• Title/Summary/Keyword: 1D $^1H-NMR$

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Synthesis of Poly(glycidyl azide-co-glycidyl ferrocenyl ether) (Poly(glycidyl azide-co-glycidyl ferrocenyl ether)의 합성)

  • Jung, Haeji
    • Journal of the Korea Institute of Military Science and Technology
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    • v.22 no.1
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    • pp.35-41
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    • 2019
  • Ferrocene and ferrocene derivatives have been widely used as a burning rate catalyst for composite solid propellants. However, its tendency to migrate through the propellant grain and to crystallize at the surface changes the composition of propellant which results in unpredictable burning rate. To overcome the weakness of ferrocene catalyst, we designed a polymer containing ferrocene, poly(glycidyl azide-co-glycidyl ferrocenyl ether) (GAFP). GAFPs were synthesized from poly(epichlorohydrin-co-glycidyl ferrocenyl ether) (PEGF) which has ferrocenyl ethers in its pendant groups. The structures of GAFPs were confirmed by FT-IR, $^1H$ and $^{13}C$ NMR spectral analyses. Thermal properties of the GAFPs were evaluated using differential scanning calorimeter (DSC). As the contents of ferrocene increased, the glass transition temperature ($T_g$) of the GAFPs shifted to a higher temperature, and the decomposition temperature ($T_d$) decreased because the ferrocene worked as a burning rate catalyst.

Preparation and Properties of Phytosphingosine Ascorbate with Retaining Skin Development Effects (피부 활성을 갖는 Phytosphingosine Ascorbate의 합성)

  • Min, Seok-Kee;Jin, Yong-Hoon;Park, Woo-Jung;Eom, Sang-Yong;Kim, Jong-Heon
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.30 no.2
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    • pp.167-172
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    • 2004
  • In the human skin, vitamin C (L -ascorbic acid) that is well known as the activated materials has effects that is skin anti-aging and wrinkle repair by giving impetus to collagen biosynthesis and anti-oxidation, and that is the sun screen, a wound recovering, inhibition melanogenesis and so on. In spite of its effects, vitamin C has the defects of the skin stimulation and easily oxidized instability by water, air, heat and light. For solving their matters, many investigation is advanced and its results are synthesized the various vitamin C derivatives. And yet they have not solved the unstable property of vitamin C and were still insufficient for the comparing with the effect of the pure vitamin C itself. In this study, in order to prepare vitamin C derivative of being improved the stability and to apply vitamin C effect in the skin, we prepared new vitamin C derivative, phytosphingosine ascorbate, by using phytosphingosine, one of sphingolipids, which have a distinguished skin affinity. Phytosphingosine ascorbate can be prepared as the ionic bond between amine group (-NH$_2$) of phytosphingosine and hydroxy group (-OH) of vitamin C by way of the relatively simple reaction. So the structure and properties of the synthesized phytosphingosine ascorbate was confirmed the use of elemental analysis (C 58.3 : H 9.3 : N 2.8 : O 29.5), MALDI TOF-MS (Mw=492.58), Ultraviolet spectra (268.5nm), lH NMR, FT-IR spectra, thermal analysis (m.p=l54$^{\circ}C$), HPLC and so on. And we could confirm the anti-bacterial and anti-oxidation effects. Based on these results, we could confirm to prepare a new material that was expected of both effects of vitamin C and phytosphingosine and that is improved properties of vitamin C.

Antitumor Activity and Nephrotoxicity of the Novel Platinum(II) Coordination Complex (새로운 Platinum (II) Complex [Pt (II)(trans-d-dach)(DPPE)] $(NO_3)_2$의 항암효과 및 신독성에 관한 연구)

  • Jung Jee-Chang;Lee Moon-Ho;Chang Sung-Goo;Rho Young-Soo
    • The Korean Journal of Pharmacology
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    • v.31 no.1 s.57
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    • pp.103-114
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    • 1995
  • Platinum coordination complexes are currently one of the most compounds used in the treatment of solid tumors. However, its use is limited by severe side effects such as renal toxicity. Our platinum-based drug discovery program is aimed at developing drugs capable of diminishing toxicity and improving antitumor activity. We synthesized new Pt (Ⅱ) complex analogue containing 1,2-diaminocyclohexane (dach) as carrier ligand and 1,2-bis(diphenylphosphino) ethane (DPPE) as a leaving group. Furthermore, nitrate was added to improve the solubility. A new series of [Pt(trans-ddach)(DPPE).$2NO_3(PC)$ was synthesized and characterized by their elemental analysis and by various spectroscopic techniques [infrared (IR), $^{13}carbon$ nuclear magnetic resonance (NMR)]. PC demonstrated acceptable antitumor activity aganist P388, L-1210 lymphocytic leukemia cells and SK=OV3 human ovarian adenocarcinoma cells, and significant. activity as compared with that. cisplatin. The toxicity of PC was found quite less than thar of cisplatin using MTT, $[^3H]$ thymidine uptake and glucose consumption tests in rabbit proximal tubule cells, human kidney cortical cells and human renal cortical tissues. Based on these results, this novel platinum compound represent a valuable lead in the development of a new anticancer chemotherapeutic agent capable of improving antitumor activity and low toxicity.

