58897-67-9

Upstream product

• 108-32-7 1,2-propylene cyclic carbonate 
• 1765-93-1 4-fluoroboronic acid 
• 14823-09-7 6-iodopyridazin-3(2H)-one 
• 66548-52-5 3-chloro-6-(4-fluorophenyl)pyridazine 
• 39499-62-2 6-(4-Fluoro-phenyl)-4,5-dihydro-2H-pyridazin-3-one 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 267401-66-1 2-(2-fluoroethyl)-6-(4-fluorophenyl)-3-(2H)-pyridazinone 
• 66548-73-0 6-(4-fluoro-phenyl)-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine 
• 66548-51-4 6-(p-fluorophenyl)-1,2,4-triazolo[4,3-b)pyridazine 
• 105538-28-1 6-Amino-1-(3-ethoxycarbonyl-propyl)-3-(4-fluoro-phenyl)-pyridazin-1-ium; bromide 
• 88490-21-5 [6-(4-Fluoro-phenyl)-pyridazin-3-yl]-hydrazine 
• 105538-07-6 3-amino-6-(4-fluorophenyl)pyridazine 
• 66548-52-5 3-chloro-6-(4-fluorophenyl)pyridazine 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed Alkynylation of 4-Arylphthalazin-1(2H)-one Scaffolds via C-H Bond Activation

Selective C–H bond alkynylation toward modular access to material and pharmaceutical molecules is of great desire in modern organic synthesis. Disclosed herein is rhodium(III)-catalyzed selective C–H bond mono-/bialkynylation of 4-aryl phthalazin-1(2H)-one was developed. The silver salt AgSbF6 are demonstrated to play a vital role in promoting the bialkynylation reactions. The present alkynylation strategy is simple, efficient, and features high functional group tolerance and broad substrate scope under an air atmosphere. Additionally, 6-aryl pyridazin-3(2H)-one scaffold is amenable to the selective monoalkynylation and sequential bialkynylation, respectively.

Scope and limitation of propylene carbonate as a sustainable solvent in the Suzuki-Miyaura reaction

The Suzuki-Miyaura reaction is one of the most used transformations in drug research. Thus making this reaction more sustainable is of considerable current interest. Here we show that propylene carbonate (PC) can be used as a solvent for the Suzuki-Miyaura reaction. PC is one of the greenest solvents since it is synthesized under green conditions by the use of carbon dioxide in the air. All reactions proceeded well and good or excellent yields were observed for the biaryl products. Nonetheless in the case of pyridazinones, 2-hydroxypropyl- chain containing side-products were observed. Importantly, this fact allowed the isolation of several novel compounds which were generated under prominently green conditions.

Synthesis and Bioevaluation of 3,6-Diaryl-[1,2,4]triazolo[4,3-b] Pyridazines as Antitubulin Agents

A series of 3,6-diaryl-[1,2,4]triazolo[4,3-b]pyridazines were designed as a class of vinylogous CA-4 analogues. The easily isomerized (Z,E)-butadiene linker of vinylogous CA-4 was replaced by a rigid [1,2,4]triazolo[4,3-b]pyridazine scaffold. Twenty-one target compounds were synthesized and exhibited moderate to potent antiproliferative activity. The compound 4q with a 3-amino-4-methoxyphenyl moiety as the B-ring, comparable to CA-4 (IC50 = 0.009-0.012 μM), displayed the highly active antiproliferative activity against SGC-7901, A549, and HT-1080 cell lines with IC50 values of 0.014, 0.008, and 0.012 μM, respectively. Tubulin polymerization experiments indicated that 4q effectively inhibited tubulin polymerization, and immunostaining assay revealed that 4q significantly disrupted tubulin microtubule dynamics. Moreover, cell cycle studies revealed that compound 4q dramatically arrested cell cycle progression at G2/M phase in A549 cells. Molecular modeling studies showed that 4q could bind to the colchicine binding site on microtubules.

Discovery of substituted 6-pheny-3H-pyridazin-3-one derivatives as novel c-Met kinase inhibitors

We report a series of phenyl substituted pyridazin-3-ones substituted with morpholino-pyrimidines. The SAR of the phenyl was explored and their c-Met kinase and cell-based inhibitory activity toward c-Met driven cell lines were evaluated. Described herein

Copper(II) chloride as an efficient reagent for the dehydrogenation of pyridazinone derivatives

A new procedure is described for the preparation of pyridazinones from 4,5-dihydropyridazinones under mild conditions with CuCl2 in MeCN via halogenation and spontaneous HCl elimination. For the trans-hexahydrophthalazin-8(1H)-one 1B*, the HCl elimination is five times faster than for the corresponding cis isomer 1B.

Herbicidal agent

A method for combatting weeds by applying to the weeds or their environment, a phenylpyridazine, wherein the phenyl group is substituted by hydroxy, halogen, cyano, nitro, amino, alkyl, alkoxy, cycloalkyl, cycloalkoxy, phenyl, phenoxy, alkylthio or an alkylsulfonyl group and wherein the pyridazinyl ring is substituted in the 4-position by hydroxy or by a --O--C(O)-- derivative.

One-pot preparation of 6-substituted 3(2H)-pyridazinones from ketones

A one-pot process for the preparation of 6-phenyl-3(2H)-pyridazinone from acetophenone and glyoxylic acid has been investigated and shown to have wide utility in the preparation of 6- and 5,6-substituted 3(2H)-pyridazinones. Limitations to the process encountered with 2'-hydroxyacetophenone and with basic hetero-aromatic ketones have been overcome, and the processes described offer the rapid and efficient synthesis of many 6-substituted pyridazinones from readily available ketones.

Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents

Substituted 6-phenyl-3(2H)-pyridazinone compounds are useful as cardiotonic agents. Said compounds cause a significant increase in myocardial contractility in the anesthetized dog. Said compounds are produced by reacting substituted γ-oxobenzenebutanoic acids with suitably substituted hydrazines to provide 6-phenyl-4,5-dihydro-3(2H)-pyridazinones which are dehydrogenated to the desired product. The intermediate 6-phenyl-4,5-dihydro-3(2H)-pyridazinones are themselves useful as cardiotonic agents.

Synthesis and Anxiolytic Activity of 6-(Substituted-phenyl)-1,2,4-triazolopyridazines

The synthesis of a series of 6-(substituted-phenyl)-1,2,4-triazolopyridazines (VIII) is reported.Some of these derivatives show activity in tests predictive of anxiolytic activity (a) protection against pentylenetetrazole-induced convulsions; (b)

Method for treating anxiety in mammals

This disclosure describes compositions of matter useful as anxiolytic agents and the method of meliorating anxiety in mammals therewith; the active ingredients of said compositions of matter being certain substituted 6-phenyl-1,2,4-triazolo[4,3-b]pyridazines or the pharmacologically acceptable acid-addition salts thereof.