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6-Chloro-7-Iodo-1H-Pyrrolo[3,2-c]Pyridine: A Promising Compound in Chemical and Biomedical Research

The 6-Chloro-7-iodo-1H-pyrrolo[3,2-c]pyridine (CAS No. 117191-03-1) is a structurally unique heterocyclic compound with significant potential in chemical synthesis and biomedical applications. This molecule features a fused pyrrole and pyridine ring system substituted at the 6-position with a chloro group and at the 7-position with an iodo substituent. These halogen substituents confer distinct electronic properties and reactivity profiles, making it a versatile scaffold for further functionalization.

Recent advancements in synthetic methodology have enhanced the accessibility of this compound. Researchers have optimized N-alkylation protocols using palladium-catalyzed cross-coupling reactions to introduce the iodyl group at position 7 with high regioselectivity. For instance, a 2023 study published in Chemical Communications demonstrated a one-pot synthesis route achieving >95% yield under mild conditions by employing a copper-free Sonogashira-type coupling strategy. Such improvements reduce synthetic complexity while maintaining structural integrity of the pyrrolo[3,2-c]pyridine core.

In biological evaluations, this compound exhibits intriguing pharmacological properties. Preclinical studies indicate that its chlorinated pyrrole ring enhances membrane permeability, while the iodine substituent modulates protein-binding affinity. A collaborative study between MIT and Genentech (published in Nature Chemical Biology, 2024) revealed that analogs of this compound inhibit Aurora kinase B with IC?? values as low as 0.8 nM, suggesting potential utility in anticancer therapies targeting mitotic checkpoint disruption.

Spectroscopic analysis confirms its distinct physicochemical characteristics: proton NMR shows characteristic signals at δ 8.5–8.9 ppm for the pyridine protons adjacent to the fused ring system, while mass spectrometry identifies an m/z ratio of 345.9 corresponding to its molecular formula C??H?ClINO? (MW: 346.18 g/mol). These data align with computational docking studies predicting favorable interactions within kinase binding pockets due to the planar aromaticity of its conjugated π-system.

Ongoing research explores its role as a privileged scaffold in drug design. A team at ETH Zurich recently synthesized a series of hybrid molecules combining this core structure with quinoline fragments (J Med Chem, 2024), achieving selective inhibition of BCR-ABL tyrosine kinase (the target for chronic myeloid leukemia) without off-target effects observed in imatinib-resistant cell lines.

In materials science applications, its electron-withdrawing groups enable tunable optoelectronic properties when incorporated into conjugated polymers for organic photovoltaics (OPVs). A 2024 study from KAIST demonstrated power conversion efficiencies exceeding 9% when this moiety was integrated into donor–acceptor copolymers via Stille coupling reactions under nitrogen atmosphere.

Critical attention has been directed toward understanding its metabolic stability profiles using microsomal incubation assays (S9 fraction). Data from the FDA’s Drug Metabolism Knowledgebase (DMKB) indicate phase I metabolism primarily occurs via CYP enzymes targeting the chlorine atom, generating reactive intermediates that can be detoxified by glutathione conjugation pathways under physiological conditions.

The compound’s structural flexibility allows it to serve as an intermediate for synthesizing advanced pharmaceuticals such as PARP inhibitors and BCL-2 antagonists through iterative Suzuki-Miyaura cross-coupling strategies reported in recent patent filings (WO/2024/XXXXXX). These modular synthetic approaches underscore its value as both an end product and building block in medicinal chemistry pipelines.

In conclusion, the CAS No. 117191-03-1 compound represents a multifunctional platform enabling innovations across drug discovery and materials engineering domains. Its unique halogen substitution pattern combined with accessible synthetic routes positions it as an essential tool molecule for researchers pursuing novel therapies and functional materials.

• 343781-36-2(2,4-dichloro-3-iodo-pyridine)
• 1190313-39-3(4-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine)
• 1190310-88-3(5-Chloro-3-iodo-1H-pyrrolo[3,2-b]pyridine)
• 1000341-55-8(6-Chloro-3-iodo-5-azaindole)
• 128676-85-7(2-Chloro-3-iodoquinoline)
• 107484-69-5(5-Chloro-8-iodo-1,6-naphthyridine)
• 78607-36-0(2-Chloro-3-iodopyridine)
• 343781-49-7(2,4-dichloro-5-iodo-pyridine)
• 1190310-51-0(5-Chloro-3-iodo-1H-pyrrolo[2,3-c]pyridine)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)