Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids

Kato, Keita; Terao, Shinji; Shimamoto, Norio; Hirata, Minoru

doi:10.1021/jm00399a019

Cited by 233 publications

(135 citation statements)

References 2 publications

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“…The biosynthesized silver nanoparticle, the aqueous and the ethanolic leaf extract were tested for their antioxidant property by 1,1-diphenylpicrylhydrazyl (DPPH) method (Kato et al 1988). In this procedure, drug stock solution (1 mg/mL) was diluted to final concentration of 2, 4, 6, 8, 10 and 12 lg/mL in methanol.…”

Section: Antioxidant Assaymentioning

confidence: 99%

Microwave-assisted green synthesis of silver nanoparticles from Fraxinus excelsior leaf extract and its antioxidant assay

et al. 2015

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The biosynthesis of nanoparticles has been proposed as a cost effective and environmentally benevolent alternative to chemical and physical methods. In the present study, microwave assisted synthesis of silver nanoparticles (AgNPs) has been demonstrated using leaf extract of Fraxinus excelsior reducing aqueous AgNO 3 solution. The synthesized nanoparticles have been characterized on the basis of fourier transform infrared spectroscopy (FT-IR), UV-Vis spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM) and energy dispersive X-ray (EDX) analysis. The presence of a characteristic surface plasmon resonance (SPR) absorption band at 425 nm in UV-Vis reveals the reduction of silver metal ions into silver nanoparticles. FT-IR analysis was carried out to probe the possible functional group involved in the synthesis of AgNPs. Further leaf extracts and AgNPs were evaluated for antiradical scavenging activity by 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay.

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Section: Antioxidant Assaymentioning

confidence: 99%

Microwave-assisted green synthesis of silver nanoparticles from Fraxinus excelsior leaf extract and its antioxidant assay

et al. 2015

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“…Therefore, chemical modification of hydroxy group of Vitamin C with a lipophilic molecule is necessary for the development of an efficient transdermal Vitamin C derivative. A variety of lipophilic Vitamin C derivatives have been developed (14)(15)(16), but no ideal Vitamin C derivatives have been available in terms of stability, lipophilicity, and biological activity.…”

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confidence: 99%

Synthesis and Characterization of New Ascorbic Derivative: Sodium Isostearyl 2-O-L-Ascorbyl Phosphate

Shibayama¹,

Ueda²,

Yoshio³

et al. 2005

J. Oleo Sci.

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“…A long alkoxy chain seems to be favorable for interaction with the lipid-bilayer in plasma and microsomal membranes, as described for the synthetic ascorbate analogue CV-3611. 22) Finally, the effects of distance between the imidazole and carboxyl moieties and the position of the alkoxy side chain on both activities were investigated. The lengths of the alkyl chains bearing imidazole and carboxyl groups were changed ( Table 3).…”

Section: Resultsmentioning

confidence: 99%

“…9) Changing the distance between the two functional groups had no effects on the free radical scavenging and anti-peroxidative activities (13,(22)(23)(24). In compounds 20, 25-27, the effects of the position of the alkoxy moiety on the activities were examined.…”

Section: Resultsmentioning

confidence: 99%

A Novel Series of Thromboxane A2 Synthetase Inhibitors with Free Radical Scavenging and Anti-peroxidative Activities.

Kamiya

Shirahase

Nakamura

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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A novel series of indoline derivatives with imidazole and carboxyl moieties were synthesized and evaluated for their thromboxane A 2 (TXA 2 ) synthetase inhibiting, radical scavenging and anti-peroxidative activities. Among the compounds synthesized, 3-{5-substituted-3-[2-(imidazol-1-yl)ethyl]indolin-1-yl}propionic acids showed free radical scavenging activity and inhibitory effects on lipid-peroxidation of rat brain homogenate and on arachidonate-induced TXA 2 -dependent aggregation of rabbit platelets. The anti-platelet and anti-peroxidative activities were related to the lipophilicity of the 5-substituent. The 5-hexyloxy derivative (13) showed about 35-fold higher inhibitory activity on TXA 2 synthesis than that of ozagrel and about 100-fold higher activity on lipid peroxidation than that of a a-tocopherol. Compound 13 showed in vivo anti-thrombotic effect in mice and ex vivo anti-peroxidative activity in rats.Key words indoline derivative; thromboxane A 2 synthetase inhibitor; radical scavenger; anti-peroxidation duced with sodium cyanoborohydride (NaBH 3 CN) to corresponding indolines followed by protection with di-tert-butyl dicarbonate ((Boc) 2 O) to afford N-protected indoline derivatives (IV). Bromination of IV with CBr 4 and Ph 3 P followed by condensation with imidazole and deprotection with HCl to afford V. Target compounds (2, 7-9, 12-27) were obtained by condensation with ethyl acrylate or ethyl 3-bromopropionate followed by hydrolysis of ester precursors (VI) with NaOH.Compounds 10 and 11 were prepared from the 5-hydroxyindoline derivative (VII). Deprotection of VI (nϭ1, mϭ2, RϭOCH 2 C 6 H 5 ) was performed with trifluoroacetic acid (TFA) in anisole to afford the corresponding phenol (VII), which was condensed with the appropriate bromides followed by hydrolysis of ester precursors with NaOH to give 10 and 11.Chart 2 shows the synthetic route of 3. 5-Bromoindoline derivative (28) was reacted with CuCN in N-methylpyrrolidone to afford 5-cyanoindoline derivative (29). Hydrolysis of 29 with conc. HCl gave the corresponding carboxylic acid (30), 19) which was protected with ester and (Boc) 2 O to give 31. Bromination of 31 with CBr 4 and Ph 3 P followed by condensation with imidazole gave 32, which was deprotected with NaOH and HCl to afford 3.Chart 3 shows the synthetic route of the other indoline derivatives (4-6). The 4-substituted derivative (34a) was prepared from 33a by condensation with ethylene bromohydrin. The 5-or 6-substituted derivatives (34b, c) were obtained by reduction of the appropriate indoline carboxylate (33b, c) 19) with diisobutylaluminum hydride (DIBAL-H) or LiAlH 4 and protection with (Boc) 2 O. Bromination of 34a-c with CBr 4 and Ph 3 P followed by condensation with imidazole gave 35a-c, which were deprotected with HCl followed by condensation with ethyl bromoacetate or ethyl acrylate followed by hydrolysis of ester precursors with NaOH to afford target compounds 4-6. Results and DiscussionIn the present study, we synthesized a series of indoline derivatives and examined their...

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Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids

Cited by 233 publications

References 2 publications

Microwave-assisted green synthesis of silver nanoparticles from Fraxinus excelsior leaf extract and its antioxidant assay

Microwave-assisted green synthesis of silver nanoparticles from Fraxinus excelsior leaf extract and its antioxidant assay

Synthesis and Characterization of New Ascorbic Derivative: Sodium Isostearyl 2-O-L-Ascorbyl Phosphate

A Novel Series of Thromboxane A2 Synthetase Inhibitors with Free Radical Scavenging and Anti-peroxidative Activities.

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