• Title/Summary/Keyword: naphthyl group

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Photopolymerization of Methyl Methacrylate with Primarty Aryl- and Alkylsilanes

  • 우희권;홍란영;양수연;박선희;송선정;함희석
    • Bulletin of the Korean Chemical Society
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    • v.16 no.11
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    • pp.1056-1059
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    • 1995
  • The bulk photopolymerization of methyl methacrylate (MMA) with primary arylsilane (e.g., phenylsilane) and various primary alkylsilanes (e.g., benzylsilane, 3-phenoxyphenyl-1-silabutane, 3-naphthyl-1-silabutane, and 3-chlorophenyl-1-silabutane) was performed to produce poly(MMA)s containing the corresponding silyl moiety as an end group. It was found for the phenylsilane that while the polymerization yields increased and then decreased with a turning point at the molar ratio of MMA:silane=10:1 as the relative silane concentration increases, the polymer molecular weights decreased, and the TGA residue yields and the relative intensities of SiH IR stretching bands increased with increment of molar ratio of silane over MMA. The photopolymerization yield of MMA with the arylsilane was found to be higher than those with the alkylsilanes and without the silanes. Thus, the silanes seemed to significantly influence on the photopolymerization as both chain initiation and chain transfer agents.

Chiral Recognition Models of Enantiomeric Separation on Cyclodextrin Chiral Staionary Phases

  • 이선행;김병학;이영철
    • Bulletin of the Korean Chemical Society
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    • v.16 no.4
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    • pp.305-309
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    • 1995
  • The enantiomeric separation of several amino acid derivatives by reversed-phase liquid chromatography using two (R)-and (S)-naphthylethylcarbamate-β-cyclodextrin(NEC-β-CD) bonded stationary phases was studied to illustrate the chiral recognition model of the enantiomeric separation. The retention and enantioselectivity of the chiral separations with (R)-and (S)-NEC-β-CD bonded phases were compared with similar separations with the native β-CD stationary phases. Especially, the enantioselectivity and elution orders between the derivatized amino acid enantiomers are carefully examined. These results can be illustrated by the chiral recognition models involving inclusion complexation, π-π interaction, and/or hydrophobic interaction. Inclusion complexation and hydrophobic interaction of the naphthyl group of the NEC moiety seem to be major chiral recognition components in the enantiomeric separation of 2,4-dinitrophenyl amino acids and dabsyl amino acids on (R)-and (S)-NEC-β-CD columns. For dansyl amino acids, only the inclusion complexation is the dominant factor. Three different chiral recognition models containing π-π interaction, inclusion complexation and hydrogen bonding were proposed for the separation of the 3,5-dinitrobenzoyl amino acid enantiomers, depending on the size and shape of amino acids.

Preparation of A New HPLC Chiral Stationary Phase from (S)-Naproxen and Application in Elucidating Chiral Recognition Models

  • 현명호;김광자;정경규
    • Bulletin of the Korean Chemical Society
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    • v.18 no.10
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    • pp.1085-1089
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    • 1997
  • A new HPLC chiral stationary phase (CSP 3) has been prepared by connecting N-phenyl N-propyl amide of (S)-naproxen to silica gel through the 6-methoxy-2-naphthyl group of (S)-naproxen. The new CSP has been applied in resolving a homologous series of N-(3,5-dinitrobenzoyl)-α-amino acid esters and a homologous series of N-(3,5-dinitrobenzoyl)-α-(4-alkylphenyl)alkylamines. The separation factors, α, for resolving a homologous series of N-(3,5-dinitrobenzoyl)-α-amino esters and a homologous series of N-(3,5-dinitrobenzoyl)-α-(4-alkylphenyl)alkylamines on the new CSP have been found to remain almost constant throughout the wide range of the length of the alkyl substituent of the analytes while those on the previously reported CSPs (CSP 1 and 2) which were prepared by connecting N-phenyl N-propyl amide of (S)-naproxen to silica gel through the N-propyl group increase or decrease continuously. These results are concluded to support the chiral recognition models which utilize the intercalation of the alkyl substituent of the racemic analytes between the adjacent strands of CSP 1 or 2 to rationalize the increasing or decreasing trends of separation factors.

Effect of Substituents on Benzenesulfonyl Motif of 4-Phenyl-1-arylsulfonylimidazolidinones for Their Cytotoxicity

  • Lee, Hui-Soon;Park, Kyung-Lae;Choi, Sang-Un;Lee, Chong-Ock;Jung, Sang-Hun
    • Archives of Pharmacal Research
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    • v.23 no.6
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    • pp.579-584
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    • 2000
  • To explore the effect of substituents' on phenyl motif on sulfonyl function of novel anticancer 4-phenyl-1-benzenesulfonylimidazolidinones (1), electron donating or withdrawing sub-stituents were introduced at 3 or 4-position and the analogs were tested against human lung (A549) and colon (HCT-15) cancer cell lines. Quantitative structure activity relation-ship of the 4-substituted series shows that only STERIMOL L values are well correlated. The increment of substituent's volume enhances the activity against both cell lines. The small substituent at 3-position additionally increases the activity. However naphthyl group in place of phenyl reduces the activity, Therefore the phenyl motif with sterically large substituent at 4-position and small substituent at 3-position may be important for their activity. Integration of these substituents' effects into the structural design led to discover the more potent analog, 4-phenyl-1-(N-acetylindoline-5-sulfonyl) imidazolidinone (1n).

