Superoxide Anion-Scavenging Effect of 2-Amino-1,3-selenazoles

Sekiguchi, Akihiro; Nishina, Atsuyoshi; Kimura, Hirokazu; Fukumoto, Ryo-hei; Kanoh, Koichi; Ishihara, Hideharu; Koketsu, Mamoru

doi:10.1248/cpb.53.1439

Cited by 41 publications

(21 citation statements)

References 28 publications

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“…Thus, the 1 H NMR spectrum of 8a showed a signal at δ 4.93 ppm equivalent to the NH 2 group (D 2 O exchangeable), a singlet at δ 6.62 ppm indica-ting the coumarin H-4 and a multiplet at δ 7.26-7.40 ppm for the C 6 H 4 group. In addition, the 13 C NMR spectrum signals were consistent with the assigned structure. The reaction of either compound 8a or 8b with phenylisothiocyanate (9) gave the 7-phenylthiazolo [4',5':4,5] thieno [2,3-d]pyrimidine-6(7H)-thione derivatives 10a and 10b, respectively.…”

Section: Resultssupporting

confidence: 68%

“…Thus, the 1 H NMR spectrum showed a singlet at δ 4.28 ppm equivalent to the thiazole CH 2 group, a singlet at δ 6.52 ppm indicating the coumarin 4H, a multiplet at δ 7.28-7.38 ppm for the C 6 H 4 group. Moreover, the 13 C NMR spectrum shoSheme 1. Synthesis of compounds 3, 6a-c and 7a-c wed beside the expected signals, δ 58.6 ppm indicating the presence of the thiazole CH 2 , two signals at δ 164.3, 168.6 ppm equivalent to the two CO groups and a signal at δ 170.3 ppm for the C=N.…”

Section: Resultsmentioning

confidence: 97%

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Anti-inflammatory and Anti-ulcer Activities of New Fused Thiazole Derivatives Derived from 2-(2-Oxo-2H-chromen-3-yl)thiazol-4(5H)-one

Mohareb

Al‐Omran

Abdelaziz

et al. 2017

ACSi

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The reaction of the 2-(4-oxo-4,5-dihydrothiazol-2-yl)acetonitrile (1) with salicylaldehyde (2) in 1,4-dioxane containing a catalytic amount of piperidine gave the coumarin derivative 3. The latter reacted with different reagents to give pyrano that compounds 7a, 8a, 10b, 13b, 15b, 18a, 19b, 19c, and 19d showed higher activity compared to the rest of the compounds. In addition to this, toxicity of such active compounds was studied against shrimp larvae where compounds 10b, 18a, 19c and 19d showed to be non-toxic against the tested organisms.

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Section: Resultssupporting

confidence: 68%

Section: Resultsmentioning

confidence: 97%

Anti-inflammatory and Anti-ulcer Activities of New Fused Thiazole Derivatives Derived from 2-(2-Oxo-2H-chromen-3-yl)thiazol-4(5H)-one

Mohareb

Al‐Omran

Abdelaziz

et al. 2017

ACSi

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“…Previously, we systematically synthesized various organic selenium compounds, including selenocarbamates, selenoureas, thioureas, tertiary selenoamide compounds, 2-amino-1,3-selenazoles, and bis-(2-amino-5-selenazoyl) ketones, and demonstrated their SOSA by using the same chemiluminescence method. The IC 50 values of these compounds ranged from approximately 0.1 to 100 µM (Takahashi et al, 2004;Sekiguchi et al, 2005;Takahashi et al, 2005a;Takahashi et al, 2005b;Sekiguchi et al, 2006). The SOSA of compound b might be relatively low compared with that of other compounds such as selenocarbamates, selenoureas, thioureas, tertiary selenoamide, and ebselen.…”

Section: Discussionmentioning

confidence: 97%

A superoxide anion-scavenger, 1,3-selenazolidin-4-one suppresses serum deprivation-induced apoptosis in PC12 cells by activating MAP kinase

