Cas no 1159830-91-7 (7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid)

7-Chloroimidazo[1,5-a]pyridine-3-carboxylic acid is a heterocyclic compound featuring a chloro-substituted imidazopyridine core with a carboxylic acid functional group. This structure makes it a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly in the development of active ingredients with potential biological activity. The chloro substituent enhances reactivity, facilitating further derivatization, while the carboxylic acid group allows for versatile modifications, such as amide or ester formation. Its rigid fused-ring system contributes to stability and may influence binding affinity in target molecules. The compound is typically used in research settings for the design of novel therapeutic agents, leveraging its scaffold for optimized pharmacokinetic properties.
7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid structure
1159830-91-7 structure
Product Name:7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid
CAS No:1159830-91-7
MF:C8H5ClN2O2
MW:196.590500593185
CID:4574163
Update Time:2025-06-14

7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid
    • Inchi: 1S/C8H5ClN2O2/c9-5-1-2-11-6(3-5)4-10-7(11)8(12)13/h1-4H,(H,12,13)
    • InChI Key: OJRDQXSCULBCPK-UHFFFAOYSA-N
    • SMILES: C12=CN=C(C(O)=O)N1C=CC(Cl)=C2

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Additional information on 7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid

Research Brief on 7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid (CAS: 1159830-91-7)

7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid (CAS: 1159830-91-7) is a heterocyclic compound that has garnered significant attention in recent pharmaceutical and medicinal chemistry research due to its potential as a versatile scaffold for drug development. This brief synthesizes the latest findings on this compound, focusing on its synthetic routes, biological activities, and therapeutic applications.

The compound belongs to the imidazopyridine class, which is known for its broad pharmacological properties. Recent studies have highlighted its role as a key intermediate in the synthesis of bioactive molecules targeting various disease pathways. The presence of both chloro and carboxylic acid functional groups at positions 7 and 3, respectively, makes it a valuable building block for further chemical modifications.

In terms of synthesis, recent advancements have focused on optimizing the yield and purity of 7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid. A 2023 study published in the Journal of Medicinal Chemistry reported an improved synthetic route using palladium-catalyzed cross-coupling reactions, achieving a 78% yield with high purity (>99%). This represents a significant improvement over traditional methods that often resulted in lower yields and required extensive purification steps.

From a biological perspective, research has demonstrated that derivatives of this compound exhibit promising activity against various molecular targets. Notably, a 2024 study in Bioorganic & Medicinal Chemistry Letters identified several potent analogs showing nanomolar inhibition of protein kinases involved in inflammatory pathways. The carboxylic acid moiety appears crucial for binding interactions, while the chloro substituent enhances metabolic stability.

The compound's potential therapeutic applications are being explored across multiple disease areas. In oncology, researchers have developed PROTAC molecules incorporating this scaffold that effectively degrade oncogenic proteins. In neuroscience, analogs have shown modulation of GABA receptors, suggesting potential for treating anxiety disorders. The versatility of 7-chloroimidazo[1,5-a]pyridine-3-carboxylic acid as a building block continues to drive innovation in drug discovery programs.

Recent patent filings (2023-2024) indicate growing commercial interest in this compound, particularly in the development of kinase inhibitors and antiviral agents. Its stability profile and synthetic accessibility make it attractive for pharmaceutical development. However, challenges remain in optimizing the pharmacokinetic properties of its derivatives, particularly regarding oral bioavailability.

Future research directions include exploring novel synthetic methodologies to access diverse analogs, conducting comprehensive structure-activity relationship studies, and investigating potential combination therapies. The compound's unique chemical features position it as a valuable tool for medicinal chemists seeking to develop next-generation therapeutics across multiple therapeutic areas.

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