Lak Shin Jeong

Summary

Affiliation: Ewha Womans University
Country: Korea

Publications

  1. ncbi request reprint Discovery of a new nucleoside template for human A3 adenosine receptor ligands: D-4'-thioadenosine derivatives without 4'-hydroxymethyl group as highly potent and selective antagonists
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 50:3159-62. 2007
  2. ncbi request reprint Asymmetric synthesis of cyclopropyl-fused 2'-C-methylcarbanucleosides as potential anti-HCV agents
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 26:1021-4. 2007
  3. ncbi request reprint Design and synthesis of 3'-ureidoadenosine-5'-uronamides: effects of the 3'-ureido group on binding to the A3 adenosine receptor
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, South Korea
    Bioorg Med Chem Lett 14:4851-4. 2004
  4. ncbi request reprint Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, South Korea
    Antivir Chem Chemother 15:235-50. 2004
  5. ncbi request reprint Stereoselective synthesis of 1'-functionalized-4'-thionucleosides
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 26:1011-4. 2007
  6. pmc Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 51:6609-13. 2008
  7. ncbi request reprint Structure-activity relationships of 2-chloro-N6-substituted-4'-thioadenosine-5'-uronamides as highly potent and selective agonists at the human A3 adenosine receptor
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 49:273-81. 2006
  8. ncbi request reprint Design, synthesis, and biological activity of N6-substituted-4'-thioadenosines at the human A3 adenosine receptor
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem 14:4718-30. 2006
  9. doi request reprint Structure-activity relationships of 2-chloro-N6-substituted-4'-thioadenosine-5'-N,N-dialkyluronamides as human A3 adenosine receptor antagonists
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem Lett 18:1612-6. 2008
  10. ncbi request reprint First synthesis of 4'-selenonucleosides showing unusual Southern conformation
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Org Lett 10:209-12. 2008

Collaborators

Detail Information

Publications84

  1. ncbi request reprint Discovery of a new nucleoside template for human A3 adenosine receptor ligands: D-4'-thioadenosine derivatives without 4'-hydroxymethyl group as highly potent and selective antagonists
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 50:3159-62. 2007
    ..An N6-(3-chlorobenzyl)purine analogue 9b displayed a Ki value of 1.66 nM at the human A3 AR. Thus, truncated D-4'-thioadenosine is an excellent template for the design of novel A3 AR antagonists to act at both human and murine species...
  2. ncbi request reprint Asymmetric synthesis of cyclopropyl-fused 2'-C-methylcarbanucleosides as potential anti-HCV agents
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 26:1021-4. 2007
    ..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...
  3. ncbi request reprint Design and synthesis of 3'-ureidoadenosine-5'-uronamides: effects of the 3'-ureido group on binding to the A3 adenosine receptor
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, South Korea
    Bioorg Med Chem Lett 14:4851-4. 2004
    ....
  4. ncbi request reprint Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, South Korea
    Antivir Chem Chemother 15:235-50. 2004
    ..Furthermore, the review includes valuable information for designing and synthesizing novel carbocyclic nucleosides...
  5. ncbi request reprint Stereoselective synthesis of 1'-functionalized-4'-thionucleosides
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 26:1011-4. 2007
    ..Stereoselective functionalization of the 1'-position of 4'-thionucleosides was achieved using a stereoselective S(N)2 reaction controlled by 5-membered ring coordination...
  6. pmc Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 51:6609-13. 2008
    ..5 nM), but a N(6)-(3-bromobenzyl) derivative 7d showed the optimal species-independent binding affinity...
  7. ncbi request reprint Structure-activity relationships of 2-chloro-N6-substituted-4'-thioadenosine-5'-uronamides as highly potent and selective agonists at the human A3 adenosine receptor
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 49:273-81. 2006
    ..In several cases for which the corresponding 4'-oxonucleosides have been studied, the 4'-thionucleosides showed higher binding affinity to the A(3) AR...
  8. ncbi request reprint Design, synthesis, and biological activity of N6-substituted-4'-thioadenosines at the human A3 adenosine receptor
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem 14:4718-30. 2006
    ..N6-(3-Iodobenzyl) derivative 19g was demonstrated to be an A3AR-selective partial agonist displaying a Ki value of 3.2 nM...
