• Title/Summary/Keyword: methoxy groups

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Synthesis of Nucleophilic Adducts of Thiols (Ⅰ). Addition of Cysteine to $\beta$-Nitrostyrene Derivatives

  • Kim, Tae-Rin;Choi, Sung-Yong
    • Bulletin of the Korean Chemical Society
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    • v.2 no.4
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    • pp.125-129
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    • 1981
  • The addition reactions of cysteine without blocking amino and carboxyl groups to substituted and unsubstituted ${\beta}$-nitro-styrene derivatives were investigated. ${\beta}$-Nitrostyrene(1a), p-methyl-${\beta}$-nitrostyrene(1b), 3,4,5-trimethoxy-$[\beta}$ -nitrostyrene(1c), $[\varpi}$-3,4-methylenedioxy-${\beta}$ -nitrostyrene(1d), o-, m- and p-chloro-${\beta}$ -nitrostyrene (1e, 1f, 1g) and o-, m- and p-methoxy-${\beta}$-nitrostyrene (1h, 1i, 1j) easily undergo addition reactions with cysteine to form S-(2-nitro-1-phenylethyl)-L-cysteine(3a), S-[2-nitro-1-(p-methyl)phenyl-ethyl]-L-cysteine(3b), S-[2-nitro-1-(3',4',5'-trimethoxy) phenylethyl]-L-cysteine(3c), S-[2-nitro-1-($[\vatpi}$ -3',4'-methylenedioxy)phenylethyl]-L-cysteine(3d), S-[2-nitro-1-(o-chloro)phenylethyl]-L-cysteine(3e), S-[2-nitro-1-(m-chloro)-phenylethyl]-L-cysteine(3f), S-[2-nitro-1-(p-chloro)phenylethyl]-L-cysteine(3g), S-[2-nitro-1-(o-methoxy)phenylethyl]-L-cysteine(3h), S-[2-nitro-1-(m-methoxy)phenylethyl]-L-cysteine(3i) and S-[2-nitro-1-(p-methoxy)phenylethyl]-L-cysteine(3j), respectively. The structure of adducts were confirmed by means of UV-spectrum, IR-spectrum, molecular weight measurement and elemental analysis. The various factors effecting the yield of cysteine adducts to ${\beta}$-nitrostyrene derivatives were also studied.

Steric Effect on the Molecular Hyperpolarizabilities of β-Nitrostyrene Derivatives

  • 조봉래;제종태;김현수;전승준;송옥근;Wang, C. H.
    • Bulletin of the Korean Chemical Society
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    • v.17 no.8
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    • pp.693-695
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    • 1996
  • The steric effect on the first order hyperpolarizability of the β-nitrostyrene derivatives has been investigated by comparing the β values and the dihedral angles between the aryl and nitroalkenyl groups. In general the β value increased with the electron-donating ability of the substituent. The larger β value for 3,4-dimethoxy-β-nitrostyrene than that for p-methoxy-β-nitrostyrene has been attributed to the lower charge transfer energy for the former. The most striking substituent effect was observed in the β-methyl-β-nitrostyrene derivatives. Thus the β values for 3,4-dimethoxy- and p-methoxy derivatives of the latter decreased to near zero, probably because of the large distortion from planarity caused by the steric repulsion between the β-methyl and the aryl groups. The larger β value for p-dimethylamino-β-methyl-β-nitrostyrene has been interpreted with an increased electron-donating ability of the substituent and increased co-planarity.

