Pyridazine Derivatives. I. Some Amebacidal 3-Pyridazones

Steck, Edgar A.; Brundage, R. Pauline; Fletcher, Lynn T.

doi:10.1021/ja01101a032

Cited by 29 publications

(14 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Condensation of the appropriate γ-keto acid with hydrazine hydrate resulted in the previously described C-6 substituted dihydropyridazinones 2a–h,j,k [21,26–32] and the new 2i in good yields (Scheme 1). A further synthetic step was required to obtain compound 2l , which was generated by melting and spontaneous decarboxylation of the carboxylic acid 2k at 160 °C [33].…”

Section: Chemistrymentioning

confidence: 99%

Further studies on 2-arylacetamide pyridazin-3(2H)-ones: Design, synthesis and evaluation of 4,6-disubstituted analogs as formyl peptide receptors (FPRs) agonists

Giovannoni

Schepetkin

Cilibrizzi

et al. 2013

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

Formyl peptide receptors (FPRs) play an essential role in the regulation of endogenous inflammation and immunity. In the present studies, a large series of pyridazin-3(2H)-one derivatives bearing an arylacetamide chain at position 2 was synthesized and tested for FPR agonist activity. The pyridazin-3(2H)-one ring was confirmed to be an appropriate scaffold to support FPR agonist activity, and its modification at the 4 and 6 positions led to the identification of additional active agonists, which induced intracellular Ca2+ flux in HL-60 cells transfected with either FPR1, FPR2, or FPR3. Seven formyl peptide receptor 1 (FPR1)-specific and several mixed FPR1/FPR2 dual agonists were identified with low micromolar EC50 values. Furthermore, these agonists also activated human neutrophils, inducing intracellular Ca2+ flux and chemotaxis. Finally, molecular docking studies indicated that the most potent pyridazin-3(2H)-ones overlapped in their best docking poses with fMLF and WKYMVM peptides in the FPR1 and FPR2 ligand binding sites, respectively. Thus, pyridazinone-based compounds represent potential lead compounds for further development of selective and/or potent FPR agonists.

show abstract

Section: Chemistrymentioning

confidence: 99%

Further studies on 2-arylacetamide pyridazin-3(2H)-ones: Design, synthesis and evaluation of 4,6-disubstituted analogs as formyl peptide receptors (FPRs) agonists

Giovannoni

Schepetkin

Cilibrizzi

et al. 2013

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…Whereas in most cases the free carboxylic acids (R 4 ¼ H) are employed, esters are also frequently used [28]. For the latter case, a protocol suitable for high-throughput organic synthesis has been developed that is based on construction of the oxo ester precursor by silver(I)-catalyzed addition of zirconocenes to epoxy esters [29].…”

Section: 22mentioning

confidence: 99%

Six‐Membered Heterocycles: 1,2‐, 1,3‐, and 1,4‐Diazines and Related Systems

Cabal

2011

Modern Heterocyclic Chemistry

View full text Add to dashboard Cite

“…Some pyridazines have been examined for activity against sporozoan, and flagellate parasites but not for antiamebic activity. 1 6-Aryl-4,5-dihydro-3(2H)-pyridazinones exhibited a strong platelet aggregation inhibiting action coupled with a hypotensive action. Three para-substituted dihydropyridazinones were conspicuous in exerting a strong hypotensive action on anesthetized rats.…”

Section: Introductionmentioning

confidence: 97%

Synthesis of 1,3,4‐Oxadiazoles and 1,3‐Thiazolidinones Containing 1,4,5,6‐Tetrahydro‐6‐pyridazinone

Tao

Cao

Wang

et al. 2006

J Chinese Chemical Soc

View full text Add to dashboard Cite

The reaction of 1,4,5,6-tetrahydro-6-pyridazinone-3-carboxylic acid hydrazides (1) with aromatic aldehydes afforded 1,4,5,6-tetrahydro-6-pyridazinone-3-carbonyl aromatic aldehyde hydrazones (2a-2g). Heterocyclic derivatives linked 1,3,4-oxadiazole obtained by cyclocondensation of 2a-2g with acetic anhydride in absolute ethanol, and 2a-2g cyclized with mercaptoacetic acid in DMF in the presence of anhydrous ZnCl 2 afforded the 1,3-thiazolidinone derivatives. The structures of the new compounds were established by elemental analyses, IR, 1 H NMR and MS spectral data.

show abstract

Pyridazine Derivatives. I. Some Amebacidal 3-Pyridazones

Cited by 29 publications

References 0 publications

Further studies on 2-arylacetamide pyridazin-3(2H)-ones: Design, synthesis and evaluation of 4,6-disubstituted analogs as formyl peptide receptors (FPRs) agonists

Further studies on 2-arylacetamide pyridazin-3(2H)-ones: Design, synthesis and evaluation of 4,6-disubstituted analogs as formyl peptide receptors (FPRs) agonists

Six‐Membered Heterocycles: 1,2‐, 1,3‐, and 1,4‐Diazines and Related Systems

Synthesis of 1,3,4‐Oxadiazoles and 1,3‐Thiazolidinones Containing 1,4,5,6‐Tetrahydro‐6‐pyridazinone

Contact Info

Product

Resources

About