• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1993년도 제2회 신약개발 연구발표회 초록집
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• pp.118-118
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• 1993

퀴놀론 모핵의 합성은 기존에 알려진 합성 방법인 Could-Jacobs방법과 Bayer방법에 의해서 Intermediate로 사용된 7-chloro-1-ethyl-6-fluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid와 1-cyclopropyl-7-chloro-6-Fluoro-1,4-dihydro-4-oxoquinolne-3-carboxylic acid를 합성하였다. Heteroaromatic tin compound는 furan, thiophene, 3-bromopyridine, 2-fluoropyridine에 n-BuLi을 사용하여 metallation 한후 electrophile로 tributyltin chloride를 사용하여 2-tributylstannofuran, 2-tributylst-annothiophene, 3-tributylstannopyridine, 2- fluoro-2-tributylstannop-yridine을 합성할 수 있었다. 이상의 Intermediate와 tin compounds를 p-alladium 촉매하에서 반응시켜 1-ethyl-7-(2-furanyl)-6-fluoro-1,4-dihy-dro-4-oxo-3-quinoline-carboxylic acid (compound 3), 1-ethyl-7-(2-th-iophenyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinol in carboxylic acid(compound 5), 1-ethyl-7-(3-pyridinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 7), 1-ethyl-7-(2-fluoro-3-pyrid-nyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 9), 1-cyclopropyl-7-(2-furanyl) -6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 4), 1-cyclopropyl-7-(2-thiophenyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 6) ,1-cyclopropyl-7-(3-pyridinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 8), 1-cyclopropyl-7-(2-fluoro-3-pyridinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 10)를 합성하였다.

• 약학회지
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• 제31권2호
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• pp.92-97
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• 1987

The N-[1H-6-fluoro-1,4-dihydro-4-oxo-7-chloroquinoline-3-carboxy] succinimide was reacted with amoxicillin, ampicillin and 6-APA to give 6-[D-(-)-$\alpha$-{1H-6-fluoro-1,4-dihydro-4-oxo-7-chloroguinoline-3-carboxamido} p-hydroxyphanyl acetamido] penicillanic acid [1], 6-[D-(-)-$\alpha$-{1H-6-fluoro-1,4-dihydro-4-oxo-7-chloroquinoline-3-carboxamido} phenylacetamido] penicillanic acid [10] and 6-[1H-6-fluoro-1,4-dihydro-4-oxo-7-chloroquinoline-3-carboxamido] penicillanic acid [19]. The 1-alkyl-6-fluoro-1,4-dihydro-4-oxo-7-substituted quinoline-3-carboxylic acids were reacted with ethyl chloroformate for making mixed anhydride; these mixed anhydrides were reacted with amoxicillin, ampilcillin and 6-APA to give 6-[D-(-)-$\alpha$-{1-alkyl-6-fluoro-1,4-dihydro-4-oxo-7-substituted quinoline-3-carboxamido} p-hydroxyphenylacetamido] penicillanic acid [2-9], 6-[D-(1)-$\alpha$-{1-alkyl-6-fluoro-1,4-dihydro-4-oxo-7-substituted quinoline-3-carboxamido} phenylacetamidod penicillanic acid [11-18] and 6-[1-alkyl-6-fluoro-1,4-dihydro-4-oxo-7-substituted quinoline-3-carboxamido] penicillanic acid [20-27].

• Archives of Pharmacal Research
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• 제12권1호
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• pp.1-4
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• 1989

6-Arylamino-3,7-dihydro-3,7-dimethy-2-oxo-1H-purine and 2-arylimino-6-arylamino-3,7-dihydro-3,7-dimethyl-1H-purine were obtained in a one-pot reaction when 3,7-dihydro-3,7-dimethyl-1H-purine-3,6-dione, phosphorus pentaoxide, triethylamine hydrochloride and appropriate amine amino are heated at $170^{\circ}$. Some derivatives were tested for their antitumor activity.

