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Studies on insecticidal activity and synthesis of Bis (trichlorophenoxy) ethane (Bis(trichlorophenoxy) ethane(BTPE)의 합성 및 살충효력에 관한 연구(I))

  • Kim C. S.;Kim H. W.;Kim M. Y.;Kang S. W.;Lee D. S.;Lee E. S.
    • Korean journal of applied entomology
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    • v.4
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    • pp.47-50
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    • 1965
  • Many of the chlorophenol derivatives are widely used as insecticides, herbicides and plant growth regulators. The function and use of these chemicals would be different according to the number of chlorine and their chemical structures. It was reported in this article that 1) Bis(trichlorophenoxy) ethane was synthesized with 2 mol-trichlorophenol and 1 moi-dibromoethane in 2 moi-Sodium hydroxide alcohol solution, and 3) the insecticidal activity of Bis(trichlorophenoxy) ethane was compared with Phenkapton, Tedion V-18, BHC, and DDT, on Citrus red mite, Bombix mori (Silk worm), and Daikon leaf beetle(Phaedon brassicae) 3) The toxicity of Bis(2, 4, 5-trichlorophenoxy) ethane and Bis(2, 4, 5-trichlorophenoxy) ethane was studied on mice. The following results were obtained. 1) Yield of Bis(2, 4, 5-trichlorophenoxy) ethane, $50.06\%$, m.p. $157-159^{\circ}C$, and yield of Bis(2,4, 6-trichlorophenoxy) ethane, $32.60\%$, m.p. $162-163^{\circ}C$. 2) Insecticidal activity of Bis(2, 4, 5-trichlorophenoxy) ethane to Citrus red mite is stronger than that of Tedion V-18, and weaker than that of Phenkapton. 3) Insecticidal activity of Bis(2, 4, 5-trichlorophenoxy) ethane to Bombix mori is weaker than those of BHC and DDT. 4) Insecticidal activity of Bis(2. 4, 5-trichlorophenoxy) ethane to Daikon leaf beetle proved to be ineffective. 5) Five rams of Bis(2, 4, 5-trichlorophenoxy) ethane and Bis(2, 4, 6-trichlorophenoxy) ethane pet kg of body weight respectively were given to mice orally, and none of the mouse was killed by it after a period of 72 hours. Therefore it seems that there is almost no toxicity.

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Down-modulation of Bis reduces the invasive ability of glioma cells induced by TPA, through NF-κB mediated activation of MMP-9

  • Lee, Young Dae;Cui, Mei Nu;Yoon, Hye Hyeon;Kim, Hye Yun;Oh, Il-Hoan;Lee, Jeong-Hwa
    • BMB Reports
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    • v.47 no.5
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    • pp.262-267
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    • 2014
  • Bcl-2 interacting cell death suppressor (Bis) has been shown to have anti-apoptotic and anti-stress functions. Recently, increased Bis expression was reported to correlate with glioma aggressiveness. Here, we investigated the effect of Bis knockdown on the acquisition of the invasive phenotype of A172 glioma cells, induced by 12-O-Tetradecanoylphorbol-3-acetate (TPA), using a Transwell assay. Bis knockdown resulted in a significant decrease in the migration and invasion of A172 cells. Furthermore, Bis knockdown notably decreased TPA-induced matrix metalloproteinase-9 (MMP-9) activity and mRNA expression, as measured by zymography and quantitative real time PCR, respectively. A luciferase reporter assay indicated that Bis suppression significantly down-regulated NF-${\kappa}B$-driven transcription. Finally, we demonstrated that the rapid phosphorylation and subsequent degradation of $I{\kappa}B-{\alpha}$ induced by TPA was remarkably delayed by Bis knockdown. These results suggest that Bis regulates the invasive ability of glioma cells elicited by TPA, by modulating NF-${\kappa}B$ activation, and subsequent induction of MMP-9 mRNA.

Syntheses New Bis-Crown Ethers Containing Imine Group(III) (새로운 이민기를 포함하는 비스 크라운 에테르의 합성)

  • Lee, Sang-Hwoon;Jang, Dong-Chun;Chang, Seung-hyun
    • Journal of the Korean Society of Industry Convergence
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    • v.6 no.1
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    • pp.73-80
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    • 2003
  • We report herein synthetic results obtained six new types of bis-benzocrown ethers containing imine group. Bis crown ethers1~3 are aminobenzo-15-crown-5-ether linked with terephthalaldehyde, isophthalaldehyde, phthaldehyde respectively by imine reaction. Bis crown ethers1~3 are different distances in each crown ether rings. Bis crown ether 4 has large cavity in crown ethers. Functionalized crown ether 5 is synthesized amonobenzo-15-crown-5-ether and terephthaladehyde same ratio at one to one. Bis crown ether 6 has photosensitive linkage between crown ethers. Bis crown ether 7 is prepared by amonobenzo-15-crown-5-ether and triethyl ortho formate. 4'-Nitrobenzo-crown ethers and 3',4'-dinitrobenzo-crown ethers were prepared by nitration of benzo crown ethers, obtained from the reaction of catechol and oligoethylene glycol ditosylate. Crown ethers containing aldehyde group were synthesized from the reaction of 3,4-dihydroxybenzaldehyde and corresponding ditosylate respectively. The synthesized crown ethers were characterized respectively by IR, NMR, GC-Mass.