Effects of Chrysanthemum Extract Drinks on Sociopsychological Stress (사회.심리적 스트레스에 미치는 국화 추출 음료의 영향)

  • 최진호;김대익;박수현;김동우;조원기;유병팔
    • Journal of Life Science
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    • v.9 no.5
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    • pp.604-611
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    • 1999
  • The effects of anti-stress chrysanthemum flower (ASCF) extract drink (ASCF-0.1% and ASCF-0.5% concentrations) were tested for the anti-stress action. ICR male mice (20$\pm$2 g) were fed with basic experimental diets and given free access to water containing these ingredients for 18 days. Psychological stress/sociopsychologcal stress exposed by foot-shock for 1 hour for 3 days. Both ASCF-0.1 and ASCF-0.5 groups in the sociopsychological stress resulted in a significant decrease of 28.1% and 27.3% in plasma corticosterone (CS) secretion compared with psychological stress (control group). Noradrenaline (NA) secretions in the brain were significantly increased 49.7% and 53.9%, respectively, in ASCF-0.1 and ASCF-0.5 groups compared with control group. MHPG-SO4 (3-Methoxy-4-hydroxyphenylethy-leneglycol sulfate) levels in the brain resulted in a marked decreases of 12.9% and 16.6%, respectively in ASCF-0.1 and ASCF-0.5 groups. NA/MHPG-SO4 ratios in the brain of ASCF-0.1 and ASCF-0.5 groups resulted in a significantly increase of 71.3% and 81.0%, respectively, compared with control group. These results suggest that anti-stress chrysanthemum flower (ASCF) drink can effectively ridded the sociopsychological stress.

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Effects of Mind Tonic Drinks on Sociopsychological Stress (사회.심리적 스트레스에 미치는 마인드 토닉(Mind Tonic) 음료의 영향)

  • 최진호;김대익;박수현;김동우;조원기;유병팔
    • Journal of Life Science
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    • v.9 no.5
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    • pp.596-603
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    • 1999
  • The effects of anti-stress mind tonic (ASMT) drink (ASMT-0.1% and ASMT-0.5% concentration) were tested for the anti-stress action. ICR male mice (20$\pm$2 g) were fed with basic experimental diets free access to water containing these ingredients for 18 days. Psychological stress/sociopsychological stress were exposed by foot-shock for 1 hour for 3 days. Both ASMT-0.1 and ASMT-0.5 groups in the sociopsychological stress resulted in a significant decrease of 19.1% and 41.9% in plasma corticosterone (CS) secretion compared with psychological stress (control group). Noradrenaline (NA) secretions in the brain were significantly increased 23.4% and 35.9%, respectively, in ASMT-0.1 and ASMT-0.5 groups compared with control group. MHPG-SO4 (3-Methoxy-4-hydroxyphenylethyleneglycol sulfate) levels in the brain resulted in a marked decreases of 27.1% and 19.6%, respectively in ASMT-0.1 and ASMT-0.5 groups. NA/MHPG-SO4 ratios in the brain of ASMT-0.1 and ASMT-0.5 groups resulted in a significantly increase of about 70% compared with control group. These suggest that mind tonic anti-stress drink can effectively ridded the sociopsychological stress.

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Synthesis and Luminescent Properties of Tetrafluorophenyl Containing Poly(p-phenylenevinylene) Derivatives

  • Ahn, Taek
    • Transactions on Electrical and Electronic Materials
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    • v.16 no.3
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    • pp.162-167
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    • 2015
  • To investigate the effect of fluoro groups substitution on poly(p-phenylenevinylene) derivatives, poly(2,3,5,6- tetrafluoro-p-phenylenevinylene-alt-N-ethylhexyl-3,6-carbazolevinylene), PCTF-PPV, and poly[2,3,5,6-tetrafluoro-p-phenylenevinylene-alt-2-methoxy-5-(2-ethylhexyloxy)-p-phenylenevinylene], PMTF-PPV, were synthesized by the well-known Wittig condensation polymerization process. To compare the influences of fluoro groups, no fluoro groups containing model polymers, poly(p-phenylenevinylene-alt-N-ethylhexyl-3,6-carbazolevinylene), PCPPPV and poly[p-phenylenevinylene-alt-2-methoxy-5-(2-ethylhexyloxy)-p-phenylenevinylene], p-PMEH-PPV, were also synthesized. The resulting polymers were completely soluble in common organic solvents and exhibited good thermal stability up to 300℃. The polymers showed UV-visible absorbance and photoluminescence (PL) in the ranges of 259~452 nm and 500~580 nm, respectively. The tetrafluorophenyl containing PCTF-PPV and PMTF-PPV showed relatively red-shifted PL peaks at 521 nm and 580 nm, respectively, compared to that of non-fluoro groups containing polymers (PCP-PPV: 500 nm and p-PMEH-PPV: 539 nm). The single-layer light-emitting diode was fabricated in a configuration of ITO/polymer/Al. Electroluminescene (EL) emissions of PCP-PPV, PCTF-PPV, p-PMEH-PPV and PMTF-PPV were shown at 507, 524, 556, and 616 nm, respectively.

