Polymer‐Supported Copper Complex for C—N and C—O Cross‐Coupling Reactions with Aryl Boronic Acids.

Chiang, Gary C. H.; Olsson, Thomas

doi:10.1002/chin.200450050

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“…The synthetic procedure to obtain pyridazine analogs 15a,b and 18 is depicted in Figure . The previously described 3‐chloro‐6‐phenylpyridazin‐4‐ol, compound 12 [Sircar, ] was converted into intermediate 13 by performing a cross‐coupling reaction with the appropriate aryl boronic acids, using copper acetate as catalyst and a weak base (triethylamine) in CH 2 Cl 2 [Quach and Batey, ; Chiang and Olsson, ]. Compound 13 was then treated with saturated ethanolic ammonia at 180°C to obtain the corresponding 3‐amino derivative 14 , which was directly reacted under standard conditions with the 4‐bromophenylisocyanate or the 4‐bromobenzoyl chloride to obtain the urea 15a and the amide 15b , respectively.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Pharmacological Evaluation of New Pyridazin‐Based Thioderivatives as Formyl Peptide Receptor (FPR) Agonists

Crocetti¹,

Vergelli²,

Cilibrizzi³

et al. 2013

Drug Development Research

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A new series of pyridazinone-based thioderivatives and pyridazine analogs was synthesized and tested for their ability to bind to the three human formyl peptide receptor (FPR) isoforms (FPR1, FPR2, and FPR3) and to activate intracellular calcium mobilization and chemotaxis in human neutrophils. Among the pyridazin-3(2H)-one derivatives tested, analogs 8b and 8c were mixed FPR1/FPR2 agonists, with median effective concentration values in the micromolar range, and were able to activate chemotaxis and Ca 2+ flux in human neutrophils in the low micromolar range. Molecular docking studies showed that interaction of a ligand with Arg205 of FPR1 is important for FPR1 agonist activity. For FPR2, differences in activity between oxygen-containing compounds and their thio-analogs were due to steric bulkiness of sulfur-containing groups. Drug Dev Res 74 : 259-271, 2013.

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Section: Methodsmentioning

confidence: 99%