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Syntheses Bis or Tri Crown Ethers Containing Imine Group(V) (이민기를 포함하는 비스 또는 트리 크라운에테르의 합성 (V))

  • Chang, Seung-Hyun;Kim, Jung-Sung
    • Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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    • pp.110-113
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    • 2003
  • We report herein synthetic results obtained six new types of bis-benzocrown ethers containing imine group. Bis crown ethers l~3 are aminobenzo-15-crown-5-ether linked with terephthalaldehyde, isophthalaldehyde, phthaldehyde respectively by imine reaction. Bis crown ethers l~3 are different distances in each crown ether rings. Bis crown ether 4 has large cavity in crown ethers. Functionalized crown ether 5 is synthesized amonobenzo-l5-crown-5-ether and terephthaladehyde same ratio at one to one. Bis crown ether 6 has phothosensitive linkage between crown ethers. Bis crown ether 7 is prepared by amonobenzo-l5-crown-5-ether and triethyl ortho formate. 4'-Nitrobenzo-crown ethers and 3',4'-dinitrobenzo-crown ethers were prepared by nitration of benzo crown ethers, obtained from the reaction of catechol and oligoethylene glycol ditosylate. Crown ethers containing aldehyde group were synthesized from the reaction of 3,4-dihydroxybenzaldehyde and corresponding ditosylate respectively. The synthesized crown ethers were characterized respectively by IR, NMR. GC-Mass.

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Synthesis of 1,1-Dimethyl-2,5-bis(trimethylsilyl)-3,4-diphenyl-1-silacyclopenta-2,4-diene (1,1-Dimethyl-2,5-bis(trimethylsilyl)-3,4-diphenyl-1-silacyclopenta-2,4-diene의 합성)

  • Young Kun Kong;Wan-Chul Joo
    • Journal of the Korean Chemical Society
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    • v.30 no.6
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    • pp.521-525
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    • 1986
  • From the reaction of phenyltrimethylsilylacetylene with lithium, 1,4-bis(trimethylsilyl)-2,3-diphenyl-1,4-butadene dianion was formed. The reaction of dianion with dichlorodimethylsilane affords 1,1-dimethyl-2,5-bis(trimethylsilyl)-3,4-diphenyl-1-silacyclopenta-2,4-diene. In addition 1,4-bis(trimethylsilyl)-2,3-diphenyl-1,3-butadiene was isolated. It seems to be hydrolized product in alkali medium.

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Improvement of Thermal Stability of Polyethylene Lithium-ion Battery Separator via Coating with Polymers Synthesized from Bis-GMA Derivatives (Bis-GMA 유도체로부터 제조된 고분자 코팅에 의한 리튬이차전지용 폴리에틸렌 격리막의 고온 안정성 향상)

  • Im, Hyun-Gu;Hong, Ji-Hye;Kim, Chang-Keun
    • Polymer Korea
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    • v.34 no.6
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    • pp.517-521
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    • 2010
  • Microprous polyethylene (PE) membranes are widely used as lithium-ion battery separators. A separator having higher meltdown temperature than PE separator is still required for useful safety feature at a high temperature. To enhance meltdown temperature of PE separator, it was coated with polymers synthesized from bis-GMA derivatives by radical polymerization. Polymer was not formed when bis-GMA monomer having a high viscosity was used, while polymers were formed when bis-GMA derivatives having a low viscosity were used. When the separator was coated with polymer synthesized from reaction mixture containing proper amount of bis-GMA derivative, its meltdown temperature were increased up to $160^{\circ}C$ without reduction in the air permeability.

Synthesis of $\pi$-Allyl-type Cobalt, Palladium, Platinum Complexes Having a $C_2$-Chiral Ligand ($C_2$ 손대칭 리간드를 배위하는 $\pi$-Allyl-Cobalt, Palladium, Platinum 착물의 생성)

