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새로운 의약품의 합성에 관한 연구 : 6-Thiocyanopenicillanic Acid 유도체의 합성
이영행,이채호,최원식,Lee Young-Haeng,Lee Chai-Ho,Choi Won-Sik 대한화학회 1992 대한화학회지 Vol.36 No.5
A new ${\beta}$-lactam compound, 6-thiocyanopenicillanic acid(1a) was prepared by the reaction of diazonium salt of 6-aminopenicillanic acid with sodium thiocyanate. Reaction of 6-thiocyanopenicillanic acid(1a) with p-nitrobenzyl bromide, chloromethylpivalate and 1-chlorodiethylcarbonate, respectively, afforded the corresponding esters(1b∼d) 6-aminopenicillanic acid의 diazo화 반응과 sodium thiocyanate와 반응으로 새로운 ${\beta}$-lactam 화합물인 6-thiocyanopenicillanic acid(1a)를 합성하고 p-nitrobenzyl bromide, chloromethylpivalate 및 1-chlorodiethylcarbonate들과의 반응에 의해 각각 해당되는 esters(1b∼d)를 합성하였다
7-티아지닐 세파로스포린 유도체의 합성과 생리활성에 관한 연구
이영행(Young Haeng Lee),채규윤(Kyu Yun Chai),황선암(Sun Am Hyang),최원식(Won Sik Choi) 대한약학회 1997 약학회지 Vol.41 No.4
New cephalosporin antibiotics, 7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido]-3-substituted-3-cephem-4-carboxylic acid derivatives 2a-2d, 7-[(3,4-dihydro-6-ethoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl)acetamido] -3-substituted-3-cephem-4-carboxylic acid derivatives 3a-3d and 7-[(3,4-dihydro-6-methoxycarbonyl-2,2-dimethyl-2H-1,4-thiazin-3-yl-1-(S)-oxide)acetamido]-3-substituted-3-cephem-4-carboxylic acid derivatives 4a-4d were synthesized. Antibacterial activities of these new cephalosporin derivatives and the relationship between their structures and their activities were examined. Among them, 7-[(3,4-dihydro-6-methoxycaronyl-2,2-dimethyl-2H-1,4-thiazin-3-yl-1-(S)oxide)-acetamido]-3-[(1,2,3-triazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid 4d exhibited the antibacterial activities against Gram(+)and Gram(-) bacteria.
3-[(4-카르복시-3-히드록시이소티아졸-5-일)티오메틸] 세파로스포린 유도체들의 합성 및 항균력
이영행(Young Haeng Lee),박규종(Kyu Jong Park),김하정(Ha Jung Kim),최원식(Won Sik Choi) 대한약학회 1998 약학회지 Vol.42 No.4
New cephalosporin antibiotics. 7-[(1H-tetrazolyl)acetamidol]-3-[(4-carboxy-3-hydroxyisothiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid trisodium salt 2,7-[(5-ethylthio-3-hydroxyisothiazol-4-yl)carbox-amidol-3-[(4-carboxy-3-hydroxyisothiazo1-5-yl)thiomethyl)-3-cephem-4-carboxylic acid 3,7-[(2-aminothiazol-4-yl)acetamido]-3-[(4-carboxy-3-hydroxyisothiazol-5-yl]thiomethyl]-3-cephem-4-caboxylic acid 4,7-[(Z)-2-(2-aminothiazol-4-yl)-2-(alkoxyimino)acetamido)-3-[(4-carboxy-3-hydroxyisothiazol-5-yl)thiomethyl)-3-cephem-4-carboxylic acid 5-9 were synthesized. Antibacterial activities of these new cephalosporin derivatives and the relationship between their structures and activities were examined. Among them, 7-((Z)-2-(2-aminothiazol-4-yl)-2-(carboxymethoxyimino)acetamido)-3-[(4-carboxy-3-hydroxyisothiazol-5-yl)thiomethyl)-3-cephem-4-carboxylic acid 8 and 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(l-carboxy-1-methylethoxyimino)acetamido]-3-[(4-carboxy-3-hydroxyisothiazol-5-yl)thiomethyl)-3-cephem-4-carboxylic acid 9 exhibited good antibacterial activities compared with those of cefotaxime and ceftriaxone.
