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

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 22, 2004, Pages 5641-5644

  Moon, Hyung Ryong ^a   Lee, Hyun Joo ^b   Kim, Kyung Ran ^a   Lee, Kang Man ^b   Lee, Sang Kook ^b   Kim, Hea Ok ^b   Chun, Moon Woo ^c   Jeong, Lak Shin ^b  

^a Pusan National University   (South Korea)

^b University of Seoul   (South Korea)

^c Seoul National University   (South Korea)

Author keywords

Cytotoxicity; Fluoro neplanocin A; Hydrogen bonding donor; Phosphorylation.; S Adenosylhomocysteine hydrolase

Indexed keywords

ADENOSYLHOMOCYSTEINASE; ANTIVIRUS AGENT; CYCLOPENTENONE DERIVATIVE; HYDROXYL GROUP; NEPLANOCIN A; ADENOSINE; DRUG DERIVATIVE;

ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGEN BOND; PROTEIN PHOSPHORYLATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ADENOSINE; ADENOSYLHOMOCYSTEINASE; CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; HYDROGEN BONDING; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 5144233594     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.08.047     Document Type: Article

References (18)

1. P.M. Ueland Pharmacol. Rev. 34 1982 223
2. J.L. Palmer, and R.H. Abeles J. Biol. Chem. 254 1979 1217
3. G. de la Haba, and G.L. Cantoni J. Biol. Chem. 234 1959 603
4. P.K. Chiang D.M. Paton Methods in Pharmacology Vol. 6 1985 Plenum New York 127
5. M. Hasobe, J.G. McKee, and R.T. Borchardt Antimicrob. Agents Chemother. 33 1989 828
6. M. Cools, and E. De Clercq Biochem. Pharmacol. 40 1990 2259
7. D.B. Ault-Riche, Y. Lee, C.-S. Yuan, M. Hasobe, M.S. Wolfe, D.R. Borcherding, and R.T. Borchardt Mol. Pharmacol. 43 1993 989
8. E. De Clercq Biochem. Pharmacol. 36 1987 2567
9. R. Borchardt, B. Keller, and U. Patel-Thrombe J. Biol. Chem. 259 1984 4353
10. L.S. Jeong, S.J. Yoo, K.M. Lee, M.J. Koo, W.J. Choi, H.O. Kim, H.R. Moon, M.Y. Lee, J.G. Park, S.K. Lee, and M.W. Chun J. Med. Chem. 46 2003 201
11. R.T. Borchardt, and M.S. Wolfe J. Med. Chem. 34 1991 1521 and references cited therein
12. H.O. Kim, S.J. Yoo, H.S. Ahn, W.J. Choi, H.R. Moon, K.M. Lee, M.W. Chun, and L.S. Jeong Bioorg. Med. Chem. Lett. 14 2004 2091
13. W.J. Choi, H.R. Moon, H.O. Kim, B.N. Yoo, J.A. Lee, D.H. Shin, and L.S. Jeong J. Org. Chem. 69 2004 2634
14. E. Djuardi, P. Bovonsombat, and E. McNelis Synth. Commun. 27 1997 2497
15. V.E. Marquez, M.-I. Lim, C.K.-H. Tseng, A. Markovac, M.A. Priest, M.S. Khan, and B. Kaskar J. Org. Chem. 53 1988 5709
16. J.L. Luche J. Am. Chem. Soc. 100 1978 2226
17. A.B. Smith III, and R.E. Richmond J. Am. Chem. Soc. 105 1983 575
18. L.S. Jeong, Y.A. Lee, H.R. Moon, and M.W. Chun Nucleos. Nucleot. 17 1998 1473