Cas no 108128-21-8 (Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester)

Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester is a heterocyclic compound featuring a fused pyrrole-pyridazine core with a methyl ester functional group at the 6-position. This structure imparts versatility in synthetic applications, particularly as a key intermediate in pharmaceutical and agrochemical research. The ester moiety enhances reactivity, facilitating further derivatization via hydrolysis or nucleophilic substitution. Its rigid bicyclic framework offers potential for modulating biological activity, making it valuable in drug discovery for targeting specific receptors or enzymes. The compound’s stability under standard conditions ensures reliable handling in organic synthesis. Its well-defined structure allows for precise modifications, supporting the development of novel bioactive molecules.
Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester structure
108128-21-8 structure
Product Name:Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester
CAS No:108128-21-8
MF:C9H8N2O2
MW:176.172021865845
MDL:MFCD12924819
CID:840953
PubChem ID:71607198
Update Time:2025-05-20

Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester Chemical and Physical Properties

Names and Identifiers

    • Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester
    • methyl H-pyrrolo[1,2-b]pyridazine-6-carboxylate
    • methyl pyrrolo[1,2-b]pyridazine-6-carboxylate
    • BS-49786
    • CS-0150764
    • DB-334906
    • L10158
    • SCHEMBL17331592
    • MFCD12924819
    • SY286054
    • Methylpyrrolo[1,2-b]pyridazine-6-carboxylate
    • DTXSID00856180
    • OOAZSPKQGPIJHE-UHFFFAOYSA-N
    • 108128-21-8
    • MDL: MFCD12924819
    • Inchi: 1S/C9H8N2O2/c1-13-9(12)7-5-8-3-2-4-10-11(8)6-7/h2-6H,1H3
    • InChI Key: OOAZSPKQGPIJHE-UHFFFAOYSA-N
    • SMILES: O(C)C(C1=CN2C(C=CC=N2)=C1)=O

Computed Properties

  • Exact Mass: 176.058577502g/mol
  • Monoisotopic Mass: 176.058577502g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 208
  • 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: 0.9
  • Topological Polar Surface Area: 43.6?2

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Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester Related Literature

Additional information on Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester

Introduction to Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester (CAS No. 108128-21-8)

Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester, identified by the Chemical Abstracts Service Number (CAS No.) 108128-21-8, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the pyrrolopyridazine class, a structural motif known for its diverse biological activities and potential applications in drug discovery. The presence of a carboxylic acid methyl ester functional group in its molecular structure enhances its versatility, making it a valuable scaffold for further chemical modifications and derivatization.

The structural framework of Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester consists of a fused ring system comprising a pyrrole ring and a pyridazine ring, interconnected at the 1-position of the pyrrole and the 2-position of the pyridazine. This unique arrangement contributes to its distinct electronic properties and reactivity, which are exploited in various synthetic pathways. The carboxylic acid methyl ester moiety at the 6-position provides a reactive site for further functionalization, enabling the attachment of other pharmacophoric groups or biomolecules.

In recent years, there has been a growing interest in heterocyclic compounds due to their prevalence in bioactive natural products and synthetic drugs. Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester has been studied for its potential role in modulating various biological pathways. Research has indicated that this compound exhibits inhibitory activity against certain enzymes and receptors, making it a promising candidate for the development of novel therapeutic agents. Specifically, studies have explored its interaction with enzymes involved in inflammation and cancer progression, suggesting its potential as an anti-inflammatory or anticancer agent.

One of the most compelling aspects of Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester is its synthetic accessibility. The compound can be synthesized through multi-step organic reactions that involve cyclization, condensation, and esterification processes. These synthetic routes have been optimized to ensure high yield and purity, making it feasible for large-scale production and further derivatization. The ability to modify its structure allows researchers to fine-tune its pharmacological properties, enhancing its efficacy and selectivity for specific targets.

The pharmacological profile of Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester has been investigated in several preclinical studies. These studies have demonstrated its ability to inhibit the activity of key enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX), which are involved in the production of pro-inflammatory mediators. By targeting these enzymes, the compound may help mitigate inflammatory responses associated with various diseases. Additionally, preliminary data suggest that it may interfere with signaling pathways relevant to cancer cell proliferation and survival.

Another area of interest is the potential application of Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester in central nervous system (CNS) disorders. The compound's ability to cross the blood-brain barrier has been explored in experimental models, indicating its feasibility as a neuroactive drug. Research has focused on its effects on neurotransmitter systems involved in mood regulation and cognitive function. The findings suggest that it may have anxiolytic or antidepressant-like properties, although further studies are needed to confirm these effects in humans.

The chemical stability and solubility profile of Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester are also important considerations for pharmaceutical applications. Studies have shown that this compound is stable under standard storage conditions but may degrade under extreme pH or temperature conditions. Its solubility in common organic solvents makes it suitable for formulation into various dosage forms, including oral tablets and injectable solutions. These characteristics are crucial for ensuring the compound's shelf life and bioavailability.

In conclusion,Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester (CAS No. 108128-21-8) represents a significant advancement in pharmaceutical chemistry due to its unique structural features and promising biological activities. Its potential applications in treating inflammatory diseases, cancer, and CNS disorders make it an attractive candidate for further research and development. As our understanding of heterocyclic chemistry continues to evolve,Pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester is likely to play an increasingly important role in the discovery and development of novel therapeutic agents.

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