Effects of Rose Fruit Extract Drinks on Sociopsychological Stress (사회.심리적 스트레스에 미치는 장미 추출 음료의 영향)

  • 최진호;김대익;박수현;김동우;조원기;유병팔
    • Journal of Life Science
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    • v.9 no.5
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    • pp.612-619
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    • 1999
  • The effects of anti-stress rose fruit (ASRF) extract drink (ASRF-0.1% and ASRF-0.5% concentrations) were tested for the anti-stress action. ICR male mice (20$\pm$2 g) were fed with basic experimental diets and given free access to water containing these ingredients for 18 days. Psychological stress/sociopsychological stress exposed by foot-shock for 1 hour for 3 days. Both ASRF-0.1 and ASRF-0.5 groups in the sociopsychological stress resulted in a significant decrease of 24.3% and 38.0% in plasma corticosterone (CS) secretion compared with psychological stress (control group). Noradrenaline (NA) secretion in the brain were significantly increased 35.9% in ASRF-0.5 group, but NA secretion in ASRF-0.1 group could not be obtained significant result compared with control group. MHPG-SO4 (3-Methoxy-4-hydroxy-phenylethy leneglycol sulfate) levels in the brain resulted in a marked decreases of 16.5% and 18.9% respectively in ASRF-0.1 and ASRF-0.5 groups. NA/MHPG-SO4 ratios in the brain of ASRF-0.1 and ASRF-0.5 groups resulted in a significantly increase of 16.5% and 67.0%, respectively, compared with control group. These results suggest that anti-stress rose fruit (ASRF) drink also can effectively ridded the sociopsychological stress.

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Synthesis and Characterization of Thermosensitive Poly(organophosphazenes) with Methoxy-Poly(ethylene glycol) and Alkylamines as Side Groups

  • Lee, Bae-Hoon;Lee, Young-Moo;Sohn, Yoon-Soo;Song, Soo-Chang
    • Bulletin of the Korean Chemical Society
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    • v.23 no.4
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    • pp.549-554
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    • 2002
  • Thermosensitive poly(organophosphazenes) bearing methoxy-poly(ethylene glycol) (MPEG) and alkylamines as substituents have been synthesized and characterized by elemental analysis, NMR spectroscopy, GPC, and DSC. All the polymers exhibited crystallinity, which was probably induced by the MPEG side chain of the polymers. All the polymers exhibited the lower critical solution temperature (LCSTs) in the range of 28 to $94^{\circ}C$ depending on several factors such as mole ratio of the substituents, kinds of PEG and alkylamines. The higher content of MPEG and shorter chain length of alkylamines of the polymers afforded the higher LCST. The LCSTs of the polymers exhibited almost concentration-independent behavior in the range of 3-30 wt % of the polymers in aqueous solutions. The polymers showed the higher LCSTs in the acidic solutions than in the neutral and basic solutions. The ionic strength of the polymer solution affected the LCST, which decreased with increased NaCl concentration. The polymer bearing almost equimolar substitutuents with the -N-P-N- unit has shown the LCST more sensitive to NaCl and pH than that with the -N-P-O- unit. The polymers were found to degrade in acidic solution but be very stable in alkali solution as well as in the buffer solution of pH 7.4.

