A correlative IR, MS, 1H, 13C and 15N NMR and theoretical study of 4-arylthiazol-2(3H)-onesElectronic supplementary information (ESI) available: NMR data, including graphs; Cartesian coordinates for 3a and 4. See http://www.rsc.org/suppdata/p2/b1/b106322g/

Pihlaja, Kalevi; Ovcharenko, V. V.; Kolehmainen, Erkki; Laihia, Katri; Fabian, Walter M. F.; Dehne, H.; Perjéssy, A.; Kleist, Marion; Teller, Joachim; Šusteková, Zora

doi:10.1039/b106322g

Cited by 18 publications

(10 citation statements)

References 16 publications

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“…1.12 mmol of K 2 CO 3 and 0.67 mmol (for 2a – f ) of the appropriate 2-chloro- N -phenylacetamide were added to a suspension of intermediate 1a – c [21–23] (0.56 mmol) in anhydrous CH 3 CN (3 mL). The mixture was stirred at reflux for 6–7 h. After evaporation of the solvent, ice-cold water (20 mL) was added, and the precipitate was recovered by vacuum filtration.…”

Section: Methodsmentioning

confidence: 99%

“…A mixture of intermediate of type 1 ( 1a – c ) [21–23] (0.62 mmol) the appropriate phenylboronic acid (1.24 mmol), Cu(Ac) 2 (0.93 m mol), and Et 3 N (1.24 mmol) in dry CH 2 Cl 2 (3 mL), was stirred at room temperature overnight. The organic layer was washed with water (3 × 15 mL) and then with 33% aqueous ammonia (3 × 10 mL).…”

Section: Methodsmentioning

confidence: 99%

“…To a suspension of the substrate of type 1 ( 1a , b ) [21, 23] (0.54 mmol) in anhydrous CH 3 CN (3 mL), 1.08 mmol of K 2 CO 3 and 0.65 mmol of the appropriate commercially available intermediate 4a , b were added. The mixture was stirred at reflux for 8 h ( 5a , b and 6a , b ) or for 3 h ( 5c- and 6c ).…”

Section: Methodsmentioning

confidence: 99%

“…1.02 mmol of K 2 CO 3 and 0.61 mmol of dibenzyl chloromethyl phosphate ( 7 ) [27] were added to a suspension of the substrate 1a – c [21–23] (0.51 mmol) in anhydrous CH 3 CN (4 mL). The mixture was stirred at reflux for 6 h. After evaporation of the solvent, ice-cold water (20 mL) was added and the suspension was recovered by extraction with CH 2 Cl 2 (3 × 15 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Products 2a – f were obtained by standard alkylation on precursors 1a – c [21–23], using appropriately substituted 2-chloro- N -phenylacetamides and K 2 CO 3 in anhydrous acetonitrile at reflux. The N-aryl derivatives 3a – f were obtained through a coupling reaction on 1a – c with commercially available phenylboronic acids in the presence of EtN 3 and (Ac) 2 Cu (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and analytical characterization of new thiazol-2-(3H)-ones as human neutrophil elastase (HNE) inhibitors

Crocetti

Bartolucci

Cilibrizzi

et al. 2017

Chemistry Central Journal

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Human neutrophil elastase (HNE) is a potent serine protease belonging to the chymotrypsin family and is involved in a variety of pathologies affecting the respiratory system. Thus, compounds able to inhibit HNE proteolytic activity could represent effective therapeutics. We present here the synthesis of new thiazol-2-(3H)-ones as an elaboration of potent HNE inhibitors with an isoxazol-5-(2H)-one scaffold that we recently identified. Two-dimensional NMR spectroscopic techniques and tandem mass spectrometry allowed us to correctly assign the structure of the final compounds arising from both tautomers of the thiazol-2-(3H)-one nucleus (N-3 of the thiazol-2-(3H)-one and 3-OH of the thiazole). All new compounds were tested as HNE inhibitors, and no activity was found at the highest concentration used (40 µM), demonstrating that the thiazol-2-(3H)-one is not a good scaffold for HNE inhibitors. Molecular modelling experiments indicate that the low-energy pose might limit the nucleophilic attack on the endocyclic carbonyl group of the thiazolone-based compounds by HNE catalytic Ser195, in contrast to isoxazol-5-(2H)-one analogues. Electronic supplementary materialThe online version of this article (10.1186/s13065-017-0358-1) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and analytical characterization of new thiazol-2-(3H)-ones as human neutrophil elastase (HNE) inhibitors

Crocetti

Bartolucci

Cilibrizzi

et al. 2017

Chemistry Central Journal

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Microwave‐Assisted Diversity‐Oriented Synthesis of Thiazol‐2(3H)‐ones and Its Interaction with Biomacromolecules

et al. 2022

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An expeditious catalyst-free heteroannulation has been accomplished to access functionalized thiazol-2(3H)ones by the reaction of isothiocyanates and 2-bromoketones in EtOH under controlled microwave irradiation heating. The synthetic strategy is simple, straightforward, and offers two points of structural diversity to expand the product versatility. Further, the biological relevance of the synthesized thiazol-2(3H)-ones has been examined for their possible use as putative acetylcholinesterase inhibitors through molecular docking analysis.

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Synthesis of Five‐ and Six‐Membered N‐Phenylacetamido Substituted Heterocycles as Formyl Peptide Receptor Agonists

Vergelli

Schepetkin

Ciciani

et al. 2016

Drug Development Research

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Formyl peptide receptors (FPRs) are G-protein-coupled receptors that play an important role in the regulation of inflammatory process and cellular dysfunction. In humans, three different isoforms are expressed (FPR1, FPR2 and FPR3). FPR2 appears to be directly involved in the resolution of inflammation (ROI), an active process carried out by specific pro-resolving mediators that modulate specific receptors. Previously, we identified 2-arylacetamido pyridazin-3(2H)-ones as FPR1- or FPR2-selective agonists, as well as a large number of mixed-agonists for the three isoforms. Here, we report a new series of 2-arylacetamido pyridazinones substituted at position 5 and their development as FPR agonists. We also synthesized a new series of 2-oxothiazolones bearing a 4-bromophenylacetamido fragment, which was fundamental for activity in the pyridazinone series. The compounds of most interest were 4a, a potent, mixed FPR agonist recognized by all three isotypes (FPR1 EC50 = 19 nM, FPR2 EC50 = 43 nM, FPR3 EC50 = 40 nM), and 4b, which had potent activity and a preference for FPR2 (EC50 = 13 nM). These novel compounds may represent valuable tools for studying FPR activation and signaling.

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A correlative IR, MS, 1H, 13C and 15N NMR and theoretical study of 4-arylthiazol-2(3H)-onesElectronic supplementary information (ESI) available: NMR data, including graphs; Cartesian coordinates for 3a and 4. See http://www.rsc.org/suppdata/p2/b1/b106322g/

Cited by 18 publications

References 16 publications

Synthesis and analytical characterization of new thiazol-2-(3H)-ones as human neutrophil elastase (HNE) inhibitors

Synthesis and analytical characterization of new thiazol-2-(3H)-ones as human neutrophil elastase (HNE) inhibitors

Microwave‐Assisted Diversity‐Oriented Synthesis of Thiazol‐2(3H)‐ones and Its Interaction with Biomacromolecules

Synthesis of Five‐ and Six‐Membered N‐Phenylacetamido Substituted Heterocycles as Formyl Peptide Receptor Agonists

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