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N1 - Alkylisoguanosines ( Doridosine 유도체 ) 의 합성과 특성에 관한 연구
윤인권,김용해 ( In Kwon Youn,Yong Hae Kim ) 생화학분자생물학회 1981 BMB Reports Vol.14 No.2
N¹-Alkylisoguanosines were synthesized. Their chemical and physical properties, and biological activities were compared with those of the marine natural product, doridosine (1). N¹-Alkylisoguanosine appears to exist in the structure of N¹-alkyl-6-amino-2-oxo-9-β-D-ribofuranosyl purine (1`), in water, dioxane, acetonitrile and dimethylsulfoxide solution. The biological activity of N¹-ethylisoguanosine was run on guinia pig atria and the same type of activity of doridosine was found, but ca. half of that from doridosine (N¹-methylisoguanosine).
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윤인권,김환철,Yun, In-Gwon,Kim, Hwan-Cheol 배재대학교 자연과학연구소 1995 自然科學論文集 Vol.7 No.-
입체 이성질체를 합성하는 방법으로 최근에 알려진 입체선택성 촉매를 이용한 유기반응을 연구 하기 위하여 비천연 아미노산인 인돌린-2- 카르본산으로 부터카르본산그룹의 환원,2차아민기의 보호화,메실화,아지도치환,환원에 의한 아민기로의 전환, 술폰화, 보호기제거등의 총 5단계의 합성과정을 거쳐 목적하는 술폰아미드를 합성하였다. 각 생성물은 관 크로마토그래피에 의하여 분리 정제후 핵자기공명스펙트럼($^1H,^13C $ NMR) 적외선 스펙트럼 등에 의하여 구조를 확인 하였다. In order to develope new asymmetric catalyst, we synthesized the following new sulfonamide derivatives start from S-Indoline-2-Carboxylic Acid via the following 5 steps. Hydroxy methyl derivative(1) was thus treated with methane sulfonyl chloride in the presence of triethylamine as base to give mesylated derivative(2) in 85% of isolated yield. The mesylate compound (2) was treated with excess sodium azide to give Azido derivative (4) in 95% isolated yield. Azido compound (3) was then reduced to the corresponding amino derivative in near quntitative yield by the hydrogenation under hydrogen atmospere in the presence of catalytic amount of Pd-C. The amino derivative (4) was converted to its sulfonamide derivatives by the treatment of compound(4) with triisopropyl benzene sulfonyl chloride in the presence of triethyl amine as base. Finally t-BOC group of the compound(5) was removed by the treatement of excess Trifluoro-acetic acid in near quantitative yield to give the target sulfonamide derivative (7) .in this paper we prepared compound(6) in 49% overall yield via the 5 steps of synthesis starting from t-Boc- 2-hydroxy methyl indoline(1) which cab be easily prepared from commercial available S-indoline-2-carboxylic acid by known methods. we plan to apply this new catalyst for the asymmetric reduction , diels-alder reaction, aldolcondensation reaction in due courses.
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Synthesis and Characterization of $N^1$-Alkylisoguanosines (Doridosine Derivatives)
윤인권,김용해,Youn, In-Kwon,Kim, Yong-Hae 생화학분자생물학회 1981 한국생화학회지 Vol.14 No.2
$N^1$-Alkylisoguanosines을 합성하고 천연물인 doridosine과 생리작용에 관해서 비교 검토하였다. $N^1$-Alkylisoguanosines 은 물, 디오기산, 아세트나이트릴, 디메틸술폭사이드 등의 용액에서는 $N^1$-alkyl-6-amino-2-oxo-9-${\beta}$-D-ribofuranosyl purine으로 존재함이 확인되었다. 이 화합물의 생리작용을 guinia pig atria를 사용하여 조사하였고, 천연물인 doridosine과 같은 형의 활성을 나타냄이 발견됐고 그 효과는 doridosine의 약 반정도였다. $N^1$-Alkylisoguanosines were synthesized. Their chemical and physical properties, and biological activities were compared with those of the marine natural product, doridosine ($\underline{1}$). $N^1$-Alkylisoguanosine appears to exist in the structure of $N^1$-alkyl-6-amino-2-oxo-9-${\beta}$-D-ribofuranosyl purine ($\underline{1}'$), in water, dioxane, acetonitrile and dimethylsulfoxide solution. The biological activity of $N^1$-ethylisoguanosine was run on guinia pig atria and the same type of activity of doridosine was found, but ca. half of that from doridosine ($N^1$-methylisoguanosine).
