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InChI:InChI=1/C8H8N4S/c9-10-8-4-3-6(11-12-8)7-2-1-5-13-7/h1-5H,9H2,(H,10,12)

Upstream product

• 28657-41-2 3-chloro-6-(2'-thienyl)pyridazine 
• 54558-07-5 6-(thien-2-yl)-2,3-dihydropyridazin-3-one 
• 4653-08-1 4-oxo-4-thiophen-2-yl-butyric acid 
• 52240-00-3 6-(thien-2-yl)-2,3,4,5-tetrahydropyridazin-3-one 

Relevant academic research and scientific papers

Synthesis and Structure-Activity Relationships of Series of Aminopyridazine Derivatives of γ-Aminobutyric Acid Acting as Selective GABA-A Antagonists

We have recently shown that an aryloaminopyridazine derivarive of GABA, SR 95103 , is a selective and competitive GABA-A receptor antagonist.In order to further explore the structural requirements for GABA receptor affinity, we synthesized a series of 38 compounds by attaching various pyridazinic structures to GABA or GABA-like side chains.Most of the compounds displaced GABA from rat brain membranes.All the active compounds antagonized the GABA-elicited enhancement of diazepam binding, strongly suggesting that all these compounds are GABA-A receptor antagonists.None of the compounds that displaced GABA from rat brain membranes interacted with other GABA recognition sites (GABA-B receptor, GABA uptake binding site, glutamate decarboxylase, GABA-transaminase).They did not interact with the Cl- ionophore associated with the GABA-A receptor and did not interact with the benzodiazepine, strychnine, and glutamate binding sites.Thus these compounds appear to be specific GABA-A receptor antagonists.In terms of structure-activity, it can be concluded that a GABA moiety bearing a positive charge is necessary for optimal GABA-A receptor recognition.Additional binding sites are tolerated only if they are part of a charge-delocalized amidinic or guanidinic system.If this delocalization is achieved by linking a butyric acid moiety to the N(2) nitrogen of a 3-aminopyridazine, GABA-antagonistic character is produced.The highest potency (ca.250 times bicuculline) was observed when an aromatic ? system, bearing electron-donating substituents, was present on the 6-position of the pyridazine ring.

Synthesis and antihypertensive activity of new 6-heteroaryl-3-hydrazinopyridazine derivatives

The synthesis and pharmacological activity of new 6-heteroaryl-3-hydrazinopyridazines with antihypertensive action are described. The introduction of pyrrole, pyrazole, imidazole, triazole, tetrazole, thiophene, indole, and carbazole heterocyclic rings into the 6 position of the pyridazine nucleus has been carried out by three different methods of synthesis. The hypotensive action has been examined on normotensive and spontaneously hypertensive rats by comparison with dihydralazine (I). 6-Imidazol-1-yl derivatives have proved particularly active. Of these derivatives 3-hydrazino-6-(2-methylimidazol-1-yl)pyridazine (7c) achieves 4.9 times the activity of dihydralazine when administered orally to spontaneously hypertensive rats. The LD50 values of 7c and dihydralazine are very similar.