Stereoselective, solid phase-based synthesis of trans 3-alkyl-substituted β-lactams as analogues of cholesterol absorption inhibitors

Tetrahedron

Volumn 68, Issue 52, 2012, Pages 10780-10786

  Delpiccolo, Carina M L ^a   Testero, Sebastián A ^a   Leyes, Federico N ^a   Boggián, Dora B ^a   Camacho, Cristián M ^a   Mata, Ernesto G ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

Beta lactam derivatives; Cholesterol absorption inhibitors; Solid phase synthesis

Indexed keywords

AGENTS AFFECTING LIPID METABOLISM; BETA LACTAM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; SOLID PHASE SYNTHESIS; STAUDINGER REACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TRANS ISOMER;

EID: 84869498275     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.01.072     Document Type: Article

References (58)

1. R.E. Dolle, B. Le Bourdonnec, K. Worm, G.A. Morales, C.J. Thomas, and W. Zhang J. Comb. Chem. 12 2010 765
2. R.E. Dolle, B. Le Bourdonnec, A.J. Goodman, G.A. Morales, C.J. Thomas, and W. Zhang J. Comb. Chem. 11 2009 739
3. R.E. Dolle, B. Le Bourdonnec, A.J. Goodman, G.A. Morales, C.J. Thomas, and W. Zhang J. Comb. Chem. 10 2008 753
4. R.E. Dolle, B. Le Bourdonnec, A.J. Goodman, G.A. Morales, J.M. Salvino, and W. Zhang J. Comb. Chem. 9 2007 855
5. R.E. Dolle, B. Le Bourdonnec, G.A. Morales, K.J. Moriarty, and J.M. Salvino J. Comb. Chem. 8 2006 597
6. R.E. Dolle J. Comb. Chem. 7 2005 739
7. A.A. Poeylaut-Palena, and E.G. Mata Org. Biomol. Chem. 8 2010 3947
8. D.D. Young, and A. Deiters Angew. Chem., Int. Ed. 46 2007 5187
9. S. Mazur, and P. Jayalekshmy J. Am. Chem. Soc. 101 1979 677
10. L.I. Llarrull, S.A. Testero, J.F. Fisher, and S. Mobashery Curr. Opin. Microbiol. 13 2010 551
11. S.A. Testero, J.F. Fisher, and S. Mobashery β-Lactam Antibiotics D.J. Abraham, D.P. Rotella, Burger's Medicinal Chemistry, Drug Discovery and Development 7th ed. 2010 John Wiley & Sons New York, NY 257 402
12. G.S. Singh Mini-Rev. Med. Chem. 4 2004 69
13. G.S. Singh Mini-Rev. Med. Chem. 4 2004 93
14. For different biological applications of β-lactams, see: P.D. Mehta, N.P.S. Sengar, and A.K. Pathak Eur. J. Med. Chem. 45 2010 5541
15. N.M. O'Boyle, M. Carr, N.O. Keely, A.J.S. Knox, T. McCabe, D.G. Lloyd, D.M. Zisterer, and M.J. Meegan Eur. J. Org. Chem. 46 2011 4595
16. B.K. Banik, I. Banik, and F.F. Becker Eur. J. Med. Chem. 45 2010 845
17. B.K. Banik, I. Banik, and F.F. Becker Bioorg. Med. Chem. 13 2005 3611
18. B.K. Banik, F.F. Becker, and I. Banik Bioorg. Med. Chem. 12 2004 2523
19. L. Sun, N.I. Vasilevich, J.A. Fuselier, S.J. Hocart, and D.H. Coy Bioorg. Med. Chem. Lett. 14 2004 2041
20. I. Banik, F.F. Becker, and B.K. Banik J. Med. Chem. 46 2003 12
21. V.K. Srivastava, G. Palit, S. Singh, R. Dhawan, and K. Shanker J. Indian Chem. Soc. 67 1990 335
22. T.M. Miller, and D.W. Cleveland Science 307 2005 361
23. B. Alcaide, and P. Almendros Chem. Rec. 11 2011 311
24. B. Alcaide, P. Almendros, and C. Aragoncillo Chem. Rev. 107 2007 4437
25. B. Alcaide, and P. Almendros Curr. Med. Chem. 11 2004 1921
26. A.R.A.S. Deshmukh, B.M. Bhawal, D. Krishnaswamy, V.V. Govande, B.A. Shinkre, and A. Jayanthi Curr. Med. Chem. 11 2004 1889
27. B. Alcaide, and P. Almendros Synlett 2002 381
28. C. Palomo, J.M. Aizpurua, I. Ganboa, and M. Oiarbide Synlett 2001 1813
29. B. Alcaide, and P. Almendros Chem. Soc. Rev. 30 2001 226
30. D.A. Burnett, M.A. Caplen, H.R. Davis, R.E. Burrier, and J.W. Clader J. Med. Chem. 37 1994 1733