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윤인권,백기현,Youn, In-Kwon,Beak, Gi-Hueon 배재대학교 자연과학연구소 1997 自然科學論文集 Vol.9 No.1
We synthesized the following series of 3', 5'hydroxy modified thymidine analogs to check the potential asymmetric catalytic effects. 3'-monomethylammino and dimethylaminothymidine was synthesized from thymidine via 8 step and 7 step in 38%, 20% overall yields respectively. 5'Acetyl-3'-dimethylamino thymidine was prepared from thymidine via 8 step in 40% overall yield. 5‘-TBS-3'-up-t BOC methylamino thymidine was prepared from thymidine via 6 step in 30% overall yield. 3'-acetyl-5'-t BOC amino thymidine was prepared from thymidine via 7 step in 31% overall yield. 본 연구에서는 thymidine으로부터 시작하여 3'-OH과 5'-OH의 각각의 변형, 동시의 변형을 통해 크게 5종의 amino thymidine 골격의 촉매를 합성하였다. 다양한 thymidine 화합물들이 새로운 키랄 보조체로서의 촉매효과를 위해 우선 3'-OH 자리에 mono-methylamino thymidine과 dimethylamino thymidine을 합성하고, 이들의 합성과정을 응용하여 5'-OH을 Ac-O로 변환한 5'-acetyl-3'-dimethylamino thymidine과 5'-OH를 TBS로 변환하고 up위치의 azido화합물인 5'-TBS-3'-Up-tBOC methylamino thymidine을 합성하였다. 그리고, 5'-OH를 amino group으로 변환하고 3'-OH를 -Me로 변환한 화합물 3'-acetyl-5'-tBOC-amino thymidine을 합성하였다.
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윤인권,서시우,Youn, In-Kwon,Seo, S.U. 배재대학교 자연과학연구소 2002 自然科學論文集 Vol.12 No.1
식물 중 단자엽을 제외한 쌍자엽 식물은 선택적으로 제거할 수 있는 헤테로 고리 화합물을 기존에 알려진 방법보다 용이하게 합성할 수 있는 방법을 연구하였으며, 과정에 일부 헤테로 고리 치환기의 4위치에 염소기가 치환된 화합물 5a를 70%수율로 하는 5b는 74%수율로 각각 수득하였다. 술폰 산화제로 potassium percarbonate를 사용하였을 때 1)의 화합물을 90%수율로 고순도 화합물을 수득하였으며 2)의 경우 85%의 고수율, 고순도 화합물을 수득하였다. Sodium hypochlorite의 경우 피리미딘 헤테로 고리에 염소가 치환되는 불순물 생성으로 적합지 않음이 판명되었다. We developed new process for the large scale preparation of pyrazole sulfonyl urea and pyrazole sulfonyl urea carboalkoxyl benzene sulfonyl urea 1) in high yields and convenience. As compound with know procedure this procedure have found to be far large scale preparation. During the preparation we obtains two new sulfonyl urea 5a and 5b in 70% and 74% ( purified by crystallization).
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Synthesis of Dithioacetal containing α-Pyrone and Enone Derivatives
Yoon,In-Kwon 培材大學校 1997 培材論叢 Vol.2 No.-
활성화 되어있지않은 키틴 디 치오아세탈의 경우 케톤류로부터 강한 염기를 사용하여 카르본디설파이드와의 반응으로 합성할 수 있다. 그러나 β-케토 에스테르와 같이 활성화되어 있는 경우는 포타시움 카보네이트를 염기로 사용하고 DMF를 용매로 사용하면 쉽게 탈 양성자가 일어나 원하는 키틴디치오아세탈을 수득할 수 있었다. 이로부터 락톤을 합성하는 것은 다음과 같다. 즉 에틸 α-(1,3-디치올란-2-일리덴)아세테이트를 NaH 또는 Mg(OCH₃)₂로 처리한 후 알데히드 또는 케톤을 가한 뒤 실온에서 3-4시간 교반하여 주는 것이다. 합성한 락톤을 열분해 하여 디 이논을 높은 수율로 수득할 수 있었다. Synthesis of none activated α-oxoketene dithioacetals are usually prepared from ketones by using strong base such as sodium tert-amylate, lithium 4-methyl-2,6-di-tert-butyphenoxide and sodium hydride etc. to deprotonate ketones in the presence of carbon disulfide but β-ketoesters were acidic enough to be deprotonated by potassium carbonate in DMF. The preparation of δ-lactones was straight forward, namely, ethyl α-(1,3-dithiolan-2-ylidene)acetate in THF was treated with NaH and aldehyde or ketone was added. Then stirring at room temperature 3-4hrs gave the various δ-lactone in high yields. Condensation with aromatic aldehyde was performed with 1.05eq. of NaH, but in case of ketone 2eq. of NaH was necessary to ensure the reaction. Aliphatic aldehyde was self condensed before reaction with ketene dithioacetals thus 2eq. of magnesium methoxide was used for the condensation of base labile aldehydes. α-Pyrones prepared here was thermally degraded to give dienone in high yields.
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Sythesis of 3'-Methylamino Pyrimidine as Potential Anti AIDS Agents
백기현,윤인권,Beak, Gi-Hyeon,Youn, In-Kwon 배재대학교 자연과학연구소 1995 自然科學論文集 Vol.7 No.-
3'-Methylamino pyrimidine 3 was prepared from deoxy pyrimidine via the following 8 step reaction sequences; silyl protection, mesylation, cyclization, azide substitution, hydrogenation, t-Boc protection, methylation, and deprotection in 23% overall yield as a potential anti-AIDS agents.
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