• 농약과학회지
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• 제7권2호
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• pp.155-158
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• 2003

2-Imino-1,3-thiazloine 1은 새로운 작용기작에 의하여 벼도열병원균에 대하여 선택적인 항균력을 나타낸다. 화합물 1의 C-2 위치의 imino기에 cyano 기가 치환된 새로운 화합물 2-cyanoimino-1,3-thiazoline 유도체 2를 합성하였다. Cyano 기의 강한 전자끌기와 더불어 1,3-thiazoline 고리의 황 및 질소원자의 비공유전자쌍은 2-imino-1,3-thiazloine 계열의 생물활성에 영향을 줄 것으로 예상되었다. Thiourea 4 의 $\gamma$-chloro-$\beta$-ketoacetoacetanilide 3에 대한 위치 특이적인 친핵적 공격 및 산촉매 하의 탈수에 의해서 2가 생성되었다.

• Archives of Pharmacal Research
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• 제23권2호
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• pp.104-111
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• 2000

Stereochemical isomers with hydroxy groups were synthesized by reacting 2-(dimethoxy-methyl)cyclohexanone with propargylmagnesium bromide. The stereo chemical structures were identified by NMR spectral interpretation and the geometry optimization. To assist the NMR interpretation, geometry optimization based on semi-empirical AM1 and PM3 methods was applied. Throughout this study, the structures of the two isomers were all determined and $^{1}H$ and $^{13}C$ NMR spectra were fully assigned. It was proven that the less polar isomer is an axial alcohol and the more polar one is an equatorial alcohol.

• Current Research on Agriculture and Life Sciences
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• 제5권
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• pp.168-172
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• 1987

광학성체인 isopropylidene glycerols로 부터 mercaptogiycerol을 합성하였다. 1,2-Isopropylideneglycerol을 tosyl화 하고 다시 tosyl group을 thiolacetate로 치환하였다. 염기성 가수분해와 산화에 의해 1,1'-dithiobis-2,3-isopropylidene-2,3-propanediol이 생성되었다. 이 화합물을 mercaptogiycerol 합성을 위해 사용함으로써 1-decenyl lithium으로 cis-S-dec-1'-enyl-2,3-isopropylidene-1-mercapto-2,3-propanediol을 생성하였다. 본 생성물은 plasmalogenase용 thioplasmaloger 기질 조제에 사용된다.

• Bulletin of the Korean Chemical Society
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• 제9권6호
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• pp.379-381
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• 1988

Racemic nuciferal(1) and nuciferol(2), the terpenic natural perfumeries, have been synthesized by a simple procedure. The benzylic halide 6; 1-(1-chloroethyl)-4-methylbenzene, was prepared by converting p-tolualdehyde(4) into 1-(p-tolyl)-1-ethanol(5), followed by convertion of 5 into corresponding chloride. The Grignard reagent of 6 was reacted with the bromoacetal 7, 2-(2-bromoethyl)-1,3-dioxolane, to give a crosscoupling product 8, which was hydrolysed to 4-(p-tolyl)-pentanal (9). The Wittig reaction of isopropylide 10 with 9 yielded arcurcumen(11). The stereospecific allylic oxidation of the gem-dimethyl olefin 11 with selenium dioxide afforded a trans-aldehyde, (${\pm}$)-1, which was reduced to corresponding alcohol, (${\pm}$)-2.

• Bulletin of the Korean Chemical Society
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• 제7권6호
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• pp.472-477
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• 1986

The reaction of (E)- or (Z)-1-alkenylmercuric chlorides with acrylic acid derivatives in the presence of 10 mol% of lithium trichloropalladate ($LiPdCl_3$) and an equimolar amount of cupric chloride, as a reoxidant for the palladium, in acetonitrile at room temperature gave the corresponding (E,E)- or (E,Z)-2,4-dienoic acid derivatives stereospecifically in moderate to good yields. The reaction of (E)- or (Z)-3-chloromercuripropenoic acid with olefins under the reaction condintion described above similarly gave good yields of (E,E)- or (Z,E)-2,4-dienoic acids stereospecifically. A side reaction, the homocoupling of alkenylmercuric chlorides, could be minimized by employing the condition described above. However, in the reaction of 3-chloromercuripropenoic acid with olefins under the present condition, the homocoupled side reaction product was not produced.

