From β-Amino-γ-sultone to Unusual Bicyclic Pyridine and Pyrazine Heterocyclic Systems: Synthesis and Cytostatic and Antiviral Activities

ChemMedChem

Volumn 6, Issue 4, 2011, Pages 686-697

  deCastro, Sonia ^a   Familiar, Olga ^a   Andrei, Graciela ^b   Snoeck, Robert ^b   Balzarini, Jan ^b   Camarasa, María José ^a   Velázquez, Sonsoles ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antitumor agents; Antiviral agents; Cyclization; Nitrogen heterocycles; Sultones

Indexed keywords

3 BENZYL 3 ETHYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3 BENZYL 3 ETHYL 4 (2 FORMYL 1 BENZYLIDENEAMINO)AMINE 5H 1,2 OXATHIOLE 2,2 DIOXIDE; 3 BENZYL 3 ETHYL 5 METHYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3 BENZYL 3 ETHYL 6 CARBAMOYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3 BENZYL 3 ETHYL 6 HYDROXYMETHYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3 BENZYL 3 ETHYL 6 METHOXYCARBONYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3 BENZYL 3 ETHYL 6 METHYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3 BENZYL 3 ETHYL 6 METHYLCARBAMOYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3 BENZYL 3 ETHYL 6 METHYLSULFONYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3 BENZYL 3 ETHYL 7 METHYL 3H [1,2] OXATHIOLE[4,5 B]PYRIDINE 1,1 DIOXIDE; 3 BENZYL 6 (4 CHLOROPHENYL) 3 ETHYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE; 3,3 DIBENZYL 5,7 DIMETHYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 6 ACETYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 6 CARBAMOYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 6 CARBOXY 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 6 HYDROXYMETHYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 6 METHOXYCARBONYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 6 METHYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 6 METHYLCARBAMOYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 6 METHYLETHYLCARBAMOYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 6 PHENYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; 3,3 DIBENZYL 7 METHYL 3H [1,2] OXATHIOLE[4,3 B]PYRIDINE 1,1 DIOXIDE; ANTIVIRUS AGENT; BENZYL 3 ETHYL 4 (2 FORMYLPROP 1 ENYLAMINO)AMINE 5H 1,2 OXATHIOLE 2,2 DIOXIDE; BETA AMINO GAMMA SULTONE; CYTOSTATIC AGENT; PYRAZINE DERIVATIVE; PYRIDINE DERIVATIVE; SULTONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CYTOSTASIS; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL;

AMINES; ANTIVIRAL AGENTS; CELLS, CULTURED; CYTOSTATIC AGENTS; HETEROCYCLIC COMPOUNDS, 2-RING; HIV INFECTIONS; HIV-1; PYRAZINES; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES; VIRUS REPLICATION;

EID: 79953030674     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201000546     Document Type: Article

References (45)

