A versatile strategy for the solid-phase synthesis of penicillin derivatives: Efficient preparation of 2β-methyl substituted penams as β-lactamase inhibitor analogues

Synthesis

Volumn , Issue 20, 2006, Pages 3397-3404

  Boggián, Dora B ^a   Mata, Ernesto G ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

Combinatorial chemistry; Penicillins; Rearrangement; Solid phase synthesis; Sulfoxides

Indexed keywords

ENZYME INHIBITION; REACTION KINETICS; RESINS; SYNTHESIS (CHEMICAL);

COMBINATORIAL CHEMISTRY; PENICILLIN DERIVATIVES; REARRANGEMENT; SOLID PHASE SYNTHESIS; SULFOXIDES;

ANTIBIOTICS;

BETA LACTAMASE INHIBITOR; METHYL 6,6 DIBROMO 2BETA (BROMOMETHYL) 2ALPHA METHYLPENAM 3ALPHA CARBOXYLATE 1,1 DIOXIDE; METHYL 6,6 DIBROMO 2BETA (CHLOROMETHYL) 2ALPHA METHYLPENAM 3ALPHA CARBOXYLIC ACID; PENAM DERIVATIVE; PENICILLIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MEDICAL LITERATURE; MEDICAL RESEARCH; METHODOLOGY;

EID: 33750603690     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950214     Document Type: Article

References (46)

