Cas no 454685-89-3 (7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide)

7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide is a heterocyclic compound featuring a fused pyrrolo[2,3-d]pyrimidine core with a carboxamide functional group at the 5-position. This structure serves as a versatile intermediate in medicinal chemistry, particularly in the synthesis of kinase inhibitors and other biologically active molecules. Its rigid bicyclic scaffold offers favorable binding properties to target proteins, while the carboxamide group enhances solubility and facilitates hydrogen bonding interactions. The compound is valued for its potential in drug discovery, especially in oncology and inflammation research, due to its ability to modulate key enzymatic pathways. High purity and well-characterized synthetic routes ensure reproducibility for research applications.
7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide structure
454685-89-3 structure
Product Name:7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide
CAS No:454685-89-3
MF:C7H6N4O
MW:162.148740291595
CID:1017931
PubChem ID:45084617
Update Time:2025-06-15

7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide Chemical and Physical Properties

Names and Identifiers

    • 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide
    • 1H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide(9CI)
    • 454685-89-3
    • SCHEMBL15173466
    • 1H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBOXAMIDE
    • DB-259689
    • DTXSID40665637
    • Inchi: 1S/C7H6N4O/c8-6(12)4-2-10-7-5(4)1-9-3-11-7/h1-3H,(H2,8,12)(H,9,10,11)
    • InChI Key: DYMCRSCIKQMSRP-UHFFFAOYSA-N
    • SMILES: O=C(C1=CNC2C1=CN=CN=2)N

Computed Properties

  • Exact Mass: 162.05416083g/mol
  • Monoisotopic Mass: 162.05416083g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 196
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.5
  • Topological Polar Surface Area: 84.7?2

7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide Pricemore >>

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Additional information on 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide

Recent Advances in the Study of 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide (CAS: 454685-89-3) in Chemical Biology and Pharmaceutical Research

7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide (CAS: 454685-89-3) is a heterocyclic compound that has garnered significant attention in recent years due to its potential applications in medicinal chemistry and drug development. This compound belongs to the pyrrolopyrimidine class, which is known for its diverse biological activities, including kinase inhibition, antiviral effects, and anticancer properties. Recent studies have explored its role as a key scaffold in the design of novel therapeutic agents, particularly in targeting protein kinases and other enzymes involved in critical cellular pathways.

One of the most notable advancements in the study of 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide is its application in the development of kinase inhibitors. Kinases play a pivotal role in signal transduction and are often implicated in diseases such as cancer, inflammation, and neurodegenerative disorders. Researchers have synthesized derivatives of this compound to enhance its selectivity and potency against specific kinases. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated that modifications at the 5-carboxamide position significantly improved the compound's inhibitory activity against JAK2 kinase, a target in myeloproliferative neoplasms.

In addition to its kinase inhibitory properties, 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide has shown promise as an antiviral agent. A recent preprint on bioRxiv highlighted its efficacy against RNA viruses, including SARS-CoV-2. The study revealed that the compound interferes with viral replication by inhibiting the RNA-dependent RNA polymerase (RdRp) enzyme. This finding opens new avenues for repurposing this scaffold in the fight against emerging viral pathogens.

The synthetic routes to 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide have also been optimized in recent years. A 2022 paper in Organic Letters described a novel one-pot synthesis method that improves yield and reduces the number of purification steps. This advancement is critical for scaling up production and facilitating further pharmacological evaluations. Moreover, computational studies have provided insights into the compound's binding modes and interactions with biological targets, aiding in the rational design of more effective derivatives.

Despite these promising developments, challenges remain in the clinical translation of 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide-based therapeutics. Issues such as bioavailability, metabolic stability, and off-target effects need to be addressed through structural optimization and formulation strategies. Ongoing research is focused on overcoming these hurdles, with several derivatives currently in preclinical testing. The compound's versatility and broad-spectrum activity make it a valuable candidate for further investigation in multiple therapeutic areas.

In conclusion, 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxamide (CAS: 454685-89-3) represents a promising scaffold in chemical biology and pharmaceutical research. Its applications span kinase inhibition, antiviral therapy, and beyond, supported by recent advancements in synthesis and mechanistic understanding. As research continues to unravel its full potential, this compound is poised to contribute significantly to the development of next-generation therapeutics.

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