31. M. Van Heek, C.F. France, D.S. Compton, R.L. McLeod, N.P. Yumibe, K.B. Alton, E.J. Sibertz, and H.R. Davis J. Pharmacol. Exp. Ther. 283 1997 157
32. G. Müller Drug Discovery Today 8 2003 681
33. B.G. Salisbury, H.R. Davis, R.E. Burrier, D.A. Burnett, G. Boykow, M.A. Caplen, A.L. Clemmons, D.S. Compton, L.M. Hoos, D.G. McGregor, R. Schnitzer-Polokoff, A.A. Smith, B.C. Weig, D.L. Zilli, J.W. Clader, and E.J. Sybertz Atherosclerosis 115 1995 45
34. M. Garcia-Calvo, J. Lisnock, H.G. Bull, B.E. Hawes, D.A. Burnett, M.P. Braun, J.H. Crona, H.R. Davis, D.C. Dean, P.A. Detmers, M.P. Graziano, M. Hughes, D.E. MacIntyre, A. Ogawa, K.A. O'Neil, S.P.N. Iyer, D.E. Shevell, M.M. Smith, Y.S. Tang, A.M. Makarewicz, F. Ujjainwalla, S.W. Altmann, K.T. Chapman, and N.A. Thornberry Proc. Natl. Acad. Sci. U.S.A. 102 2005 8132
35. X. Xu, R. Fu, J. Chen, S. Chenc, and X. Baia Bioorg. Med. Chem. Lett. 17 2007 101
36. Y. Wang, H. Zhang, W. Wenlong Huang, J. Kong, J. Zhou, and B. Zhang Eur. J. Med. Chem. 44 2009 1638
37. A short communication of part of this work has already been published, see: C.M.L. Delpiccolo, and E.G. Mata Tetrahedron Lett. 45 2004 4085
38. N. Fu, and T.T. Tidwell Tetrahedron 64 2008 10465
39. M. Michalac, M. Stodulski, S. Stecko, A. Mames, I. Panfil, M. Soluch, B. Furman, and M. Chmielewski J. Org. Chem. 76 2011 6931
40. J. Limanto, S.W. Krska, B.T. Dorner, E. Vazquez, N. Yoshikawa, and L. Tan Org. Lett. 12 2010 512
41. B.M. Banik, I. Banik, and F.F. Becker Eur. J. Med. Chem. 45 2010 846
42. M.R. Linder, and J. Podlech Org. Lett. 3 2001 1849
43. B.M. Banik, and F.F. Becker Tetrahedron Lett. 41 2000 6551
44. S.B. Rosenblum, T. Huynh, A. Afonso, and H.R. Davis Jr. Tetrahedron 56 2000 5735
45. G. Wu, Y. Wong, X. Chen, and Z. Ding J. Org. Chem. 64 1999 3714
46. R. Annunziata, M. Benaglia, M. Cinquini, and F. Cozzi Tetrahedron: Asymmetry 10 1999 4841
47. M. Browne, D.A. Burnett, M.A. Caplen, L.-Y. Chen, J.W. Clader, M. Domalski, S. Dugar, P. Pushpavanam, R. Sher, W. Vaccaro, M. Viziano, and H. Zhao Tetrahedron Lett. 36 1995 2555
48. C.M.L. Delpiccolo, L. Méndez, M.A. Fraga, and E.G. Mata J. Comb. Chem. 7 2005 331
49. C.M.L. Delpiccolo, and E.G. Mata Tetrahedron: Asymmetry 13 2002 905
50. Formation of a related oxazinone has been previously described in homogeneous phase, see: T.E. Gunda, S. Vieth, K.E. Köver, and F. Sztaricskai Tetrahedron Lett. 31 1990 6707
51. J. Xu ARKIVOC ix 2009 21
52. L. Jiao, Y. Liang, and J. Xu J. Am. Chem. Soc. 128 2006 6060
53. Y. Wang, Y. Liang, L. Jiao, D.-M. Du, and J. Xu J. Org. Chem. 71 2006 6983
54. Previous evidence for the formation of trans-β-lactams in thermodynamics conditions have been described, see: B. Alcaide, P. Almendros, N.R. Salgado, and A. Rodríguez-Vicente J. Org. Chem. 65 2000 4453
55. S.A. Testero, and E.G. Mata Org. Lett. 8 2006 4783
56. No more product was obtained after new treatments of the resin with higher concentrations of TFA (30 and 50%) and longer reaction times, showing that complete separation from the solid support was achieved with 10% TFA. Additionally, oxidative cleavage was tested (using CAN as reagent), but a not identifiable mixture of products was obtained, see: S. Kobayashi, and R. Akiyama Tetrahedron Lett. 39 1998 9211
57. C.M.L. Delpiccolo, M.A. Fraga, and E.G. Mata J. Comb. Chem. 5 2003 208
58. W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2923