New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A

Journal of Medicinal Chemistry

Volumn 39, Issue 19, 1996, Pages 3847-3852

  Obara, Takumi ^a   Shuto, Satoshi ^b   Saito, Yasuyoshi ^a   Snoeck, Robert ^c   Andrei, Graciela ^c   Balzarini, Jan ^c   De Clercq, Erik ^c   Matsuda, Akira ^b  

^a ASAHI CHEMICAL INDUSTRY CO   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUORONEPLANOCIN A; 6' C METHYLNEPLANOCIN A; ANTIBIOTIC AGENT; DEHYDROXYMETHYLNEPLANOCIN A; NEPLANOCIN A; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARENAVIRUS; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HUMAN CYTOMEGALOVIRUS; MEASLES VIRUS; MUMPS VIRUS; NONHUMAN; PARAINFLUENZA VIRUS; REOVIRUS; VACCINIA VIRUS; VERO CELL; VESICULAR STOMATITIS VIRUS;

ADENOSINE; ANIMALS; ANTIVIRAL AGENTS; ARENAVIRIDAE; CERCOPITHECUS AETHIOPS; CYTOMEGALOVIRUS; MOLECULAR STRUCTURE; PARAINFLUENZA VIRUS 3, HUMAN; REOVIRIDAE; VACCINIA VIRUS; VERO CELLS; VESICULAR STOMATITIS-INDIANA VIRUS;

EID: 0029844278     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960145+     Document Type: Article

References (40)