• Bulletin of the Korean Chemical Society
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• 제27권8호
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• pp.1211-1218
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• 2006

The enantiomerically pure (2R,3S)- and (2R,3R)-3-amino-2-hydroxy-4-phenylbutanoic acids (AHPBA) 1 and 3 are readily obtained from D-glucono-a-lactone. Both AHPBAs are the structural key units of KMI derivatives which are the potent inhibitors of BACE 1 ($\beta$-secretase) and HIV protease. Additionally, the obtained AHPBAs 1 and 3 are converted to dipeptides of bestatin stereoisomers 2 and 4.

• 대한화학회지
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• 제41권9호
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• pp.465-470
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• 1997

입체특이성 반응을 나타내는 키랄성 다섯자리 리간드, 1,9-bis(S)-prolyl-1,9-dioxo-2,5,8-triaza-nonane(S,S-prochen)를 S-proline과 diethylenetriamine (dien)으로부터 합성하여 $^{13}C-NMR$스펙트럼으로 확인하고, $CoCl_2{\cdot}6H_2O$와 반응시켜 적자색의 착물인 $[Co(SS-prodien)H_2O]ClO_4$ 를 합성하였다. 원소분석, 전자흡수스펙트럼, $^{13}C-NMR$스펙트럼 자료에 따라 S,S-prodian은 5자리로 배위되면서 중심의 dien부분은 fac형태로 결합하고, 한자리 리간드인 $H_2O$는 dien에 있는 2차질소원자에 대하여 cis 위치에 존재하는 ${\alpha}{\beta}$ (ffm)-형임을 알게되었다. 또한 CD스펙트럼에 따라 킬레이트된 리가드는 입체선택적으로 배위되어 ${\Lambda}$-${\alpha}{\beta}$ (ffm)-$[Co(SS-prodien)H_2O]^+$의 절대구조를 갖는다고 생각하였다.

• 대한의생명과학회지
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• 제9권4호
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• pp.177-181
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• 2003

The baculovirus/Spodoptera frugiperda (Sf) cell system has become popular for the production of large amounts of the human erythrocyte glucose transporter, GLUT1, heterologously. However, it was not possible to show that the expressed transporter in insect cells could actually transport glucose. The possible reason for this was that the activity of the endogenous insect glucose transporter was extremely high and so rendered transport activity resulting from the expression of exogenous transporter very difficult to detect. Sf21-AE cells are commonly employed as the host permissive cell line to support the baculovirus AcNPV replication and protein synthesis. The cells grow well on TC-100 medium that contains 0.1 % D-glucose as the major carbon source, strongly suggesting the presence of endogenous glucose transporters. However, unlike the human glucose transporter, very little is known about properties of the endogenous sugar transporter(s) in insect cells. Thus, the uptake of 2-deoxy-D-glucose (2dGlc) by Sf21-AE cells and the inhibition of 2dGlc transport in the insect cells by fructose and cytochalasin B were investigated in the present work. The binding assay of cytochalasin B was also performed, which could be used as a functional assay for the endogenous glucose transporter(s) in the insect cells. Sf21-AE cells were infected with the recombinant virus AcNPV-GT or no virus, at a multiplicity of infection (MOI) of 5. Infected cells were resuspended in PBS plus and minus 300 mM fructose, and plus and minus 20 $\mu$M cytochalasin B for use in transport assays. Uptake was measured at 28$^{\circ}C$ for 1 min, with final concentration of 1 mM deoxy-D-glucose, 2-[1,2-$^3$H]- or glucose, L-[l,$^3$H]-, used at a specific radioactivity of 4 Ci/mol. The results obtained demonstrated that the sugar uptake in uninfected cells was stereospecific, and was strongly inhibited by fructose but only poorly inhibitable by cytochalasin B. It is therefore suggested that the Sf21-AE glucose transporter has very low affinity for cytochalasin B, a potent inhibitor of human erythrocyte glucose transporter.