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Development of Biologically Active Compounds from Edible Plant Sources-XIX. Isolation of Inhibitory Compound on LDL-Oxidation from the Aerial Parts of Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk) (식용식물자원으로부터 활성물질의 탐색-XIX. 사자발쑥(Artemisia princeps PAMPANINI, Sajabalssuk)의 전초로부터 저밀도 지질 단백질(LDL) 산화 억제물질의 분리)

  • Bang, Myun-Ho;Song, Myoung-Chong;Han, Min-Woo;Lee, Dae-Young;Jo, Jin-Kyung;Chung, Hae-Gon;Jeong, Tae-Sook;Lee, Kyung-Tae;Choi, Myung-Sook;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.50 no.3
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    • pp.224-227
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    • 2007
  • Sajabalssuk (Artemisia princeps PAMPANINI) was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_{2}O$, successively. From the EtOAc fraction, two phenylpropanoids were isolated through the repeated silica gel and ODS column chromatographies. From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the phenylpropanoids were determined as eugenol (1) and (-)-sesamin (2). They were the first to be isolated from Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk). Also, eugenol inhibited LDL-oxidation with the inhibitory activity of 87.8 ${\pm}$ 1.0% at a concentration of 40 ${\mu}g/ml$.

All-trans Retinoic Acid-Associated Low Molecular Weight Water-Soluble Chitosan N anoparticles Based on Ion Complex

  • Kim Dong-Gon;Choi Changyong;Jeong Young-Il;Jang Mi-Kyeong;Nah Jae-Woon;Kang Seong-Koo;Bang Moon-Soo
    • Macromolecular Research
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    • v.14 no.1
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    • pp.66-72
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    • 2006
  • The purpose of this study is to develop novel nanoparticles based on polyion complex formation between low molecular weight water-soluble chitosan (LMWSC) and all-trans retinoic acid (atRA). LMWSC nanoparticles encapsulating atRA based on polyion complex were prepared by mixing of atRA into LMWSC aqueous solution using ultrasonication. In FTIR spectra, the carbonyl group of atRA at 1690 $cm^{-1}$ disappeared or decreased when ion complexes were formed between LMWSC and atRA. In ${1}^H$ NMR spectra, specific peaks of atRA disappeared when atRA-encapsulated LMWSC (RAC) nanoparticles were reconstituted into $D_{2}O$ while specific peaks both of atRA and LMWSC appeared in $D_{2}O$/DMSO (1/3, v/v) mixture. XRD patterns also showed that the crystal peaks of atRA were disappeared by encapsulation into LMWSC nanoparticles. LMWSC nanoparticles encapsulating atRA have spherical shapes with particle size below 200 nm. The mechanism of encapsulation of atRA into LMWSC nanoparticles was thought to be an ion complex formation between LMWSC and atRA. LMWSC nanoparticles showed high atRA loading efficiency over 90$\%$ (w/w). AtRA was continuously released from nanoparticles over 10 days. In in vitro cell cytotoxicity test, free atRA showed higher cytotoxic effect against CT 26 colon carcinoma cell line on 1 day. However, RAC nanoparticles showed similar cytotoxicity against CT 26 cells on 2 day. These results suggest the potential for the introduction of LMWSC nanoparticles into various biomedical fields such as drug delivery.

Two New Diphenylethylenes from Arundina graminifolia and Their Cytotoxicity

  • Li, Yin-Ke;Zhou, Bin;Ye, Yan-Qing;Du, Gang;Niu, De-Yun;Meng, Chun-Yang;Gao, Xue-Mei;Hu, Qiu-Fen
    • Bulletin of the Korean Chemical Society
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    • v.34 no.11
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    • pp.3257-3260
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    • 2013
  • Two new diphenylethylenes, gramniphenols H and I (1 and 2), together with six known diphenylethylenes (3-8), were isolated from Arundina graminifolia. The structures of 1-8 were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques. Compounds 1 and 2 were evaluated for their cytotoxicity against five human tumor cell lines. Compound 1 showed cytotoxicity against PC3 cells with $IC_{50}$ value of 3.5 ${\mu}M$. Compound 2 showed cytotoxicity against NB4 and PC3 cells with $IC_{50}$ values of 3.6 and 3.8 ${\mu}M$, respectively.

