• Title/Summary/Keyword: T3T-dimethyl

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Synthesis and Cytotoxic Effects of Deoxy-tomentellin

  • Han, Du-Seok;Jung, Kui-Ho;Jung, Woo-Jung;Oh, In-Kyo;Kang, Kil-Ung;Baek, Seung-Hwa
    • Archives of Pharmacal Research
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    • v.23 no.2
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    • pp.121-127
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    • 2000
  • Cannabigerol (1, CBG), methyl 4-[(2E)-3,7-dimethyl-2,6-octad ienyl)oxy]-3-methoxybenzoate (2, DTM), 5-fluorouracil (3, FU) as a reference, and cannabidiol (4, CBD) were tested for their growth inhibitory effects against KB(ATCC NO, OCL 17) cell lines using two different assays, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazoliumbromide (MTT) assay and the sulforhod-amine B protein (SRB) assay. These compounds showed inhibitory activity in vitro in the micromolar range against KB cell lines. In general, the antitumor activities of these compounds (1, 2, 3 and 4) were dose-dependent over the micromolar concentration range of 1 to 100 M. The comparison of $IC_{50}$ values of these compounds in tumor cell lines showed that their susceptibility to these compounds decreases in the following order: DTM > CBD > 5-FU > CBG by MTT assay and DTM = CBD > 5-FU > CBG by SRB assay. CBG 1, DTM 2, 5-FU 3, and CBD 4 were tested for their cytotoxic effects on NIH 3T3 fibroblasts using two different assays, the MTT assay and SRB assay. These compounds exhibited potent cytotoxic activities in vitro in the micromolar range against NIH 3T3 fibroblasts. In general, the cytotoxic acivities of these compounds (1, 2, 3 and 4) were dose-dependent over the micromolar concentraion range of 1 to 100 M. The comparison of $CD_{50}$ values of these compounds in NIH 3T3 fibroblasts shows that their susceptibility to these compounds in decreases the following order(:) CBD > 5-FU > DTM > CBG by MTT assay, CBD > 5-FU > CBG > DTM by SRB assay. These results suggest that DTM 2 has the most growth-inhibitory activity against KB cell lines.

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Improvement of Emission Performance in a 3.3 Liter DI Diesel Engine by Using Dimethyl Ether Fuel (디메틸에테르 연료를 사용하는 3.3리터 디젤기관의 배기성능 개선)

  • Pyo, Young-Dug;Lee, Young-Jae;Kim, Mun-Heon
    • Transactions of the Korean Society of Automotive Engineers
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    • v.15 no.4
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    • pp.178-185
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    • 2007
  • A study is improvement of power and emission in a inline-pump Dr diesel engine by using Dimethyl ether Fuel. Dimethyl ether (DME) is an oxygenated fuel with a cetane number higher than that of diesel oil. It meets the ULEV emission regulation and reduces the smoke to almost zero when used in a diesel engine. But NOx emission is almost same and CO, THC emissions are lower than that of diesel engine. The emissions aren't satisfied the stronger emission regulation in the further. Generally DOC (Diesel Oxidation Catalyst) is used to reduce CO & THC emissions and EGR (Exhaust Gas Recirculation) system is used to reduce NOx emission. Test results showed that the torque and the power with DME were almost same as those of pure diesel oil, but the brake thermal efficiency increased a little. also the BSEC (Brake Specific Energy Consumption) with DME was similar that of diesel. The test results showed that the DOC was the vary effective method to reduce the CO emission in case of Dimethyl Ether Fuel in diesel engine. But, THC emission is showed a little reduction rates. Also EGR system was the very effective method to reduce the NOx emission in case of Dimethyl Ether Fuel in diesel engine.

Kinetics and Mechanism of the Pyridinolysis of (2R,4R,5S)-(+)-2-Chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine 2-Sulfide in Acetonitrile

  • Barai, Hasi Rani;Lee, Hai-Whang
    • Bulletin of the Korean Chemical Society
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    • v.33 no.3
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    • pp.1047-1051
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    • 2012
  • The nucleophilic substitution reactions of (2R,4R,5S)-(+)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine 2-sulfide with X-pyridines are investigated kinetically in acetonitrile at $5.0^{\circ}C$. The free energy relationships for substituent X variations in the nucleophiles exhibit biphasic concave upwards with a break point at X = 3-Ac. Unusual positive $\rho_X$ (= +4.73) and negative ${\beta}_X$ (= -0.75) values are obtained with the weakly basic pyridines, and rationalized by the isokinetic relationship with isokinetic temperature at $t_{ISOKINETIC}=39.3^{\circ}C$. A concerted mechanism involving a change of nucleophilic attacking direction from a frontside attack with the strongly basic pyridines to a backside attack with the weakly basic pyridines is proposed on the basis of greater magnitudes of selectivity parameters ($\rho_X$ = -6.15 and ${\beta}_X$ = 1.11) with the strongly basic pyridines compared to those ($\rho_X$ = 4.73 and ${\beta}_X$ = -0.75) with the weakly basic pyridines.

