Synthesis and Anti-inflammatory Activity of Antioxidants, 4-Alkylthio-o-anisidine Derivatives.

Komeshima, Nobuyasu; Osawa, Toshihiko; Nishitoba, Tsuyoshi; Jin-no, Yasunari; Kiriu, Takahiro

doi:10.1248/cpb.40.351

Cited by 9 publications

(5 citation statements)

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“…The same reaction carried out in boiling chlorobenzene gave about 50% conversion of the starting 8a after 16 h, and the product 2a was isolated in 12% yield along with 8% of thiazole 5 . The required sulfoxide 8a was smoothly obtained in 68% isolated yield by periodate oxidation of either amidine 6a or its hydrochloride 6a · HCl . 1 H NMR and combustion analyses demonstrated that sulfoxide 8a crystallizes with one molecule of water.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Liquid Crystalline 4H-Benzo[1,2,4]thiadiazines and Generation of Persistent Radicals

et al. 2007

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Four substituted 4H-benzo[1,2,4]thiadiazines 2 were prepared by condensation of the appropriate anilines and benzonitriles followed by oxidative cyclization. The preparation of three fluorinated derivatives 2b-2d proceeded smoothly, while the synthesis of 2a was problematic, presumably due to the relatively high electron density of the benzene ring. The four-ring derivatives 2c and 2d exhibited liquid crystalline properties (2c: Cr 95 SmA 158 I and 2d: Cr 142 SmA 212 I). 4H-Benzo[1,2,4]thiadiazines 2 were oxidized with AgO to generate the corresponding persistent radicals 1 (g=2.0057). The stability of the radicals followed the order 1b approximately 1d>1c>1a, and the two fluorinated radicals 1b and 1d were isolated as crude solids. The lower stability of 1c is presumably due to the presence of the reactive benzylic CH position, and 1a lacks the stabilizing effect of the three fluorine atoms. ESR spectra for 1 were simulated using DFT-derived hfcc as the starting point.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Liquid Crystalline 4H-Benzo[1,2,4]thiadiazines and Generation of Persistent Radicals

et al. 2007

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“…Also, low levels of lipid peroxides can activate both cyclo-oxygenase and lipoxygenase enzymes and thereby increase eicosanoid formation (Lands & Marshall 1985;Riendeau et al 1989). A number of anti-inflammatory agents have been shown to inhibit lipid peroxidation, and this has been proposed as a part of the mechanism of their antiinflammatory activity (Cheeseman & Forni 1988;Cynshi et a1 1990;Komeshima et al 1992;Andreadou et al 1992). Furthermore, compounds which react with lipid peroxyls may suppress the enzymatic oxygenation of arachidonic acid to form bioactive lipid peroxides (Reddana et a1 1985;Seeger et al 1988).…”

Section: Discussionmentioning

confidence: 99%

Effect of Aminoethylpyrroles on Carrageenan-induced Inflammation and on Lipid Peroxidation in Rats: Some Structural Aspects

Demopoulos

Rekka

1994

Journal of Pharmacy and Pharmacology

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Nine 3-(2-aminoethyl)pyrrole derivatives were investigated as anti-inflammatory agents in the carrageenan-induced rat paw oedema model and as antioxidants in the non-enzymatic lipid peroxidation assay. It was found that the derivatives which were substituted with a p-toluenesulphonyl group exhibited considerable anti-inflammatory activity and some also showed antioxidant properties. However, the presence of a p-toluenesulphonyl group did not invariably lead to activity. A structural feature which was essential for both activities was the aminoethyl side chain. Although a relationship between the antiinflammatory and the antioxidant activities was not apparent, the combination of these properties could be useful.

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“…in which “n” and “n′” indicate the difference in thickness between the first and second measurements of hind paws in the placebo control and test groups, respectively23–27 The results were expressed as mean ± standard error of the mean, and the significant difference between groups was tested by using one-way analysis of variance followed by Tukey’s honestly significant difference test at P < 0.05.…”

Section: Methodsmentioning

confidence: 99%

Novel N-phenylcarbamothioylbenzamides with anti-inflammatory activity and prostaglandin E2 inhibitory properties

Limban

Missir²,

Fahelelbom³

et al. 2013

DDDT

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A number of 2-((4-ethylphenoxy)methyl)-N-(substituted-phenylcarbamothioyl) benzamides (1a–h) were synthesized via reaction of 2-((4-ethylphenoxy)methyl)benzoyl isothiocyanate (2) as a key intermediate with several substituted primary aromatic amines. The new compounds were characterized by proton nuclear magnetic resonance (1H-NMR), carbon-13 nuclear magnetic resonance (13C-NMR), infrared spectrometry (IR), mass spectrometry (MS), and elemental analysis. The anti-inflammatory activity of 1a–h was investigated by acute carrageenan-induced paw edema in mice using the reference drug indomethacin. The results obtained indicated that, of the derivatives developed, 1a and 1d–h exhibited significantly higher anti-inflammatory activity (26.81%–61.45%) when compared with the reference drug indomethacin (22.43%) (P = 0.0490 for 1a, 0.0015 for 1d, 0.0330 for 1f, and P < 0.001 for 1e and 1h). Moreover, the ulcer incidence of 20% for 1e and 1h was clearly lower when compared with the indomethacin group (in which the ulcer incidence was 80%). Of particular note, the ulcer index of 0.2 for 1e was significantly less than that in the indomethacin group (0.6, P = 0.014). Additionally, prostaglandin E2 (PGE2) inhibitory properties were found to be high with 1e (68.32 pg/mL), significantly different from those of the placebo group (530.13 pg/mL, P < 0.001), and equipotent to the effect observed in the indomethacin-pretreated group (96.13 pg/mL, P > 0.05). Moreover, the PGE2 level of 54.15 pg/mL with 1h was also significantly different from that of the placebo group (P < 0.001) and of the indomethacin group (P < 0.05). The significant inhibition of PGE2 observed with 1e (68.32 pg/mL) and 1h (54.15 pg/mL) agree with their observed ulcer incidences. Our overall findings for N-phenylcarbamothioylbenzamides 1a–h clearly suggest that the compounds exhibit an anti-inflammatory effect, potently inhibit PGE2 synthesis, and markedly demonstrate low ulcer incidence.

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Synthesis and Anti-inflammatory Activity of Antioxidants, 4-Alkylthio-o-anisidine Derivatives.

Cited by 9 publications

References 0 publications

Synthesis of Liquid Crystalline 4H-Benzo[1,2,4]thiadiazines and Generation of Persistent Radicals

Synthesis of Liquid Crystalline 4H-Benzo[1,2,4]thiadiazines and Generation of Persistent Radicals

Effect of Aminoethylpyrroles on Carrageenan-induced Inflammation and on Lipid Peroxidation in Rats: Some Structural Aspects

Novel N-phenylcarbamothioylbenzamides with anti-inflammatory activity and prostaglandin E2 inhibitory properties

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