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7-Methoxy-3-phenylsulfonyl-1(3H)-isobenzofuranone의 合成 : 항암제 Anthracycline의 중간체合成
노영쇠 全北大學校 基礎科學硏究所 1983 基礎科學 Vol.6 No.1
In cinjunction to our efforts toward the synthesis of anthracycline antitumor antibiotics, 7-methoxy-3-phenylsulfonyl-1(3H)-isobenzofuranone(6), a key intermediate that could furnish1,4-dihydroxy polrsubstituted naphthalenes via Michael condensation with various α, β-unsaturated carbonyl systems, was prepared by two different routes. One method involved dibromination on the aromatic methyl group of 6-methoxy o-toluate(8), followed by hydrolysis of the resulting dibromobenzoate to give phthalaldehydic acid(10), which was converted to phthalide sulfide(11), them finally to sulfone 6 by oxidation with m-CPBA.An alternative method involved disulfenylation on the aromatic methyl group of 6-methoxy o-toluate(5) which was partially hydrolyzed to give sulfide(11), then converted to sulfone (6) by the aforementioned oxidation.
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.
노영쇠,최병진,송영기,이국행 全北大學校 科學敎育硏究所 1981 과학과 과학교육 논문지 Vol.6 No.-
Measure the degrees of water pollution of the Jeonju river that is not measured wholly in spite of the importance of the Jeonbug area. The experimental values were compared with standard values of environment and checked the reasonableness for beverage and irrigation water Also propose the management methods of the results which are different along the sampling area.
Dibenzotetraazapentalene들의 염기도와 protonation의 위치
노영쇠 全北大學校 基礎科學硏究所 1981 基礎科學 Vol.4 No.1
Dibenzo-1, 3a, 6, 6a-tetraazapentalene(DBTA-1) and dibenzo-1, 3a, 4, 6a-tetraazape-ntalene(DBTA-2) were prepared by known method. The mechanism through which 1-NPB and 2-NPB are formed as the intermediates in the synthetic route is discussed, and their derivatives such as 3-chlorodibenzo-1, 3a, 6, 6a-tetraazapentalene was also synthesized. With the pK values of dibenzotetraazapentalene derivatives measured by UV-spectrophotometer, their degrees of delocalization are confirmed to be almost the same in all cases, then are presented their basicities and the sites of protonation.
노영쇠 全北大學校 基礎科學硏究所 1984 基礎科學 Vol.7 No.1
The kinetics of the hydrolysis of acetaldehyde diethyl acetaldehyde diethyl acetal, cyclohexanone ethyleneglycol ketal, benzaldehyde ethylenglycol acetal, and furfural ethylenglycol acetal have been studies in 20% dioxane-water(V/V). The rates of the hydrolysis in the bufferolution of pH 1.95 to 12.40 were measured by UV spectrophotometry. A pronounced general acid catalysis by acid species of the buffer solution can be observed.
Michael 반응을 이용한 Naphthacenone 유도체의 합성
노영쇠,유진호,박시호,조인호,권윤자,Rho, Young S.,Yoo, Jin H.,Park, Si H.,Cho, In H.,Kwon, Yoon J. 대한화학회 1996 대한화학회지 Vol.40 No.7
3-Carbomethoxy-1(3H)-isobenzofuraneme(9)과 .alpha., .beta.-불포화 에스테르 화합물 3a-b를 각각 반응시켜서 naphthacene-6, 7-dione 11a-b를 좋은 수율로 얻었다. 이들 중 C-9 위치에 에틸기가 없는 11a는 산화시켰을 때 naphthacene-5, 12-dione 13a가 생성되는 반면, 에틸기를 갖고 있는 11b는 naphthacene-5, 7, 12-trione 12b와 naphthacene-5, 12-dione 13b가 3:2로 생성되어졌다. 3-Carbomethoxy-1(3H)-isobenzofuranone(9) underwent condensation with ${\alpha}{\beta}-unsaturated$, esters 3a-b to produce the corresponding naphthacene-6,7-diones 11a-b with high yields in one pot procedure. Among the naphthacene-6,7-diones formed, compound 11a without an ethyl group at C-9 position was oxidized to give the naphthacene-5,12-dione 13a, while compound 11b containing the ethyl group was oxidized to give a 3:2 mixture of the naphthacene-5,7,12-trione 12b and naphthacene-5,12-dione 13b under the same experimental conditions.
Syntheses of Idarubicin Analogues Containing a Glucose or Galactose Moiety as a Glycone
노영쇠,Ran Park,Seon-Young Kim,유동진 대한화학회 2010 Bulletin of the Korean Chemical Society Vol.31 No.1
The new idarubicin analogues (12 and 13) with a glucose or galactoseas as a glycone were synthesized from daunomycin (2). (+)-4-Demethoxydaunomycinone (6) obtained from reaction of 2 with AlCl3 was converted to 4-trifluoromethanesulfonyl daunomycinone (7) through reaction with trifluoromethanesulfonic anhydride. The treatment of 7 with 1,1-bis-(diphenylphospino)ferrocene/Pd(OAc)2 in triethylamine/formic acid/dioxane provided the idarubicinone (5b). Glycosylation of 7-hydroxy group of 5b with two kinds of tetraacetyl pyranosyl halide (8 and 9) by a modified Koenigs-Knorr procedure and then deacetylation using aqueous 0.1 N LiOH solution and amberlite cationic resin gave the objective materials. The in vitro MTT assay of the analogues (12b and 13a) in comparison with idarubicin (5a) on peripheral blood human promyelocytic-leukemia cell line and human breast cancer cell line were also described.
노영쇠,김선자,조인호,No, Yeong-Soe,Kim, Sun-Ja,Jo, In-Ho 대한약학회 1997 약학회지 Vol.41 No.1
A regiospecific total synthesis on the precursor(18b) of rhodomycinones is described. The anion of 3-carbomethoxy-1(3H)-isobenzofuranone(13) was respectively condensed wi th naphthalenone (12) and butenoate(8) derivatives which were, prepared by two different synthetic routes to afford 9-ethyl-6,7-dihydroxy 7,8,9,10-tetrahydronaphthacene-5,12 dione(18b) after oxidation and reduction.
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.
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).