Synthesis and antiinflammatory activities of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones

Ikuta, Hironori; Shirota, Hiroshi; Kobayashi, Shigeya; Yamagishi, Youji; Yamada, Kazuhiro; Yamatsu, Isao; Katayama, Kouichi

doi:10.1021/jm00394a011

Cited by 77 publications

(62 citation statements)

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“…23 Therefore, compounds with antioxidant properties would be expected to be potential inhibitors of 5-LO. [24][25][26][27][28] Furthermore, oxygen free radicals, which are inflammatory mediators of considerable importance, may be inactivated by such Compounds. 29 » 30 Although there have been attempts to develop new therapeutically effective derivatives of anthralin, such as triacetoxyanthracene 31 2 and butantrone 12 (3) for which initial reports were promising, later reports have indicated that these compounds were less effective and more irritating than anthralin itself.…”

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confidence: 99%

Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase

Müller

Gürster²,

Piwek³

et al. 1993

J. Med. Chem.

112

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The syntheses, the biological evaluation, and the structure-activity relationships of a novel series of l,8-dihydroxy-9(10H)-anthracenones bearing acyl-, alkyl-, or alkylidene-linked aromatic substituents in the 10-position are described. The phenylacyl and phenylalkylidene analogs were far more potent inhibitors of 5-lipoxygenase (5-LO) from bovine polymorphonuclear leukocytes (IC50 values in the 10 -7 M range) than the antipsoriatic drug anthralin, whereas phenylalkyl analogs were only weak inhibitors. Among the active compounds were both potent generators of hydroxyl radicals, as determined by deoxyribose degradation, and strong reducers of the stable free radical 2,2-diphenyl-l-picrylhydrazyl (DPPH). However, several derivatives of this series maintained 5-LO inhibitory activity but did not generate hydroxyl radicals and were not reactive with DPPH. In particular, phenylacyl analogs were also 6 times more efficient in inhibition of lipid peroxidation in model membranes than anthralin. Structure-activity relationships have shown that the presence of free phenolic groups in the attached aromatic ring is beneficial but not required for 5-LO inhibitory potency. The inhibitory potency in the 10-phenylacyl series increased with the length of the acyl chain with three methylene units being the optimum, suggesting a specific enzyme interaction which would not be expected for nonspecific redox inhibitors.Psoriasis is a widespread, chronic inflammatory and scaling skin disease, mainly characterized by increased cell proliferation of the epidermis.

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confidence: 99%

Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase

Müller

Gürster²,

Piwek³

et al. 1993

J. Med. Chem.

112

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“…A solution of 2,4-dibromobutyroyl chloride 23 (2; 1.32 g; 4.95 mmol) in dry DCM (30 mL) was added at À20…”

Section: -Benzyloxy-3-bromopyrrolidin-2-one (5a)mentioning

confidence: 99%

5-Membered cyclic hydroxamic acids as HDAC inhibitors

Mutule

Borovika

Rozenberga

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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The new histone deacylases inhibitors (HDACi) were synthesized in the class of 5-membered cyclic hydroxamic acids (5-CHA), showing medium size CHA as a new Zn-binding group. New reaction sequence was proposed for the synthesis of 5-membered alkylidene-cyclic-hydroxamic acids starting from butyrolactone. Compound 10c showed low mM activity on HeLa cell extracts. From these results, cyclic hydroxamic acids will be further investigated to find more potent compounds.

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“…After 6 h, the mice were sacrificed; the stomach was removed and opened along the greater curvature, washed with distilled water and cleaned gently by dipping in saline. The mucosa damage for each stomach was examined using a stereoscopic microscope and compared with the reference drug indomethacin according to the reported procedure [36].…”

Section: Ulcerogenic Activitymentioning

confidence: 99%

Synthesis and Pharmacological Activities of Some New Triazolo- and Tetrazolopyrimidine Derivatives

et al. 2013

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Abstract:A new series of fused triazolo-and tetrazolopyrimidine derivatives 2-14 were synthesized and their anti-inflammatory and ulcerogenic activities were evaluated. The pharmacological screening showed that many of these obtained compounds have good anti-inflammatory activities, comparable to the reference drug. The toxicity of the compounds was also assayed via the determination of their LD 50 values. The structures of newly synthesized compounds were confirmed by IR, 1 H-NMR, MS spectral data and elemental analysis.

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Synthesis and antiinflammatory activities of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones

Cited by 77 publications

References 0 publications

Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase

Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase

5-Membered cyclic hydroxamic acids as HDAC inhibitors

Synthesis and Pharmacological Activities of Some New Triazolo- and Tetrazolopyrimidine Derivatives

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