• Molecules and Cells
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• v.20 no.3
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• pp.364-370
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• 2005

We show that sulforaphane inhibits osteoclastogenesis in the presence of macrophage colony-stimulating factor (M-CSF) and receptor for activation of nuclear factor-${\kappa}B$ ligand (RANKL) in osteoclast (OC) precursors. Sulforaphane, an aliphatic isothiocyanate, is a known cancer chemo-preventative agent with anti-oxidative properties. Nuclear factor-${\kappa}B$ (NF-${\kappa}B$) is a critical transcription factor in RANKL-induced osteoclastogenesis, and electrophoretic mobility shift assays (EMSAs) and assay of NF-${\kappa}B$-mediated secreted alkaline phosphatase (SEAP) revealed that sulforaphane selectively inhibited NF-${\kappa}B$ activation induced by RANKL. Inhibition may involve interaction of sulforaphane with thiol groups, since it was prevented by reducing agents.

• YAKHAK HOEJI
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• v.26 no.2
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• pp.91-96
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• 1982

In an attempt to design prodrugs for the Derivatives of the Isothiocyanates R-N=C=S were synthesized eleven novel bis-dithiocarbamates. The best way of preparing the dithiocarbamates was the formation of the dithiocarbonates followed by the reaction of the dithiocarbonates with amines. Thus, the treatment of the diols with carbon disulfide in the presense of potassium hydroxide afforded the potassium salts of the ditniocarbonic acids. The potassium salts were then reacted with alkyl halides to give the dithiocarbonates, which upon treatment with amines produces the dithiocarbamates. In case of vicinal diol (n=o in the above formula), only one of the hydroxy groups was reacted to give the mono-dithiocarbonate. The dithiocarbonates failed to react with amides and aromatic amines. Dithiocarbonates of the different types were obtained when the active double bonds, such as $CH_{2}=CH-Z$ , (Z are electron withdrawing groups), were allowed to react with the free dithiocarbonic acids produced in situ by carefully neutralizing the Potassium salts of the corresponding acids. These compounds are considered to be of some value as prodrugs for the active double bonds.

• YAKHAK HOEJI
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• v.37 no.2
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• pp.113-118
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• 1993

3-Phenyl-5, 6, 7, 8-tetrahydrothiazolo[3, 2-$\alpha$][1, 3]diazepine, which has pharmaceutical activities, was reacted with phenyl isothiocyanate to give 3-phenyl-9-phenyl(thiocarbamoyl)-5, 6, 7, 8-tetrahydrothiazolo[3, 2-$\alpha$][1, 3]diazepi nium-betaine. New biheterocyclic compounds were prepared by the ring transformation reaction of the above reactive betaine with $\alpha$-haloesters and $\alpha$-haloketones such as ethyl bromoacetate, methyl bromoacetate, chloroacetone, and 4'-methoxyphenacyl bromide, respectively. In each ring transformation reaction, two major products supposed to be geometrical isomers were obtained.

• Bulletin of the Korean Chemical Society
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• v.28 no.5
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• pp.751-757
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• 2007

To develop new COX-2 inhibitors, 1,5-diarylhydantoins and 1,5-diaryl-2-thiohydantoins were synthesized from phenylacetic acids by esterification, bromination, C-N bond formation and cyclization. Esters 1-3 were efficiently synthesized from the starting materials by reflux in absolute methanol for 3 h containing concentrated sulfuric acid as catalyst. Bromination was carried out with N-bromosuccinimide at rt in dichloromethane. Bromides 4-6 were reacted with aniline, p-anisidine, sulfanilamide in ethanol (or N,N-dimethylformamide) to provide the amines 7-15. Hydantoins and 2-thiohydantoins 16-46 were synthesized from amines 7-15 by treating them with potassium isocyanate (or potassium thiocyanate) and triethylamine. The synthetic process from alkyl α-anilinophenylacetate 7-15 to 3-alkylhydantoins was carried out in a one-pot reaction using alkyl isocyanate (alkyl isothiocyanate).

• 산림경영
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• s.148
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• pp.54-55
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• 2001

산림청 임업연구원(원장 서승진)은 몬트리올의정서에서 오존층 파괴물질로 지정되어 2005년부터 세계적으로 사용이 금지되게 되는 훈증농약인 메틸브로마이드(Methyl Bromide : MB)를 대체할 수 있는 훈증활성물질 이소치오시아네트(Isothiocyanate)를 양고추냉이(겨자무)로부터 추출하는데 성공하였다. 메틸브로마이드는 세계적으로 토양소득, 검역, 시설물 훈증에 약 7만톤이 사용되는 유독성 물질로서 대체물질 개발을 위해 여러나라에서 연구 중에 있으며 우리나라도 OECD 가입국으로서 환경친화적 무공해 농약의 개발이 시급한 실정이었다. 이소치오시아네이트는 쌀, 옥수수, 콩 등 각종 곡물에 피해를 주는 쌀바구미, 팥바구미, 화랑곡나방, 권연벌레 등 저장곡물해충에 메틸보로마이드와 대등한 살충효과가 있는 무공해 천연물로서 메틸브로마이드를 대체할 수 있을 것으로 전망하고 있다. 앞으로 제형개발 등 상품화가 되면 수입에 의존하고 있는 저장곡물 방충농약을 대체할 수 있어 연간 300만 달러의 외화 절감은 물론 지구환경파괴를 막을 수 있는 획기적 계기를 마련하였다.

