Synthesis of novel 8-substituted carbocyclic analogs of 2′,3′-dideoxyadenosine with activity against hepatitis B virus

Nucleosides, Nucleotides and Nucleic Acids

Volumn 21, Issue 11-12, 2002, Pages 891-901

  Gudmundsson, Kristjan S ^a   Daluge, Susan M ^a   Condreay, Lynn D ^a   Johnson, Lance C ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYADENOSINE; [3 (6 AMINO 8 BROMO 9H PURIN 9 YL)CYCLOPENTYL]METHANOL; [3 (6 AMINO 8 CHLORO 9H PURIN 9 YL)CYCLOPENTYL]METHANOL; [3 (6 AMINO 8 METHYL 9H PURIN 9 YL)CYCLOPENTYL]METHANOL; [3 [6 AMINO 8 (METHYLAMINO) 9H PURIN 9 YL]CYCLOPENTYL]METHANOL; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; BROMINATION; DEAMINATION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HALOGENATION; HEPATITIS B VIRUS; LITHIATION; NONPHOTOCHEMICAL QUENCHING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERASE CHAIN REACTION; STEREOCHEMISTRY; VIRUS INHIBITION;

ANTIVIRAL AGENTS; DIDEOXYADENOSINE; HEPATITIS B VIRUS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

HEPATITIS B VIRUS;

EID: 0036909328     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120016613     Document Type: Article

References (30)