  • Uhm, Jae Kook;Lee, Jong O;An, Hee Won
    • Journal of the Korean Chemical Society
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    • v.42 no.2
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    • pp.177-183
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    • 1998
  • By the reactions of a $C_{2}$-chiral ligand, (+)-11S,12S-bis[2,2'-(diphenylphosphino)benzanilido]-9,10-dihydro-9,10-ethanoanthracene(6) with $[\pi-allyl chloroplatinum(II)]_4$, and $CpCo(CO)_2$ respectively, three new complexes, ($\pi$-allyl)platinum(II)(+)-11S,12S-bis[2,2'-(diphenylphosphino)benzanilido]-9,10-dihydro-9,10-ethanoanthracene perchlorate(1), ($\pi$-allyl)platinum(II)(+)-11S,12S-bis[2,2'-(diphenylphosphino)benzanilido]-9,10-dihydro-9,10-ethanoanthracene chloride(2), ($\eta^5$-cyclopentadienyl)cobalt(I)-(+)-11S,12S-bis[2,2'-(diphenylphosphino)benzanilido]-9,10-dihydro-9,10-ethanoanthracene(3) were prepared. $\eta^3$-Cyclohexenyl)palladium(II)1,2-bis(diphenylphosphino)ethane perchlorate(4) was obtained by the reaction of ($\eta^3$-cyclohexenyl)palladium(II) chloride dimer with a symmetric ligand, 1,2-bis(diphenylphosphino)ethane and lithium perchlorate. These complexes were identified by NMR-, IR-, and Mass-Spectrophotometers and elemental analyzer.

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Bis is Induced by Oxidative Stress via Activation of HSF1

  • Yoo, Hyung Jae;Im, Chang-Nim;Youn, Dong-Ye;Yun, Hye Hyeon;Lee, Jeong-Hwa
    • The Korean Journal of Physiology and Pharmacology
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    • v.18 no.5
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    • pp.403-409
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    • 2014
  • The Bis protein is known to be involved in a variety of cellular processes including apoptosis, migration, autophagy as well as protein quality control. Bis expression is induced in response to a number of types of stress, such as heat shock or a proteasome inhibitor via the activation of heat shock factor (HSF)1. We report herein that Bis expression is increased at the transcriptional level in HK-2 kidney tubular cells and A172 glioma cells by exposure to oxidative stress such as $H_2O_2$ treatment and oxygen-glucose deprivation, respectively. The pretreatment of HK-2 cells with N-acetyl cysteine, suppressed Bis induction. Furthermore, HSF1 silencing attenuated Bis expression that was induced by $H_2O_2$, accompanied by increase in reactive oxygen species (ROS) accumulation. Using a series of deletion constructs of the bis gene promoter, two putative heat shock elements located in the proximal region of the bis gene promoter were found to be essential for the constitutive expression is as well as the inducible expression of Bis. Taken together, our results indicate that oxidative stress induces Bis expression at the transcriptional levels via activation of HSF1, which might confer an expansion of antioxidant capacity against pro-oxidant milieu. However, the possible role of the other cis-element in the induction of Bis remains to be determined.

Studies on the Synthesis of Mannich Bases of Hexachlorophene and their Antimicrobial Activities (Hexachlorophene의 Mannich Bases 합성 및 항미생물작용에 관한 연구)

  • Kim, Jong-Ho;Bae, Moo;Lee, Gye-Jun
    • Microbiology and Biotechnology Letters
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    • v.1 no.1
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    • pp.43-50
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    • 1973
  • Thirty-three Mannich bases of 2,2'-methylene bis (3,4, 6-trichlorophenoxy-acetic acid) were synthesized hexachlorophene as potential antimicrobial agents and tested against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Trichophyton rubrum, Microsporum gypseum, Epidermophyton floccosum, Aspergillus niger and Aspergillus oryzae in vitro. It was found that: 1) 2,2'-Methylene bis [${\alpha}$-(3, 4, 6-trichlorophenoxy)-${\beta}$- (N,N -diethylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(N, N-dimethynlamo) propionoic acid] were active against Staphylococcus aureus and Bacillus subtilis at the concn. of 1 $\mu\textrm{g}$/$m\ell$ respectively; 2) 2,2'-Methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxyphenylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3, 4, 6-trichlorophenoxy)-${\beta}$-(cyclohexylamino) propionic acid] were active against Trichophyton-rubrum at the concn. of 2 $\mu\textrm{g}$/$m\ell$ respectively; 3) 2,2'-Methylene bis [${\alpha}$-3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxyphenyl-amino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trcihlorophenoxy)-${\beta}$-(piperidino) propionic acid] were active against Microsporum gypseum at the concn. of 2 $\mu\textrm{g}$/$m\ell$ respectively; 4) 2,2'-Methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxyphenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3, 4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxy phenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(o-chlorophenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(o-chloro-p-nitrophenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$- (3,4,6-trichlorophenoxy)-${\beta}$-(methylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(hydroxylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(cyclohexylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorphenoxy)-${\beta}$-(morpholino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(p-sulfophenylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(4-sulfu-l-nayphthlamino) aoi!c rppioncd (were active against Epidermophyton floccosum at the concn. of 1 $\mu\textrm{g}$/$m\ell$ respectively; 5) 2,2'-Methlene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxyphenylamino) propionic acid], 2,2'-methylene bis (a-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxyphenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(p-methylphenylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(hydroxylamino) propionic acid] were active against Aspergillus niger and Aspergillus oryzae at the concn. of 1 $\mu\textrm{g}$/$m\ell$ respectively.

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