• Bulletin of the Korean Chemical Society
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• v.33 no.7
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• pp.2260-2264
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• 2012

The kinetics and mechanism of the pyridinolysis ($XC_5H_4N$) of dimethyl isothiocyanophosphate are investigated in acetonitrile at $55.0^{\circ}C$. The Hammett and Br$\ddot{o}$nsted plots for substituent X variations in the nucleophiles exhibit two discrete slopes with a break region between X = 3-Ac and 4-Ac. These are interpreted to indicate a mechanistic change at the break region from a concerted to a stepwise mechanism with a rate-limiting expulsion of the isothiocyanate leaving group from the intermediate. The relatively large ${\beta}x$ values imply much greater fraction of frontside nucleophilic attack TSf than that of backside attack TSb. The steric effects of the two ligands play an important role to determine the pyridinolysis rates of isothiocyanophosphates.

• Bulletin of the Korean Chemical Society
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• v.34 no.2
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• pp.539-544
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• 2013

$Ag@SiO_2@SiO_2$(FITC) nanocomposites were prepared by the simple polyol process and St$\ddot{o}$ber method. Fluorescence enhancement of fluorescein moiety (fluorescein isothiocyanate, FITC) was investigated in the presence of silver nanoparticles in $Ag@SiO_2@SiO_2$(FITC) system with varying thickness (X nm) of first silica shell. Maximum enhancement factor of 4.3 fold was achieved in $Ag@SiO_2@SiO_2$(FITC) structure with the first silica shell thickness of 8 nm and the average separation distance of 11 nm between the surface of silver nanoparticle and fluorescein moiety. The enhancement is believed to be originated from increased excitation rate of fluorescein moiety due to concentrated local electromagnetic field which was improved by interaction of light with silver nanoparticles.

• Bulletin of the Korean Chemical Society
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• v.34 no.8
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• pp.2317-2320
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• 2013

Thiourea and vinyl sulfoxide derivatives were designed based on the structures of sulforaphane and gallic acid, prepared and tested for HO-1 inducing activity as a measure of Nrf2 activation, and inhibitory effect on NO production as a measure of anti-inflammatory activity. Both series of compounds showed moderate activity on HO-1 induction, and no inhibitory effect on NO production. Interestingly the thiourea compound 6d showed better HO-1 induction (71% SFN) than the corresponding isothiocyanate compound 6a (55% SFN). Overall, it seemed that more efficient electrophile is needed to get more effective Nrf2 activator.

• Archives of Pharmacal Research
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• v.29 no.11
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• pp.1061-1065
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• 2006

A new chiral derivatization agent with sugar moiety, 2,3,4,6-tetra-O-acetyl-${\beta}$-D-galactopyranosyl isothiocyanate (GATC) was synthesized. Several ${\beta}-blockers$ were investigated for the possible separation of the enantiomers by reversed-phase HPLC after derivatization with this new chiral derivatization agent (GATC). GATC was reacted readily with ${\beta}-blockers$ at room temperature and the reaction mixture could directly be injected into the HPLC system. The corresponding diastereomers were well resolved on an ODS column with acetonitrile-ammonium acetate buffer as a mobile phase and monitored at UV 254 nm. The optimization of the derivatization procedure (concentration of GATC, reaction temperature and time) and HPLC conditions (pH and ionic strength of mobile phase) were investigated and compared with GITC.

• Archives of Pharmacal Research
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• v.22 no.6
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• pp.559-564
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• 1999

In order to discover new cancer chemopreventive agents from natural or synthetic products, a structurally diverse class of chemopreventive agents was evaluated using in vitro biomarker of inhibition of 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ornithine decarboxylase (ODC) activity in cultured mouse epidermal 308 (ME)308 cells. As a results, apigenin, benzylisothiocyanate, curcumin, diallyl disulfide, N-(4-hydroxyphenyl)retinamide (4-HPR), menadione, miconazole, nordihydroguaiaretic acid (NDGA) and phenethyl isothiocyanate showed potent inhibitory effects in this process. A chemically diverse group of compounds was included in the evaluation, such as flavonoids, retinoids, isothiocyanates, sulfur-containing compounds and phenolic antioxidant compounds. These data are suggestive to understand the cancer chemopreventive potential mediated by these substances.