1. (a) Herdewijn, P.; Balzarini, J.; De Clercq, E.; Pauwels, R.; Baba, M.; Broder, S.; Vanderhaeghe, H. J. Med. Chem. 1987, 30, 1270-1278;
2. (b) Huryn, D.M.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768;
3. (c) Mansour, T. S.; Storer, R. Current Pharmaceutical Design 1997, 3, 227-264.
4. For C8 Bromination of Ribose and 2′-deoxyribose Derivatives see: (a) Holmes, R.E.; Robins, R.K. J. Am. Chem. Soc. 1964, 86, 1242-1245; (b) Srivastava, P.C.; Nagpal, K.L. Experientia 1970, 26, 220; For Lithiation, Followed by Electrophile Quenching for Furanose Derivatives see: (c) Hayakawa, H.; Tanaka, H.; Sasaki, K.; Haraguchi, K.; Saitoh, T.; Takai, F.; Miyasaka, T. J. Heterocycl. Chem. 1989, 26, 189-192; (d) Hayakawa, H.; Haraguchi, K.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 72-79; (e) Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 787-790; (f) For Reviews see: Srivastava, P.C.; Robins, R.K.; Meyer, R.B. Jr. Synthesis and properties of purine nucleosides and nucleotides. In Chemistry of Nucleosides and Nucleotides; Townsend, Leroy B. Ed.; Plenum Press, New York, 1988; 113-281.
5. For C8 Bromination of Ribose and 2′-deoxyribose Derivatives see: (a) Holmes, R.E.; Robins, R.K. J. Am. Chem. Soc. 1964, 86, 1242-1245; (b) Srivastava, P.C.; Nagpal, K.L. Experientia 1970, 26, 220; For Lithiation, Followed by Electrophile Quenching for Furanose Derivatives see: (c) Hayakawa, H.; Tanaka, H.; Sasaki, K.; Haraguchi, K.; Saitoh, T.; Takai, F.; Miyasaka, T. J. Heterocycl. Chem. 1989, 26, 189-192; (d) Hayakawa, H.; Haraguchi, K.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 72-79; (e) Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 787-790; (f) For Reviews see: Srivastava, P.C.; Robins, R.K.; Meyer, R.B. Jr. Synthesis and properties of purine nucleosides and nucleotides. In Chemistry of Nucleosides and Nucleotides; Townsend, Leroy B. Ed.; Plenum Press, New York, 1988; 113-281.
6. For C8 Bromination of Ribose and 2′-deoxyribose Derivatives see: (a) Holmes, R.E.; Robins, R.K. J. Am. Chem. Soc. 1964, 86, 1242-1245; (b) Srivastava, P.C.; Nagpal, K.L. Experientia 1970, 26, 220; For Lithiation, Followed by Electrophile Quenching for Furanose Derivatives see: (c) Hayakawa, H.; Tanaka, H.; Sasaki, K.; Haraguchi, K.; Saitoh, T.; Takai, F.; Miyasaka, T. J. Heterocycl. Chem. 1989, 26, 189-192; (d) Hayakawa, H.; Haraguchi, K.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 72-79; (e) Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 787-790; (f) For Reviews see: Srivastava, P.C.; Robins, R.K.; Meyer, R.B. Jr. Synthesis and properties of purine nucleosides and nucleotides. In Chemistry of Nucleosides and Nucleotides; Townsend, Leroy B. Ed.; Plenum Press, New York, 1988; 113-281.
7. For C8 Bromination of Ribose and 2′-deoxyribose Derivatives see: (a) Holmes, R.E.; Robins, R.K. J. Am. Chem. Soc. 1964, 86, 1242-1245; (b) Srivastava, P.C.; Nagpal, K.L. Experientia 1970, 26, 220; For Lithiation, Followed by Electrophile Quenching for Furanose Derivatives see: (c) Hayakawa, H.; Tanaka, H.; Sasaki, K.; Haraguchi, K.; Saitoh, T.; Takai, F.; Miyasaka, T. J. Heterocycl. Chem. 1989, 26, 189-192; (d) Hayakawa, H.; Haraguchi, K.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 72-79; (e) Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 787-790; (f) For Reviews see: Srivastava, P.C.; Robins, R.K.; Meyer, R.B. Jr. Synthesis and properties of purine nucleosides and nucleotides. In Chemistry of Nucleosides and Nucleotides; Townsend, Leroy B. Ed.; Plenum Press, New York, 1988; 113-281.
8. For C8 Bromination of Ribose and 2′-deoxyribose Derivatives see: (a) Holmes, R.E.; Robins, R.K. J. Am. Chem. Soc. 1964, 86, 1242-1245; (b) Srivastava, P.C.; Nagpal, K.L. Experientia 1970, 26, 220; For Lithiation, Followed by Electrophile Quenching for Furanose Derivatives see: (c) Hayakawa, H.; Tanaka, H.; Sasaki, K.; Haraguchi, K.; Saitoh, T.; Takai, F.; Miyasaka, T. J. Heterocycl. Chem. 1989, 26, 189-192; (d) Hayakawa, H.; Haraguchi, K.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 72-79; (e) Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 787-790; (f) For Reviews see: Srivastava, P.C.; Robins, R.K.; Meyer, R.B. Jr. Synthesis and properties of purine nucleosides and nucleotides. In Chemistry of Nucleosides and Nucleotides; Townsend, Leroy B. Ed.; Plenum Press, New York, 1988; 113-281.
9. For C8 Bromination of Ribose and 2′-deoxyribose Derivatives see: (a) Holmes, R.E.; Robins, R.K. J. Am. Chem. Soc. 1964, 86, 1242-1245; (b) Srivastava, P.C.; Nagpal, K.L. Experientia 1970, 26, 220; For Lithiation, Followed by Electrophile Quenching for Furanose Derivatives see: (c) Hayakawa, H.; Tanaka, H.; Sasaki, K.; Haraguchi, K.; Saitoh, T.; Takai, F.; Miyasaka, T. J. Heterocycl. Chem. 1989, 26, 189-192; (d) Hayakawa, H.; Haraguchi, K.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 72-79; (e) Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 787-790; (f) For Reviews see: Srivastava, P.C.; Robins, R.K.; Meyer, R.B. Jr. Synthesis and properties of purine nucleosides and nucleotides. In Chemistry of Nucleosides and Nucleotides; Townsend, Leroy B. Ed.; Plenum Press, New York, 1988; 113-281.
10. Nair, V.; Buenger, G.S. J. Org. Chem. 1990, 55, 3695-3697.
11. Nair, V.; Buenger, G.S. Synthesis 1990, 962-966.
12. (a) Van Aerschot, A.A.; Mamos, P.; Weyns, N.J.; Ikeda, S.; De Clercq, E.; Herdewijn, P.A. J. Med. Chem. 1993, 36, 2938-2942;
13. (b) Van Aerschot, A.; Herdewijn, P.; Balzarini, J.; Pauwels, R.; De Clercq, E. J. Med. Chem. 1989, 32, 1743-1749.
14. (a) Gala, D.; Schumacher, D.P. Synlett 1992, 1, 61-63;
15. (b) Comin, M.J.; Rodriguez, J.B. Anales de la Asociacion Quimica Argentina 1998, 86, 131-138;
16. (c) Saksena, A.K.; Girijavallabhan, V.M.; Ganguly, A.K. Process for Preparing Cyclopentyl Purine Derivatives. US 4999428, 1991;
17. (d) Vince, R.; Hua M.; Brownell, J.; Daluge, S.; Lee, F.; Shannon, W.M.; Lavelle, G.C.; Qualls, J.; Weislow, O.S. Biochem. Biopharm. Res. Commun. 1988, 156, 1046-1053;
18. (e) Wang, P.; Gullen, B.; Newton, M.G.; Cheng, Y.-C.; Schinazi, R.F.; Chu, C.K. J. Med. Chem. 1999, 42, 3390-3399;
19. (f) Wang, P.Y.; Schinazi, R.F.; Chu, C.K. Bioorg. Med. Chem. Lett. 1998, 31, 1585-1588;
20. (g) Yoshio, T.; Takumi, H.; Marumoto, R.; Yamamoto, N. Preparation of Carbocyclic Derivatives of Purine Nucleosides as Virucides. EP 236935, 1987;
21. (h) Coward, J.K.; Slisz, E.P. J. Med. Chem. 1973, 16, 460-463;
22. (i) For Synthesis of Carbocyclic 2′,3′-dideoxydidehydroadenosine Derivatives, see: Daluge, S.M. Synthesis and Antiviral Activity of (1R,4S)-4-(6-amino-9H-purin-9-yl)-2-cyclopentene-1-methanol. WO 200047581, 2000.
23. (a) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, R.; Earl, R.A.; Guedj, R. Tetrahedron 1994, 50, 10,611-10,670;
24. (b) Zhu, X.-F. Nucleosides, Nucleotides and Nucleic Acids 2000, 19, 651-690;
25. (c) Daluge, S.M.; Martin, M.T. et al. Nucleosides, Nucleotides and Nucleic Acids 2000, 19, 297-327 and references therein;
26. (d) Tan, X.; Chu, C.K.; Boudinot, F.D. Advanced Drug Delivery Reviews 1999, 39, 117-151;
27. (e) Crimmins, M.T. Tetrahedron 1998, 54, 9229-9272.
28. 50 > 10 μM.
29. Jansen, R.W.; Johnson, L.C.; Averett, D.R. Antimicrobial Agents and Chemotherapy 1993, 37, 441-447.
30. Sells, M.A.; Chen, M.-L.; Acs, G. Proc. Natl. Acad. Sci. USA. 1987, 84, 1005-1009.