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박노상(No Sang Park),김현숙(Hyun Sook Kim),임희종(Hee Jong Lim),정영식(Young Shik Jung),최중권(Joong Kwon Choi),함원훈(Won Hoon Ham) 대한약학회 1991 약학회지 Vol.35 No.2
Quinoline, pyrazolo-[5,4-b]-pyridine, isoxazolo-[5,4-b]-pyridine, pyrazolo-[4,3-c]-quinoline, isoxazolo-[5,4-e]-thiazine, and isothiazolo-[5,4-e]-thiazine derivatives were prepared as possible antiinflammatory agents. Some of the synthesized compounds showed antiinflammatory activities comparable to Aspirin and Naproxen.
새로운 Quinolone 誘導體의 合成에 關한 硏究(Ⅱ)
함원훈,고윤석,배형준,이기영,정영훈 성균관대학교 약학연구소 1995 成均藥硏論文集 Vol.7 No.1
Abstract - Palladium catalyzed cross-coupling reactions of aryl halides with organo tin reagents and π-sufficient aromatic heterocycles proceeded easily and efficiently during carbon-carbon bond formation. We used this method for the anti bacterial agents, and synthesis of new quinolone derivatives which have C-C bond at C-7 position of general quinolone moieties. Quinolone moieties, and aryl tin or aromatic heterocycles in the presence of palladium catalyst were coupled to afford new quinolone derivatives. The synthesis and structure-activity relationship are presented.
배형준,정윤성,함원훈,정영훈 성균관대학교 약학연구소 1996 成均藥硏論文集 Vol.8 No.1
The class of β-lactam containing compounds known as carbapenems has been the focus of countless chemical and biological studies since the naturally occurring structural type was reported in 1976. The discovery of thienamycin, with its extraordinary potent broad-spectrum antibacterial profile, prompted a rigorous search for efficient and general routes to total and partial synthesis of carbapenems. Wile many strategies of carbapenem construction have been brought to fruit, only two approaches (and conceptually related ones) have emerged with the general usefulness. In fact, they have been applied relentlessly in analogue programs around the world. This thesis utilize a rhodium catalyzed carbene insertion to establish the bicyclic ring system. The resulting β-keto ester is transformed into carbapenem via vinyl phosphate. Thiol addition-phosphate elimination occurs readily to incorporate the new side-chain thiol. New carbapenem derivative, {ally(1R, 5S, 6S)-2-(N-carboben-oxycarboxydiethylamido cysteine)-6-[(IR)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylate} was synthesized via 10 steps.
Bouvardin의 구성요소인 광학활성 베타-하이드록시 아미노산 유도체의 합성에 관한 연구
정영훈,배형준,고윤석,송정남,오창영,함원훈 성균관대학교 약학연구소 1995 成均藥硏論文集 Vol.7 No.1
Abstract - Synthesis of the optically active unnatural β-hydroxy amino acid, which is building block of oligopeptide anticancer Bouvardin, was carried out for the total synthesis of Bouvardin. Oxazolidonic acid 2 was synthesized from p-bromobenzaldehyde as a starting material in 20% overall yield through five steps. And L-3-(3-hydroxy-4-methoxyphenyl)alanine methyl ester 3 was also synthesized from L-tyrosine in 46% overall yield using a known synthetic methodology. The Ullmann coupling reaction of amide 18 obtained from 2 and 3, was investigated under various reaction conditions.