• Archives of Pharmacal Research
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• 제21권4호
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• pp.465-469
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• 1998

The search for platinum (II)-based compounds with improved therapeutic properties was prompted to design and synthesize a new family of water-soluble, third generation cis-diaminedichloroplatinum (II) complexes linked to uracil and uridine. Six heretofore unreported uracil and uridine-platinum (II) complexes are; [N-(uracil-5-yl-methyl)ethane-1,2-di-amine]dichloroplatinum (II) (3a), [N-(uracil-6-yl-methyl)ethane-1,2-diaminel dichloroplatinum (II) (3b), t[N-($2^1$, $3^1$,$5^1$-tri-O-acetyl)uridine-5-yl-methyl] ethane-1,2-diamineldichloroplatinum (II) (6a), {[N-($2^1$,$3^1$, $5^1$-tri-O-acetyl) uridine-6-yl-methyl]ethane-1,2-diamine)dichloroplatinum (II) (6b),[N-(uridine- 5-yl-methyl)ethane-1,2-diamine]dichloroplatinum (II) (7a), [N-(uridine-6-yl- methyl)ethane-1,2-diamine]dichloroplatinum (II) (7b). These analogues were prepared from the key starting materials, 5-chloromethyluracil (1a) and 6-chloromethyluracil (1b) which were reacted with ethylenediamine to afford the respective 5-[(2-aminoethyl)aminol methyluracil (2a) and 6-[(2-aminoethyl)amino]methyluracil (2b). The cis-platin complexes 3a and 3b were obtained through the reaction of the respective 2a and 2b with potassium tetrachloroplatinate (II). The heterocyclic nucleic acid bases 1a and 1b were efficiently introduced on the .betha.-D-ribose ring via a Vorbruggen-type nucleoside coupling procedure with hexamethyldisilazane, trimethylchlorosilane and stannic chloride under anhydrous acetonitrile to yield the stereospecific .betha.-anomeric 5-chloromethyl- $2^1$,$3^1$,$5^1$-tri-O-acetyluridine (4a) and 6-chloromethyl-$2^1$,$3^1$,$5^1$-tri-O-acetyluridine (4b), respectively. The nucleosides 4a and 4b were coupled with ethylenediamine to provide the respective 5-[(amino-ethyl)aminolmethyl-$2^1$,$3^1$,$5^1$-tri-O-acetyluridine (5a) and 6-[(aminoethyl)amino] methyl-$2^1$,$3^1$,$5^1$-tri-O-acetyluridine (5b). The diamino-uridines 5a and 5b were reacted with potassium tetrachloroplatinate (II) to give the novel nucleoside complexes, 6a and 6b, respectively which were deacetylated into the free nucleosides, 7a and 7b by the treatment with CH$_{3}$ONa. The cytotoxic activities were evaluated against three cell lines (FM-3A, P-388 and J-82) and none of the synthesized compounds showed any significant activity.

• 대한화학회지
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• 제39권9호
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• pp.715-721
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• 1995

Trans-$[Co(py)_4/Ci_2]^+(py=pyridine)$과 L-proline 및 diimine(=2,2'-bipyridine,1,10-phenanthroline)과의 반응에서 $[Co(L-pro)_2/(bipy)]^+$(L-pro=bipy=2,2'-bipyridine)과 $[Co(L-pro)_2(phen)]^+$(phen=1,10-phenathroline)이 각각 생성되었다. 관 크로마토그래피상에서 입체특이성을 가지는 L-prolinato의 입체선택성으로 인하여 $[Co(L-pro)_2(bipy)]^+$에서는 $Lambda$-trans(N)만이 얻어졌고 $[Co(L-pro)_2(bipy)]^+$에서는 ${\Delta}$-trans(N)과 $Lambda$-cis(O)cis(N)이 얻어졌다. 결정구조 연구의 결과는 다음과 같다: $Lambda$-trans(N)-$[Co(L-pro)_2(bipy)]CIO_4{\cdot}2H_2O$ (1): monoclinic, space group $P2_1(#4)$, a = 9.807(3), b = 10.421(1), c = 12.778(2)${\AA}$, ${\beta}=109.90(2)^{\circ}$, V = 1227.8(5)${\AA}^3$, Z = 2; 1571 data(I>3.0${\sigma}$(I)) R = 0.060 and $R_W = 0.067$; ${\Delta}$-trans(N)-$[Co(L-pro)_2(phen)]Cl{\cdot}_3H_2O$ (2): monoclinic, space group $P2_1(#4)$, a = 9.838(2), b = 12.892(2), c = 10.747(2)${\AA}$, ${\beta}=113.79(2)^{\circ}$, V = 1247.2(4)${\AA}^3$, Z = 2; 2433 data(I>3.0${\sigma}$(I)) R = 0.043 and $R_W = 0.050$.