• 공업화학
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• 제8권4호
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• pp.700-703
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• 1997

Phthalic anhydride를 출발물질로 halogenation, phosphorylation하여 diethyl phthalimidoalkylphosphonate를 합성하였다. 이 화합물을 chlorination하여 O-ethyl phthalimidoalkylphosphonate을 만든후 diphenylmethyl 7-$\beta$-amino-3-acetoxymethyl-3-cephem-4-carboxylate와 coupling하여 지금까지 알려져 있지 않은 화합물 diphenylmethyl-7-$\beta$-(O-ethylphthalimidomethylphosphony1)-3-acetoxymethyl-3-cephem-4-carboxylate와 diphenylmethyl-7-$\beta$-[O-ethylphthalimidoethylphosphonyl]-3-acetoxymethyl-3-cephem-4-carboxylate를 각각 19%, 43%의 수율로 합성하였다.

• Bulletin of the Korean Chemical Society
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• 제34권11호
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• pp.3317-3321
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• 2013

A series of new 3-alkylamino-6-allylthio-pyridazine derivatives was synthesized through allythiolation and amino-de-halogenation and were expected to have anti-proliferative activity. 6-Allylthio-3-chloropyridazine was prepared from the reaction of 3,6-dichloropyridazine with allylmercaptan and sodium hydroxide. The alkylamines such as methylamine and the dialkylamines such as dimethylamine were introduced into the 3-position of the pyridazine ring. These new compounds showed anti-proliferative activities against MCF-7 human breast cancer cells in CCK-8 assays. These compounds are thus promising candidates for chemotherapy of breast cancer. Two compounds, 14 and 15, showed higher potencies for inhibiting growth of breast cancer cells than did 5FU. This suggests the potential anti-proliferative activity of these compounds.

• Bulletin of the Korean Chemical Society
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• 제26권8호
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• pp.1190-1196
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• 2005

Halopyrroles, N-substituted 2-halopyrroles were prepared by halogenation of N-substituted pyrroles with NBS, NCS, or surfuryl chloride. N-Substituted 3-halopyrroles were synthesized by acid-catalyzed thermal and photochemical isomerization reactions of N-substituted 2-halopyrroles. Both the thermal and photochemical reactions were acid-catalyzed. For the acid-catalyzed isomerization, a mechanism of [1,3] bromine shift followed by deprotonation is operated. For the acid-catalyzed photoisomerization, an excited triplet state of 2-protonated N-benzyl-2-halopyrrole produces an intermediate N-substituted pyrrole complex with halonium ion which is equilibrated with N-substituted pyrrole plus halonium ion, and then the halonium ion newly adds to 3-position of N-substituted pyrrole followed by deprotonation to afford N-benzyl-3-halopyrrole.

• Bulletin of the Korean Chemical Society
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• 제34권8호
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• pp.2276-2280
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• 2013

The accurate prediction of vertical excitation energies is very important for the development of new materials in the dye and pigment industry. A time-dependent density functional theory (TD-DFT) approach coupled with 22 different exchange-correlation functionals was used for the prediction of vertical excitation energies in the halogenated copper phthalocyanine molecules in order to find the most appropriate functional and to determine the accuracy of the prediction of the absorption wavelength and observed spectral shifts. Among the tested functional, B3LYP functional provides much more accurate vertical excitation energies and UV-vis spectra. Our results clearly provide a benchmark calibration of the TD-DFT method for phthalocyanine based dyes and pigments used in industry.

• Bulletin of the Korean Chemical Society
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• 제22권2호
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• pp.149-153
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• 2001

A new methodology for construction of dihydro-1,4-dioxin skeleton was described. Introduction of thio group at the ${\alpha}-position$ of 8 followed by chlorination gave 11, which was to prevent an enolization as well as to promote the facile nucleophilic substitution reaction of ethylene glycol giving 16 in equilibrium with cyclic ether 19. Removal of thio group of 19 and dehydration in the presence of an acid catalyst gave dihydro-1,4-dioxin 21. In case of electron withdrawing trifluoromethyl group is subsituted in C-2, 18 was converted to the corresponding dihydro-1,4-dioxin 20 by the halogenation of hydroxy followed by treatment of triethylamine.

• 약학회지
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• 제50권6호
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• pp.393-397
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• 2006

The synthesis of new 3-substituted 7-halocephalosporanates was described. 7-ACA was reacted with thiols at pH 6.5${\sim}$6.8 to afford the 3-substituted 7-ACA (1), which was treated with diphenyldiazomethane to give diphenylmethyl 7-aminocephalosporanate (2). The Halogenation of 7-aminocephalosporanate (2) with NaNO$_2$, KBr and H$_2$SO$_4$ gave 7-bro-mocephalosporanate (3) and with NaNO$_2$, HCI gave 7-chlorocephalosporanate (4). Diphenylmethyl cephalosporanate (2${\sim}$4) were deprotected by AIC1$_3$ in anisole and neutralized to give the sodium cephalosporanate (5${\sim}$7).

