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N-Alkyl-N-Nitrosocarbamoyl-3alpha-Amino-와 3beta-Amino-5alpha-Cholestane 유도체들의 합성 및 항암작용 평가
김정균(Jack C. Kim),최순규(Soon Kyu Choi),조인섭(In Seop Cho),유동식(Dong Sik Yu),류성호(Sung Ho Ryu),문경호(Kyung Ho Moon) 대한약학회 1985 약학회지 Vol.29 No.2
The isomeric intermediates, 3alpha- and 3beta-amino-5alpha-cholestane required for the synthesis of N-nitrosoureas, N-(2-chloroethyl)-N-nitrosocarbamoyl-3alpha-amino-5alpha-cholestane (9), N-methyl-N-nitrosocarbamoyl-3alpha-amino-5alpha-cholestane (10), N-(2-chloroethyl)-N-nitrosocarbamoyl-3beta-amino-5alpha-cholestane (7), and N-methyl-N-nitrosocarbamoyl-3beta-amino-5alpha-cholestane (8) were obtained through the LiAlH4 reduction of 5alpha-cholestan-3-one oxime, followed by the chromatographic separation: the assignment of the stereochemistry of both isomers were based on the shape and chemical shift of C3-proton resonances on their NMR spectra and on the elution mobility on the TLC. The urea intermediates, N-(2-chloroethyl)carbamoyl-3alpha-amino-5alpha-cholestane (13), N-methylcarbamoyl-3alpha-amino-5alpha-cholestane (14), N-(2-chloroethyl)carbamoyl-3beta-amino-5alpha-cholestane (11) and N-methyl-3beta-amino-5alpha-cholestane (12) were prepared by the treatment of each isomers (3alpha-amino- and 3beta-amino-5alpha-cholestane) with alkyl isocyanates in anhydrous CHCl3, and the corresponding nitrosoureas, 7~10 were obtained by the nitrosation of the ureas, 11~14, with AcOH (or HCOOH)/NaNO2 in ice-cold condition. The inhibitory activity of the nitrosoureas, 7~10, and their intermediates, 12~14 towards the growth of L1210 murine leukemia cells, were examined. Among them, the compounds 9 and 10 exhibited high activity having ED50 to be 5.5g/ml and 6.1g/ml, respectively.
N-메틸-N'-치환페닐우레아화합물들의 니트로소화 반응에 있어서 니트로소화 화학종의 반응성 및 위치화학적 영향
김정균,조인섭,최순규,Jack C. Kim,In-Seop Cho,Soon-Kyu Choi 대한화학회 1991 대한화학회지 Vol.35 No.3
비대칭우레아화합물, N-메틸-N'-치환페닐우레아화합물들 ($CH_3NHCONHC_6H_4-G$; G = H, p-$CH_3,\;m-CH_3,\;m-CH_3O$, p-F, m-F, m-Br) 7종 합성하고 이들을 NaN$O_2$와 4종류의 산(d-HCl, HCOOH, C$H_3$COOH, CF$_3$COOH)을 사용하여 니트로소화시킬 때 이 니트로소화 반응의 위치선택성을 조사하였다. 이들 반응 모든 경우에서 두 가지 위치이성질체생성물, N-니트로소-N-메틸-N'-치환페닐우레아생성물(A)들과 N'-니트로소-N-메틸-N'-치환페닐우레아생성물(B)들이 주생성물로 생성되었으며, 이들 생성몰비 B/A를 이들 반응혼합물의 $^1$H-NMR에서의 메틸피이크의 면적을 측정하여 이를 결정하였다. 전자공급체치환기(ㅎ)가 우레아화합물의 페닐기에 치환된 경우 일반적으로 B/A의 비가 증가되었다. 이들 위치이성체 생성물비 B/A로부터 니트로소화 화학종(HONO, HCOONO, CH$_3$ COONO, CF$_3$ COONO)의 페닐치환기에 의한 질소원자 위의 전자밀도변화에 대한 반응민감도를 얻었으며 반응민감도의 상대적 크기는 1.00 : 0.93 : 0.78 : > ∼ 0.7(HONO : HCOONO : CH$_3$ COONO : CF$_3$ COONO)로 나타났다. The regioselectivity in the nitrosation of seven N-methyl-N'-substituted phenylureas ($CH_3NHCONHC_6H_4-G$; G = H, p-CH$_3$, m-CH$_3$, m-CH$_3$O, p-F, m-F, m-Br) was examined using NaNO$_2$ and 4 different acids (diluted HCl, HCOOH, CH$_3$COOH, CF$_3$COOH). In all cases, the two regioisomeric products, N-nitroso-N-methyl-N'-substituted phenylureas (A) and N'-nitroso-N-methyl-N'-substituted phenylureas (B) were observed to be formed as major products and product ratios were determined by the integration of their methyl peaks in $^1$H-NMR. Electron donating substitutent(G) on phenyl of the ureas generally led to increase the ratio of B to A. The data have revealed that the relative sensitivity of the nitrosonium species (HONO, HCOONO, CH$_3$COONO, CF$_3$COONO) toward the change of electron density on nitrogen with phenyl substitutents are 1.00 : 0.93 : 0.78 : > ∼ 0.7.
