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항암항생제 6-Deoxybisanhydrodaunomycinone의 합성
조인호,노영쇠,박시호,안구현,신홍식,한병구,Cho, In Ho,Rho Young Soy,Park, Si Ho,Ahn Koo Hyeon,Sin Hong Sig,Han Byoung Ku 대한화학회 1993 대한화학회지 Vol.37 No.1
항암항생제 Danuorubicin(1b)의 aglycone인 daunomycinone의 전이물질 6-deoxybisanhydrodaunomycinone(20)의 전 합성이 이루어졌다. 만들어진 enone 화합물 4를 phthalide sulfone 7과 반응시킨 뒤 oxidation과 methylation을 시켜서 anthraquinone 화합물 10을 얻었다. 화합물 10의 benzyl기를 bromination시켜서 얻은 monobromo 화합물 11을 bis(tetrabutylammonium) dichromate로 고리화반응을 시켜서 hydroxyanthraquinone 화합물 16을 얻은 뒤 OH기를 thiophenol로 치환시켰다. sulfide 화합물 17은 phosphate buffer 용액속에서 m-CPBA로써 산화시켜서 anthraquinonyl sulfone 화합물 18을 얻은 뒤 methyl vinyl ketone(19)과 결합시켜서 화합물 20을 얻었다. A brief route for total synthesis of 6-deoxybisanhydrodaunomycinone(20) was described, namely the precursor of the daunomycinone, the aglycone of the anticancer antibiotic daunorubicin (1b). The prepared enone 4 was condensed with phthalide sulfone 7 to afford anthraquinone 10 after oxidation and methylation. The benzylic group of 10 was brominated, and subsequent oxidation with bis(tetrabutylammonium) dichromate followed by cyclization give hydroxyanthraquinone 16, which was displaced with thiophenol. Oxidation of 17 with m-CPBA in phosphate buffer solution afforded anthraquinonyl sulfone 18 which was condensed with methyl vinyl ketone (19) to furnish 20.
고지방식이에 의한 비만 동물모델에서 유산균 마분말의 항비만 효과
박영미(Young Mi Park),오홍근(Hong Geun Oh),강양규(Yang Gyu Kang),김영필(Young Pill Kim),신홍식(Hong Sig Sin),장승환(Seung Hwan Jang),김희정(Hee Jeong Kim),이상왕(Sang Wang Lee),이학용(Hak Yong Lee) 한의병리학회 2015 동의생리병리학회지 Vol.22 No.2
The purpose of this study was to examine the antiobesity effects of lactic acid bacteria-fermented Dioscoreae Rhizoma powder (LDR) in Sprague-Dawley rats with high-fat diet (HFD)-induced obesity. Rats were divided into 5 groups: normal diet group, control (high fat diet-vehicle) group, 0.4 g/kg LDR (high fat diet + 0.4 g/kg lactic acid bacteria-fermented Dioscoreae Rhizoma powder) group, 1 g/kg LDR (high fat diet + lactic acid bacteria-fermented Dioscoreae Rhizoma powder) group, 2.5g/kg LDR (high fat diet + lactic acid bacteria-fermented Dioscoreae Rhizoma powder) group. Our results indicate that LDR administration has effects on decreasing of body weight, fat weight, blood parameters and adipocyte size in the obesity animals. In addition, verified that fat degeneration and ballooning degeneration were alleviated in the experimental group fed on a high fat diet combined with LDR groups. These results indicate that lactic acid bacteria-fermented Dioscoreae Rhizoma powder may reduce elevating body weight and lipid accumulation in rat fed a high fat diet, suggesting its usefulness as a functional food for reducing body fat and obesity.
노영쇠(Young S. Rho),김선자(Sun Ja Kim),조인호(In Ho Cho),신홍식(Hong Sig Sin) 대한약학회 1999 약학회지 Vol.43 No.1
A brief route for regiospecific synthesis of novel 10-oxodaunomycinone derivatives (10a, b) is described. Dimethoxy-1-tetralone 4 was converted to acetyl tetralone (5a, b) which was oxidized with oxygen to obtain cis-diol compound (8a, b). The construction of (10a, b) was completed by the condensation of phthaloyl dichloride 9 with cis-diol (8a, b).
항암항생제 11-Deoxy-beta-rhodomycinone의 합성
노영쇠(Young S. Rho),강혼수(Heun Soo Kang),신홍식(Hong Sig Sin) 대한약학회 1993 약학회지 Vol.37 No.6
Methyl 3-[(phenylsulfonyl)methyl]-1,4,8-trimethoxy-2-naphthoate(7) preparad by 3 steps was condensed with 5-ethyl-2-cyclohexen-l-one(8) to afford the teracyclic aromatic ring system compound 10, which was stepwise converted into the precursor of 11-Deoxy-beta-rhodomycinone by means of various functional groups transformation.
항암항생제 11-Deoxy-β-rhodomycinone 의 합성
노영쇠,강혼수,신홍식 全北大學校 基礎科學硏究所 1994 基礎科學 Vol.16 No.-
Methyl 3-[(phenylsulfonyl)methyl]-1,4,8-trimethoxy-2-naphthoate(7) preparad by 3 steps was condensed with 5-ethyl-2-cyclohexen-1-one(8) to afford the teracyclic aromatic ring system compound 10, which was stepwise converted into the precursor of 11-Deoxy-β-rhodomycinone by means of various functional groups transformation.
항암항생제 6-Deoxybisanhydrodaunomycinone의 합성
趙仁鎬,魯永釗,朴時浩,안구현,申洪植,韓秉九 全北大學校 基礎科學硏究所 1994 基礎科學 Vol.16 No.-
항암항생제 Danuorubicin(1b)의 aglycone인 daunomycinone의 전이물질 6-deoxybisanhydrodaunomycinone(20)의 전 합성이 이루어졌다. 만들어진 enone 화합물 4를 phthalide sulfone7과 반응시킨 뒤 oxidation과 methylation을 시켜서 anthraquinone 화합물 10을 얻었다. 화합물 10의 benzy기를 bromination 시켜서 얻은 monobromo 화합물 11을 bis(tetrabutylammoumum) dichromate로 고리화반응을 시켜서 hydrox-yanthraquinone 화합물 16을 얻은 뒤 OH기를 thiophenol로 치환시켰다. sulfide 화합물 17은 phoshate buffer 용액속에서 m-CPBA로써 산화시켜서 anthraquinonyl sulfone 화합물 18을 얻은뒤 methy vinyl ketone(19)과 결합시켜서 화합물 20을 얻었다. A brief route for total synthesis of 6-deoxybisanhydrodaunomycinone(20) was described, namely the precursor of the daunomycinone, the aglycone of the anticancer antibiotic daunorubicin (1b). The prepared enone 4 was condensed with phthalide sulfone 7 to afford anthraquinone 10 after oxidation and methylation. The benzylic group of 10 was brominated, and subsequent oxidation with bis(tetrabutylammonium) dichromate followed by cyclization give hydroxyanthraquinone 16, which was displaced with thiophenol. Oxidation of 17 with m-CPBA in phosphate buffer solution afforded anthraquinonyl sulfone 18 which was condensed with metyl mvynyl ketone (19) to furnish 20.