Antioxidant Effect of Salvia miltiorrhiza

  • Kang, Hye-Sook;Chung, Hae-Young;Jung, Jee-Hyung;Kang, Sam-Sik;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.20 no.5
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    • pp.496-500
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    • 1997
  • A strong antioxidant activity, which was measured by the radical scavenging effect on 1, 1-diphenyl-2-picrylhydrazyl(DPPH) radical, was detected in the methanol extract of Salvia miltiorrhiza Bunge (Labiatae). By activity-directed fractionation, compounds 1 and 2 were isolated as antioxidant principles of S. miltiorrhiza. Compounds 1 and 2 were identified as dimethyl lithospermate and 3-(3, 4-dihydroxyphenyl)lactamide, respectively, on the basis of spectral data. The radical scavenging effect of compounds 1 and 2 on DPPH radical exceeded that of L-ascorbic acid which is a well known antioxidant. These two compounds also showed prominent inhibitory activity against free radical generation in dichlorofluorescein (DCF) method and cytoprotective effect against t-BHP in cultured liver cell.

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Synthesis of Permethrin using Ester Enolate Claisen Rearrangement (에스테르엔올 음이온의 Claisen 자리옮김 반응에 의한 Permethrin의 합성)

  • In-Kyu Kim;Suk-Ku Kang;Jang-Hoo Hong
    • Journal of the Korean Chemical Society
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    • v.30 no.6
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    • pp.548-552
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    • 1986
  • A stereoselective synthesis of 3-phenoxybenzyl (${\pm}$)-cis and trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid starting from readily available 2-methyl-3-buten-2-ol($\underline{2}$) is described. Allylic rearrangement of 2-methyl-3-buten-2-ol, in the presence of acetic acid and acetic anhydride gave 3-methyl-2-butenyl acetate($\underline{3}$). The [3,3] sigmatropic rearrangement of the allyl acetate($\underline{3}$), as the silylketene acetal, produced the ${\gamma},\;{\delta}$-unsaturated acid($\underline{4}$). Treatment of 3,3-dimethyl-4-pentenoic acid($\underline{4}$) with SOCl2 followed by esterification with 3-phenoxybenzyl alcohol yielded 3, 3-dimethyl-4-pentenoic acid ester($\underline{5}$). Addition of carbon tetrachloride to the olefin ester($\underline{6}$) furnished 4,6,6,6-tetrachloro-3,3-dimethylhexanoic acid ester ($\underline{7}$). Cyclization with potassium t-butoxide and elimination of hydrogen chloride afforded 3-phenoxybenzyl (${\pm}$) cis- and trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid.

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Ice-Binding Protein Derived from Glaciozyma Can Improve the Viability of Cryopreserved Mammalian Cells

  • Kim, Hak Jun;Shim, Hye Eun;Lee, Jun Hyuck;Kang, Yong-Cheol;Hur, Young Baek
    • Journal of Microbiology and Biotechnology
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    • v.25 no.12
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    • pp.1989-1996
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    • 2015
  • Ice-binding proteins (IBPs) can inhibit ice recrystallization (IR), a major cause of cell death during cryopreservation. IBPs are hypothesized to improve cell viability after cryopreservation by alleviating the cryoinjury caused by IR. In our previous studies, we showed that supplementation of the freezing medium with the recombinant IBP of the Arctic yeast Glaciozyma sp. (designated as LeIBP) could reduce post-thaw hemolysis of human red blood cells and increase the survival of cryopreserved diatoms. Here, we showed that LeIBP could improve the viability of cryopreserved mammalian cells. Human cervical cancer cells (HeLa), mouse fibroblasts (NIH/3T3), human preosteoblasts (MC3T3-E1), Chinese hamster ovary cells (CHO-K1), and human keratinocytes (HaCaT) were evaluated. These mammalian cells were frozen in dimethyl sulfoxide (DMSO)/fetal bovine serum (FBS) solution with or without 0.1 mg/ml LeIBP at a cooling rate of -1℃/min in a -80℃ freezer overnight. The minimum effective concentration (0.1 mg/ml) of LeIBP was determined, based on the viability of HeLa cells after treatment with LeIBP during cryopreservation and the IR inhibition assay results. The post-thaw viability of mammalian cells was examined. In all cases, cell viability was significantly enhanced by more than 10% by LeIBP supplementation in 5% DMSO/5% FBS: viability increased by 20% for HeLa cells, 28% for NIH/3T3 cells, 21% for MC3T3-E1, 10% for CHO-K1, and 20% for HaCaT. Furthermore, addition of LeIBP reduced the concentrations of toxic DMSO and FBS down to 5%. Therefore, we demonstrated that LeIBP can increase the viability of cryopreserved mammalian cells by inhibiting IR.

Microbial Transformation of a Monoterpene, Geraniol, by the Marine-derived Fungus Hypocrea sp.