Epsilon-N-[(2-Chloroethyl) nitrosocarbamoyl]-L-lysine의 합성
김정균(Jack C. Kim),조인섭(In Seop Cho) 대한약학회 1983 약학회지 Vol.27 No.2
A copper complex of epsilon-N-[(2-chloroethyl)carbamoyl]-L-lysine was prepared by the treatment of the L-lysine copper complex with 2-chloroethyl isocyanate in cold water. Within the L-lysine copper complex molecule, the alpha-amino and carboxyl groups are bounded to Cu2+, but the epsilon-amino group is free and can react with carbamoylating agents. A potential antitumor agent, epsilon-N-[(2-chloroethyl) nitrosocarbamoyl]-L-lysine was synthesized by nitrosation of this copper complex with Na N02 in anhydrous formic acid, followed by the passage of H2S gas.
변비형 과민성 장증후군과 기능성 변비 환자에서 직장 감각능의 차이
양재훈 ( Jae Hoon Yang ),이준성 ( Joon Seong Lee ),홍수진 ( Su Jin Hong ),임희혁 ( Hee Hyuk Im ),황경란 ( Kyung Ran Hwang ),김현정 ( Hyun Jung Kim ),이상호 ( Sang Ho Lee ),고봉민 ( Bong Min Koh ),정인섭 ( In Seop Jung ),유창범 ( C 대한소화기기능성질환·운동학회 2005 Journal of Neurogastroenterology and Motility (JNM Vol.11 No.1
목적: 변비형 과민성 장증후군과 기능성 변비 환자에서 바로스타트를 이용한 팽창에 대한 직장 감각능의 차이를 알아보고자 하였다. 대상 및 방법: 로마진단기준 II에 의한 변비형 과민성 장증후군 환자 31명과 기능성 변비 환자 38명을 대상으로 바로스타트를 이용한 직장 감각검사 및 팽창도를 측정하였다. 직장 내 위상성 팽창자극을 2mmHg씩 단계적으로 증량하여 환자의 첫 감각, 배변 긴박감, 최대감내 압력의 역치를 구하였고, 감각지수 % [100×(최대감내 Background/Aims: The differential diagnosis of constipation-predominant irritable bowel syndrome (IBS-C) and functional constipation (FC) is difficult in many cases, even though the suggested pathophysiologies are quite different. The presence of visceral
형태가 고정된 ${\beta}$-아미노케톤의 탈케탈화 (반응) 의 연구
김정균,이용태,윤웅찬,조인섭,문성환,한선홍,Jack C. Kim,Yong Tae Lee,Ung Chan Yoon,In-Seop Cho,Sung Hwan Moon,Sun Hong Han 대한화학회 1988 대한화학회지 Vol.32 No.6
구조 형태가 고정된 ${\beta}$-아미노 케탈의 탈케탈화 실패요인으로서, 반응 중간체의 정전기적 반발, 구조상 특징에 의한 전이상태의 각스트레인의 증가, 그리고 고정된 구조형태에서 오는 물분자의 $SN_2$ 형태공격의 입체적 차단에 의한 것으로 추정하고 그들 요인의 중요성을 분리 평가하였다. 2-에틸렌디옥시-1-아세나프테닐아민, N-(2-에틸렌디옥시-1-아세나프테닐)아세트 아미드, 그리고 트리메틸-2-에틸렌디옥시-1-아세나프테닐암모니움 요오드를 합성하여 그들의 탈케탈화 반응을 검토함으로서 이중 양이온의 정전기적 반발요인에 의한 실패요인 정도를 평가하였다. ${\beta}$-아미노기에 전자흡인기인 아세틸기를 넣어 아미노기의 양성자화 정도를 감소시킴으로서 탈케탈화를 용이하게 일으킬 수 있었다. 이 결과는 정전기적 반발요인이 ${\beta}$-아미노 케탈화의 탈케탈화 방해요인으로 매우 중요하게 작용하고 있음을 보여준다. 그리고 구조상 특징에 의한 방해요인을 검토하기 위해 구조형태가 고정되지 않은 ${\beta}$-아미노케탈, 2-아미노-1-에틸렌디옥시아세토페논과 아미노아세탈, 디메틸 아미노 포름알데히드 디메틸아세탈과 2-아미노아세트알데히드 디메틸아세탈의 탈케탈화 및 탈아세탈화 용이도를 검토한 결과 용이하게 탈아세탈화되었다. 