  9. doi request reprint Structure-activity relationships of 2-chloro-N6-substituted-4'-thioadenosine-5'-N,N-dialkyluronamides as human A3 adenosine receptor antagonists
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem Lett 18:1612-6. 2008
    ..A N(6)-(3-bromobenzyl) derivative 6c (K(i)=9.32 nM) exhibited the highest binding affinity at the human A(3)AR with very low binding affinities to other AR subtypes...
  10. ncbi request reprint First synthesis of 4'-selenonucleosides showing unusual Southern conformation
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Org Lett 10:209-12. 2008
    ..All stereoelectronic effects shown in 4'-oxonucleosides were overwhelmed by the size of selenium and steric interactions, driving the conformation to the C2'-endo/ C3'-exo twist (Southern) conformation...
  11. ncbi request reprint Synthesis and anti-HCV activity Of 2''-beta-hydroxymethylated nucleosides
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 26:725-8. 2007
    ..Adenine nucleoside 3 showed potent anti-HCV activity, implying that 2' -beta-hydroxymethyl group has the appropriate electronic properties interfering with HCV polymerase...
  12. ncbi request reprint Asymmetric synthesis of novel apio carbocyclic nucleoside analogues as potential antiviral and antitumor agent
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 26:721-4. 2007
    ..Novel apio carbocyclic nucleosides 18-21 were asymmetrically synthesized as potential antiviral and antitumor agent, starting from D-ribose employing aldol reaction, RCM reaction and Mitsunobu reaction as key reactions...
  13. ncbi request reprint Synthesis of N6-substituted 3'-ureidoadenosine derivatives as highly potent agonists at the mutant A3 adenosine receptor
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 26:717-9. 2007
    ..Among compounds tested, 3 '-ureido-N6-(3-iodobenzyl)adenosine (2c) exhibited the highest binding affinity (Ki = 0.22 micro M) at the H272E mutant A3 AR without binding to the natural A3AR...
  14. ncbi request reprint Synthesis and antitumor activity of fluorocyclopentenyl-pyrimidines
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 26:713-6. 2007
    ..Cytosine analog 8 was found to exhibit significant anticancer activity in various human tumor cell lines...
  15. ncbi request reprint Design, synthesis, and anti-tumor activity of 4'-thionucleosides as potent and selective agonists at the human A3 adenosine receptor
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Nucleosides Nucleotides Nucleic Acids 26:1565-8. 2007
    ..38 nM and 0.28 nM, respectively) at the human A(3)AR. These compounds showed anti-growth effects on HL-60 leukemia cell, which resulted from the inhibition of Wnt signaling pathway...
  16. doi request reprint Design and synthesis of novel 2',3'-dideoxy-4'-selenonucleosides as potential antiviral agents
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem 16:9891-7. 2008
    ....
  17. ncbi request reprint Synthesis and biological evaluation of halo-neplanocin A as novel mechanism-based inhibitors of S-adenosylhomocysteine hydrolase
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 22:589-92. 2003
    ..Halogenated analogues of neplanocin A were synthesized from the key intermediate 1, among which fluoro-neplanocin A was found to be novel mechanism-based irreversible inhibitor of S-Adenosylhomocysteine hydrolase...
  18. ncbi request reprint Synthesis of halogenated 9-(dihydroxycyclopent-4'-enyl) adenines and their inhibitory activities against S-adenosylhomocysteine hydrolase
    Lak Shin Jeong
    College of Pharmacy, Ewha Womans University, Seoul, South Korea
    Nucleosides Nucleotides Nucleic Acids 22:919-21. 2003
    ..Novel halovinyl analogues of neplanocin A without 4'-hydroxymethyl group were easily synthesized starting from D-ribose via cyclopentenone 5 as a key intermediate and their inhibitory activity against SAH hydrolase was assayed...
  19. ncbi request reprint Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 46:201-3. 2003
    ..A new mechanism of irreversible inhibition discovered in this work might provide new alternatives in the design of a different class of antiviral agents operating via SAH inhibition...