1. This paper constitutes Part 149 of Nucleosides and Nucleotides. Part 148: Shuto, S.; Obara, T.; Saito, Y.; Andrei, G.; Snoeck, R.; De Clercq, E, Matsuda, A. New Neplanocin analogues VI. Synthesis and potent antiviral activity of 6′-homoneplanocin A (HNPA). J. Med. Chem. 1996, 39, 2392-2399.
2. (a) Yaginuma, S; Muto, N.; Tsujino, M.; Sudate, Y.; Hayashi, M.; Otani, M. Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation and characterization. J. Antibiot. 1981, 34, 359-366.
3. (b) Hayashi, M.; Yaginuma, S.; Yoshioka, H.; Nakatsu, K. Studies on neplanocin A, new antitumor antibiotic. II. Structure determination. J. Antibiot. 1981, 34, 675-680.
4. De Clercq, E. Antiviral and antimetabolic activities of neplanocins. Antimicrob. Agents Chemother. 1985, 28, 84-89.
5. (a) Glazer, R. I.; Knode, M. C. Neplancin A. A cyclopentenyl analog of adenosine with specificity for inhibiting RNA methylation. J. Biol. Chem. 1984, 259, 12964-12969.
6. (b) Inaba, M.; Nagashima, S.; Tsukagoshi, S.; Sakurai, Y. Biochemical mode of cytotoxic action of neplanocin A in L1210 leukemic cells. Cancer Res. 1986, 46, 1063-1067.
7. (c) Hoshi, A.; Yoshida, M.; Iigo, M.; Tokuzen, R.; Fukukawa, K.; Ueda, T. J. PharmacobioDyn. 1986, 9, 202-206.
8. Tsujino, M.; Yaginuma, S.; Fujii, T.; Hayano, K.; Matsuda, T.; Watanabe, T.; Abe, J. Neplanocins, new antitumor agents: biological activities. Curr. Chemother. Infect. Dis. 1981, 3, 1559.
9. (a) Shuto, S.; Obara, T.; Toriya, M.; Hosoya, M.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. New neplanocin analogues. I. Synthesis of 6′-modified neplanocin A derivatives as broad-spectrum antiviral agents. J. Med. Chem. 1992, 35, 324-331.
10. (b) Shigeta, S.; Mori, S.; Baba, M.; Ito, M.; Honzumi, K.; Nakamura, K.; Oshitani, H.; Numazaki, Y.; Matsuda, A.; Obara, T.; Shuto, S.; De Clercq, E. Antiviral activities of ribavirin, EICAR, and (6′R)-6′-C-methylneplanocin A against several ortho- and paramyxoviruses. Antimicrob. Agents Chemother. 1992, 36, 435-439.
11. (c) Shuto, S.; Obara, T.; Kosugi, Y.; Toriya, M.; Yaginuma, S.; Shigeta, S.; Matsuda, A. New neplanocin analogues. III. 6′R-Configuration is essential for the antiviral activity of 6′-C-methyl-3-deazaneplanocin A's. BioMed. Chem. Lett. 1994, 4, 605-608.
12. (d) Obara, T.; Shuto, S.; Saito, Y.; Toriya, M.; Ogawa, K.; Yaginuma, S.; Shigeta, S.; Matsuda, A. New neplanocin analogues. V. A potent adenosylhomocysteine hydrolase inhibitor lacking antiviral activity. Synthesis and antiviral activity of 6′-carboxylic acid derivatives of neplanocin A. Nucleosides Nudeotides, in press.
13. (e) Shuto, S.; Obara, T.; Saito, Y; Andrei, G.; Snoeck, R.; De Clercq, E. New neplanocin analogues. VI. Synthesis and potent antiviral activity of 6′-homoneplanocin A (HNPA). J. Med. Chem. 1996, 39, 2392-2399.
14. For examples: (a) Borcherding, D. R.; Narayanan, S.; Hasobe, M.; McKee, J. G.; Keller, B. T.; Borchardt, R. T. Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase. J. Med. Chem. 1988, 31, 1729-1738. (b) Tseng, C. K. H.; Marquez, V. E.; Fuller, R. W.; Goldstein, B. M.; Haines, D. R.; Mc Pherson, H.; Parsons, J. L.; Shannon, W. M.; Arnett, G.; Hollingshead, M.; Driscoll, J. S. Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities. J. Med. Chem. 1989, 32, 1442-1446. (c) Hasobe, M.; McKee, J. G.; Borcherding, D. R.; Borchardt, R. T. 9-(trans-2′,trans-3′-Dihydroxycyclopent-4′-enyl)-adenine and 3-deazaadenine: analogs of neplanocin A which retain potent antiviral activity but exhibit reduced cytotoxicity. Antimicrob. Agents Chemother. 1987, 31, 1849-1851.
15. For examples: (a) Borcherding, D. R.; Narayanan, S.; Hasobe, M.; McKee, J. G.; Keller, B. T.; Borchardt, R. T. Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase. J. Med. Chem. 1988, 31, 1729-1738. (b) Tseng, C. K. H.; Marquez, V. E.; Fuller, R. W.; Goldstein, B. M.; Haines, D. R.; Mc Pherson, H.; Parsons, J. L.; Shannon, W. M.; Arnett, G.; Hollingshead, M.; Driscoll, J. S. Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities. J. Med. Chem. 1989, 32, 1442-1446. (c) Hasobe, M.; McKee, J. G.; Borcherding, D. R.; Borchardt, R. T. 9-(trans-2′,trans-3′-Dihydroxycyclopent-4′-enyl)-adenine and 3-deazaadenine: analogs of neplanocin A which retain potent antiviral activity but exhibit reduced cytotoxicity. Antimicrob. Agents Chemother. 1987, 31, 1849-1851.
16. For examples: (a) Borcherding, D. R.; Narayanan, S.; Hasobe, M.; McKee, J. G.; Keller, B. T.; Borchardt, R. T. Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase. J. Med. Chem. 1988, 31, 1729-1738. (b) Tseng, C. K. H.; Marquez, V. E.; Fuller, R. W.; Goldstein, B. M.; Haines, D. R.; Mc Pherson, H.; Parsons, J. L.; Shannon, W. M.; Arnett, G.; Hollingshead, M.; Driscoll, J. S. Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities. J. Med. Chem. 1989, 32, 1442-1446. (c) Hasobe, M.; McKee, J. G.; Borcherding, D. R.; Borchardt, R. T. 9-(trans-2′,trans-3′-Dihydroxycyclopent-4′-enyl)-adenine and 3-deazaadenine: analogs of neplanocin A which retain potent antiviral activity but exhibit reduced cytotoxicity. Antimicrob. Agents Chemother. 1987, 31, 1849-1851.