Differential Effects of Methoxylated p-Coumaric Acids on Melanoma in B16/F10 Cells

  • Yoon, Hoon Seok;Lee, Nam-Ho;Hyun, Chang-Gu;Shin, Dong-Bum
    • Preventive Nutrition and Food Science
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    • v.20 no.1
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    • pp.73-77
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    • 2015
  • As an approach to search for chemopreventive agents, we tested p-coumaric acid, 3-methoxy-p-coumaric acid (ferulic acid), and 3,5-dimethoxy-p-coumaric acid (sinapic acid) in B16/F10 melanoma cells. Intracellular melanin contents were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay and cytotoxicity of the compounds were examined by lactate dehydrogenase (LDH) release. p-Coumaric acid showed inhibitory effect on melanogenesis, but ferulic acid increased melanin content, and sinapic acid had almost no effect on melanogenesis. Treatment with ferulic acid resulted in a 2 to 3 fold elevation in the production of melanin. Correlatively, cell viability decreased in a dose-dependent manner when treated with ferulic acid. However, ferulic acid did not affect the LDH release from the cells. Treatment with sinapic acid resulted in a 50~60% elevation in the release of LDH when treated with a $200{\mu}g/mL$ concentration and showed neither cytostasis nor increase of melanin synthesis in a dose-dependent manner. Taken together, p-coumaric acid inhibits melanogenesis, ferulic acid induces melanogenesis, and sinapic acid exerts cytotoxic effects in B16/F10 murine melanoma cells. The results indicate that the addition of methoxy groups to p-coumaric acid shows the melanogenic or cytotoxic effects in melanoma cells compared to the original compound. Therefore, this study suggests the possibility that methoxylated p-coumaric acid, ferulic acid can be used as a chemopreventive agent.

Synthesis, Crystal structure, and Magnetic Properties of Dinuclear Iron(III) Complexes with Methoxo Bridges

  • Shin, Jong-Won;Han, Jeong-Hyeong;Rowthu, Sankara Rao;Kim, Bong-Gon;Min, Kil-Sik
    • Bulletin of the Korean Chemical Society
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    • v.31 no.12
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    • pp.3617-3622
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    • 2010
  • The reaction of stoichiometric amount of $FeCl_2{\cdot}4H_2O$, (2-pyridylmethyl, 3-pyridylmethyl)amine (2,3-pyma) and sodium azide/sodium thiocyanate in methanol under aerobic conditions affords the dinuclear Fe(III) complexes, [(2,3-pyma) $(N_3)_2Fe({\mu}-OCH_3)_2Fe(N_3)_2$(2,3-pyma)]${\cdot}CH_3OH$ (1) and [(2,3-pyma)$(NCS)_2Fe({\mu}-OCH_3)_2Fe(NCS)_2$(2,3-pyma)] (2) in good yield. Two bis-methoxy-bridged diiron(III) complexes are isolated and characterized. The coordination geometries around iron(III) ions in 1 and 2 are the same tetragonally distorted octahedron. The iron(III) ions are coordinated by two nitrogens of a 2,3-pyma, two nitrogens of two azide/thiocyanate ions, and two oxygens of two methoxy groups. Both compounds are isomorphous. The structures of 1 and 2 display the C-$H{\cdots}\pi$ and/or $\pi-\pi$ stacking interactions as well as hydrogen bonding interactions, respectively. Compounds 1 and 2 show significant antiferromagnetic couplings through the bridged methoxy groups between the iron(III) ions in the temperature range from 5 to 300 K ($H=-2JS_1{\cdot}S_2$, J=-19.1 and $-13.9\;cm^{-1}$ for 1 and 2).

Rapid and Efficient Debromination of vic-Dibromides with VCl3/Indium System

  • Yoo, Byung Woo;Park, Jee Yeon;Shin, Hyo Jong
    • Journal of the Korean Chemical Society
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    • v.62 no.4
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    • pp.275-278
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    • 2018
  • The $VCl_3$/In system was found to be a new protocol for debromination of a variety of vic-dibromides to the corresponding alkenes in high yields with short reaction times under mild conditions. This new methodology is highly chemoselective, tolerating several functional groups such as chloro, bromo, fluoro, keto, ester, carboxyl, and methoxy groups.