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서정진,이봉용,Suh, Jung-Jin,Lee, Bong-Yong 대한약학회 1989 약학회지 Vol.33 No.1
As potential xanthine bronchodilators related to Doxofylline (1b), 2-(7-theophyllineethyl)-1,3-dioxolane (3), 7-(3,3-dimethoxypropyl) theophylline(5), 2-methyl, 2-(7-theophyllinemethyl)-1,3- dioxolane (8a), 2-phenyl, 2-(7-theophyllinemethyl)-1,3-dioxolane (8b) and 2-(7-theophyllinemethyl)-1,3-benzodioxolane(14) were synthesized from theophylline (1a).
1,4-Dihydropyridine의 Dialkylaminomethyl화 유도체의 합성
서정진(Jung Jin Suh),홍유화(You Hwa Hong) 대한약학회 1989 약학회지 Vol.33 No.5
When 2,6-Dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-mono methyl ester(3) was reacted with dimethyl methylene ammonium chloride (5a) and K2CO3 in DMF, 2,6-dimethyl-4-(3''-nitrophenyl)-5-(N,N-dimethylamino)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6a) was obtained in 41% yield. As the same procedure with compound (3) and the other dialkylaminomethylating reagents (5b, c, d, e), 2,6-dimethyl-4-(3''-nitrophenyl)-5-(N,N-diethylamino)methyl-1,4-dihydropyridine-3-carboxylic acid methylester(6b), 2,6-dimethyl-4-(3''-nitrophenyl)-5-(1''-pyrrolidinyl)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6c), 2,6-dimethyl-4-(3''-nitrophenyl)-5-(1''-piperidinyl)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6d) and 2,6-dimethyl-4-(3''-nitrophenyl)-5-(1''-morpholinyl)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6e) were obtained in 28%, 49%, 48% and 18% yield respectively.
서정진(Jung Jin Suh),홍유화(You Hwa Hong) 대한약학회 1989 약학회지 Vol.33 No.2
2,6-Dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl 5-(2''-phenylsulfinyl) ethyl ester (10) or 2,6-Dimethyl-4-(2''or 3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-alkyl 5-(2-methylsulfonyl) ethyl ester (14a, b, c) were hydrolyzed by treatment with NaOH in aqueous EtOH solution to give 2,6-Dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester (4b), 2,6-Dimethyl-4-(2''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester (4c) and 2,6-Dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monoisopropyl ester (4d) in 80-90% yield. By the same procedure, 2,6-Dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3,5-bis(2''-methylsulfonyl) ethyl ester (15) gave 2,6-Dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid (4e) in 96% yield.
서정진(Jung Jin Suh),홍유화(You Hwa Hong) 대한약학회 1989 약학회지 Vol.33 No.4
2,6-dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl 5-(2''-methylthio)ethyl ester methyl iodide salt (7a) was hydrolyzed by treatment with NAOH in aquous EtOH solution to give 2,6-dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid mono methyl ester (2b) in 88% yield. By the same procedure, 2,6-dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridinine-3,5-dicarboxylic acid 3-mono isopropyl ester (2c), 2,6-dimethyl-4-(2''-nitrophenyl)1,4-dihydropyridine-3,5-dicarboxylic acid 3-mono methyl ester (2d), 2,6-dimethyl-4-(2'',3''-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-mono methyl ester (2e) and 2,6-dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridin-3,5-dicarboxylic acid (2f) were obtained from the methyl iodide salts in 91-98% yield.
서정진(Jung Jin Suh),홍유화(You Hwa Hong) 대한약학회 1987 약학회지 Vol.31 No.1
2-Substituted-3,4-dihydro-2H-1,2-benzothiazin-4-one 1,1-dioxide 6 was reatced with magnesium methyl carbonate to form magnesium chelate 7, which could be hydrolized in cold hydrochloric acid solution to give 2-substituted-4-hydroxy-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide 2 in good yield.
1-[(2-Phenyl-1,3-benzodioxol-2-yl)methyl]-1H-imidazole 유도체의 합성 및 항진균작용
서정진(Jung Jin Suh),김재규(Jae Kyu Kim),강희일(Heui Il Kang) 대한약학회 1991 약학회지 Vol.35 No.4
The synthesis of 1-[(2-phenyl-1,3-benzodioxol-2-yl)methyl]-1H-imidazole derivatives is described starting with 2-bromoacetophenones and catechols. l-[(2-Phenyl-1,3-benzodioxol-2-yl)methyl]-1H-imidazole (9-12) showed potent broad-spectrum activity, not only against Candida species but also Cr. neoformans, S. cerevisiae and T. mentagrophytes.
The Solvent-Independent Structure of Piroxicam
김봉희,서일환,지옥인,서종명,서정진,Kim, Bong-Hee,Suh, Il-Hwan,Jhee, Ok-In,Suh, Jong-Myung,Suh, Jung-Jin 한국약제학회 1988 Journal of Pharmaceutical Investigation Vol.18 No.4
The three-dimensional structures of piroxicam crystallized from two different solvents, toluene and toluene/hexane mixture respectively, are proved identical: $C_{15}H_{13}N_3O_4S,\;M\;=\;331.35$, monoclinic, a = 7.128(1), b = 15.146(2), c = 13.956(2) ${\AA},\;{\beta}=\;97.33(1)^{\circ},\;V\;=\;1494.37{\AA}^{3},\;Dx\;=\;1.472\;g/cm^{3},\;Z\;=\;4,\;space\;group\;P2_{1}/c,\;Mo\;K{\alpha}(\lambda=\;0.71073\;{\AA})$, F(000) = 688, T = 295 K, R = 0.0611 for 1993 unique observed reflections. The thiazine ring exhibits a half chair conformation. An amide group is involved in an intramolecular hydrogen bond to the hydroxy group, O(17)-H(17)${\cdots}O(15){\AA}$. The molecule is planar within 2 ${\AA}$ with the interplanar angle $127.9(4)^{\circ}$ between pyridine and benzene rings. A molecular chain parallel to [011] is formed by two intermolecular hydrogen bonds N(16)-H(6)${\cdots}O(11)$ and C(6)-H(6)${\cdots}O(11)$, and the molecular chains are held together by van der Waals forces.
1,4-Dihydropyridine-5-Formyl 유도체의 합성
홍유화(You Hwa Hong),서정진(Jung Jin Suh) 대한약학회 1989 약학회지 Vol.33 No.5
2,6-Dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester (1) was formulated to 2,6-dimethyl-4-(3''-nitrophenyl)-5-formyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (2) in 76% yield. At the elevated temperature, 2,6-dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-monomethyl ester (3) was also converted into compound 2 in 46% yield. The compound 2 was reduced to 2,6-dimethyl-4-(3''-nitrophenyl)-5-hydroxymethyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (4) in 91% yield. Compound 2 was reacted with triethyl phosphonoacetate to give 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-ethoxycarbonyl ethenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester (5) in 50% yield. Reaction between compound 2 and amines (methylamine, ethylamine, methoxylamine, hydroxylamine, phenyl hydrazine and 1-amino-4-methyl piperazine) gave six schiff bases 7a, 7b, 7c, 7e, 7f in 81%, 91%, 82%, 81%, 50% and 84% yield, respectively.