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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.
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.
김상건,류지연 德成女子大學校 藥學硏究所 1996 藥學論文誌 Vol.7 No.1
Dimethyl-4,4′-dimethoxy-5,6,5′,6′-dimethylenedioxy-biphenyl-2,2′-dicarboxylate(PMC)의 간장보호효과 기전의 일부를 규명하기 위하여 PMC가 cytochrome P450(P450), microsomal epoxide hydrolase(mEH), glutathione S-transferase(GST) 효소발현에 미치는 효과를 관찰하였다. PMC를 5∼100㎎/㎏의 용량으로 5일간 투여한 후 간조직중의 효소발현을 측정하였을 때 P450 2B1/2 단백질발현이 PMC 투여용량에 의존적으로 증가하여 1일 50 또는 100 ㎎/㎏용량에서 4∼5배 증가하였다. P450 2E1의 단백질 양은 PMC를 고용량으로 투여한 군에서만 감소하였다. P450 1A1/2의 발현은 PMC투여에 의하여 변화하지 않았으나, P450 2C11은 PMC를 투여한 후 용량의존적으로 감소하였다. mEH와 GST 단백질발현은 PMC투여 약물용량에 관계없이 대조군과 유사하였다. PMC를 단독으로 EH는 garlic oil(GO)과 병용하여 투여할 때의 알콜성지방간 형성에 미치는 효과를 측정하였다. PMC와 GO (1:2 비율)의 혼합물 150㎎/㎏을 3일간 전처치하였을 때 ethanol투여로 유발되는 간장중의 triglyceride (TG) 함량증가를 대조군에 비하여 71%로 감소시켰다. PMC, GO를 각각 전처치할 때에는 isopropanol에 의하여 유도되는 TG 함량증가가 각각 50%, 0%로 감소되었으나, 이들 약제를 병용투여할 때는 감소되는 효과가 소실되었다. Ethanol로 유발되는 지방간 모델에서 cholesterol함량을 측정한 결과 PMC, GO 또는 PMC+GO를 전처치 한 동물군에서 cholesterol증가를 각각 22%, 33% 또는 26%로 감소시켰으며, isopropanol을 투여하여 유발되는 cholesterol의 함량증가는 동일한 전처치에 의하여 각각 30%, 0%, 80%로 저하되었다. 요약하면, PMC는 간장 대사효소중 P450 2B1/2를 유도발현하며, P450 2C11은 억제적으로 발현시키나, mEH, GST의 발현에는 영향을 미치지 않는 것으로 나타났으며, PMC와 GO을 병용하여 투여할 때 지방간형성에 대한 약한 방어효과가 있는 것으로 보인다.
Biphenyl Dimethyl Dicarboxylate가 간내 Cytochrome P450 1A1과 2B1 및 CCl4 유도 간독성에 미치는 영향
김순선(Soon Sun Kim),오현영(Hyun Young Oh),김학림(Hak Rim Kim),양지선(Ji Sun Yang),김동섭(Dong Sup Kim),신윤용(Yhun Yhong Sheen),최기환(Ki Hwan Choi) 대한약학회 1999 약학회지 Vol.43 No.6
In this study, we have investigated the effect of Biphenyl Dimethyl Dicarboxylate (DDB), a synthetic analogue of Schizandrin C isolated from Schizandrae Fructus on cytochrome P450 1A1 and 2B1, and the protective mechanism against CCl4-induced hepatotoxicity in rat liver. After DDB was administered into male rats for different periods of time (1-7 days) and with different doses (25, 50, 100 and 200mg/kg), mRNA levels of CYP1A1 and CYP2B1 were measured by polymerase chain reaction (PCR) and assayed the activities of CYP1A1 specific ethoxyresorufin-0-dealkylase (EROD) and CYP2B1 specific benzyloxyresorufin-0-dealkylase (BROD). DDB treatment resulted in increase in CYP2B1 mRNA level and BROD activity, whereas there was no change in CYP1A1 mRNA level and EROD activity. This effect of DDB was time- and dose-dependent and reached maximal level by 3 day and 200mg/kg treatment. In addition, rats were pretreated with DDB at doses of 25, 50 or 100mg/kg daily for 4 days, 3-hr after final treatment on the 4th day, CCl4 0.3ml/kg was intraperitonially injected into the rats to examine the effect of DDB on CCl4-induced hepatic injury. Serum levels of ALT and AST were determined and histopathological examination was done in rat liver. Furthermore, we have measured hepatic microsomal malondialdehyde (MDA) level, a parameter of lipid peroxidation. Based on serum ALT level and lipid peroxidation, pretreatment of DDB, 50mg/kg appeared the most protective effect against CCl4-induced hepatotoxity. These results indicate that DDB stimulates CYP2B1 mRNA level and BROD activity in time and dose dependent manner and suggest that protective effect of DDB on CCl4-induced hepatotoxicity may be mediated through free radical scavenging.
Huasheng Lu,Hengbo Yin,Aili Wang,Jun Shen,Xiaobo Yan,Yumin Liu,Changhua Zhang 한국화학공학회 2014 Korean Journal of Chemical Engineering Vol.31 No.1
Diethyl 3,4-ethylenedioxythiophene-2,5-dicarboxylate was efficiently synthesized via the O-alkylation of disodium salt of diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate with 1,2-dichloroethane over ionic type phase transfer catalysts, such as tetrabutyl ammonium bromide and benzyltriethyl ammonium chloride. The ionic type phase transfer catalysts showed higher catalytic activities than the nonionic type phase transfer catalysts, such as triethylamine,pyridine, 18-crown-6, and polyethylene glycol 400/600, in the O-alkylation reaction. The conversion of the disodium salt of more than 97% and the selectivity of diethyl 3,4-ethylenedioxythiophene-2,5-dicarboxylate of more than 98%were achieved when the O-alkylation reaction was synergistically catalyzed by tetrabutyl ammonium bromide and potassium iodide.
민동원,이순원 대한화학회 2002 Bulletin of the Korean Chemical Society Vol.23 No.7
Three-dimensional terbium coordination polymers with the formulas of [Tb4(NDC)6(H2O)5]·2H2O (1) and [Tb2(BPDC)3(H2O)3]·H2O (2) (NDC = 2,6-naphthalenedicarboxylate; BPDC = 2,2'-bipyridine-4,4'-dicarboxylate) were prepared by hydrothermal reactions. Both compounds were structurally characterized by X-ray diffraction. Compound 1 has a polymeric structure that contains four distinct Tb metals. Three Tb metals have a square-antiprismatic structure, and the remaining one has a 9-coordinate, triply capped trigonal-prismatic structure. Compound 2 is also a polymer with two distinct Tb metals, both of which have a square-antiprismatic structure. The pyridine nitrogen atoms of the BPDC2− ligand do not coordinate to the metal centers in compound 2.