2-Amino-6-bromopyrido[2,3-d]pyrimidin-4(3H)-one
[CAS# 120040-42-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: 2-Amino-6-bromopyrido[2,3-d]pyrimidin-4(3H)-one
• Molecular Formula: C₇H₅BrN₄O
• Molecular Weight: 241.04
• CAS Registry Number: 120040-42-8
• SMILES: C1=C(C=NC2=C1C(=O)NC(=N2)N)Br

Properties

• Density: 2.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.862, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H332-H335
• Precautionary Statements: P261-P280-P305+P351+P338

Discovory and Applicatios

2-Amino-6-bromopyrido[2,3-d]pyrimidin-4(3H)-one is a heterocyclic compound that has garnered attention in medicinal chemistry and pharmaceutical research. This molecule belongs to the class of pyridopyrimidines, known for their biological activities and structural resemblance to purines, which are essential components of nucleic acids. The modification of pyridopyrimidine scaffolds, as seen with 2-amino and 6-bromo substituents, has led to the exploration of new properties and applications in diverse areas, including antiviral and anticancer research.

The discovery of 2-amino-6-bromopyrido[2,3-d]pyrimidin-4(3H)-one can be traced to studies aimed at synthesizing compounds with enhanced bioactivity and selectivity toward specific molecular targets. By altering the substitution patterns of pyridopyrimidines, researchers have identified potential leads with activity against various enzymes and receptors that play roles in human diseases. The inclusion of bromine at the sixth position of the compound’s structure increases its molecular weight and electron density, enhancing interactions with biomolecules and contributing to its biological potential.

Applications of 2-amino-6-bromopyrido[2,3-d]pyrimidin-4(3H)-one primarily revolve around its use as an intermediate in drug design and discovery. This compound serves as a key structure for developing inhibitors that target kinases, a type of enzyme involved in cellular signaling and growth regulation. Given that aberrant kinase activity is implicated in many cancers, compounds based on the pyridopyrimidine framework have been investigated for their antitumor effects. The amino group at position 2 and the bromo group at position 6 allow for further functionalization, enabling scientists to create derivatives with improved pharmacological properties.

Beyond oncology, 2-amino-6-bromopyrido[2,3-d]pyrimidin-4(3H)-one and its derivatives show promise in the field of virology, where similar compounds have been tested for activity against viral enzymes. Structural modifications to this molecule could inhibit viral replication processes by mimicking or interfering with the natural substrates of viral enzymes. Such inhibition mechanisms are valuable for combating diseases caused by RNA viruses, which pose significant public health challenges.

The compound's ability to serve as a versatile intermediate also extends to materials science and biochemistry, where it is used to synthesize new polymers and study enzyme-substrate interactions. Its bromine-containing structure, when incorporated into polymers, may influence properties like thermal stability, making it relevant for specialized material applications. Additionally, in biochemical research, derivatives of 2-amino-6-bromopyrido[2,3-d]pyrimidin-4(3H)-one are valuable for probing the active sites of enzymes and examining molecular interactions due to their heterocyclic nature and electronic characteristics.