5,6,7,8-Tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one
[CAS# 859826-41-8]

Identification

• Name: 5,6,7,8-Tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one
• Molecular Formula: C₇H₉N₃O
• Molecular Weight: 151.17
• CAS Registry Number: 859826-41-8
• SMILES: C1CNCC2=C1C(=O)NC=N2

Properties

• Solubility: Slightly soluble (3.8 g/L) (25 °C), Calc.^*
• Density: 1.51±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

5,6,7,8-Tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one, commonly known as THPP, is a heterocyclic compound first synthesized during the mid-20th century as part of the exploration into pyrimidine derivatives. The synthesis and study of THPP were driven by the need to develop novel compounds with potential pharmacological applications. Researchers focused on pyrido[3,4-d]pyrimidine frameworks due to their structural similarity to purines, which are biologically significant molecules. The discovery of THPP added to the growing library of nitrogen-containing heterocycles, opening up new avenues for medicinal chemistry and drug development.

THPP serves as a valuable scaffold in the design of new drugs. Its structure allows for various substitutions, making it a versatile template for developing compounds with diverse biological activities. Researchers have investigated THPP derivatives for their potential as anti-cancer, anti-inflammatory, and antimicrobial agents. The ability to modify its chemical structure enables the creation of molecules that can interact with specific biological targets, leading to the development of new therapeutic agents.

THPP derivatives have shown promise as enzyme inhibitors. Their ability to bind to enzyme active sites and interfere with enzyme function makes them potential candidates for treating diseases where enzyme dysregulation is a factor. For example, certain THPP derivatives are being studied for their ability to inhibit kinases, enzymes involved in cell signaling pathways that are often overactive in cancer. By inhibiting these enzymes, THPP compounds may help to control abnormal cell growth and proliferation.

The neuroprotective potential of THPP compounds is another area of active research. Their structural resemblance to purines, which play critical roles in brain function, suggests that THPP derivatives might modulate neurological processes. Studies are exploring their potential to protect neurons from damage in conditions such as Alzheimer's disease and Parkinson's disease. The ability to prevent or mitigate neuronal damage could lead to new treatments for these debilitating disorders.

In recent years, THPP derivatives have been evaluated for their antiviral properties. Researchers are investigating their ability to inhibit the replication of viruses by targeting viral enzymes or host cell pathways essential for viral reproduction. This application is particularly relevant in the development of new treatments for viral infections that are resistant to existing drugs.

Beyond specific therapeutic applications, THPP is also used as a platform for drug development. Its core structure can be easily modified to produce libraries of compounds for high-throughput screening. This approach accelerates the identification of lead compounds with desirable biological activities, streamlining the drug discovery process.

References

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