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Jeong, Lak Shin,Shantanu Pal,Choe, Seung Ah,Choi, Won Jun,Kenneth A. Jacobson,Zhan-Guo Gao,Athena M. Klutz,Xiyan Hou,Kim, Hea Ok,Lee, Hyuk Woo,Lee, Sang Kook,Dilip K. Tosh,Moon, Hyung Ryong 이화여자대학교 약학연구소 2009 藥學硏究論文集 Vol.- No.19
Novel D- and L-4´-thioadenosine derivatives lacking the 4´-hydroxymethyl moiety were synthesized, starting from D-mannose and D-gulonic γ-lactone, respectively, as potent and selective species-independent A₃ adenosine receptor (AR) antagonists. Among the novel 4´-truncated 2-H nucleosides tested, a N^(6)-(3-chlorobenzyl) derivative 7c was the most potent at the human A₃ AR (K_(i) = 1.5 nM), but a N^(6)-(3-bromobenzyl) derivative 7d showed the optimal species-independent binding affinity.
Lak Shin, Jeong,Dilip K. Tosh,Won Jun, Choi,Sang Kook, Lee,You-Jin, Kang,Sun, Choi,Jin Hee, Lee,Hankil, Lee,Hyuk Woo, Lee,Hea Ok, Kim 이화여자대학교 약학연구소 2010 藥學硏究論文集 Vol.- No.20
The first synthesis of 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl pyrimidines as potent anticancer agents was accomplished using the DAST fluorination as a key step. It was first revealed that selenium atom participated in the DAST fluorination of 4'-selenonucleosides and that conformational bias induced by bulky selenium acted as a decisive factor in the DAST fluorination. Among compounds tested, 2'-F-4'-seleno-ara-C (4a) exhibited highly potent anticancer activity in all cancer cell lines tested and was more potent than ara-C (1).
Hou, Xiyan,Lee, Hyuk-Woo,Tosh, Dilip K.,Zhao, Long Xuan,Jeong, Lak-Shin 대한약학회 2007 Archives of Pharmacal Research Vol.30 No.10
Improved syntheses of potent and selective $A_3$ adenosine receptor agonists, CI-IB-MECA and thio-CI-IB-MECA were accomplished from cheap stating material, D-ribose. New synthetic methods were found to be superior to old methods from the viewpoint of use of cheap starting material, number of steps, and overall yields.
Xiyan Hou,Hyuk Woo Lee,Dilip K. Tosh,Long Xuan Zhao,Lak Shin Jeong 대한약학회 2007 Archives of Pharmacal Research Vol.30 No.10
Improved syntheses of potent and selective A3 adenosine receptor agonists, Cl-IB-MECA and thio-Cl-IB-MECA were accomplished from cheap stating material, D-ribose. New synthetic methods were found to be superior to old methods from the viewpoint of use of cheap starting material, number of steps, and overall yields.
Lee, Jeong A,Kim, Hea Ok,Tosh, Dilip K.,Moon, Hyung Ryong,Kim, Sanghee,Jeong, Lak Shin 이화여자대학교 약학연구소 2008 藥學硏究論文集 Vol.- No.17
◁화학식 삽입▷ (원문을 참조하세요) Stereoselective synthesis of 2´-C-methyl-cycloprophy-fused carbanucleosides was accomplished via stereoselective cyclopropanation, regioselective cleavage of the isopropylidene group, stereoselective Grignard reaction, and cyclic sulfate chemistry."
Wang, Ting,Lee, Hyun Joo,Tosh, Dilip K.,Kim, Hea Ok,Pal, Shantanu,Choi, Sun,Lee, Yoonji,Moon, Hyung Ryong,Zhao, Long Xuan,Lee, Kang Man,Jeong, Lak Shin 이화여자대학교 약학연구소 2008 藥學硏究論文集 Vol.- No.18
5'-Deoxy-5'-ureidoadenosine was designed and synthesized as a potent inhibitor of S-adenosylhomocysteine hydrolase(SAH), in which 5'-ureido group as multiple hydrogen bonding donor in binding with active site residues of SAH in the molecular modeling study.
Asymmetric Synthesis of Cyclopropyl-fused 2'-C-Methylcarbanucleosides as Potential Anti-HCV Agents
Jeong, Lak Shin,Lee, Jeong A.,Kim, Hea Ok,Tosh, Dilip K.,Moon, Hyung Ryong,Lee, Seung-Jin,Lee, Kang Man,Sheen, Yhun Y.,Chun, Moon Woo Taylor Francis 2007 NUCLEOSIDES NUCLEOTIDES AND NUCLEIC ACIDS Vol. No.
<P> Novel 2 '-C-methyl-cyclopropyl-fused carbocyclic nucleosides as potential anti-HCV agents were stereoselectively synthesized, utilizing regioselective cleavage of the isopropylidene group and cyclic sulfate chemistry as key steps.</P>
Stereoselective Synthesis of 1'-Functionalized-4'-Thionucleosides
Jeong, Lak Shin,Gunaga, Prashantha,Kim, Hea Ok,Tosh, Dilip K.,Lee, Hyuk Woo,Choe, Seung Ah,Moon, Hyung Ryong,Gao, Zhan-Guo,Jacobson, Kenneth A.,Chun, Moon Woo Taylor Francis 2007 NUCLEOSIDES NUCLEOTIDES AND NUCLEIC ACIDS Vol. No.
<P> Stereoselective functionalization of the 1'-position of 4'-thionucleosides was achieved using a stereoselective SN2 reaction controlled by 5-membered ring coordination.</P>
Jeong, Lak Shin,Choe, Seung Ah,Gunaga, Prashantha,Kim, Hea Ok,Lee, Hyuk Woo,Lee, Sang Kook,Tosh, Dilip K.,Patel, Amit,Palaniappan, Krishnan K.,Gao, Zhan-Guo,Jacobson, Kenneth A.,Moon, Hyung Ryong 이화여자대학교 약학연구소 2008 藥學硏究論文集 Vol.- No.18
Truncated D-4'-thioadenosine derivatives lacking the 4'-hydroxymethylene moiety were synthesized starting from D-mannose, using cyclization to the 4-thiosugar and one-step conversion of the diol to the acetate as key steps At the human A₃ adenosine receptor (AR), N^(6)-substituted purine analogues bound potently and selectively and acted as antagonists in a cyclic AMP functional assay An N^(6)-(3-chlorobenzyl)purine analogue 9b displayed a K, value of 1 66 nM at the human A₃ AR Thus, truncated D-4'-thioadenosine is an excellent template for Ihe design of novel A₃ AR antagonists to act at both human and murine species.
Jeong, Lak Shin,Alexander, Varughese,Choi, Won Jun,Chun, Jeong ha,Kim, Hea Ok,Jeon, Ji Hye,Tosh, Dilip K,Lee, Hyuk Woo,Chandra, Girish,Choi, Jung won 梨花女子大學校 藥學硏究所 2011 藥學硏究論文集 Vol.- No.21
The first synthesis of 4'-selenothymidine (1), a novel DNA building block, and 4'-seleno-AZT (2) was accomplished from 2-deoxy-d-ribose via stereoselective formation of 2-deoxy-4-seleno-d-furanose 17 and a Pummerer-type base condensation as key steps. 4'-Selenothymidine (1) was discovered to adopt the same 2'-endo/3'-exo conformation as thymidine, which is unusual in that 4'-selenouridine has the opposite conformation to that of uridine.