  • Leutou, Alain S.;Yang, Guohua;Nenkep, Viviane N.;Siwe, Xavier N.;Feng, Zhile;Khong, Thang T.;Choi, Hong-Dae;Kang, Jung-Sook;Son, Byeng-Wha
    • Journal of Microbiology and Biotechnology
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    • v.19 no.10
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    • pp.1150-1152
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    • 2009
  • Geraniol (1) is the biogenetic precursor of a number of monoterpenes. We tested various marine-derived microorganisms to determine their ability to biotransform 1. Only Hypocrea sp. was capable of transforming 1 into its oxidized derivative, 1,7-dihydroxy-3,7-dimethyl-(E)-oct-2-ene (2). The structure of the metabolite obtained was assigned on the basis of detailed spectroscopic data analyses.

Reaction of Lithium (2,3-Dimethyl-2-butyl)-t-butoxyborohydride with Selected Organic Compounds Containing Representative Functional Groups

  • Cha, Jin-Soon;Lee, Dae-Yon
    • Bulletin of the Korean Chemical Society
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    • v.23 no.6
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    • pp.856-861
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    • 2002
  • The general reducing charagteristics of a newly synthesized reducing agent, lithium(2.3-dimethyl-2-butyl)-${\iota}$-butoxyborohydride (Li $Thx'BuOB_2$, 1), in tetrahydrofuran (THF) toward selected organic compounds containing representative fundtional groups under practical has been examined. The reagent revealed an interesting and unique reducing characteristics. Especially, the stereoselectivity in the reduction of cyclic ketones was extraordinary. Thus, the introduction of bulky alkyl and alkoxy groups into the parent borohydride affonds a high stereoselectivity. In general, the reducing power of the reagent is somewhere between the dialiylborohydride and the parent borohydride. This permits the reagent to be a reagent of choice for selecitive reduction of organic compounds with an improved selectivity.

Ab Initio Study of Mechanism of Forming Germanic Bis-Heterocyclic Compound between Dimethyl-Germylene Carbene (Me2Ge=C:) and Acetone

  • Lu, Xiuhui;Che, Xin;Lian, Zhenxia;Li, Yongqing
    • Bulletin of the Korean Chemical Society
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    • v.32 no.1
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    • pp.89-94
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    • 2011
  • The mechanism of the cycloaddition reaction of forming germanic bis-heterocyclic compound between singlet dimethylgermylene carbene and acetone has been investigated with CCSD(T)//B3LYP/6-$31G^*$ method. From the potential energy profile, it can be predicted that, this reaction has one dominant channel. The presented rule of this dominant channel is that the two reactants firstly form a four-membered ring carbene (RC4) through the [2+2] cycloaddition reaction. Due to $sp^2$ hybridization of carbene C atom in RC4, RC4 further combines with acetone to form a reactant complexe (RC5). Due to the further $sp^3$ hybridization of carbene C atom in RC4, RC5 isomerizes to a germanic bisheterocyclic compound (P6) via the transition state (TS5).

A Themotropic Behavior of Egg PC Liposome Containing the Very Long Chain Fatty Acyl Component,${\alpha},{\omega}$-13,16-Dimethyloctacosanedioate Dimethyl Ester(DME C30) Isolated from The Thermophilic Anaerobic Bacteria, Thermoanaerobacter ethanolicus

  • Kim, Hyeon Myeong;Gang, Se Byeong;Jeong, Seung Ho
    • Bulletin of the Korean Chemical Society
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    • v.22 no.9
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    • pp.979-983
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    • 2001
  • Thermoanaerobacter ethanolicus is a strictly anaerobic and thermophilic bacterium whose optimum temperature ranges over $65-68^{\circ}C.$ T. ethanolicus was known to contain a bipolar very long chain fatty acyl component such as $\alpha$, $\omega-1316-dimethyloctacosanedioate$, as one of the major membrane components. However, exact physiological role of this unusual component in the membrane remains unknown. Such a very long chain fatty acyl component, $\alpha$, ${\omega}-1316-dimethyloctacosanedioate$, dimethyl ester (DME C30), was isolated, and purified from the membrane of T. ethanolicus. As a function of added concentrations of the $\alpha$, $\omega-1316-dimethyloctacosanedioate$, dimethyl ester (DME C30) or cholesterol into the standard liposomes, the acyl chain ordering effect was investigated by the steady-state anisotropy with 1,6-diphenyl-1,3,5-hexatriene (DPH) as a fluorescent probe. Acyl chain order parameter (S) of vesicles containing DME C30 is higher comparing with phosphatidylcholine (PC) only vesicles. This result was discussed thermodynamically with the aid of the simulated annealing molecular dynamics simulations. Through the investigation of all the possible conformational changes of DME C30 or cholesterol, we showed that DME C30 is very flexible and its conformation is variable depending on the temperature comparing with cholesterol, which is rigid and restricted at overall temperature. We propose that the conformational change of DME C30, not the configurational change, may be involved in the regulation of the membrane fluidity against the changes of external temperature.