• Title/Summary/Keyword: Dimerization

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Synthesis of Asymmetric Dimer of Quinolone Derivatives Using p-TSA (p-TSA를 이용한 퀴놀론 유도체의 비대칭 이합체 합성)

  • 박명숙
    • YAKHAK HOEJI
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    • v.48 no.3
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    • pp.202-206
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    • 2004
  • New asymmetric dimers, N,N'-dialkyl-4'-hydroxy-4-oxo-2,2',3,3'-tetrahydro-2,2'-diphenyl-4,4'-quinolones 3a-f were synthesized through the dehydration and dea1coholation of N-alkylanilines and ethyl benzoylacetate. Dimers 3a-f were identified by NMR, IR and GC-MS. A series of dimer 3a-f has been synthesized using acid-catalyzed one-pot reaction that involved the condensation, cyc1ization and dimerization. Similarly, the 6,6'-methoxy (or 7,7'-methoxy) substituted dimers were prepared from N-alkyl-meta-(or para)-anisidines. Formation of dimers was undertaken with p-toluenesulfonic acid (p-TSA) at 90∼11$0^{\circ}C$ in toluene for 2∼6 hours over the Dean-Stark apparatus.

Anti-inflammatory Effects of Phytochemicals Having Michael Addition Acceptors by the Modulation of Toll-like Receptor Signaling Pathways (Michael addition acceptor 그룹을 가지고 있는 phytochemicals의 toll-like receptor 신호전달체계 조절을 통한 항염증 효과)

  • Youn, Hyung-Sun
    • Korean Journal of Food Science and Technology
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    • v.41 no.5
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    • pp.477-482
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    • 2009
  • Toll-like receptors (TLRs) play a critical role in the induction of innate immune responses that are essential for host defense against invading microbial pathogens. In general, TLRs have two major downstream signaling pathways, namely MyD88- and TRIF-dependent pathways, leading to the activation of nuclear factor-${\kappa}B$ (NF-${\kappa}B$) and interferon regulatory factor 3 (IRF3) and the expression of inflammatory mediators. TLR4 dimerization is required for the activation of downstream signaling pathways and may be one of the first lines of regulation in activating TLR-mediated signaling pathways. In this paper, the molecular targets of curcumin, 6-shogaol, and cinnamaldehyde in TLR signaling pathways will be discussed. Curcumin, 6-shogaol, and cinnamaldehyde with ${\alpha},{\beta}$-unsaturated carbonyl groups inhibit the dimerization of TLR4 induced by lipopolysaccharide, resulting in the downregulation of NF-${\kappa}B$ and IRF3. These results suggest that phytochemicals with the structural motif conferring Michael addition inhibit TLR4 dimerization, suggesting a novel mechanism for the anti-inflammatory activity of phytochemicals.

Photo-Alignment Mechanism Study of Poly(siloxane cinnamate) (폴리(실록산 신나메이트)의 광배향 메커니즘 연구)

  • Choi Ji-Won;Lim Ji-Chul;Song Ki-Gook
    • Polymer(Korea)
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    • v.30 no.5
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    • pp.417-421
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    • 2006
  • Photo -alignment of poly (siloxane cinnamate) (PSCN) was studied to better understand the alignment mechanism of cynnamoyl groups under various process conditions. DSC and polarized microscope studies showed that the isotropic temperature oi PSCN was about $105^{\circ}C$ and the liquid crystallinity, once formed, did not completely disappear even when the temperature went into the isotropic regions. UV/Vis absorption study suggested that the photo - dimerization was the main photo alignment mechanism and it's efficiency could be enhanced through the self-alignment of PSCN. It was also found that photo-dimerization was in competition with photo-fries reaction and the photo- alignment of PSCN was interfered with the excessive UV because of the strong photo-fries reaction. However, photo - fries reaction could be suppressed by adjusting the UV wavelength.

Reaction of Potassium Fluoride with Organic Halogen Compounds. (Part I) Reactions of Potassium Fluoride with Organic Halides, Acids, and Esters in presence of Dimethyl Formamide and their Pyrolytic Decaboxylation in presence of Potassium Fluoride (有機 할로겐 化合物과 弗化加里의 反應 (第1報) 有機 할라이드, 酸 및 에스테르와 弗化加里의 디메칠 호름아마이드 溶媒系反應 및 高溫-脫炭酸-熱分解反應)

  • You Sun Kim
    • Journal of the Korean Chemical Society
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    • v.7 no.3
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    • pp.189-196
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    • 1963
  • Reactions between potassium fluoride with organic halogen-containing carboxylic acids in dimethyl formamide solvent gave a decarboxylation reaction for the case of fluoro carboxylic acids of the type of $CF_3\;COOH,\;C_3F_7COOH,\;and\;C_2F_5COOH,$ whereas an additional partial fluorination together with dimerization reaction occurred for the chlorine containing acids of the type of $CH_2ClCOOH,\;CH_3CHClCOOH, \;CHCl_2COOH\;and\;o-Cl-C_6H_4-COOH.$ The phenyl halides showed no reactivity, but the halides with two electron attracting substituents on the benzene ring gave mainly dimerization reaction. The esters and alcohols gave an usual fluorination reaction. The same reactions in absence of the solvent at the elevated temperature increase the yield of the dimerized product and gave the cyclized product, fluorenone, in case of ο-chlorobenzoic acid. It was found that the fluorination usually precede the decarboxylation reaction by checking the stiochemical sequence of reaction. Catalytic influence of potassium fluoride were discussed and the mechanism of the reaction was considered.

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Promoting Effect of AlCl_3 on the Fe-catalyzed Dimerization of Bicyclo[2.2.1]hepta-2,5-diene

  • Nguyen, Mai Dao;Nguyen, Ly Vinh;Lee, Je-Seung;Han, Jeong-Sik;Jeong, Byung-Hun;Cheong, Min-Serk;Kim, Hoon-Sik;Kang, Ho-Jung
    • Bulletin of the Korean Chemical Society
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    • v.29 no.7
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    • pp.1364-1368
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    • 2008
  • The activity of the catalytic system composed of Fe$(acetylacetonate)_3$ (Fe$(acac)_3$), triphenylphosphine, and diethylaluminum chloride for the dimerization of bicyclo[2.2.1]hepta-2,5-diene (2,5-norbornadiene, NBD) to produce hexacyclic endo-endo dimer (hexacyclo[$7.2.1.0^{2,8}.1^{3,7}.1^{5,13}.0^{4,6}$]tetradec-10-ene, Hnn) was significantly enhanced by the presence of $AlCl_3$, especially at the molar ratios of NBD/Fe$(acac)_3$ of 500. XPS analysis of the catalytic systems clearly demonstrates that $AlCl_3$ facilitates the reduction of Fe$(acac)_3$ to form active species, Fe(II) and Fe(0) species. The layer separation was observed when [BMIm]Cl was used along with $AlCl_3$, but catalyst recycle was not very successful.