  20. doi request reprint Discovery of a new template for anticancer agents: 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl-cytosine (2'-F-4'-seleno-ara-C)
    Lak Shin Jeong
    Department of Bioinspired Science, Division of Life and Pharmaceutical Sciences, College of Pharmacy, Ewha Womans University, Seoul, Korea
    J Med Chem 52:5303-6. 2009
    ..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)...
  21. ncbi request reprint N6-substituted D-4'-thioadenosine-5'-methyluronamides: potent and selective agonists at the human A3 adenosine receptor
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 46:3775-7. 2003
    ..28 +/- 0.09 nM). 4 was also selective for A(3) vs human A(1) and human A(2A) receptors by 4800- and 36000-fold, respectively...
  22. ncbi request reprint Design, synthesis and binding affinity of 3'-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands
    Moo Hong Lim
    College of Pharmacy, Seoul National University, Seoul 151 742, South Korea
    Bioorg Med Chem Lett 13:817-20. 2003
    ....
  23. ncbi request reprint Synthesis of 3'-ureidoadenosine analogues and their binding affinity to the A3 adenosine receptor
    Moon Woo Chun
    Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 24:1119-21. 2005
    ..However, all synthesized 3'-ureidoadenosine analogues have lost their binding affinities to the all subtypes of adenosine receptors, indicating that bulky 3'-urea moiety led to conformational distortion...
  24. pmc Design and synthesis of N(6)-substituted-4'-thioadenosine-5'-uronamides as potent and selective human A(3) adenosine receptor agonists
    Won Jun Choi
    Department of Bioinspired Science and Division of Life and Pharmaceutical Sciences, College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem 17:8003-11. 2009
    ..4 nM). Bulky substituents at the 5'-uronamide position, such as cyclohexyl and 2-methylbenzyl, in this series of 2-H nucleoside derivatives were tolerated in A(3)AR binding, although small alkyl analogues were more potent...
  25. pmc Structure-activity relationships of truncated adenosine derivatives as highly potent and selective human A3 adenosine receptor antagonists
    Shantanu Pal
    Department of Bioinspired Science and Division of Life and Pharmaceutical Sciences, Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem 17:3733-8. 2009
    ..Although the 4'-oxo series were less potent than the 4'-thio series, this class of human A(3) AR antagonists is also regarded as another good template for the design of A(3) AR antagonists and for further drug development...
  26. ncbi request reprint Stereoselective synthesis of conformationally rigid apio carbanucleosides as potential antiviral agents
    Hyung Ryong Moon
    College of Pharmacy, Pusan National University, Pusan 609 735, Korea
    Nucleosides Nucleotides Nucleic Acids 24:709-11. 2005
    ..Introduction of hydroxymethyl substituent was efficiently and stereoselectively accomplished by aldol and retro-aldol reaction and fixed conformation was achieved from a modified Simmons-Smith cyclopropanation on a cyclopentane ring...
  27. ncbi request reprint Design, synthesis, and molecular modeling studies of 5'-deoxy-5'-ureidoadenosine: 5'-ureido group as multiple hydrogen bonding donor in the active site of S-adenosylhomocysteine hydrolase
    Ting Wang
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem Lett 17:4456-9. 2007
    ....
  28. ncbi request reprint Structure-activity relationship of 5'-substituted fluoro-neplanocin a analogues as potent inhibitors of S-adenosylhomocysteine hydrolase
    Hyung Ryong Moon
    College of Pharmacy, Pusan National University, Pusan 609 735, Korea
    Nucleosides Nucleotides Nucleic Acids 24:707-8. 2005
    ....
  29. pmc Structure-activity relationships of truncated C2- or C8-substituted adenosine derivatives as dual acting A₂A and A₃ adenosine receptor ligands
    Xiyan Hou
    Laboratory of Medicinal Chemistry, College of Pharmacy, and Department of Bioinspired Science, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 55:342-56. 2012
    ..Compound 4g was the most potent ligand acting dually as hA(2A)AR agonist and hA(3)AR antagonist, which might be useful for treatment of asthma or other inflammatory diseases...
