Cas no 1581750-56-2 (5H-Pyrrolo[2,3-b]pyrazine, 3-chloro-7-iodo-)

3-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine is a heterocyclic compound featuring a fused pyrrolopyrazine core with chloro and iodo substituents at the 3- and 7-positions, respectively. This structure offers versatility as a key intermediate in pharmaceutical and agrochemical synthesis, particularly in the development of biologically active molecules. The presence of halogen atoms enhances its reactivity, enabling selective cross-coupling reactions such as Suzuki or Sonogashira couplings. Its rigid scaffold is valuable for constructing complex heterocyclic systems, making it useful in medicinal chemistry for target-oriented synthesis. The compound’s high purity and stability under standard conditions ensure reliable performance in research and industrial applications.
5H-Pyrrolo[2,3-b]pyrazine, 3-chloro-7-iodo- structure
1581750-56-2 structure
Product Name:5H-Pyrrolo[2,3-b]pyrazine, 3-chloro-7-iodo-
CAS No:1581750-56-2
MF:C6H3ClIN3
MW:279.465591669083
CID:5560353
Update Time:2026-03-11

5H-Pyrrolo[2,3-b]pyrazine, 3-chloro-7-iodo- Chemical and Physical Properties

Names and Identifiers

    • 5H-Pyrrolo[2,3-b]pyrazine, 3-chloro-7-iodo-
    • Inchi: 1S/C6H3ClIN3/c7-4-2-9-5-3(8)1-10-6(5)11-4/h1-2H,(H,10,11)
    • InChI Key: HRNCNOHPDJTILY-UHFFFAOYSA-N
    • SMILES: C12NC=C(I)C1=NC=C(Cl)N=2

Experimental Properties

  • Density: 2.284±0.06 g/cm3(Predicted)
  • pka: 9.14±0.50(Predicted)

5H-Pyrrolo[2,3-b]pyrazine, 3-chloro-7-iodo- Pricemore >>

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Additional information on 5H-Pyrrolo[2,3-b]pyrazine, 3-chloro-7-iodo-

Introduction to 3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine (CAS No. 1581750-56-2)

3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine (CAS No. 1581750-56-2) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of pyrrolopyrazines, which are known for their diverse biological activities and potential therapeutic applications. The unique substitution pattern of 3-chloro and 7-iodo groups on the pyrrolopyrazine scaffold imparts distinct chemical and biological properties, making it a valuable candidate for various research endeavors.

The molecular structure of 3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine is characterized by a fused ring system consisting of a pyrrole and a pyrazine ring. The presence of the chloro and iodo substituents at specific positions on the ring system not only enhances its stability but also modulates its interactions with biological targets. This structural feature has been exploited in the design of novel drugs and probes for various diseases, including cancer, neurodegenerative disorders, and infectious diseases.

In recent years, significant advancements have been made in understanding the biological activities of 3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine. Studies have shown that this compound exhibits potent antiproliferative effects against various cancer cell lines, making it a promising lead compound for the development of anticancer agents. The mechanism of action involves the inhibition of key signaling pathways involved in cell proliferation and survival, such as the PI3K/AKT/mTOR pathway and the MAPK/ERK pathway.

Beyond its anticancer properties, 3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine has also been investigated for its potential neuroprotective effects. Research has demonstrated that this compound can effectively reduce oxidative stress and inflammation in neuronal cells, thereby protecting against neurodegeneration. These findings suggest that 3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine may have therapeutic potential in treating neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease.

The pharmacokinetic properties of 3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine have also been studied to evaluate its suitability as a drug candidate. Preliminary data indicate that this compound exhibits favorable absorption, distribution, metabolism, and excretion (ADME) properties. Its oral bioavailability is moderate to high, and it shows good plasma stability. These characteristics make it an attractive candidate for further preclinical and clinical development.

In addition to its direct therapeutic applications, 3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine has been used as a building block in the synthesis of more complex molecules with enhanced biological activities. The versatility of this compound allows chemists to introduce various functional groups at different positions on the pyrrolopyrazine scaffold, thereby fine-tuning its pharmacological profile. This approach has led to the discovery of several novel compounds with improved potency and selectivity.

The synthetic accessibility of 3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine is another factor contributing to its widespread use in research. Several efficient synthetic routes have been developed to prepare this compound on both small and large scales. These methods typically involve multi-step reactions starting from readily available starting materials, such as 2-chloropyrrole and 4-chloropyridazine. The robustness and scalability of these synthetic protocols make it feasible to produce sufficient quantities of the compound for extensive biological testing.

In conclusion, 3-Chloro-7-Iodo-5H-Pyrrolo[2,3-b]pyrazine (CAS No. 1581750-56-2) is a promising compound with a wide range of potential applications in medicinal chemistry and pharmaceutical research. Its unique structural features and favorable biological properties make it an attractive candidate for further investigation and development. As research in this area continues to advance, it is likely that new insights into the therapeutic potential of this compound will emerge, paving the way for innovative treatments for various diseases.

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