• 대한화학회지
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• 제44권5호
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• pp.435-440
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• 2000

2-Methoxycarbonylmethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(5)을 hydrazine hydrate와 ethylenediamine을 반응시켜 2-hydrazinocarbonylmethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(6)과 2-aminoethylcarbamoylmethylene-1,2-dihydro-4H-pyrido[2,3-b]pyrazin-3-one(7)을 각각 합성하였다. 화합물 6 또는 7을 치환 벤즈알데히드류 및 헤테로아릴 알데히드류와 반응시켜 pyrido[2,3-b]pyrazin류(8-13)를 각각 합성하였다. 몇가지 pyrido[2,3-b]pyrazin은 용액에서 enamine형,methylene imine형, methylene imine형,enaminol형 사이에 토토머화 현상을 나타내었는데, 이들의 토토머 비는 1H NMR로서 측정하였다.

• 약학회지
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• 제41권2호
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• pp.181-186
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• 1997

A series of 7-deazahypoxanthine and 7-deazaadenine derivatives[6,7.8.9.10,13] as purine antagonists was prepared. The pyrrolidine-5-one derivatives[4,11] were treated vith $(C_2H_5)_3OBF_4$ to give 3- aryl-5-ethoxy-2H-3,4-dihydropyrrole[5,12], which were converted to 7-aryl-7,8-dihydro-7(9H)-deazahy-poxanthine[6,7,8,9,10] and 7-phenyl-2-methyl-7,8- dihydro-7(9H)-deazaadenine[13].

• 한국식품영양학회지
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• 제17권2호
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• pp.156-162
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• 2004

미이용자원인 어류 carotenoid에 관한 비교 생화학적 연구의 일환으로서, 메기과의 자연산 및 양식산 메기와 한국 특산의 담수어류인 미유기의 표피 carotenoid를 TLC, column chromatography 및 HPLC로 분리하고 NaBH$_4$에 의한 환원반응, I$_2$에 의한 이성화반응 및 UV-visible spectrophotometer로 비교하고 IR 및 Mass spectrum을 측정하여 carotenoid를 동정한 결과는 다음과 같다. 자연산 메기 표피의 총 carotenoid 함량은 0.27 mg($\pm$0.7)%였으며 carotenoid의 조성은 zeaxanthin 25.8%, diatoxanin 9.7% 및 cynthiaxanthin 9.1%로서 주성분을 이루고 있었으며 그 외 isocryptoxanthin 6.5%, $\beta$-carotene 5.1%, $\beta$-cryptoxanthin 4.3%, lutein 3.4% 및 $\alpha$-cryptoxantin 2.4%의 순으로 함유하고 있었다. 양식산 메기 표피의 총 carotenoid 함량은 0.07 mg($\pm$0.03)%로서 자연산 메기에 비해 다소 낮았으며, carotenoid의 조성은 lutein 48.5%, zeaxanin 13.9% 및 isocryptoxanin 13.3%로서 주성분을 이루고, 그 외 $\beta$-carotene 9.5%, $\beta$-cryptoxantin 1.4% 및 $\alpha$-cryptoxanthin 4.6%의 순으로 함유하고 있었다. 한편 미유기 표피의 총 carotenoid 함량은 0.75 mg($\pm$0.25)%로서 메기과의 다른 어종에 비해 함량이 높았으며, carotenoid 조성은 zeaxanthin 24.5%, 7'8'-dihydro-$\beta$ -carotene-4-ol 24.1%, 7'8'-dihydro-$\beta$-carotene 17.9% 및 7'8'-dihydro-$\beta$-carotene-3-ol 10.8%로서 주성분을 이루고 있었으며 그 외 diatoxanthin 8.7%, cynthiaxanthin 6,7% 및 lutein 5.0%의 순으로 함유하고 있었다. 이러한 결과는 parasiloxanthin과 7',8'-dihyo-parasiloxanthin을 주성분으로 함유하는 biwa호수 메기, P. asotus 표피 carotenoid 조성과 비교하여, 미유기에서는 7'8'-dihydro-$\beta$-carotene의 구조를 가진 carotenoid가 존재하였으나 자연산 및 양식산 메기에서는 발견되지 않아 특이하였다.