6${\beta}$-Bromopenicillanate로부터 6-(Carboxymethylthio) penicillanic Acid 유도체의 합성
최원식,이영행,이채호,Won-Sik Choi,Young-Haeng Lee,Chai-Ho Lee 대한화학회 1991 대한화학회지 Vol.35 No.5
6${\beta}$-bromopenicillanic acid(4a)와 p-nitrobenzylbromide, 3-bromophthalide, chloromethylpivalate 및 1-chlorodiethylcarbonate의 반응으로 6${\beta}$-bromopenicillanates(4b~4e)을 합성하였으며, 6${\beta}$-bromopenicillanic acid(4a)와 그의 ester(4b~4e)를 thioglycolic acid와 친핵성 치환반응시켜 새로운 $\beta$-lactam계 화합물인 6-(carboxymethylthio)penicillanic acid(5a)와 그의 ester(5b~5e)를 얻었다. Reaction of 6${\beta}$-bromopenicillanic acid(4a) with p-nitrobenzylbromide, 3-bromophthalide, chloromethylpivalate and 1-chlorodiethylcarbonate afforded 6${\beta}$-bromopenicillanates(4b~4e). New ${\beta}$-lactam compound, 6-(carboxymethylthio)penicillanic acid(5a) and the other esters(5b~5e) were prepared by nucleophilic substitution reaction of 6${\beta}$-bromopenicillanic acid(4a) and the other esters(4b~4e) with thioglycolic acid.
1-Benzyl-4-Iodomethyl-2-Azetidinone의 합성과 Iodo기에 대한 전기화학적 환원반응
김일광,이영행,이채호,채규윤,김윤근,Kim Il Kwang,Lee Young Haeng,Lee Chai Ho,Chai Kyu Yun,Kim Yoon Geun 대한화학회 1991 대한화학회지 Vol.35 No.1
1-Benzyl-4-iodomethyl-2-azetidinone(BIMA)을 합성하여 iodomethyl기에 대한 전기화학적 환원을 direct current, differential pulse polarography, cyclic voltammetry 그리고 controlled potential coulometry 방법으로 연구하였다. BIMA의 환원과정은 1단계(-1.35 volts vs. Ag-AgCl)에서 완전비가역과 2전자이동후에 양성자가 첨가되는 EEC 반응기구로 진행되었으며 1-benzyl-4-methyl-2-azetidinone이 생성되었다. 양이온 계면활성제(cetyltrimethylammonium bromide)의 농도가 진하여질수록 양전위 이동이 있었으나 음이온 계면활성제(sodium lauryl sulfate)의 경우에는 2단계로 세분화되는 현상이 나타났다. pH변화에 따른 전극환원과정과 생성물 분석의 결과를 바탕으로 전기화학적 반응기구를 제안하였다. 1-Benzyl-4-iodomethyl-2-azetidinone(BIMA) was synthesized and its electrochemical reduction was investigated by direct current, differential pulse polarography, cyclic voltammetry and controlled potential coulometry. The irreversible two electron transfer on reductive dehalogenation of iodo group proceeded to form 1-benzyl-4-methyl-2-azetidinone by EEC electrode reaction mechanism at the first reduction step(-1.35 volts vs. Ag-AgCl). The polarographic reduction waves separated into two reduction steps due to anionic surfactant (sodium lauryl sulfate) effects, while the waves were shifted to the positive potential as the concentration of cationic surfactant (cetyltrimethylammonium bromide) increased. Upon the basis of results on the product analysis and interpretation of polarogram with pH variable, EEC electrochemical reaction mechanism was suggested.
6,6-Dibromopenicillanic acid 1,1-Dioxide 분자내 탄소 6-위치 브롬기의 전극촉매 수소화반응과 전극반응기구
김일광,이영행,이채호,Il Kwang Kim,Young Haeng Lee,Chai Ho Lee 대한화학회 1991 대한화학회지 Vol.35 No.2
The electrochemical reduction of carbon-6-dibromo groups on 6,6-dibromo penicillanic acid 1,1-oxide(DBPA) was investigated by direct current, differential pulse polarography, cyclic voltammetry and controlled potential coulometry. The irreversible two electrons transfer on the reductive debromination of each bromo group proceeded by EC,EC mechanism at the two electrode reduction steps(-0.48, -1.62 volts). The 6-bromo-PA and 6,6-dihydro-PA was synthesized by controlled potential electrolysis. Upon the basis of results on the products analysis and interpretation of polarograms obtained at various pH, electrochemical reaction mechanism was suggested. 6,6-dibromopenicillanic acid 1,1-oxide(DBPA)의 6위치 dibromo기의 전기화학적 환원을 direct current, differential pulse polarography, cyclic voltammetry, 조절전위 전기량법으로 연구하였다. DBPA 환원과정은 2단계-0.48, -1.62 volts)에서 모두 완전비가역으로 2전자씩 이동하는 EC, EC 반응기구로 진행하였다. 조절전위 전기분해를 이용하여 6-bromo-PA와 6,6-dihydro-PA를 단계적으로 합성하였으며, pH 변화에 다른 폴라로그램의 해석과 생성물 분석의 결과를 바탕으로 전기화학적 반응기구도 제안하였다.