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고옥현,강형룡,유진철,김경수,홍석순,김영수,황화영,하재천 조선대학교 약학연구소 1992 藥學硏究誌 Vol.14 No.1
7β[5-(Substituted) phenyl-2H-tetrazol-2-yl]acetamidocephalospranic acid, 7β-(5-Diphnenyl-methyl-2H-tetrazol-2-yl) acetamidocephalosporanic acid and 7β-[5-(Substituted)-4-phenyl-1.2.4-triazol2-yl]thioacetamidocephalosporanic acid were synthesized and tested in vitro antimicrobial activity. These compounds exhibited good antimicrobial activity against Gram-positive bacteria whereas most compounds showed decreased antimicrobial activity against Gram-negative bacteria
트리아조릴 티오메칠피로리딘을 3번 측쇄에 가진 세파로스포린 유도체의 합성
고옥현,홍준희 대한약학회 2002 약학회지 Vol.46 No.5
Synthesis of 7$\beta$-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[[(3S, 5S)-5-[4-phenyl-5-(4-methylphenyl or 2-thiophenyl)-4H-l, 2, 4- triazol-3-yl]thiomethylpyrrolidin-3-yl]]thiomethyl-3-cephem-4-carboxylic acids (7a, 7b) were described. (2S, 4S)-4-acethylthio-2-[4-phenyl-5-(4-methylphenyl or 2-thiophenyl)-4 H-1, 2, 4-triazol-3-yl]thiomethyl-1-tert-butoxycarbonylpyrrolidines (4a, 4b) were prepared from trans-4-hydroxy-L-proline with (2S, 4R)-absolute configuration as starting material. 4-Phenyl-5-(4-methylphenyl or 2-thiophenyl)-4 H-l, 2, 4-triazol-3-thiols (2a, 2b) were prepared from p-toluic anhydride and 2-thiophene carboxylic acid hydrazide, respectively. p-Methoxybenzyl 7$\beta$-(Z)-2-(2-for-mamidothiazol-4-yl)-2-(1-tert-butoxycarbonylisopropylimino]acetamido-3-[[ (3S, 5S)-5-[4-phenyl-5-(4-methylphenyl or 2-thio phenyl)-4H-1, 2, 3-triazol-3-yl]thiomethyl-1- tert-butoxycarbonylpyrrolidin-3-yl]]thiomethyl-3-cephem-4-carboxylates (6a, 6b) were achieved by using p-methoxybenzyl ]7P-(Z)-2-(2-formamidothiazol-4-yl)-2-(tert-butoxycarbonylisopropylimino] acetamido-3-chloromethyl-3-cephem-4-carboxylate (5) and (2S, 4S)-4-acethylthio-2-[4-phenyl-5-(4-methyl phenyl or 2-thiophenyl)-4H-1, 2, 4-triazol-3-yl]thiomethyl-1-tert-butoxycarbonyl pyrrolidines (4a, 4b). Removal of formyl, Boc, and p-methoxybenzyl protecting groups were carried out by triflu oroacetic acid and anisole to give the target compounds.
2-Ethoxymethyl-3-(5-nitro-2-furyl)acrylamide 誘導體의 合成 및 抗菌作用에 關한 硏究
高玉鉉,姜聲龍 朝鮮大學校 1980 藥學硏究誌 Vol.3 No.1
In order to obtain some new antibacterial agents, seven new 2-ethoxymethyl-3-(5-nitro-2-furyl) acrylamide derivatives were synthesized by condensing 2-ethoxymethyl-3-(5-nitro-2-furyl) acryloyl chloride with amino compound namely 5-amino-3,4-dimethyl isoxazole, sulfamonomethoxazole, d-2-amino-1-butanol, hydroxylamine HCl, semicarbazide HCl, thiosemicarbazide, and p,p′ -diaminodiphenylsulfone, respectively. The seven synthesized compounds thus obtained were 2-ethoxymethyl-3- (5-nitro-2-furyl) acryl-5-amino-3,4-dimethylisoxazoleamide〔Ⅶ〕, N^4-〔2-ethoxymethyl-3-(5-nitro-2-furyl) acryl-N^1-(5-methyl-3-isoxazolyl) sulfanilamide〔Ⅶ〕, 2-ethoxymethyl 3-(5-nitro-2-furyl) acrylhydroxamide 〔Ⅸ〕, 2-ethoxymethyl-3-(5-nitro-2-furyl) acrylsemicarbazide 〔Ⅸ〕, 2-ethoxymethyl-3-(5-nitro-2-fury) acrylthiosemicarbazide 〔XI〕, 2-ethoxymethyl -3-(5-nitrc-2-furyl) acryl-d-2-amino-1-butanolamide 〔ⅩI〕, and 4,4′ -di〔2-ethoxymethyl-3-(5-nitro-2-furyl) acrylamido〕 diphenylsulfone 〔ⅩIII〕. These compounds, with the exception of compound ⅩIII generally showed effective antibacterial activity, especially in the following instances. Compound Ⅶ was shown to be effective against Bacillus subtilis ATCC 6633, Compound Ⅷ, against Bacillus cereus var. Mycoides ATCC 11778, and compound XI , against both Proteus vuglaris and Saccharomyces cerevisiae ATCC 9763.