Isolation and Identification of a Sterol and Three Glucosides from the Peel of Pear (Pyrus pyrifolia Nakai cv. Chuhwangbae) (추황배(Pyrus pyrifolia Nakai cv. Chuhwangbae) 과피로부터 1종의 Sterol과 3종의 배당체 화합물의 단리 · 동정)

  • Lee, Yu Geon;Cho, Jeong-Yong;Lee, Hyun Joo;Lee, Yong Hyun;Lee, Sang-Hyun;Han, Tae-Ho;Kim, Wol-Soo;Park, Keun-Hyung;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.45 no.5
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    • pp.557-564
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    • 2013
  • We isolated and identified antioxidants from acidic and neutral ethyl acetate fractions of the peel of pear (Pyrus pyrifolia N. cv. Chuhwangbae). We isolated 4 compounds from the methanol extract, by using 3 different types of column chromatography (Sephadex LH-20, silica gel, and octadecylsilane) and preparative HPLC. We identified the isolated compounds as (S)-(+)-2-cis-abscisic acid O-${\beta}$-D-glucopyranosyl ester (compound 1), 1-[4-O-${\beta}$-D-glucopyranosyl]phenyl ethanone (picroside, compound 2), ${\beta}$-sitosterol (compound 3), and ${\beta}$-sitosteryl 3-O-${\beta}$-D-glucopyranoside (compound 4) by nuclear magnetic resonance analysis. We are the first to report the identification of compounds 1, 2, and 4 from pear.

Antioxidant and Cytotoxic Activity of Compounds from the Stem of Juncus effusus (등심초로부터 분리된 화합물의 항산화 활성 및 암세포 성장 억제 효과)

  • Kim, Ye Jin;Park, Chan Ik;Park, Jae Sung;Ahn, Eun Mi
    • Journal of Applied Biological Chemistry
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    • v.57 no.1
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    • pp.47-51
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    • 2014
  • The stems of Juncus effusus were extracted with 70% aqueous ethanol and the concentrated extract was partitioned with ethyl acetate, n-butanol and $H_2O$, successively. Two compounds were isolated from the ethyl acetate fraction through the repeated silica gel and Sephadex LH-20 column chromatographies. According to the results of physico-chemical and spectroscopic data including NMR and IR, the chemical structures of the compounds were determined as dehydroeffusol (1) and effusol (2). Dehydroeffusol and effusol exhibited potent scavenging activity for DPPH and ABTS radicals with the $IC_{50}$ values as $130{\pm}3.21$ and $79{\pm}1.53{\mu}M$ in DPPH assay, and as $39{\pm}3.51$ and $24{\pm}2.73{\mu}M$ in ABTS assay, respectively. The compounds also significantly inhibited the proliferation of human cancer cell lines, AGS and A549.

A detailed study of physicochemical properties and microstructure of EmimCl-EG deep eutectic solvents: Their influence on SO2 absorption behavior

  • Zhu, Jiahong;Xu, Yingjie;Feng, Xiao;Zhu, Xiao
    • Journal of Industrial and Engineering Chemistry
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    • v.67
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    • pp.148-155
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    • 2018
  • To get a better understanding of the effect of physicochemical properties and microstructure on $SO_2$ absorption behavior of DESs with different molar ratios of EmimCl and EG (from 2:1 to 1:2), densities (${\rho}$), viscosities (${\eta}$), speeds of sound (u), refractive indices ($n_D$), and thermal decomposition temperatures ($T_d$) of EmimCl-EG DESs were measured and used to obtain the other derived properties, such as thermal expansion coefficient (${\alpha}_p$) and activation energy for viscous flow ($E_{\eta}$). Moreover, FT-IR spectra and in situ variable-temperature NMR spectroscopy were employed to study the microstructures of DESs. Based on physicochemical and spectroscopic properties, the influence of the concentrations of EmimCl on the interactions in DESs was explored to be associated with their $SO_2$ absorption behavior. The results show that the interactions between $Emim^+$ and $Cl^-$ of EmimCl is gradually weakening with increasing the concentration of EG in DESs by forming of hydrogen bond interaction of $O-H{\cdots}Cl^-$, resulting in a decrease of ${\rho}$, ${\eta}$, u, $n_D$, and $T_d$ of DESs, and hindering the charge-transfer interaction of $SO_2$ with $Cl^-$ and deceasing $SO_2$ capture capacity. Moreover, the $SO_2$ absorption capacity of DESs is proportional to their ${\rho}$ and $E_{\eta}$, respectively.

Synthesis of Dodecyl Ether Sulfates Containing Various Ethylene Oxide and Isopropylene Oxide (EO, PO가 부가된 도데실 에테르 황산화물의 합성)

  • Yoo, Young-Chang;Rho, Sung-Ho;Ju, Myung-Jong;Nam, Ki-Dae
    • Applied Chemistry for Engineering
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    • v.7 no.2
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    • pp.289-298
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    • 1996
  • Eight kinds of poly(oxyethylene, oxyisopropylene) dodecyl ethers were synthesized by adding ethylene oxide and isopropylene oxide with each 5 and 10 moles alternatively on dodecanol. The addition of EO and PO for eight kinds of sodium poly(oxyethylene, oxyisopropylene) dodecyl ether sulfates was identified with HPLC, $^1H$ NMR, hydroxy value, and IR spectrum. In order to verify the sulfation the number of EO and PO molecules was obtained by spectra and Epton method. The yields of products sulfated by chlorosulfonic acid were 90~96%.

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