17. (a) Montgomery, J. A. Has the well gone dry? The first cain memorial award lecture. Cancer Res. 1982, 42, 3911-3917.
18. (b) Montgomery, J. A. Studies on biologic activity of purine and pyrimidine analogs. Med. Res. Rev. 1982, 2, 271-308.
19. (a) Chiang, P. K.; Guranowski, A.; Segall, J. E. Irreversible inhibition of S-adenosylhomocysteine hydrolase by nucleoside analogs. Arch. Biochem. Biophys. 1981, 207, 175-184.
20. (b) Zimmerman, T. P.; Wolberg, G.; Duncan, G. S.; Elion, G. B. Adenosine analogues as substrates and inhibitors of S-adenosylhomocysteine hydrolase in intact lymphocytes. Biochemistry 1980, 19, 2252-2559.
21. Part of this work has been published in a preliminary communication: Shuto, S.; Obara, T.; Itoh, H.; Kosugi, Y.; Saito, Y.; Toriya, M.; Yaginuma, S.; Shigeta, S.; Matsuda, A. New neplanocin analogues. IV. An adenosine deaminase-resistant equivalent of neplanocin A. Chem. Pharm. Bull. 1994, 42, 1688-1690.
22. Marquez, V. E.; Lim, M.-I; Tseng, C. L.-H.; Markovac, A.; Priest, M. A.; Khan, M. S.; Kaskar, M. Total synthesis of (-)-neplanocin A. J. Org. Chem. 1988, 53, 5709-5714.
23. (a) Ali, S. M.; Ramesh, K.; Borchardt, R. T. Efficient enantioselective syntheses of carbocyclic nucleoside and prostaglandin synthons. Tetrahedron Lett. 1990, 31, 1509-1512.
24. (b) Borcherding, D. R.; Scholtz, S. A.; Borchardt, R. T. Synthesis of analogues of neplanocin A: utilization of optically active dehydroxycyclopentenones derived from carbohydrates. J. Org. Chem. 1987, 52, 5457-5461.
25. Medich, J. R.; Kunnen, K. B.; Johnson, C. R. Synthesis of carbocyclic nucleoside (-)-neplanocin A. Tetrahedron Lett. 1987, 28, 4131-4134.
26. The reaction gave one diastereoisomer at the 4-position, which suggested that the addition reaction would proceed from the least hindered β-face highly stereoselectively.
27. Compound 7 was converted to the corresponding 3-deazaadenine derivative of which configurations was determined by its X-ray crystallographic analysis (see ref 6c).
28. Oehlschlager, A. C.; Mishra, P.; Dhami, S. Metal-catalyzed rearrangements of allylic esters. Can. J. Chem. 1984, 62, 791-797.
29. Montgomery, J. A.; Hewson, K. Synthesis of potential anticancer agents. XX. 2-Fluoropurines. J. Am. Chem. Soc. 1960, 82, 463-468.
30. Brown, G. B.; Wliky, V. S. 2-Chloroadenine and 2-chloroadenosine. J. Org. Chem. 1958, 23, 125-126.
31. Kosugi, Y.; Saito, Y.; Mori, S.; Watanabe, J.; Baba, M.; Shigeta, S. Antiviral activities of mizoribine and other inosine monophosphate dehydrogenase inhibitors against several ortho- and paramyxoviruses. Antiviral Chem. Chemother. 1994, 5, 366-371.
32. (a) De Clercq, E. S-Adenosyihomocysteine hydrolase inhibitors as broad-spectrum antiviral agents. Biochem. Pharmacol. 1987, 36, 2567-2575.
33. (b) De Clercq, E. Antiviral activity spectrum and target of action of different classes of nucleoside analogues. Nucleosides Nucleotides 1994, 13, 1271-1295.
34. (a) Schols, D.; De Clercq, E.; Balzarini, J.; Baba, M.; Witvrouw, M.; Hosoya, M.; Andrei, G.; Snoeck, R.; Neyts, J.; Pauwels, R.; Nagy, M.; Gyorgyi-Edelenyi, J.; Machovich, R.; Horvath, I.; Low, M.; Gorog, S. Sulphated polymers are potent and selective inhibitors of various enveloped viruses, including herpes simplex virus, cytomegalovirus, vesicular stomatitis virus, respiratory syncytial virus, and toga-, arena- and retroviruses. Antiviral Chem. Chemother. 1990, 1, 233-240.
35. (b) De Clercq, E.; Descamps, J.; Verhelst, G.; Walker, R. T.; Jones, A. S.; Torrence, P. F.; Shugar, D. Comparative efficacy of different antiherpes drugs against different strains of herpes simplex virus. J. Infect. Dis. 1980, 141, 563-574.
36. (c) De Clercq, E.; Holy, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. A novel selective broad-spectrum anti-DNA virus agent. Nature 1986, 323, 464-467.
37. (d) Snoeck, R.; Andrei, G.; Neyts, J.; Schols, D.; Cools, M.; Balzarini, J.; De Clercq, E. Inhibitory activity of S-adenosylhomocysteine hydrolase inhibitors against human cytomegalovirus replication. Antiviral Res. 1993, 21, 197-216.
38. (e) Balzarini, J.; Naesens, L.; Herdewijn, P.; Rosenberg, I.; Holy, A.; Pauwels, R.; Baba, M.; Johns, D. G.; De Clercq, E. Marked in vivo antiretrovirus activity of 9-(2-phosphonylmethoxyethyl)adenine, a selective anti-human immunodeficiency virus agent. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 332-336.
39. (f) Cools, M.; Balzarini, J.; De Clercq, E. Mechanism of antiviral and cytotoxic action of (±)-6′β-fluoroaristeromycin, a potent inhibitor ofS-adenosylhomocysteine hydrolase. Mol. Pharmacol. 1991, 39, 718-724.
40. De Clercq, E.; Balzarini, J.; Torrence, P. F.; Mertes, M. P.; Schmidt, C. L.; Shugar, D.; Barr, P. J.; Jones, A. S.; Verhelst, G.; Walker, R. T. Thymidylate synthetase as target enzyme for the inhibitory activity of 5-substituted 2′-deoxyuridines of mouse leukemia L-1210 cell growth. Mol. Pharmacol. 1981, 19, 321-330.