17258-23-0Relevant academic research and scientific papers
Ring opening and ring closure reactions of 1,2,4-triazines with carbon nucleophiles: A novel route to functionalized 3-aminopyridazines
Rykowski, Andrzej,Wolinska, Ewa
, p. 5795 - 5796 (1996)
A novel route to functionalized 3-aminopyridazines by reaction of 6-substituted 3-chloro-1,2,4-triazines with carbon nucleophiles bearing a cyano substituent at a carbanionic center was developed and a key part of the reaction mechanism was elucidated bas
Iminopyridazine derivative as well as preparation method, application and insecticide thereof
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Paragraph 0107-0112, (2021/04/14)
The invention belongs to the technical field of pesticide chemistry, and particularly relates to an iminopyridazine derivative, a preparation method and application thereof and an insecticide. On the basis of an iminopyridazine structure, propionic acid or butyric acid side chains are introduced to the first position of the iminopyridazine structure, aryl is introduced to the third position and the fifth position of the iminopyridazine structure respectively or simultaneously, and the polysubstituted iminopyridazine derivative is synthesized and has an obvious inhibiting effect on GABA receptors of public health pests such as houseflies and agricultural pests such as prodenia litura. Meanwhile, the derivative also has good insecticidal activity on prodenia litura, and has an application prospect of preparing or developing insecticides.
Expeditive synthesis of 4-substituted 3-aminopyridazines
Bourotte, Maryline,Pellegrini, Nadia,Schmitt, Martine,Bourguignon, Jean-Jacques
, p. 1482 - 1484 (2007/10/03)
3-Aminopyridazines substituted at position 4 were prepared via palladium-catalysed cross-coupling reactions starting from 3-amino-4-bromopyridazines using Suzuki and Sonogashira experimental conditions.
1,2,4-Triazine in organic synthesis. 16. Reactivity of 3-substituted 6-phenyl-1,2,4-triazines towards phenylacetonitrile anion in polar aprotic solvents
Rykowski,Wolinska,Van Der Plas
, p. 1418 - 1423 (2007/10/03)
The reactions of 3-X-6-phenyl-1,2,4-triazines (X = SMe, SPh, SO2Ph) with phenylacetonitrile anion in DMF were studied. In these reactions the ring transformation product 3-amino-4,6-diphenylpyridazine, the covalent addition product 3-X-5-(α-cya
A new route to functionalized 3-aminopyridazines by ANRORC type ring transformation of 1,2,4-triazines with carbon nucleophiles [1]
Rykowski,Wolinska,Van Der Plas
, p. 879 - 883 (2007/10/03)
The reaction of 3-chloro-6-phenyl-1,2,4-triazine 1a with carbon nucleophiles 2a-d bearing a cyano substituent at a carbanionic center has been studied. In all reactions the formation of the corresponding 3-aminopyridazines 3a-d takes place via ANRORC mech
Synthesis and Structure-Activity Relationships of Series of Aminopyridazine Derivatives of γ-Aminobutyric Acid Acting as Selective GABA-A Antagonists
Wermuth, Camille-Georges,Bourguignon, Jean-Jacques,Schlewer, Gilbert,Gies, Jean-Pierre,Schoenfelder, Angele,et al.
, p. 239 - 249 (2007/10/02)
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.
