Tetrahydropyridine derivatives with inhibitory activity on the production of proinflammatory cytokines: Part 1

Nakao, Akira; Ohkawa, Nobuyuki; Nagasaki, Takayoshi; Kagari, Takashi; Doi, Hiromi; Shimozato, Takaichi; Ushiyama, Shigeru; Aoki, Kazumasa

doi:10.1016/j.bmcl.2009.06.094

Cited by 20 publications

(14 citation statements)

References 15 publications

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“…Column chromatography has performed on silica gel 60 (particle size 0.06–0.20 mm, Merck). Compounds 1 and 2 have prepared as reported in literature [ 26 , 27 , 28 , 30 ]. The structures of all new compounds prepared in this paper have been confirmed by their spectral data.…”

Section: Methodsmentioning

confidence: 99%

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Pyrrole and Fused Pyrrole Compounds with Bioactivity against Inflammatory Mediators

et al. 2017

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A new series of pyrrolopyridines and pyrrolopyridopyrimidines have been synthesized from aminocyanopyrroles. The synthesized compounds have been characterized by FTIR, 1H-NMR and mass spectroscopy. The final compounds have been screened for in vitro pro-inflammatory cytokine inhibitory and in vivo anti-inflammatory activity. The biological results revealed that among all tested compounds some fused pyrroles, namely the pyrrolopyridines 3i and 3l, show promising activity. A docking study of the active synthesized molecules confirmed the biological results and revealed a new binding pose in the COX-2 binding site.

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Section: Methodsmentioning

confidence: 99%

“…A series of N -pyrrolylcarboxylic acids have been reported to be potent COX-2 inhibitors [ 28 , 29 ]. Also, a group of Merck researchers have reported [ 30 ] that L-167307 (pyrrole derivative) showed potent inhibitory activity towards the pro-inflammatory cytokine TNF-α. Structures of some of these compounds are shown in Figure 1 .…”

Section: Introductionmentioning

confidence: 99%

Pyrrole and Fused Pyrrole Compounds with Bioactivity against Inflammatory Mediators

et al. 2017

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“…TNF- α production inhibition in mice (BALB/c) weighing 20–30 g was carried out using the already reported procedure31, 32.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, characterization and pharmacological evaluation of pyrazolyl urea derivatives as potential anti-inflammatory agents

Somakala

Amir

2017

Acta Pharmaceutica Sinica B

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p38α mitogen activated protein kinase (MAPK) inhibitors provide a novel approach for the treatment of inflammatory disorders. A series of fifteen pyrazolyl urea derivatives (3a—o) were synthesized and evaluated for their p38α MAPK inhibition and antioxidant potential. Compounds 3a—e, 3g and 3h showed low micromolar range potency (IC50 values ranging from 0.037 ± 1.56 to 0.069 ± 0.07 µmol/L) compared to the standard inhibitor SB 203580 (IC50 = 0.043 ± 3.62 µmol/L) when evaluated for p38α MAPK inhibition by an immunosorbent-based assay. Antioxidant activity was measured by a 2,2′-diphenyl-1-picryl hydrazyl radical (DPPH) free radical scavenging method and one of the compounds, 3c, showed better percentage antioxidant activity (75.06%) compared to butylated hydroxy anisole (71.53%) at 1 mmol/L concentration. Compounds 3a—e, 3g and 3h showed promising in vivo anti-inflammatory activity (ranging from 62.25% to 80.93%) in comparison to diclofenac sodium (81.62%). The ulcerogenic liability and lipid peroxidation activity of these compounds were observed to be less in comparison to diclofenac sodium. These compounds also potently inhibited the lipopolysaccharide (LPS)-induced TNF-α release in mice (ID50 of 3a—c = 19.98, 11.32 and 9.67 mg/kg, respectively). Among the screened compounds, derivative 3c was found to be the most potent and its binding mode within the p38α MAPK is also reported.

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“…Purely synthetic THPs are also of great interest. For example, compound 5 bearing a THP ring attached to a pyrrole nucleus can act as an anti‐inflammatory agent with superior activities compared to the corresponding piperidine and pyridine analogues . To finish with, ester 6 behaves as an antagonist for M 5 muscarinic acetylcholine receptor, a potential target for the treatment of drug abuse, whereas N ‐tosyl THP 7 is a reversible inhibitor of platelet‐activating factor acetylhydrolases, thereby causing the death of cancer cells …”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Enantioselective Synthesis of Tetrahydropyridines

et al. 2018

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Tetrahydropyridines are important heterocycles present in many molecules of natural and non‐natural origins that exhibit a wide array of biological activities. With several sp3‐hybridized carbon atoms in their structure, they often include one or several stereogenic centers, whose control represents a great synthetic challenge. For the past two decades, enantioselective organocatalysis has developed as a very powerful strategy to perform the synthesis of enantioenriched compounds, including heterocycles. In this Microreview, we wish to provide the readers with a general overview about the organocatalytic strategies that have been used to achieve the preparation of diversified families of tetrahydropyridines, thereby providing elements of reflection for further developments.

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Tetrahydropyridine derivatives with inhibitory activity on the production of proinflammatory cytokines: Part 1

Cited by 20 publications

References 15 publications

Pyrrole and Fused Pyrrole Compounds with Bioactivity against Inflammatory Mediators

Pyrrole and Fused Pyrrole Compounds with Bioactivity against Inflammatory Mediators

Synthesis, characterization and pharmacological evaluation of pyrazolyl urea derivatives as potential anti-inflammatory agents

Organocatalytic Enantioselective Synthesis of Tetrahydropyridines

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