• Bulletin of the Korean Chemical Society
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• 제31권10호
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• pp.2985-2988
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• 2010

• 대한화학회지
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• 제54권4호
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• pp.429-436
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• 2010

Guanine (1)으로부터 생물활성이 있는 halogenopurines계 화합물을 합성하였다. Guanine을 acetic anhydride와 반응시켜서 2,9-diacetylguanine (2-1)을 합성하여 얻어진 화합물을 $POCl_3$와 반응시켜서 화합물 3a를 합성하고, 다음 단계에서 2-amino-6-halogenopurines (3b-d)를 합성하였다. 2-Halogenopurines (2-2a-d, 4-2a-d, 5a-d)을 2-amino-6-substituted purines (1, 3a, 4-1)로부터 효율적으로 합성한 후에, 새로운 화합물인 2-2a, 2-2c, 2-2d, 4-2c, 4-2d, 5b, 5c 및 5d를 합성하였다. 합성한 화합물의 구조를 원소분석, $^1H$ NMR, mass spectral data로 확인하였으며, 합성한 화합물에 대한 항균 활성을 시험하였다.

• 대한화학회지
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• 제52권1호
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• pp.36-46
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• 2008

가진 1차 arylselenocarboxylic amide의 고리화는 여러가지 새로운 2,4-diaryl-1,3-selenazoles에 사용되었다. 염소, 브롬, 요오드를 사용한 2,4-diaryl-1,3-selenazoles의 할로겐화는 좋은 수율의 새로운 1,1-dihalo-2,4-diaryl-1,3-selenazoles를 준다. AIDS virus(HIV-1 and HIV-2)에 대하여 몇몇의 1,1-dihalo-2,4-diaryl-1,3-selenazoles의 항바이러스 활성도를 검사하였다. 그것들은 HIV-1에 대한 약간의 대생물활성을 보였다. 모든 화합물은 원소분석, 1H NMR 그리고 질량 분광분석 정보로 구조분석 하였다. 2-(3,4-dimethoxyphenyl)-4-(4-bromophenyl)-1,3-selenazole의 결정구조도 보였다.

• Archives of Pharmacal Research
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• 제19권5호
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• pp.416-422
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• 1996

Twenty one phenylacetylshikonin analogues were synthesized from various subsitituted phenyl acetic acids and their cytotoxicity values against A549, K562 and L1210 cell lines and antitumor action in mice bearing S-180 cells were measured. All of phenylacetylshikonin analogues expressed a potent cytotoxicity $(ED_{50}, 0.1-1.80{\mu}g/ml)$ against L1210 and K562 cells. L1210 cells were the most sensitive to shikonin analogues among these cells. Except 4-methosyphenylacetylshikonin $(0.098 {\mu}g/ml)$, and a-acetoxyphenylacetylshikonin $(0.10 {\mu}g/ml)$, all other shikonin derivatives sshowed higher $ED_{50}$ values than phenylacetylshikonin $(0.13{\mu}g/ml)$, in L1210. In K562 cell, a-substitution of phenylacetylshikonin $(0.1{\mu}g/ml)$, while other subsitutions increased it slightly; 4-methoxyphenylacetylshikonin $(0.033{\mu}g/ml)$ showed a exceptionally good cytotoxicity against K562 cell. 4-Halogenation tended to decrease the cytotoxic effect on L1210 cells, while it enhanced the effect on K562; 4-bromophenylacetyl $$[ED_{50};(L1210)=1.76{\mu}g/ml, ;ED_{50};(K 562)=0.32 {\mu}g/ml]$$ and 4-chlorophenylacetyl shikonin $$[ED_{50};(L1210)=1.64 {\mu}g/ml, ;ED_{50};(K562)=0.32 {\mu}g/ml]$$. In contrast, A549 cells were much less sensitive to these shikonin analogues which showed $ED_{50}$ values of$1.5-1.35 {\mu}g/ml)$.Most of phenylacetylshikonin derivatives showed good antitumor activity in mice bearing S-180 cells. a-A-cetoxyphenylacetylshikonin and 4-dimethylaminophenylacetylshikonin showed highest T/C value (192-195%), implying that introduction of a-acetyl or of 4-dimethylamino group enhanced the antitumor activity as shown for 4-dimethylaminophenylacetylshikonin (T/C, 192%). It might be due to improvement of water solubility by dimethylamino group in the molecule.