1. For reviews on sultone chemistry, see:
2. A. Mustafa, Chem. Rev. 1954, 54, 195-223;
3. D. W. Roberts, D. L. Williams, Tetrahedron 1987, 43, 1027-1062;
4. A. J. Buglass, J. G. Tillett in The Chemistry of Sulfonic Acids, Esters and their Derivatives (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1991, Ch.19;
5. P. Metz, J. Prakt. Chem. 1998, 340, 1-10.
6. For some recent examples on synthetic applications of sultones, see:
7. A. M. M. Ewas, K. M. Dawood, K. Spinde, Y. Wang, A. Jäger, P. Metz, Synlett 2009, 1773-1776;
8. K. C. Majumdar, S. Mondal, D. Ghosh, Tetrahedron Lett. 2009, 50, 4781-4784;
9. F. M. Koch, R. Peters, Synlett 2008, 1505-1509;
10. S. A. Wolckenhauer, A. S. Devlin, J. DuBois, Org. Lett. 2007, 9, 4363-4366, and references therein.
11. See for example:
12. E. Meschkat, M. D. Barratt, Lepoittevin, Chem. Res. Toxicol. 2001, 14, 110-117;
13. E. Meschkat, M. D. Barratt, Lepoittevin, Chem. Res. Toxicol. 2001, 14, 118-126;
14. D. W. Roberts, D. L. Williams, D. Bethell, Chem. Res. Toxicol. 2007, 20, 61-71.
15. For anti-HIV-active sultone compounds, see for example:
16. J. Balzarini, M. J. Pérez-Pérez, A. San-Félix, D. Schols, C. F. Perno, A. M. Vandamme, M. J. Camarasa, E. DeClercq, Proc. Natl. Acad. Sci. USA 1992, 89, 4392-4396;
17. M. J. Camarasa, M. J. Pérez-Pérez, A. San-Félix, J. Balzarini, E. DeClercq, J. Med. Chem. 1992, 35, 2721-2727;
18. M. J. Camarasa, A. San-Félix, S. Velázquez, M. J. Pérez-Pérez, F. Gago, J. Balzarini, Curr. Top. Med. Chem. 2004, 4, 945-963;
19. S. deCastro, E. Lobatón, M. J. Pérez-Pérez, A. San-Félix, A. Cordeiro, G. Andrei, R. Snoeck, E. DeClercq, J. Balzarini, M. J. Camarasa and S. Velázquez, J. Med. Chem. 2005, 48, 1158-1168;
20. S. K. Pavelić, M. Sedić, M. Poznić, Z. Rajić, B. Zorc, K. Pavelić, J. Balzarini, M. Mintas, Anticancer Res. 2010, 30, 3987-3994.
21. For anti-HCMV- and anti-VZV-active sultone compounds, see for example:
22. S. deCastro, C. García-Aparicio, G. Andrei, R. Snoeck, J. Balzarini, M. J. Camarasa and S. Velázquez, J. Med. Chem. 2009, 52, 1582-1591;
23. S. deCastro, M. T. Peromingo, L. Naesens, G. Andrei, R. Snoeck, J. Balzarini, S. Velázquez and M. J. Camarasa, J. Med. Chem. 2008, 51, 5823-5832;
24. S. Prekupec, D. Makuc, J. Plavec, S. Kraljević, M. Kralj, K. Pavelić, G. Andrei, R. Snoeck, J. Balzarini, E. DeClercq, S. Raić-Malić, M. Mintas, Antivir. Chem. Chemother. 2005, 16, 327-338.
25. Some recent examples:
26. D. Enders, W. Harnying, G. Raabe, Synthesis 2004, 590-594;
27. D. Enders, D. Iffland, Synthesis 2007, 1837-1840;
28. B. Bachand, M. Atfani, B. Samim, S. Lévesque, D. Simard, X. Kong, Tetrahedron Lett. 2007, 48, 8587-8589, and references therein.
29. For some examples of Diels-Alder reactions of α, β-unsaturated γ-sultones and reactions of β-halo-α, β-unsaturated γ-sultones with nucleophiles, see:
30. A. W. M. Lee, W. H. Chan, L. S. Jiang, K. W. Poon, Chem. Commun. 1997, 611-612;
31. S. Braverman, T. Pechenick-Azizi, D. T. Major, M. Sprecher, J. Org. Chem. 2007, 72, 6824-6831.
32. A. Calvo-Mateo, M.-J. Camarasa, A. Díaz-Ortiz, F. G. de las Heras, J. Chem. Soc. Chem. Commun. 1988, 1114-1115;
33. M.-J. Pérez-Pérez, M.-J. Camarasa, A. Díaz-Ortiz, A. San Félix, F. G. de las Heras, Carbohydr. Res. 1991, 216, 399-411;
34. M. J. Pérez-Pérez, J. Balzarini, M. Hosoya, E. DeClercq, M. J. Camarasa, Bioorg. Med. Chem. Lett. 1992, 2, 647-648;
35. D. Postel, A. N. VanNhien, J. L. Marco, Eur. J. Org. Chem. 2003, 3713-3726, and references therein.
36. S. deCastro, M. T. Peromingo, A. Lozano, M. J. Camarasa and S. Velázquez, Chem. Eur. J. 2008, 14, 9620-9632.
37. While aromatic sultones are relatively well studied (see reference[2a] and references therein), only one example of similar fused pyridine heterocyclic systems containing a γ-sultone moiety has been previously described: Z. R. Cai, S. Y. Jabri, H. Jin, R. A. Lansdown, S. E. Metobo, M. R. Mish, R. M. Pastor, US200858315 (A1), 2008. Other less related nitrogen heterocyclic systems containing this moiety have also been reported: L. Tian, L., L. Z. Liu, Heteroat. Chem. 2005, 16, 200-204; B. I. Alo, O. B. Familoni, F. Marsais, G. Queguiner, J. Heterocycl. Chem. 1992, 29, 61-64; J. Zhang, S. Saito, T. Koizumi, J. Org. Chem. 1998, 63, 9375-9384. To the best of our knowledge, the pyrazinosultone bicyclic system is previously unknown.
38. G. M. Coppola, G. E Hardtmann, B. S. Huegi, J. Heterocycl. Chem. 1974, 51-56.
39. B. Pita, F. C. Masaguer, E. Raviña, Tetrahedron Lett. 2000, 41, 9829-9833.
40. K. Hirota, H. Kuki, Y. Maki, Heterocycles 1994, 37, 563-570.
41. K. G. Rajeev, A. D. Broom, Org. Lett. 2000, 2, 3595-3598;
42. H. B. Cottam, H. Shih, L. R. Tehrani, D. B. Wasson, D. A. Carson, J. Med. Chem. 1996, 39, 2-9.
43. See for example:
44. Y. Kim, J. Kim, S. Jang, Y. Kang, Heterocycles 1999, 51, 857-861;
45. F. Yoneda, R. Koga, J. Heterocycl. Chem. 1982, 19, 949-951.