Synthesis and biological evaluation of nucleoside analogues having 6-chloropurine as anti-SARS-CoV agents

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 9, 2007, Pages 2470-2473

  Ikejiri, Masahiro ^a   Saijo, Masayuki ^b   Morikawa, Shigeru ^b   Fukushi, Shuetsu ^b   Mizutani, Tetsuya ^b   Kurane, Ichiro ^b   Maruyama, Tokumi ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF INFECTIOUS DISEASES   (Japan)

Author keywords

6 Chloropurine; Antiviral; Nucleoside; SARS CoV

Indexed keywords

HYDROXYL GROUP; NUCLEOSIDE ANALOG; PURINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; IC 50; NONHUMAN; QUANTUM YIELD; SARS CORONAVIRUS; STRUCTURE ACTIVITY RELATION; VIRUS PLAQUE;

ANIMALS; ANTIVIRAL AGENTS; CERCOPITHECUS AETHIOPS; CHEMISTRY, PHARMACEUTICAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; EVALUATION STUDIES; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; MOLECULAR CONFORMATION; NUCLEOSIDES; PURINES; SARS VIRUS; SEVERE ACUTE RESPIRATORY SYNDROME; VERO CELLS;

SARS CORONAVIRUS;

EID: 34047136213     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.02.026     Document Type: Article

References (28)

1. Recent reviews on SARS-CoV, see for example:. De Clercq E. Expert Rev. Anti Infect. Ther 4 (2006) 291
2. Tsunetsugu-Yokota Y., Ohnishi K., and Takemori T. Rev. Med. Virol. 16 (2006) 117
3. De Haan C.A., and Rottier P.J. Cell Microbiol. 8 (2006) 1211
4. Hsueh P.-R., and Yang P.-C. J. Microbiol. Immunol. Infect. 38 (2005) 82
5. Bartlam M., Yang H., and Rao Z. Curr. Opin. Struct. Biol. 15 (2005) 664
6. For example:. Cho J.H., Bernard D.L., Sidwell R.W., Kern E.R., and Chu C.K. J. Med. Chem. 49 (2006) 1140
7. Zhang H.-Z., Zhang H., Kemnitzer W., Tseng B., Cinatl Jr. J., Michaelis M., Doerr H.W., and Cai S.X. J. Med. Chem. 49 (2006) 1198
8. Yang S., Chen S.-J., Hsu M.-F., Wu J.-D., Tseng C.-T.K., Liu Y.-F., Chen H.- C., Kuo C.-W., Wu C.-S., Chang L.-W., Chen W.-C., Liao S.-Y., Chang T.-Y., Hung H.-H., Shr H.-L., Liu C.-Y., Huang Y.-A., Chang L.-Y., Hsu J.-C., Peters C.J., Wang A.H.-J., and Hsu M.-C. J. Med. Chem. 49 (2006) 4971
9. Hoever G., Baltina L., Michaelis M., Kondratenko R., Baltina L., Tolstikov G.A., Doerr H.W., and Cinatl Jr. J. J. Med. Chem. 48 (2005) 1256 and also see Ref. 1a and references therein.
10. Maruyama T., Sato Y., Oto Y., Takahashi Y., Snoeck R., Andrei G., Witvrouw M., and De Clercq E. Chem. Pharm. Bull. 44 (1996) 2331
11. Honjo M., Maruyama T., Horikawa M., Balzarini J., and De Clercq E. Chem. Pharm. Bull. 35 (1987) 3227
12. Ruddon R.W., Rainey C.H., and Zedeck M.S. FEBS Lett. 7 (1970) 119
13. Compound 3:. Samano V., Miles R.W., and Robins M.J. J. Am. Chem. Soc. 116 (1994) 9331
14. Compound 7:. Takamatsu S., Maruyama T., Katayama S., Hirose N., Naito M., and Izawa K. J. Org. Chem. 66 (2001) 7469
15. Compound 11:. Sato Y., Ueyama K., Maruyama T., and Richman D.D. Nucleosides Nucleotides 15 (1996) 109
16. Kappler F., and Hampton A. J. Med. Chem. 33 (1990) 2545
17. van der Wenden E.M., von Frijtag Drabbe Künzel J.K., Mathôt R.A.A., Danhof M., IJzerman A.P., and Soudijn W. J. Med. Chem. 38 (1995) 4000
18. Harnden M.R., Jarvest R.L., Bacon T.H., and Boyd M.R. J. Med. Chem. 30 (1987) 1636
19. Ikejiri M., Miyashita K., Tsunemi T., and Imanishi T. Tetrahedron Lett. 45 (2004) 1243
20. A racemic mixture of 26 was employed. Maruyama T., Hanai Y., Sato Y., Snoeck R., Andrei G., Hosoya M., Balzarini J., and De Clercq E. Chem. Pharm. Bull. 41 (1993) 516
21. Saijo M., Morikawa S., Fukushi S., Mizutani T., Hasegawa H., Nagata N., Iwata N., and Kurane I. Antiviral Res. 66 (2005) 159
22. The 6-chloropurine moiety reacts with various nucleophiles (e.g., -NH, -OH, -SH) under mild conditions. For example:. Gao Z.-G., Duong H.T., Sonina T., Kim S.-K., Rompaey P.V., Calenbergh S.V., Mamedova L., Kim M.J., Kim A.Y., Liang B.T., Jeong L.S., and Jacobsen K.A. J. Med. Chem. 49 (2006) 2689
23. Caamaño O., Gómez G., Fernández F., García M.D., García-Mera X., and De Clercq E. Synthesis (2004) 2855
24. Yadav V., Chu C.K., Rais R.H., Safarjalani O.N.A., Guarcello V., Naguib F.N.M., and el Kouni M.H. J. Med. Chem. 47 (2004) 1987
25. Zedeck and coworkers have referred to the irreversible binding of 6-halogenated purine nucleuses in their report (Ref. 4). Reviews on irreversible inhibitors, see for example:. Silverman R.B. Methods Enzymol. 259 (1995) 240
26. Powers J.C., Asgian J.L., Ekici O.D., and James K.E. Chem. Rev. 102 (2002) 4639
27. Arimilli M.N., Dougherty J.P., Cundy K.C., and Bischofberger N. In: De Clercq E. (Ed). Advances in Antiviral Drug Design Vol. 3 (1999), Jai Press, Stamford Connecticut 69-91
28. Lobucavir, [1R-(1α,2β,3α)]-9-[2,3- bis(hydroxymethyl)cyclobutyl]guanine, is known to inhibit some types of viruses after the intracellular phosphorylation. Tenney D.J., Yamanaka G., Voss S.M., Cianci C.W., Tuomari A.V., Sheaffer A.K., Alam M., and Colonno R.J. Antimicrob. Agents Chemother. 41 (1997) 2680 Therefore, compound 10, an analogue of lobucavir, might be similarly phosphorylated. However, the phosphorylated derivative showed almost no antiviral activity, probably because of low affinity to SARS-CoV.