5-Nitrofurfural 誘導體의 合成과 抗菌作用에 關한 硏究
高玉鉉 조선대학교 약학연구소 1978 藥學硏究誌 Vol.1 No.1
The many studies on the synthesis and antibacterial action of 5-Nitrofuran derivatives have been reported in pharmaceutical field. In order to find antibacterial activity, author synthesized new 2-phenyl-3-(5-nitro-2-furyl) acryl-p,p'-diaminodiphenylsulfone by the action of 2-phenyl-3-(5-nitro-2-furyl)acryl chloride on p,p'-diaminodiphenylsulfone. Antibacterial action of synthesized compound against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Shigella flexneri were carried out. This new compound exhibited good antibacterial action against Bacillus subtilis.
2-Amino-4-thio(3H)pteridines 合成에 關한 硏究
高玉鉉 조선대학교 약학연구소 1982 藥學硏究誌 Vol.4 No.1
In order to obtain some new anticancer agents, author synthesized 2-amino-3-cyano-5-methylpyrazine by condensing of aminomalononitrile tosylate and β-chloropyru-valdoxime, also, synthesized 6-methyl-2-phenylamino-4-thio (3H) pteridine, 6-methyl-2-phenyl amino-4-thio(3H)pteridine 8-oxide and 2-ethyl-6-methyl-4-thio(3H)dteridine 8-oxide by condensing of alkyl or arylisothiocyanate and 2-amino-3-cyano-5-methylpyrazine, respectively.
1-Hydroxy-2-Oxiranylmethylanthraquinone의 합성
高玉鉉 朝鮮大學校 1987 藥學硏究誌 Vol.9 No.1
근래에 epoxide ring를 가지고 있는 화합물들이 insecticidal, fungicidal, antimicrobial 그리고 antileukemic activity를 가지고 있다고 보고하였다. chang 등은 antraquinone핵을 가지고 있는 mordaparvin A, B를 Morinda parvifolia(Rubiaceae)에서 분리하여 동물에 실험한 결과 antileukemic activity[mor. A; ED50(p-388)=1.85ug/ma. T/C=129%(p-388) 10mg/kg, mor.B;ED50(KB)=4.0ug/ml]를 가지고 있다고 보고하였다. 또한 anthra1uinone계의 daunomycin, adrimycin, carminoycin 등이 항생제, 항암제등으로 사용되고 있다. 이들 화합물들의 구조식중에는 epoxide ring을 합성하려고 본실험을 실시하였다. 먼저 1-hydroxyant-hraquinone을 Tseretli, Woodgat, Andrews 등의 방법을 모방하여 allybromide를 반응시켜 allylether[II]를 합성하려고 한다. comp.[II]를 Tseretli, Woodgat, Andrews, Trabell, Jefferson, Hansen, Rhoads 등의 방법을 모방하여 N, N-dimethylaniline(N,NAMA)를 용매로 약 200‘C에서 환류시켜 claisen rearrangement를 시도하여 ortho위치에 allylradical을 도입시킨 claisen bond의 epoxidationdms Kishi 등의 방법을 모방하여 epoxidationdmf 시도하려고 한다.
抗癌劑 Psorospermin의 Epoxide Ring 部位의 合成硏究
高玉鉉 조선대학교 약학연구소 1986 藥學硏究誌 Vol.8 No.1
The epoxidation of 6-(3-methyl-2-buten-4-ol)-3, 5-dimethoxyphenol using the L-(+)-diethyltartrate (DET), titanium (Ⅳ) isopropoxide 〔Ti(oPr)_4〕 and tert-butylhy-droperoxide(TBHP) is described. 6-(3-methyl-2, 3-epoxybutan-4-ol)-3, 5-dimethoxyphenol was synthesized by means of the eight steps, such as Allylether, Claissen rearrangement, Tosylation, Oxidation, Witting reaction, Reduction, Epoxidation from 3, 5-dimethoxyphenol.
고옥현 朝鮮大學校 1998 藥學硏究誌 Vol.19 No.2
The efficient synthesis of xanthone derivatives. which are important intermediates in the synthesis of psorospermin as a anticancer agent. from 3-(benzyloxy-2-hydroxybenzoic acid and 6-allyl-3.5-dihydroxy-l-tosyk1xybemne as a starting mated will be reported herein