Imidazo[1,2-b]pyridazine

Base Information

• Chemical Name: Imidazo[1,2-b]pyridazine
• CAS No.: 766-55-2
• Molecular Formula: C6H5N3
• Molecular Weight: 119.126
• Hs Code.: 29335990
• Mol file: 766-55-2.mol

Synonyms:1,3a,4-Triazaindene;1,5-Diazaindolizine;

Chemical Property of Imidazo[1,2-b]pyridazine

Chemical Property:

• Appearance/Colour: Pale yellow to almost white crystalline powder
• Melting Point: 53 - 55oC
• Refractive Index: 1.689
• PKA: 5.30±0.30(Predicted)
• PSA: 30.19000
• Density: 1.29 g/cm³
• LogP: 0.72930
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Soluble in dimethylformamide.

Purity/Quality:

99% ^*data from raw suppliers

Imidazo[1,2]pyridazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Imidazo[1,2-b]pyridazine is a heterocyclic scaffold that has been explored in the development of dual c-Met and VEGFR2 kinase inhibitors, demonstrating potential as an antitumor agent by targeting key pathways involved in tumor growth, angiogenesis, and metastasis. Its derivatives, such as those studied in this research, exhibit significant inhibitory activity against cancer cell proliferation and in vivo efficacy, highlighting its relevance in medicinal chemistry for oncology applications.

Technology Process of Imidazo[1,2-b]pyridazine

There total 6 articles about Imidazo[1,2-b]pyridazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-aminopyridazine (5469-70-5) + 2-chloroethanal (107-20-0) → imidazo[1.2-b]pyridazine (766-55-2)

Guidance literature:

at 70 ℃;

DOI:10.1021/acs.jmedchem.0c02064

Reference yield: 87.0%

6-chloroimidazo[1,2-b]pyridazine (6775-78-6) → imidazo[1.2-b]pyridazine (766-55-2)

Guidance literature:

With palladium on activated charcoal; hydrogen; triethylamine; In tetrahydrofuran; methanol; for 16h;

Reference yield:

2H-Pyridazin-3-one (504-30-3) + 2-chloroethanamine hydrochloride (870-24-6) → imidazo[1.2-b]pyridazine (766-55-2)

Guidance literature:

With sodium sulfate; triethylamine; In chloroform; at 20 - 60 ℃; for 5h;

upstream raw materials:

C₈H₉N₅O

6-hydrazinoimidazol[1,2-b]pyridazine

3-aminopyridazine

2-chloroethanal

Downstream raw materials:

3-Bromoimidazo<1,2-b>pyridazine hydrobromide

3-bromo-imidazo[1,2-b]pyridazine

3-ethynyl-imidazo[1,2-b]pyridazine

ponatinib

Refernces

Structure-based design, synthesis, and evaluation of imidazo[1,2-b] pyridazine and imidazo[1,2-a]pyridine derivatives as novel dual c-Met and VEGFR2 kinase inhibitors

10.1016/j.bmc.2013.10.028

This research endeavored to develop novel dual c-Met and VEGFR2 kinase inhibitors with potent antitumor efficacy against various human cancers. The study aimed to synthesize compounds that could inhibit both the c-mesenchymal epithelial transition factor (c-Met) and vascular endothelial growth factor receptor 2 (VEGFR2) kinases, which play significant roles in tumor growth, invasion, metastasis, and angiogenesis. Through structure-based design and synthesis, the researchers identified imidazo[1,2-b]pyridazine and imidazo[1,2-a]pyridine derivatives, with particular emphasis on compound 26, an imidazo[1,2-a]pyridine derivative bearing a 6-methylpyridone ring. This compound strongly inhibited both c-Met and VEGFR2 enzyme activities, as well as the proliferation of c-Met-addicted MKN45 cells and VEGF-stimulated human umbilical vein endothelial cells (HUVEC), demonstrating dose-dependent antitumor efficacy in vivo in mouse xenograft models. The research concluded that compound 26 has promising therapeutic potential for the treatment of human cancers.