Cas no 252723-17-4 (5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine)

5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine is a heterocyclic compound featuring a pyrrolopyrimidine core substituted with bromo, chloro, and phenylsulfonyl functional groups. This structure imparts significant reactivity, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The bromo and chloro substituents enhance electrophilic properties, facilitating further functionalization via cross-coupling or nucleophilic substitution reactions. The phenylsulfonyl group contributes to stability and modulates electronic characteristics, broadening its utility in medicinal chemistry for kinase inhibitor development. Its well-defined reactivity profile and synthetic versatility make it a preferred building block for constructing complex heterocyclic frameworks. Suitable for controlled modifications, it is often employed in targeted drug discovery and structure-activity relationship studies.
5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine structure
252723-17-4 structure
Product Name:5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine
CAS No:252723-17-4
MF:C12H7BrClN3O2S
MW:372.62487912178
MDL:MFCD11501900
CID:1081454
Update Time:2025-05-19

5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine Chemical and Physical Properties

Names and Identifiers

    • 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine
    • 7-(benzenesulfonyl)-5-bromo-4-chloropyrrolo[2,3-d]pyrimidine
    • 5-bromo-4-chloro-7-phenylsulfonyl-7H-pyrrolo[2,3-d]pyrimidine
    • 7-Benzenesulfonyl-5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
    • AR3716
    • IXXOMMSCNWTOPX-UHFFFAOYSA-N
    • AX8280172
    • ST2406136
    • 7-Benzenesulfonyl-5-bromo4chloro-7H-pyrrolo[2,3-d]pyrimidine
    • 7-Benzenesulfonyl-5-bromo4-chloro-7H-pyrrolo[2,3-d]pyrimidine
    • 7-(Benzenesulfonyl)-5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin
    • 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine
    • MDL: MFCD11501900
    • Inchi: 1S/C12H7BrClN3O2S/c13-9-6-17(12-10(9)11(14)15-7-16-12)20(18,19)8-4-2-1-3-5-8/h1-7H
    • InChI Key: IXXOMMSCNWTOPX-UHFFFAOYSA-N
    • SMILES: BrC1=CN(C2C1=C(N=CN=2)Cl)S(C1C=CC=CC=1)(=O)=O

Computed Properties

  • Exact Mass: 370.91300
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 2
  • Complexity: 452
  • Topological Polar Surface Area: 73.2

Experimental Properties

  • PSA: 73.23000
  • LogP: 4.16500

5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine Security Information

5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine Pricemore >>

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5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine Production Method

Additional information on 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo2,3-dpyrimidine

Research Brief on 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (CAS: 252723-17-4)

5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (CAS: 252723-17-4) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential as a versatile scaffold for drug discovery. This research brief synthesizes the latest findings on this compound, focusing on its synthesis, biological activity, and applications in targeted therapies.

Recent studies have highlighted the role of 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine as a key intermediate in the development of kinase inhibitors. Its unique pyrrolopyrimidine core allows for selective interactions with ATP-binding sites of various kinases, making it a promising candidate for oncology research. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy in inhibiting JAK2 and FLT3 kinases, which are critical targets in myeloproliferative disorders and acute myeloid leukemia (AML).

The compound's synthetic pathway has been optimized in recent years to improve yield and purity. A novel one-pot synthesis method, reported in Organic Letters (2022), reduces the number of steps from traditional approaches and minimizes the use of hazardous reagents. This advancement is particularly relevant for industrial-scale production, where efficiency and safety are paramount.

In addition to its kinase inhibitory properties, 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine has shown potential in modulating protein-protein interactions (PPIs). Research published in ACS Chemical Biology (2023) revealed its ability to disrupt the interaction between MDM2 and p53, suggesting applications in p53-dependent cancer therapies. The bromo and chloro substituents at the 4 and 5 positions, respectively, were found to be critical for this activity, providing insights for structure-activity relationship (SAR) studies.

Ongoing clinical investigations are exploring derivatives of this compound for their pharmacokinetic profiles and toxicity. Preliminary data from Phase I trials (2023) indicate acceptable bioavailability and manageable side effects, though further optimization may be required to enhance blood-brain barrier penetration for CNS applications. Researchers are particularly interested in its potential for treating glioblastoma multiforme, given its dual kinase and PPI modulation capabilities.

The versatility of 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine extends beyond oncology. Recent work in Nature Chemical Biology (2023) demonstrated its utility as a chemical probe for studying nucleotide-binding proteins, opening new avenues for infectious disease research. Its ability to selectively bind to certain viral polymerases makes it a candidate for broad-spectrum antiviral development, particularly against RNA viruses.

Future research directions include exploring the compound's potential in combination therapies and further elucidating its mechanism of action at the molecular level. The development of more water-soluble derivatives remains a key challenge, with several groups investigating prodrug strategies and formulation approaches. As understanding of its polypharmacology grows, this compound class may offer solutions to complex diseases requiring multi-target interventions.

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