• Archives of Pharmacal Research
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• 제21권2호
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• pp.187-192
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• 1998

The cis- and trans-diastereomers of the 7,8-dihydro-7-deazapurine derivatives were synthesized from the corresponding diastereomers of 4-tran5-cyano-2-methyl-3-phenyl-5-oxopyrrolidine (5), which were reduced from the 2-cis- and 2-tran5-diastereomers of 4-trans-cyano-2-hydroxymethyl-3-phenyl-5-oxopyrrolidine (2) via tosylation, iodination and following elimination respectively. The prepared cis- and ttans-diastereomers of 6-amino-2-mercapto-8-methyl-7-phenyl-7,8-dihydro-7(9H)-deazapurine (8) were transferred to the corresponding 2-methylthio-diastereomers 9 and following desulfurization with Raney-nickel leaded to the cis and trans-diastereomers of 6-amino-8-methyl-7-phenyl-7,8-dihydro-7(9H)-deazapurine (10), respectively. The synthesized 7-deazapurine derivatives were tested for their antibiotic activity by the serial two-fold dilution method.

• 약학회지
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• 제37권3호
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• pp.228-234
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• 1993

A new series of 7-deazapurine derivatives[7,8] as purine antagonists was prepared. Diethyl 4-cyano-N-(diphenyimethylene)-3-arylglutamate[3] were synthesized by LDA-catalyzed Michael addition of N-(diphenylrnethylene)glycine ethyl ester with (E)-2-cyano-3-arylacrylate. Deprotection yields diethyl 4-cyano-3-arylglutamate, which were easily cyclized to 4-cyano-2-ethoxycarbonyl-5-oxo-3-arylpyrrolidine[4]. The compounds[4] were treated with NaBH$_{4}$ and then with (C$_{2}$H$_{5}$)$_{3}$OBF$_{4}$ to give 4-cyano-5-ethoxy-2H-2-ethoxymethyl-3-aryl-3,4-dihydropyrrole[6], which were converted to 7-aryl-6-amino-8-ethoxymethyl-7,8-dihydro-7(3H, 9H)-deazapurine-2-thione[7] and 7-aryl-2,6-diamino-8-ethoxymethyl-7,8-dihydro-7(9H)-deazapurine[8] with possible activity against neoplastic disease.

• Bulletin of the Korean Chemical Society
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• 제26권10호
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• pp.1607-1610
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• 2005

• 한국식품과학회지
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• 제22권5호
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• pp.549-554
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• 1990

비이온성 수지인 Amberlite XAD-2 흡착 및 메탄올 용출법에 의해 살구로부터 배당체분획을 얻은 다음 almond ${\beta}-glucosidase$ 및 산가수분해(pH3.0) 또는 pH 3.0에서 simultaneous distillation-extraction(SDE)에 의해 얻어진 가수분해물로부터 GC 및 GC-MS에 의해 40종의 휘발성 성분을 확인하였다. 3종의 가수분해물로부터 이미 배당체로서 살구에 존재하는 것으로 알려져 있는 linalool oxide, linalool, ${\alpha}-terpineol$, nerol, geraniol, benzyl alcohol 및 2-phenylethyl 이외에도 2,6-dimethyl-3,7-octadiene-2,6-diol, 3,7-dimethyl-1,5-octadiene-3,7-diol,(E)-및 (Z)-2,6-dimethyl-2,7-octadiene-1,6-diol, $3-4-dihydro-{\beta}-ionol$ $3-oxo-{\alpha}-ionol$, $3-hydroxy-7,8-dihydro{\beta}-ionol$, $3-oxo-7,8-dihydro-{\alpha}-ionol$, $3-hydroxy-{\beta}-ionone$, eugenol, 3-hydroxyethylphenyl acetate 및 2,3-dihydrobenzofuran이 살구에서 처음으로 확인되었다.