  30. ncbi request reprint Design and synthesis of A3 adenosine receptor ligands, 3'-fluoro analogues of Cl-IB-MECA
    Hea Ok Kim
    Division of Chemistry and Molecular Engineering, Seoul National University, Seoul, South Korea
    Nucleosides Nucleotides Nucleic Acids 22:923-5. 2003
    ..Synthesis of 3'-deoxy-3'-fluoro-N6-substituted adenosines as bioisosteres of Cl-IB-MECA and their binding affinities to A3 adenosine receptor are described...
  31. doi request reprint Stereoselective synthesis and conformational study of novel 2',3'-Didehydro-2',3'-dideoxy-4'-selenonucleosides
    Dilip K Tosh
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea
    J Org Chem 73:4259-62. 2008
    ..Introduction of 2',3'-double bond was achieved by treating cyclic 2',3'-thiocarbonate with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine...
  32. doi request reprint New RNA purine building blocks, 4'-selenopurine nucleosides: first synthesis and unusual mixture of sugar puckerings
    Jinha Yu
    Department of Bioinspired Science and College of Pharmacy, Ewha Womans University, Seoul, Korea
    Chemistry 19:5528-32. 2013
    ..4'-Selenoadenosine exists in an unusual mixture of north and south conformers in the solid state...
  33. doi request reprint Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity
    Won Jun Choi
    Department of Bioinspired Science and College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 55:4521-5. 2012
    ..However, its 2'-deoxycytidine derivative 5b did not show any antigrowth effects, indicating that 2'-hydroxyl group is essential for the biological activity...
  34. ncbi request reprint Design, synthesis, and biological evaluation of novel iso-D-2',3'-dideoxy-3'-fluorothianucleoside derivatives
    Kyung Ran Kim
    Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan 609 735, Republic of Korea
    Bioorg Med Chem 15:227-34. 2007
    ..43microg/mL). This result implies that iso-2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent...
  35. ncbi request reprint Design, synthesis, and in vitro evaluation of APIO analogue of neplanocin A
    Hyung Ryong Moon
    College of Pharmacy, Ewha Womans University, Seoul, South Korea
    Nucleosides Nucleotides Nucleic Acids 22:1475-7. 2003
    ....
  36. ncbi request reprint Synthesis of 5'-substituted fluoro-neplanocin A analogues: importance of a hydrogen bonding donor at 5'-position for the inhibitory activity of S-adenosylhomocysteine hydrolase
    Hyung Ryong Moon
    College of Pharmacy, Pusan National University, Pusan 609 753, Korea
    Bioorg Med Chem Lett 14:5641-4. 2004
    ..All the final compounds showed much less decreased cytotoxicity in two cancer cell lines (Col2 and A549), implying that phosphorylation of the 5'-hydroxyl group of fluoro-neplanocin A is closely related to its high cytotoxicity...
  37. ncbi request reprint Stereoselective synthesis of homo-apioneplanocin A as potential inhibitor of S-adenosylhomocysteine hydrolase
    Moon Woo Chun
    College of Pharmacy, Seoul National University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 26:729-32. 2007
    ....
  38. ncbi request reprint Stereoselective synthesis of novel thioiso dideoxy nucleosides with exocyclic methylene as potential antiviral agents
    Prashantha Gunaga
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 24:1115-7. 2005
    ..Cyclization of the dimesylate to the 4-thiosugar 6a proceeded in pure SN2 reaction in the presence of allylic functional group...
  39. ncbi request reprint Design and synthesis of A3 adenosine receptor ligands, 2'-fluoro analogues of Cl-IB-MECA
    Hea Ok Kim
    Division of Chemistry and Molecular Engineering, Seoul National University, Seoul, South Korea
    Nucleosides Nucleotides Nucleic Acids 22:927-30. 2003
    ..Synthesis of 2'-deoxy-2'-fluoro-N6-substituted adenosines as bioisosteres of Cl-IB-MECA and their binding affinities to A3 adenosine receptor are described...
  40. ncbi request reprint Synthesis of novel apio carbocyclic nucleoside analogues as selective a(3) adenosine receptor agonists
    Jeong A Lee
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Org Chem 70:5006-13. 2005
    ....