Nishina

Kimura

Kozawa

et al. 2011

Toxicology and Applied Pharmacology

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Synthetic organic selenium compounds, such as ebselen, may show glutathione peroxidaselike antioxidant activity and have a neurotrophic effect. We synthesized 1,3-selenazolidin-4-ones, new types of synthetic organic selenium compounds (five-member ring compounds), to study their possible applications as antioxidants or neurotrophic-like molecules. Their superoxide radical scavenging effects were assessed using the quantitative, highly sensitive method of real-time kinetic chemiluminescence. At 166 M, the O2− scavenging activity of 1,3-selenazolidin-4-ones ranged from 0 to 66.2%. 2-[3-(4-Methoxyphenyl)-4-oxo-1,3-selenazolidin-2-ylidene]malononitrile (compound b) showed the strongest superoxide anion-scavenging activity among the 6 kinds of 2-methylene-1,3-selenazolidin-4-ones examined. Compound b had a 50% inhibitory concentration (IC50) at 92.4 M and acted as an effective and potentially useful O2− scavenger in vitro. The effect of compound b on rat pheochromocytome cell line PC12 cells was compared with that of ebselen or nerve growth factor (NGF) by use of the MTT [3-(4, 5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide] assay. When ebselen was added at 100 M or more, toxicity toward PC12 cells was evident. On the contrary, compound b suppressed serum deprivation-induced apoptosis in PC12 cells more effectively at a concentration of 100 M. The activity of compound b to phosphorylate mitogen-activated protein kinase/extracellular signal-regulated protein kinase (ERK) 1/2 (MAP kinase) in PC12 cells was higher than that of ebselen, and the former at 100 M induced the phosphorylation of MAP kinase to a degree similar to that induced by NGF. From these results, we conclude that this superoxide anion-scavenger, compound b, suppressed serum deprivationinduced apoptosis by promoting the phosphorylation of MAP kinase. (MAP kinase) in PC12 cells was higher than that of ebselen, and the former at 100 μM induced the phosphorylation of MAP kinase to a degree similar to that induced by NGF.From these results, we conclude that this superoxide anion-scavenger, compound b, suppressed serum deprivation-induced apoptosis by promoting the phosphorylation of MAP kinase.

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“…4 Recently, it was reported that 2-piperidino-and 4-phenyl-2-piperidino-1,3-selenazoles exhibit strong superoxide anion-scavening activity 5 , while 2-piperidino-and 2-morpholino-5-chloroacetyl-1, 3-selenazoles (4a, b) show antioxidant activity and strongly inhibit lipopolysaccharide-induced nitric oxide release from microglial cells. 6 Moreover, 2-amino-1,3-selenazole derivatives found application in the synthesis of organic dyes.…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of novel functionalized 1,3-selenazoles

Kanapickaitė¹,

Martynaitis²,

Šačkus

2009

Arkivoc

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The reaction of selenourea with diethyl 2,4-dibromo-3-oxoglutarate afforded ethyl 2-(2-amino-5-ethoxycarbonyl-1,3-selenazol-4-yl)-2-bromoethanoate. Treatment of the latter with acylating agents and various nucleophiles gave a series of new 4,5-disubstituted 2-amino-1,3-selenazoles. All compounds were characterized spectroscopically. The crystal structure determination of ethyl 2-(2-amino-5-ethoxycarbonyl-1,3-selenazol-4-yl)-2-bromoethanoate is reported.

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Superoxide Anion-Scavenging Effect of 2-Amino-1,3-selenazoles

Cited by 41 publications

References 28 publications

Anti-inflammatory and Anti-ulcer Activities of New Fused Thiazole Derivatives Derived from 2-(2-Oxo-2H-chromen-3-yl)thiazol-4(5H)-one

Anti-inflammatory and Anti-ulcer Activities of New Fused Thiazole Derivatives Derived from 2-(2-Oxo-2H-chromen-3-yl)thiazol-4(5H)-one

A superoxide anion-scavenger, 1,3-selenazolidin-4-one suppresses serum deprivation-induced apoptosis in PC12 cells by activating MAP kinase

Facile synthesis of novel functionalized 1,3-selenazoles

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