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Electroluminescent Properties of Anthracene-Based Dye with ${\alpha}-Naphthylethenyl$ Subsituent ((${\alpha}-Naphthyl$ Group이 치환된 안트라센 염료의 전계발광 특성)

  • Kim, Hong-Soo;Lee, Dong-Kyu;Nam, Ki-Dae
    • Journal of the Korean Applied Science and Technology
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    • v.16 no.2
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    • pp.127-133
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    • 1999
  • New electroluminescent materials base on anthracene chromophore, [9.10-bis(${\alpha}$-naph -thylethenyl) anthracene (${\alpha}$-BNA)] were newly synthesized. The anthracene derivatives with bulky substituent possessed high melting point and they gave stable amorphous films through vacuum - sublimation methods. Three types of electroluminescent devices were fabricated with double layer and triple layer structure : ITO/TPD/emission layer/MgAg, ITO/emission layer/ OXD-7 and ITO/ TPD/ emission layer/OXD-7/MgAg, respectively. In three types of devices with the emissive layer of ${\alpha}$-BNA, efficient orange electroluminescence was observed. In the triple layer device whit a emitting layer of 20 nm thickness , maximum luminance was about 10000 cd/ $m^2$ at an applied voltage of 10v and maximum external quantum efficiency was 1.0%.

Substrate and Inhibitor Specificities of Esterase in Lucilia illustris Meigen (연두금파리 Esterase의 기질 및 억제제 특이성에 관한 연구)

  • 유종명;박천배이형철
    • The Korean Journal of Zoology
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    • v.39 no.2
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    • pp.190-197
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    • 1996
  • The optimal conditions and substrate specificity of whole body esterase (EST) activity, effects of inhibitors (Eserine, Paraoxon, p-HMB, DDVP, DFP) on the enzyme, and ontogenv of the isozymes were determined in Lucilio ilfustris Meisen. The optimal temperature was $45^{\circ}C$ regardless of kind of reacted substrate, $\alpha-naphthyl$ acetate $(\alpha-Nal,$ a.naphthvl butylate $(\alpha-N),$ and Pnaphthyl acetate $(\beta-Na),$ but the optimal pH showed some regioselectivitv to naphthvl group of the esters; PH 7.0 for Iform, pH 7.5 for a-form. The maximum reaction rate was recorded at about 2.5 $\times$ 10's M of PNa and etNa, but 1.0 $\times$ 10'S M of $\alpha-Nb.$ Among the five EST inhibitors tested, DDVP was the most powerful. However, distinction of the relative specificity of inhibitors between three body parts, head, thorax, and abdomen, was shouts, representing differences in the distribution and activity of isozvmes. Of 12 carboxyl-esterases (CE), 8 cholinesterases (ChE) and 2 arvlesterases (ArE) identified based on their inhibitor specificity throughout the development, two larval and prepupal stage specific ChEs, no pupal specific, and 2 CEs.2ChEs. and one ArE adult specific isozvmes were confirmed.

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Effect of the Length of Side Group Substitution on Optical and Electroluminescene Properties

  • Shin, Hwangyu;Kang, Hyeonmi;Kim, Beomjin;Park, Youngil;Yu, Young-Jun;Park, Jongwook
    • Bulletin of the Korean Chemical Society
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    • v.35 no.10
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    • pp.3041-3046
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    • 2014
  • Blue emitting materials, 9,10-bis-biphenyl-4-yl-anthracene (AC-P), 9,10-bis-[1,1';4',1"]terphenyl-4-yl-anthracene (AC-DP), and 9,10-bis[3",5"-deiphenyltriphenyl-4'-yl]anthracene (AC-TP) were synthesized through boration and Suzuki aryl-aryl coupling reaction. EL performance of blue light-emitters was optimized and improved by varying the chemical structures of the side groups. In the thin film state, the three materials exhibit $PL_{max}$ values in the range of 442-456 nm. EL device with the synthesized compounds in the following configuration was fabricated: ITO/4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNATA) 60nm/N,N'-bis (naphthalene-1-yl)-N,N'-bis(phenyl)benzidine (NPB) 15nm/synthesized blue emitting materials (30nm)/1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi) 20nm/LiF 1nm/Al 200nm. The current efficiency and C.I.E. value of AC-TP were 3.87 cd/A and (0.15, 0.12). A bulky and non-planar side group helps to prevent ${\pi}-{\pi}^*$ stacking interaction, which should lead to the formation of more reliable amorphous film. This is expected to have a positive effect on the high efficiency of the operating OLED device.