  41. ncbi request reprint Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides
    Won Jun Choi
    WonJun Choi Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Nucleosides Nucleotides Nucleic Acids 24:611-3. 2005
    ..The preparative and stereoselective synthesis (45- 50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions...
  42. doi request reprint Synthesis of 2-alkynyl substituted 4'-thioadenosine derivatives and their binding affinities at the adenosine receptors
    Cheng Wu Liang
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Arch Pharm Res 31:973-7. 2008
    ..Among compounds tested, only compound 3b showed moderate binding affinity at the human A3 adenosine receptor without binding affinities at other subtypes...
  43. doi request reprint A new DNA building block, 4'-selenothymidine: synthesis and modification to 4'-seleno-AZT as a potential anti-HIV agent
    Varughese Alexander
    Department of Bioinspired Science and Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Org Lett 12:2242-5. 2010
    ..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...
  44. pmc Design, synthesis, and binding of homologated truncated 4'-thioadenosine derivatives at the human A3 adenosine receptors
    Hyuk Woo Lee
    Department of Bioinspired Science, College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem 18:7015-21. 2010
    ....
  45. doi request reprint X-ray crystal structure and binding mode analysis of human S-adenosylhomocysteine hydrolase complexed with novel mechanism-based inhibitors, haloneplanocin A analogues
    Kang Man Lee
    College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Med Chem 54:930-8. 2011
    ..The inhibitory activity was decreased as the size of the halogen atom increased and/or if the 4'-CH(2)OH group was absent. These results could be utilized to design new therapeutic agents operating via AdoHcy hydrolase inhibition...
  46. ncbi request reprint Stereoselective synthesis of a novel apio analogue of neplanocin A as potential S-adenosylhomocysteine hydrolase inhibitor
    Hyung Ryong Moon
    College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Org Lett 4:3501-3. 2002
    ..reaction: see text]..
  47. doi request reprint Inhibition of cell proliferation through cell cycle arrest and apoptosis by thio-Cl-IB-MECA, a novel A3 adenosine receptor agonist, in human lung cancer cells
    Sun Jack Kim
    College of Pharmacy, Ewha Womans University, 11 1 Daehyun Dong, Seodaemun Ku, Seoul 120 750, Republic of Korea
    Cancer Lett 264:309-15. 2008
    ..The activation of Akt-mediated signaling was also inhibited by treatment with thio-Cl-IB-MECA. These data might suggest the potential therapeutic value of an adenosine analog in the treatment of human lung cancer...
  48. ncbi request reprint Synthesis of 5-azacytidine nucleosides with rigid sugar moiety as potential antitumor agents
    Moon Woo Chun
    College of Pharmacy, Seoul National University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 22:915-7. 2003
    ..The bicyclic 3'-O,5'-C-methylene-linked and 2'-O,5'-C-methylene-linked 5-azacytidine derivatives were readily synthesized from 1,2;5,6-di-O-isopropylidene-D-glucose and evaluated against several cancer cell lines...
  49. ncbi request reprint Synthesis of [1'-fluoro-2',2'-bis-(hydroxymethyl)cyclopropylmethyl]purines as antiviral agents
    Ju Hyun Park
    College of Pharmacy, Sookmyung Women s University, Yongsangu, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 22:955-7. 2003
    ..1'-Fluoro-2',2'-bis-(hydroxymethyl)cyclopropylmethyl]purines were designed, synthesized and their antiviral activity against poliovirus, HSV and HIV was evaluated...
  50. ncbi request reprint Synthesis of 3'-deoxy-3'-C-hydroxymethyl analogues of tiazofurin and ribavirin
    Moon Woo Chun
    Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 151 742, Korea
    Nucleosides Nucleotides Nucleic Acids 24:975-7. 2005
    ..On the basis of potent biological activity of 3'-branched-3'-deoxynucleoside analogues, novel ribavirin and tiazofurin derivatives with 3'-C-hydroxymethyl substituent were synthesized, starting from D-xylose...
  51. ncbi request reprint Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: effects of the bulky protecting groups to enforce facial selectivity
    Won Jun Choi
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Org Chem 69:2634-6. 2004
    ....