이 결과는 구조상 특징에 의한 요인도 매우 중요함을 보여준다. The causes of failure in the deketalization of rigid ${\beta}$-aminoketals were separately investigated by examining the deketalization of 3 ketals, 2-ethylenedioxy-l-acenaphthenylamine (2), N-(2-ethylenedioxy-l-acenaphthenyl)acetamide(13) and trimethyl-2-ethylenedioxy-1-acenaphthenylammonium iodide(14), and by examining the deketalization of non-rigid ${\beta}$-aminoketal, 2-amino-l-ethylenedioxyacetophenone(19) and non-rigid aliphatic acetals, dimethylaminoformaldehyde dimethylacetal (20) and 2-aminoactaldehyde dimethyl acetal(21). While compounds 2 and 14 were not able to be hydrolyzed in the various acidic conditions 13 was easily deketalized. The result indicated the importance of electrostatic repulsion in the possible dicationic intermediates as a factor of failure in the deketalization. The observations of easy deketalization of compounds 19, 20 and 21 indicated that the structural characters of rigid $\beta-aminoketals$ are also important factors in the hydrolysis of ${\beta}$-aminoketals.
Numerical Identification of a Streptomyces Strain Producing Thiol Protease Inhibitor
KIM, IN SEOP,KIM, HYOUNG TAE,WARD, ALAN C.,GOODFELLOW, MICHAEL,HAH, YUNG CHIL,LEE, KYE JOON 한국미생물 · 생명공학회 1992 Journal of microbiology and biotechnology Vol.2 No.3
Chemotaxonomic and numerical identification were carried out for an isolate of Streptomyces strain SMF13 producing thiol protease inhibitor. Fifty taxonomic unit characters were tested and the data were analyzed numerically using the TAXON program. The isolate SMF13 was identified to be a member of the cluster 5 of Streptomyces and best matched to Streptomyces omiyaensis which is a synonym of Streptomyces exfoliatus. Therefore, it was concluded that the isolate was identified to be a strain of Streptomyces exfoliatus.
Lithium Aluminum Hydride Reduction Studies of Rigid $\alpha$-Oximino Ketones
Kim, Jack C.,Lee, Young-Tae,Kim, Min-Sook,Woo, Young-Min,Shin, Hong-Dae,Cho, In-Seop Korean Chemical Society 1982 Bulletin of the Korean Chemical Society Vol.3 No.3
Rigid ${\alpha}$-oximino ketones containing two functional groups such as 2-oximino-1-acenaphthenone and 2-oximino-1-indanone were synthesized and the simultaneous reduction of the two functional groups of ${\alpha}$-oximino ketones by $LiAlH_4$ gave the corresponding amino alcohols, 2-amino-1-acenaphthenol and 2-amino-1-indanol. The yields of the reduction products of the ${\alpha}$ -oximino ketones remarkably increased, as the increase of molar ratio of hydride used to the reactant. The use of 24 moles of $LiAlH_4$ was found to afford the best result in the reduction of the rigid ${\alpha}$-oximino ketones to the corresponding amino alcohols. The yields was not affected by the variation of solvents such as ether, THF and diglyme.
Reconstruction of Dermal Papilla-like Tissue using Self-aggregation Technique
Youn-Ho Shin(신연호),Doo-Hoon Lee(이두훈),Hee-Hoon Yoon(윤희훈),Young-Kwon Seo(서영권),Bo-Young Yoo(유보영),Key-Yong Song(송계용),Sung-Joo Hwang(황성주),Young-Jin Kim(김영진),Eun-Kyung Yang(양은경),Chang-Seo Park(박장서),In-Seop C 한국생물공학회 2004 한국생물공학회 학술대회 Vol.2004 No.10