Cytotoxicity and Structure-activity Relationships of Naphthyridine Derivatives in Human Cervical Cancer, Leukemia, and Prostate Cancer

  • Hwang, Yu Jin;Chung, Mi Lyang;Sohn, Uy Dong;Im, Chaeuk
    • The Korean Journal of Physiology and Pharmacology
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    • v.17 no.6
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    • pp.517-523
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    • 2013
  • Naphthyridine compounds are important, because they exhibit various biological activities including anticancer, antimicrobial, and anti-inflammatory activity. Some naphthyridines have antimitotic effects or demonstrate anticancer activity by inhibiting topoisomerase II. These compounds have been investigated as potential anticancer agents, and several compounds are now part of clinical trials. A series of naphthyridine derivatives were evaluated for their in vitro cytotoxic activities against human cervical cancer (HeLa), leukemia (HL-60), and prostate cancer (PC-3) cell lines using an MTT assay. Some compounds (14, 15, and 16) were more potent than colchicine against all three human cancer cell lines and compound (16) demonstrated potency with $IC_{50}$ values of 0.7, 0.1, and $5.1{\mu}M$, respectively. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were used for quantitative structure-activity relationship (QSAR) molecular modeling of these compounds. We obtained accurate and predictive three-dimensional QSAR (3D-QSAR) models as indicated by the high PLS parameters of the HeLa ($q^2$, 0.857; $r^2$, 0.984; $r^2\;_{pred}$, 0.966), HL-60 ($q^2$, 0.777; $q^2$, 0.937; $r^2\;_{pred}$, 0.913), and PC-3 ($q^2$, 0.702; $q^2$, 0.983; $r^2\;_{pred}$, 0.974) cell lines. The 3D-QSAR contour maps suggested that the C-1 NH and C-4 carbonyl group of the naphthyridine ring and the C-2 naphthyl ring were important for cytotoxicity in all three human cancer cell lines.

Structure of a Spiro Orthocarbonate, 3,3'-Spirobi[1H, 5H-naphtho [1,8-ef] [1,3] dioxocin] (Spiro Orthocarbonate, 3,3'-Spirobi[1H, 5H-naphtho[1,8-ef] [1,3] dioxocin]의 분자구조)

  • Young Mi Song;Jung Mi Shin;Young Ja Park
    • Journal of the Korean Chemical Society
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    • v.36 no.4
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    • pp.536-539
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    • 1992
  • Eight-membered ring spiro orthocarbonate (C$_{25}H_{20}O_4$, M$_r$ = 384) is monoclinic, space group C2/c, with a = 15.319(4), b = 9.057(3), c = 13.168(3)${\AA}$, ${\beta}$ = 98.53(3)$^{\circ}$, Z = 4, F(000) = 808, T = 290 K, ${\mu}$(Mo-K${\alpha}$) = 0.55 cm$_1$, D$_c$ = 1.36 g/cm$^3$ and D$_m$ = 1.40 g/cm$^3$. The intensity data were collected with Mo-K${\alpha}$ radiation (${\lambda}$ = 0.7107 ${\AA}$) on an automatic four-circle diffractometer with a graphite monochromater. The structure was solved by direct methods and refined by full matrix least-squares methods. The final R value was 0.052 for 1412 observed reflections. The molecule has C$_2$point symmetry. The eight-membered ring has a chair conformation with pseudo-C$_s$ symmetry. The naphthyl ring is planar with the C-C bond lengths being in the range of 1.352∼1.444${\AA}$ and bond angles of 117.2∼123.5$^{\circ}$. The bond lengths of C(1)-C(9), C(8)-C(9) and C(9)-C(10) are somewhat longer than those of the other C-C bonds.

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Properties of Liquid Crystalline Polyester/Poly(ethylene 2,6-naphthalate) Blend Fibers (액정 폴리에스테르/PEN 블렌드 섬유의 성질)

  • Kim, Won;Kim, Young-Yong;Son, Jung-Sun;Yun, Doo-Soo;Han, Chul;Choi, Jae-Kon;Jo, Byung-Wook
    • Elastomers and Composites
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    • v.37 no.4
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    • pp.244-257
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    • 2002
  • A thermotropic liquid crystalline polymer(TLCP) which has flexible butylene/hexylene spacers in the main chain and a triad aromatic ester type mesogenic unit containing a naphthyl group was prepared by solution polycondensation. The in-situ composites based on poly(ethylene 2,6-naphthalate) (PEN) and a thermotropic liquid crystalline polymer(TLCP) were prepared and melt spun at different TLCP contents and different draw ratios to produce monofilaments. Blends of the TLCP with PEN were investigated in terms of thermal, mechanical properties and morphology. The TLCP synthesized showed nematic mesophasic behavior and its transition temperature to isotropic melt from mesophase was 249℃. The blends showed well dispersed TLCP phases in the PEN matrix without macroscopic phase separation. Inclusion of TLCP in the blends decreased the cold crystallization temperature of PEN in the blend, therefore, the TLCP acts as a nucleating agent in the blend and showed good interfacial adhesion between the dispersed LCP phases and PEN matrix with domain sizes 40~50 nm in diameter and well developed fibrillation in the monofilaments. The TLCP acted effectively as a reinforcing material in the PEN matrix at the 10wt% level, it led to an increase of initial modulus up to 270% and tensile strength by 235%, while the elongation rate increasing with higher draw ratios.