  52. ncbi request reprint Synthesis of D- and L-apio nucleoside analogues with 2'-hydroxyl group as potential anti-HIV agents
    Dong Zhe Jin
    College of Pharmacy, Seoul National University, Seoul 151 742, South Korea
    Bioorg Med Chem 12:1101-9. 2004
    ....
  53. pmc Synthesis of 3'-acetamidoadenosine derivatives as potential A3 adenosine receptor agonists
    Moon Woo Chun
    College of Pharmacy, Seoul National University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 27:408-20. 2008
    ....
  54. pmc Regio- and stereoselective synthesis of truncated 3'-aminocarbanucleosides and their binding affinity at the A3 adenosine receptor
    Mun Ju Choi
    Laboratory of Medicinal Chemistry, College of Pharmacy and Department of Bioinspired Science, Ewha Womans University, Seoul, 120 750, Korea
    Org Biomol Chem 9:6955-62. 2011
    ..The stereoselective synthesis of truncated 3'-aminocarbanucleosides 4a-d via a stereo- and regioselective conversion of a diol 9 to bromoacetate 11a and their binding affinity towards the human A(3) adenosine receptor are described...
  55. doi request reprint Synthesis of 3'-C-hydroxymethyl-substituted pyrimidine and purine nucleosides as potential anti-hepatitis C virus (HCV) agents
    Xiaojuan Pei
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea
    Arch Pharm Res 31:843-9. 2008
    ....
  56. ncbi request reprint Synthesis of homo-N-nucleoside with 1,2,4-triazole-3-carboxamide
    Moon Woo Chun
    Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 151 742, Korea
    Nucleosides Nucleotides Nucleic Acids 24:979-81. 2005
    ....
  57. ncbi request reprint Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase
    Hea Ok Kim
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, South Korea
    Bioorg Med Chem Lett 14:2091-3. 2004
    ..From this study, 4(')-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme...
  58. ncbi request reprint Synthesis and biological evaluation of novel tert-azido or tert-amino substituted penciclovir analogs
    Hea Ok Kim
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Org Biomol Chem 2:1164-8. 2004
    ....
  59. ncbi request reprint Synthesis and biological evaluation of novel thioapio dideoxynucleosides
    Hyung Ryong Moon
    College of Pharmacy, Ewha Womans University, Seoul 120 750, Republic of Korea
    Bioorg Med Chem 10:1499-507. 2002
    ..Although we could not find good anti-HIV agents in this study, findings of some anticancer activity in this series will allow this class of nucleosides to be the new template for the development of new anticancer agents (Fig. 1)...
  60. ncbi request reprint Stereoselective synthesis of 2'-C-methyl-cyclopropyl-fused carbanucleosides as potential anti-HCV agents
    Jeong A Lee
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Org Lett 8:5081-3. 2006
    ..reaction: see text]..
  61. ncbi request reprint Asymmetric synthesis of novel thioiso dideoxynucleosides with exocyclic methylene as potential antiviral agents
    Prashantha Gunaga
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    J Org Chem 69:3208-11. 2004
    ..On the other hand, glycosylation of 14 with 6-chloropurine under Mitsunobu conditions afforded the desired S(N)2 product 26, while palladium-catalyzed glycosylation resulted in the sole formation of S(N)2' product 34...
  62. doi request reprint Synthesis and anti-hepatitis C virus (HCV) activity of 3'-C-substituted-methyl pyrimidine and purine nucleosides
    Won Jun Choi
    Department of Bioinspired Science, Ewha Womans University, 11 1 Seodaemun gu, Daehyun dong, Seoul 120 750, Republic of Korea
    Bioorg Med Chem 18:4812-20. 2010
    ..This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents...
  63. ncbi request reprint Synthesis of 2-C-hydroxymethylribofuranosylpurines as potent anti-hepatitis C virus (HCV) agents
    Byul Nae Yoo
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Republic of Korea
    Bioorg Med Chem Lett 16:4190-4. 2006
    ..Among compounds tested, adenosine derivative 2a exhibited potent anti-HCV activity, indicating that the hydroxyl group of 2'-C-hydroxymethyl substituent led to favorable interaction with HCV polymerase...
