Selective synthesis and application to the synthesis of (E)-fluorovinyl nucleosides

Nucleosides, Nucleotides and Nucleic Acids

Volumn 27, Issue 3, 2008, Pages 213-223

  Shen, Qingbo ^a   Hong, Joon Hee ^a  

^a Chosun University   (South Korea)

Author keywords

Antiviral agent; Fluoroneplanocin A; Fluorovinyl; Neplanocin A

Indexed keywords

1 [2 FLUORO 4 HYDROXY 3 METHYL BUT 2 ENYL] 5 FLUOROURACIL; 1 [2 FLUORO 4 HYDROXY 3 METHYL BUT 2 ENYL]CYTOSINE; 9 [2 FLUORO 4 HYDROXY 3 METHYL BUT 2 ENYL] 2 AMINO 6 HYDROXYPURINE; 9 [2 FLUORO 4 HYDROXY 3 METHYL BUT 2 ENYL]ADENINE; NEPLANOCIN A; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SELECTIVITY; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN;

ANTIVIRAL AGENTS; CELL LINE; HUMANS; NUCLEOSIDES; VINYL COMPOUNDS; VIRUSES;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 38949117353     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770701845170     Document Type: Article

References (26)

1. a) Borthwick, A.D.; Biggadike, K. Synthesis of chiral carbocyclic nucleosides. Tetrahedron 1992, 48, 571-623;
2. b) Huryn, D.M.; Okabe, M. AIDS-driven nucleoside chemistry. Chem. Rev. 1992, 92, 1745-1768;
3. c) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.; Earl, R.A.; Guedj, R. Synthesis of carbocyclic nucleosides. Tetrahedron 1994, 50, 10611-10670;
4. d) Crimmins, M.T. New development in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides. Tetrahedron 1998, 54, 9229-9272;
5. e) Ariona, O.; Gómez, A.M.; López, J.C.; Plumet, J. Synthesis and conformational and biological aspects of carbasugars. Chem. Rev. 2007, 107, 1919-2036
6. Marquez, V.E.; Lim, B.B.; Barchi, J.J.; Nicklaus, M.C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents. eds, Chu, C.K., Baker, D.C.,Plenum New York, 1993, p. 265.
7. a) Houston, D.M.; Dolence, E.K.; Keller, B.T.; Patel-Thombre, U.; Borchardt, R.T. Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 9. 2′,3′-Dialdehyde derivatives of carbocyclic purine nucleosides as inhibitors of S-adenosylhomocysteine hydrolase. J. Med. Chem. 1985, 28, 471-477;
8. b) Marquez, V.E.; Lim, M.I. Carbocyclic nucleosides. Med. Res. Rev. 1986, 6, 1-40;
9. c) Shuto, S.; Obara, T.; Toriya, M.; Hosoya, M.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. Synthesis of 6′-modified neplanocin A derivatives as broad-spectrum antiviral agents. J. Med. Chem. 1992, 35, 324-331;
10. d) Shuto, S.; Obara, T.; Itoh, H. Kosugi, Y.; Saito, Y.; Toriya, M.; Yagimura, S.; Shigeta, S.; Matsudam A. 2-Fluroneplanocin A: An adenosine deaminase-resistant equivalent of neplanocin A. Chem. Pharm. Bull. 1994, 42, 1688-1690.
11. a) Ueland, P.M. Pharmacological and biological aspects of S-adenosylhomocysteine and Sadenosylhomocysteine hydrolase. Pharmacol. Rev. 1982, 34, 223-253;
12. b) Palmer, J.L.; Abeles, R.H. The mechanism of action of S-adenosylhomocysteinase. J. Biol. Chem. 1979, 254, 1217-1226.
13. a) Machida, H.; Sakata, S.; Kuninaka, A.; Yoshino, H. Antiherpesviral and anticellular effects of 1-β-D-arabinofuranosyl-E-5-(2-halogenovinyl) uracils. Antimicrob. Agents Chemother. 1981, 20, 47-52;
14. b) Choi, Y.; Li, L.; Grill, S.; Gullen, E.; Lee, C.S.; Gumina, G.; Tsujii, E.; Cheng, Y.-C.; Chu, C.K. Structureactivity relationships of (E)-5-(2-bromovinyl)uracil and related pyrimidine nucleosides as antiviral agents for herpes viruses. J. Med. Chem. 2000, 43, 2538-2546;
15. c) Gumina, G.; Schinazi, R.F.; Chu, C.K. Synthesis and potent anti-HIV activity of L-3′-fluoro-2′,3′-unsaturated cytidine. Org. Lett. 2001, 3, 4177-4180.
16. Jeong, L.S.; Yoo, S.J.; Lee, K.M.; Koo, M.J.; Choi, W.J.; Kim, H.O.; Moon, H.R.; Lee, M.Y.; Park, J.G.; Lee, S.K.; Chun, M.W. Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase. J. Med. Chem. 2003, 46, 201-203.
17. a) Kirk, K.L. Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules. J. Fluorine Chem. 2006, 127, 1013-1029;
18. b) Hertel, L.W.; Ternansky, R.J. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, eds. Filler, R., Kobayashi, Y., Yagupolski, L.M., Elsevier, Amsterdam, 1993, p. 23;
19. c) Novo, B.; Resnati, G. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets, ed. Soloshonok, V. A., John Wiley & Son, Ltd., Chichester, 1999, p. 349
20. Borcherding, D.R.; Narayanan, S.; Hasobe, M.; McKee, J.G.; Keller, B.T.; Borchardt, R.T. Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase. J. Med. Chem. 1988, 31, 1729-1738.
21. Haines, D.R.; Tseng, C.K.H.; Marquez, V.E. Synthesis and biological activity of unsaturated carboacyclic purine nucleoside. J. Med. Chem. 1987, 30, 943-947.
22. Marquez, V.E.; Tseng, C.K.; Kelly, J.A.; Mitsuya, H.; Broder, S.; Roth, J.S.; Driscoll, J.S. 2′,3′-Dideoxy-2′-fluoro-ara-A. An acid-stable purine nucleoside active against human immunodeficiency virus (HIV). Biochem. Pharmacol. 1987, 36, 2719-2722.
23. Martin, J.A.; Bushnell, D.J.; Duncan, I.B.; Dunsdon, S.J.; Hall, M.J.; Machin, P.J.; Merrett, J.H.; Parkes, K.E.; Roberts, N.A.; Thomas, G.J.; Galpin, S.A.; Kinchington, D. Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1). J. Med. Chem. 1990, 33, 2137-2145.
24. Matthes, E.; Lehmann, C.; Scholz, D.; Rosenthal, H.A.; Langen, P. Phosphorylation, anti-HIV activity and cytotoxicity of 3′-fluorothymidine. Biochem, Biophys. Res. Commun. 1988, 153, 825-831.
25. Kim, A.; Hong, J.H. Synthesis and antiviral activity of C-fluoro-branched cyclopropyl nucleosides. Eur. J. Med. Chem. 2007, 42, 487-493.
26. Hong, J.H.; Ko, O.H. Synthesis and antiviral evaluation of novel acyclic nucleosides. Bull. Kor. Chem. Soc. 2003, 24, 1284-1288.