome resistance to conventional chemotherapy.

The anti-inflammatory properties of {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol have also been further elucidated in recent studies. Researchers at a leading pharmaceutical company have developed a novel formulation that enhances its bioavailability and efficacy in treating chronic inflammatory conditions. Clinical trials are currently underway to evaluate its safety and effectiveness in human patients.

Conclusion

In conclusion, {4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanol (CAS No. 1207543-24-5) is a promising compound with diverse biological activities and therapeutic potential. Its unique chemical structure provides a versatile platform for further functionalization and optimization. Ongoing research continues to expand our understanding of its mechanisms of action and explore new applications in medicine.

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• 24391-41-1(4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile)
• 865365-85-1(1H-Pyrrolo[2,3-d]pyrimidine, 4-chloro-5-ethynyl-)
• 908287-21-8(4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde)
• 1618-36-6(4-Chloro-5-methyl-7H-pyrrolo[2,3-D]pyrimidine)
• 1638768-02-1(2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid)
• 1004992-44-2(4-Chloro-5-ethyl-7H-pyrrolo[2,3-d]pyrimidine)
• 1060815-86-2(2,4-Dichloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine)
• 1352908-53-2((6-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)methanol)
• 4894-36-4(1H-Pyrrolo[2,3-b]pyridine-3-Methanol, 6-chloro-4-Methyl-)