  64. ncbi request reprint Synthesis of novel L-N-MCd4T as a potent anti-HIV agent
    Ah Young Park
    Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan, Korea
    Org Biomol Chem 4:4065-7. 2006
    ..76 microg mL(-1)) agent without cytotoxicity up to 100 microg mL(-1), indicating that the anti-HIV-1 activity found is similar to that of ddI (EC50 = 4.95 microg mL(-1)), which is used clinically for the treatment of AIDS patients...
  65. ncbi request reprint Alternative and improved syntheses of highly potent and selective A3 adenosine receptor agonists, Cl-IB-MECA and thio-Cl-IB-MECA
    Xiyan Hou
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120 750, Korea
    Arch Pharm Res 30:1205-9. 2007
    ..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...
  66. ncbi request reprint Synthesis and biological evaluation of pyrimidine nucleosides fused with 3',4'-tetrahydrofuran ring
    Moon Woo Chun
    College of Pharmacy, Seoul National University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 22:719-21. 2003
    ..Thymine analogue 1 and its corresponding 2'-deoxy analogue 3 exhibited high cytotoxicity instead of giving antiviral activities...
  67. ncbi request reprint Synthesis of (Z)-(1-fluoro-2-hydroxymethylcyclopropylmethyl)purines
    Ju Hyun Park
    College of Pharmacy, Sookmyung Women s University, Yongsangu, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 22:659-61. 2003
    ..Z)-(1-fluoro-2-hydroxymethylcyclopropylmethyl)purines were designed, synthesized and evaluated their antiviral activity against poliovirus, HSV, and HIV...
  68. doi request reprint Synthesis of fluoroneplanocin A
    Lak Shin Jeong
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea
    Curr Protoc Nucleic Acid Chem . 2008
    ..This intermediate is synthesized using a stereoselective Grignard reaction, a ring-closing metathesis (RCM) reaction, and oxidative rearrangement as key steps...
  69. ncbi request reprint Synthesis of 2-(3'-azido- and 3'-amino-3'-deoxy-beta-D-ribofuranosyl)thiazole-4-carboxamide
    Cheng Wu Liang
    College of Pharmacy, Seoul National University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 22:2039-48. 2003
    ..In view of biological activities of tiazofurin and azido or aminosugar nucleosides, novel azido- and amino-substituted tiazofurin derivatives (1 and 2) were efficiently synthesized starting from 1,2;5,6-di-O-isopropylidene-D-glucose...
  70. ncbi request reprint A novel adenosine analog, thio-Cl-IB-MECA, induces G0/G1 cell cycle arrest and apoptosis in human promyelocytic leukemia HL-60 cells
    Eun Jin Lee
    College of Pharmacy, Ewha Womans University, 11 1 Daehyun Dong, Seodaemun Ku, Seoul 120 750, Republic of Korea
    Biochem Pharmacol 70:918-24. 2005
    ....
  71. ncbi request reprint Recent advances in 4'-thionucleosides as potential antiviral and antitumor agents
    Prashantha Gunaga
    Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, 120 750, Korea
    Curr Med Chem 11:2585-637. 2004
    ..and Walker et al. Subsequent contributions by the other authors, enhanced its standing as an important class of antiviral agents. Following is a reasonably exhaustive account of this class of compounds reported after 1990...
  72. doi request reprint Truncated fluorocyclopentenyl pyrimidines as S-adenosylhomocysteine hydrolase inhibitors
    Yeon Hee Park
    Department of Bioinspired Science and Division of Life and Pharmaceutical Sciences, College of Pharmacy, Ewha Womans University, Seoul, Korea
    Nucleosides Nucleotides Nucleic Acids 28:601-13. 2009
    ....
  73. pmc Structural determinants of efficacy at A3 adenosine receptors: modification of the ribose moiety
    Zhan Guo Gao
    Laboratory of Bioorganic Chemistry, Molecular Recognition Section, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA
    Biochem Pharmacol 67:893-901. 2004
    ....
  74. ncbi request reprint Asymmetric synthesis of novel pseudo-D-vinylcyclopropyl nucleosides bearing quaternary carbon as potential anti-herpesvirus agent
    Ah Young Park
    College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan, Korea
    Nucleosides Nucleotides Nucleic Acids 26:1001-4. 2007
    ....
