34019-61-9

Usage

Chemical structure

A pyridazine derivative with a 4-chlorophenyl group attached to the pyridazine ring

Potential applications

Pharmaceutical intermediate, synthesis of various drugs and biologically active compounds

Field of use

Organic and medicinal chemistry, development of new therapeutic agents

Importance

Interesting and important molecule for further research and exploration in the field of pharmaceutical chemistry

InChI:InChI=1/C10H7ClN2O2/c11-7-1-3-8(4-2-7)13-10(15)6-5-9(14)12-13/h1-6H,(H,12,14)

Upstream product

• 110-16-7 maleic acid 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 108-31-6 maleic anhydride 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of Novel σ1 Receptor Ligands for Treating Neuropathic Pain: 6-Hydroxypyridazinones

By use of the 6-hydroxypyridazinone framework, a new series of potent σ1 receptor ligands associated with pharmacological antineuropathic pain activity was synthesized and is described in this article. In vitro receptor binding studies revealed high σ1 receptor affinity (Ki σ1 = 1.4 nM) and excellent selectivity over not only σ2 receptor (1366-fold) but also other CNS targets (adrenergic, μ-opioid, sertonerigic receptors, etc.) for 2-(3,4-dichlorophenyl)-6-(3-(piperidin-1-yl)propoxy)pyridazin-3(2H)-one (compound 54). Compound 54 exhibited dose-dependent antiallodynic properties in mouse formalin model and rats chronic constriction injury (CCI) model of neuropathic pain. In addition, functional activity of compound 54 was evaluated using phenytoin and indicated that the compound was a σ1 receptor antagonist. Moreover, no motor impairments were found in rotarod tests at antiallodynic doses and no sedative side effect was evident in locomotor activity tests. Last but not least, good safety and favorable pharmacokinetic properties were also noted. These profiles suggest that compound 54 may be a member of a novel class of candidate drugs for treatment of neuropathic pain.

Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones

Ruthenium-catalyzed simple, cascade and one-pot synthesis of cinnoline-fused diones has been carried out by the C-H activation of phthalazinones/pyridazinones accomplished by the unusual deoxygenation of propargyl alcohols. The bond selectivity is accredited to the traceless directing nature of the hydroxyl group of propargyl alcohol. A sequential C-H activation, insertion and deoxy-oxidative annulation has been proposed based on the preliminary mechanistic study.