Pyrido[1,2-a]benzimidazole (7CI,8CI,9CI)

Base Information

• Chemical Name: Pyrido[1,2-a]benzimidazole (7CI,8CI,9CI)
• CAS No.: 245-47-6
• Molecular Formula: C11H8 N2
• Molecular Weight: 168.198
• Hs Code.: 2933990090
• Mol file: 245-47-6.mol

Synonyms:1,2-Pyrido-4,5-benzo-1,3-diazoline;NSC 660430

Chemical Property of Pyrido[1,2-a]benzimidazole (7CI,8CI,9CI)

Chemical Property:

• Melting Point: 176-177 °C
• Boiling Point: 272.1±22.0 °C(Predicted)
• PKA: 6.80±0.30(Predicted)
• PSA: 17.30000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 2.48750

Purity/Quality:

97% ^*data from raw suppliers

Pyrido[1,2-a]benzimidazole 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Pyrido[1,2-a]benzimidazole derivatives, including those with Mannich base side chains, exhibit promising antimalarial activity against both chloroquine-sensitive and multidrug-resistant *Plasmodium* strains. However, these compounds face challenges such as rapid metabolism and potential toxicity due to reactive metabolite formation. While modifications to block bioactivation reduce toxicity, they also diminish antimalarial efficacy, suggesting that further optimization is needed to balance metabolic stability and pharmacological activity. The metabolites of these derivatives remain potential candidates for future antimalarial drug development.

Technology Process of Pyrido[1,2-a]benzimidazole (7CI,8CI,9CI)

There total 5 articles about Pyrido[1,2-a]benzimidazole (7CI,8CI,9CI) 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: 59.0%

2-(2-methanesulfonylanilino)-pyridine → benzo[4,5]imidazo[1,2-a]pyridine (245-47-6) + α-carboline (244-76-8)

Guidance literature:

In tert-butyl alcohol; for 4h; Irradiation;

Reference yield: 39.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + 2-(phenylamino)pyridine (6631-37-4) → benzo[4,5]imidazo[1,2-a]pyridine (245-47-6) + 2-[(N-acetyl-N-phenyl)amino]pyridine (51263-25-3)

Guidance literature:

With palladium diacetate; acetic acid; In acetic anhydride; at 100 ℃; for 20h;

DOI:10.1021/acs.organomet.9b00113

Reference yield:

[1-(4-Fluoro-phenyl)-meth-(Z)-ylidene]-pyridin-2-yl-amine → benzo[4,5]imidazo[1,2-a]pyridine (245-47-6) + 8-fluoropyrido[1,2-a]benzimidazole (136343-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / -30 - 50 °C

2: bis(tertbutylcarbonyloxy)iodobenzene / 2.5 h / 25 °C

With bis(tertbutylcarbonyloxy)iodobenzene; In tetrahydrofuran;

DOI:10.1021/ol4015656

upstream raw materials:

N-((4-fluorophenyl)(phenyl)methyl)pyridin-2-amine

2-aminopyridine

[bis(acetoxy)iodo]benzene

2-(phenylamino)pyridine

Downstream raw materials:

2-benzimidazolecarboxylic acid

N-(2-chlorophenyl)pyridin-2-amine

Refernces

Antimalarial Pyrido[1,2- a]benzimidazole Derivatives with Mannich Base Side Chains: Synthesis, Pharmacological Evaluation, and Reactive Metabolite Trapping Studies

10.1021/acsinfecdis.8b00279

The research aims to develop new antimalarial drugs by synthesizing and evaluating a series of pyrido[1,2-a]benzimidazole derivatives with Mannich base side chains. The study investigates these compounds' antiplasmodial activity, metabolic stability, and potential to form reactive metabolites, which can cause toxicity. Key chemicals used include ethyl acetoacetate, ethyl cyanoacetate, and various reagents for functional group transformations. The research concludes that while these derivatives show good antiplasmodial activity, they are rapidly metabolized, with less than 40% of the parent compound remaining after 30 minutes in liver microsomes. Strategies to block bioactivation were successful but at the expense of antimalarial activity. The study highlights the potential of these compounds' metabolites as future leads for drug development, given their potent activity against both chloroquine-sensitive and multidrug-resistant Plasmodium strains.

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