  75. ncbi request reprint Docking studies of agonists and antagonists suggest an activation pathway of the A3 adenosine receptor
    Soo Kyung Kim
    Molecular Recognition Section, Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases NIDDK, National Institutes of Health NIH, Bethesda, MD 20892, USA
    J Mol Graph Model 25:562-77. 2006
    ..Thus, the putative conformational changes associated with A(3)AR activation indicate a shared mechanism of GPCR activation similar to rhodopsin...
  76. ncbi request reprint Synthesis of enantiopure pseudo-L-vinylcyclopropyl nucleosides bearing quaternary carbon as potential anti-herpesvirus agent
    Hyung Ryong Moon
    College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan, Korea
    Nucleosides Nucleotides Nucleic Acids 26:975-8. 2007
    ....
  77. ncbi request reprint Asymmetric synthesis of apio fluoroneplanocin A analogs as potential AdoHcy hydrolase inhibitor
    Ah Young Park
    College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan, Korea
    Nucleosides Nucleotides Nucleic Acids 26:943-7. 2007
    ..This methodology can be adapted to the synthesis of fluoro compounds extensively...
  78. ncbi request reprint Design, enantiopure synthesis, and biological evaluation of novel iso-D-2',3'-dideoxy-3'-fluorothianucleoside derivatives as a bioisostere of lamivudine
    Kyung Ran Kim
    College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan, Korea
    Nucleosides Nucleotides Nucleic Acids 26:911-5. 2007
    ..43 microg/mL). This result implies that iso 2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent...
  79. pmc Probing the binding site of the A1 adenosine receptor reengineered for orthogonal recognition by tailored nucleosides
    Krishnan K Palaniappan
    Molecular Recognition Section, Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892 0810, USA
    Biochemistry 46:7437-48. 2007
    ..This neoceptor approach should be useful for the validation of molecular modeling and the dissection of promiscuous GPCR signaling...
  80. pmc Orthogonal activation of the reengineered A3 adenosine receptor (neoceptor) using tailored nucleoside agonists
    Zhan Guo Gao
    Molecular Recognition Section, Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892, USA
    J Med Chem 49:2689-702. 2006
    ..The orthogonal pair comprising an engineered receptor and a modified agonist should be useful for elucidating signaling pathways and could be therapeutically applied to diseases following organ-targeted delivery of the neoceptor gene...
  81. ncbi request reprint The antitumor effect of LJ-529, a novel agonist to A3 adenosine receptor, in both estrogen receptor-positive and estrogen receptor-negative human breast cancers
    Heekyoung Chung
    Department of Pathology, College of Medicine, Hanyang University, 133 791 Seoul, Republic of Korea
    Mol Cancer Ther 5:685-92. 2006
    ....
  82. pmc Conversion of A3 adenosine receptor agonists into selective antagonists by modification of the 5'-ribofuran-uronamide moiety
    Zhan Guo Gao
    Molecular Recognition Section, Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA
    Bioorg Med Chem Lett 16:596-601. 2006
    ..Competitive antagonism was demonstrated by Schild analysis. The 2-(dimethylamino)-5'-(N,N-dimethyl)uronamido substitution also retained A(3)AR selectivity but lowered affinity...
  83. ncbi request reprint D-4'-thioadenosine derivatives as highly potent and selective agonists at the human A3 adenosine receptor
    Hyouk Woo Lee
    College of Pharmacy, Seoul National University, Seoul corrected Korea
    Nucleosides Nucleotides Nucleic Acids 24:607-9. 2005
    ..28 +/- 0.09 nM) at the human A3 adenosine receptor...
  84. ncbi request reprint Synthesis and biological evaluation of novel D-2'-azido-2',3'-dideoxyarabinofuranosyl-4'-thiopyrimidines and purines
    Hea Ok Kim
    Division of Chemistry and Molecular Engineering, Seoul National University, Seoul 151 742, Republic of Korea
    Bioorg Med Chem Lett 12:2403-6. 2002
    ..Most of the final nucleosides exhibited toxicity-dependent anti-HIV-1 activity, among which D-alpha-adenine analogue was found to be the most cytotoxic...