1. Kidwai, M.; Sapra, P.; Bhushan, K. R. Curr. Med. Chem. 1999, 6, 195.
2. (a) Neu, H. C. Science 1992, 257, 1064.
3. (b) Davies, J. Science 1994, 264, 375.
4. Bush, K. Curr. Pharm. Des. 1999, 5, 839.
5. (a) Mascaretti, O. A.; Boschetti, C. E.; Danelon, G. O.; Mata, E. G.; Roveri, O. A. Curr. Med. Chem. 1995, 1, 441.
6. (b) Mascaretti, O. A.; Danelon, G. O.; Setti, E. L.; Laborde, M.; Mata, E. G. Curr. Pharm. Des. 1999, 5, 939.
7. (c) Maiti, S. N.; Phillips, O. A.; Micetich, R. G.; Livermore, D. M. Curr. Med. Chem. 1998, 5, 441.
8. Micetich, R. G.; Maiti, S. N.; Spevak, P.; Hall, T. W.; Yamabe, S.; Ishida, N.; Tanaka, M.; Yamazaki, T.; Nakai, A.; Ogawa, K. J. Med. Chem. 1987, 30, 1469.
9. Iman, Z.; Nyda, K.; Avi, Y. Int. J. Pharm. 1997, 153, 115.
10. For reports on biologically active 2β-substituted penam derivatives, see: (a) Richter, H. G. F.; Angehrn, P.; Hubschwerlen, C.; Kania, M.; Page, M. G. P.; Specklin, J.-L.; Winkler, F. K. J. Med. Chem. 1996, 39, 3712.
11. (b) Danelon, G. O.; Mata, E. G.; Mascaretti, O. A.; Girardini, J.; Marro, M.; Roveri, O. A. Bioorg. Med. Chem. Lett. 1995, 5, 2037.
12. (c) Danelon, G. O.; Mascaretti, O. A.; Radice, M.; Power, P.; Calcagno, M. L.; Mata, E. G.; Gutkind, G. J. Antimicrob. Chemother. 1998, 41, 313.
13. (d) Reddy, N. A. V.; Setti, E. L.; Phillips, O. A.; Czajkowski, D. P.; Atwal, H.; Atchison, K.; Micetich, R. G.; Maiti, S. N. J. Antibiot. 1997, 50, 276.
14. (e) Czajkowski, D. P.; Reddy, A. V. N.; Setti, E. L.; Phillips, O. A.; Micetich, R. G.; Kunugita, C.; Maiti, S. N. Bioorg. Med. Chem. Lett. 1997, 7, 11.
15. (f) Buynak, J. D.; Rao, A. S.; Doppalapudi, V. R.; Adam, G.; Petersen, P. J.; Nidamarthy, D. Bioorg. Med. Chem. Lett. 1999, 9, 1997.
16. (g) Phillips, O. A.; Reddy, A. V. N.; Setti, E. L.; Spevak, P.; Czajkowski, D. P.; Atwal, H.; Salama, S.; Micetich, R. G.; Maiti, S. N. Bioorg. Med. Chem. 2005, 13, 2847.
17. (a) Boschetti, C. E.; Mata, E. G.; Mascaretti, O. A.; Cricco, J. A.; Coux, G.; Roveri, O. A. Bioorg. Med. Chem. Lett. 1995, 5, 2033.
18. (b) Boschetti, C. E.; Mata, E. G.; Mascaretti, O. A.; Cricco, J. A.; Coux, G.; Lodeyro, A.; Roveri, O. A. J. Braz. Chem. Soc. 1996, 7, 285.
19. (a) Seneci, P. Solid-Phase Synthesis and Combinatorial Technologies; Wiley: New York, 2000.
20. (b) Obrecht, D.; Villalgordo, J. M. Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries; Elsevier Science Ltd.: New York, 1998.
21. (c) Solid-Phase Organic Synthesis; Burgess, K., Ed.; Wiley: New York, 2000.
22. (d) Solid-Phase Organic Synthesis; Czarnik, A. W., Ed.; Wiley: New York, 2001:
23. (e) Dörwald, F. Z. Organic Synthesis on Solid Phase: Supports, Linkers, Reactions; Wiley-VCH: Weinheim, 2002, 2nd Ed.
24. For reviews on solid-phase synthesis of β-lactams, see: (a) Mata, E. G. Curr. Pharm. Design 1999, 5, 955.
25. (b) Laborde, M. A.; Mata, E. G. Mini-Rev. Med. Chem. 2006, 6, 107.
26. For solid-phase synthesis of 3,4-disubstituted β-lactams, see: (a) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 2002, 13, 905.
27. (b) Delpiccolo, C. M. L.; Fraga, M. A.; Mata, E. G. J. Comb. Chem. 2003, 5, 208.
28. (c) Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron Lett. 2004, 45, 4085.
29. (d) Delpiccolo, C. M. L.; Méndez, L.; Fraga, M. A.; Mata, E. G. J. Comb. Chem. 2005, 7, 331.
30. For a short publication of part of this work, see: Delpiccolo, C. M. L.; Mata, E. G. Tetrahedron: Asymmetry 1999, 10, 3893.
31. Beebe, X.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1995, 60, 4196.
32. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis; Pierce Chemical Company: Rockford, 1984, 38.
33. (a) Mata, E. G. Tetrahedron Lett. 1997, 38, 6335.
34. (b) Ma, S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1419.
35. (c) Cironi, P.; Manzanares, I.; Albericio, F.; Alvarez, M. Org. Lett. 2003, 5, 2959.
36. (d) Marfil, M.; Albericio, F.; Alvarez, M. Tetrahedron 2004, 60, 8659.
37. (e) Cironi, P.; Cuevas, C.; Albericio, F.; Alvarez, M. Tetrahedron 2004, 60, 8669.
38. (f) Olsen, C. A.; Parera, N.; Albericio, F.; Alvarez, M. Tetrahedron Lett. 2005, 46, 2041.
39. Kamiya, T.; Tevaji, T.; Hashimoto, M.; Nakaguchi, O.; Oku, T. Tetrahedron Lett. 1973, 3001.
40. Giralt, E.; Rizo, J.; Pedroso, E. Tetrahedron 1984, 40, 4141.
41. Formation of these 2β-(heterocyclyl)thiomethyl derivatives had not been previously reported in solution chemistry under similar conditions, see: Gottstein, W. J.; Haynes, U. J.; McGregor, D. N. J. Med. Chem. 1985, 28, 518.
42. Alpegiani, M.; Giudici, F.; Perrone, E.; Borghi, D. Tetrahedron Lett. 1990, 31, 3509.
43. (a) Hecker, S. C.; Cho, I.-S.; Glinka, T. W.; Zhang, Z. J.; Prince, M. E.; Lee, V. J.; Christensen, B. G.; Boggs, A.; Chamberland, S.; Malouin, F.; Parr, T. R.; Annamalai, T.; Biais, J.; Bond, E. L.; Case, L.; Chan, C.; Crase, J.; Frith, R.; Griffith, D.; Harford, L.; Liu, N.; Ludwikow, M.; Mathias, K.; Rea, D.; Williams, R. J. Antibiot. 1998, 51, 722.
44. (b) Yamazaki, H.; Tsuchida, Y.; Satoh, H.; Kawashima, S.; Hanaki, H.; Hiramatsu, K. J. Antibiot. 2000, 53, 546.
45. Aswapokee, N.; Neu, H. C. J. Antibiot. 1978, 31, 123.
46. Oxidation of resin-bound 2β-(heterocyclyl)thiomethyl penicillins to the corresponding sulfones was not carried out; however, this reaction is expected to be difficult to achieve due to the presence of two or more sulfur atoms in the molecule.