A protecting group-free synthesis of deazathiamine: A step toward inhibitor design

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 22, 2010, Pages 6472-6474

  Zhao, Hong ^a   De Carvalho, Luiz Pedro S ^b   Nathan, Carl ^b   Ouerfelli, Ouathek ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b WEILL CORNELL MEDICAL COLLEGE   (United States)

Author keywords

2,3,5 Tribromo 3 methylthiophene; 3 Deazathiamine; 3 Deazathiamine synthesis; 3 Deazathiaminediphosphate; Deazathiamine

Indexed keywords

2 HYDROXY 3 OXOADIPATE SYNTHASE; 3 DEAZATHIAMINE; 3 DEAZATHIAMINE DIPHOSPHATE; ANTIINFECTIVE AGENT; BACTERIAL ENZYME; PYRIMIDINE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; IN VITRO STUDY;

AZA COMPOUNDS; ENZYME INHIBITORS; MAGNETIC RESONANCE SPECTROSCOPY; OXO-ACID-LYASES; THIAMINE;

EID: 77958053595     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.09.053     Document Type: Article

References (29)

1. S.E. Dorman, and R.E. Chaisson Nat. Med. 13 2007 295
2. S. Shenoi, and G. Friedland Annu. Rev. Med. 60 2009 307
3. C.E. Barry 3rd, H.I. Boshoff, V. Dartois, T. Dick, S. Ehrt, J. Flynn, D. Schnappinger, R.J. Wilkinson, and D. Young Nat. Rev. Microbiol. 7 2009 845
4. G.M. Cook, M. Berney, S. Gebhard, M. Heinemann, R.A. Cox, O. Danilchanka, and M. Niederweis Adv. Microbiol. Physiol. 55 2009 81 318-319
5. J. Tian, R. Bryk, M. Itoh, M. Suematsu, and C. Nathan Proc. Natl. Acad. Sci. U.S.A. 102 2005 10670
6. J.R. Guest Philos. Trans. R. Soc. London, Ser. B: Biol. Sci. 350 1995 189
7. L.P. de Carvalho, H. Zhao, C.E. Dickinson, N.M. Arango, C.D. Lima, S.M. Fischer, O. Ouerfelli, C. Nathan, and K.Y. Rhee Chem. Biol. 17 2010 323
8. M. Muller, D. Gocke, and M. Pohl FEBS J. 276 2009 2894
9. K. Tittmann FEBS J. 276 2009 2893
10. M. Mandal, and R.R. Breaker Nat. Rev. Mol. Cell Biol. 5 2004 451
11. W. Winkler, A. Nahvi, and R.R. Breaker Nature 419 2002 952
12. S. Thore, M. Leibundgut, and N. Ban Science 312 2006 1208
13. A. Serganov, A. Polonskaia, A.T. Phan, R.R. Breaker, and D.J. Patel Nature 441 2006 1167
14. A.S. Mironov, I. Gusarov, R. Rafikov, L.E. Lopez, K. Shatalin, R.A. Kreneva, D.A. Perumov, and E. Nudler Cell 111 2002 747
15. C.M. Sassetti, and E.J. Rubin Proc. Natl. Acad. Sci. U.S.A. 100 2003 12989
16. K. Agyei-Owusu, and F.J. Leeper FEBS J. 276 2009 2905
17. W.F. Fobare, W.R. Solvibile, A.J. Robichaud, M.S. Malamas, E. Manas, J. Turner, Y. Hu, E. Wagner, R. Chopra, R. Cowling, G. Jin, and J. Bard Bioorg. Med. Chem. Lett. 17 2007 5353
18. T.E. Edwards, and A.R. Ferre-D'Amare Structure 14 2006 1459
19. S. Mann, C. Perez Melero, D. Hawksley, and F.J. Leeper Org. Biomol. Chem. 2 2004 1732
20. K.M. Erixon, C.L. Dabalos, and F.J. Leeper Chem. Commun. (Camb) 2007 960
21. D. Hawksley, D.A. Griffin, and F.J. Leeper J. Chem. Soc., Perkin Trans. 1 2001 144
22. A.A. Thomas, J. De Meese, Y. Le Huerou, S.A. Boyd, T.T. Romoff, S.S. Gonzales, I. Gunawardana, T. Kaplan, F. Sullivan, K. Condroski, J.P. Lyssikatos, T.D. Aicher, J. Ballard, B. Bernat, W. DeWolf, M. Han, C. Lemieux, D. Smith, S. Weiler, S.K. Wright, G. Vigers, and B. Brandhuber Bioorg. Med. Chem. Lett. 18 2008 509
23. R.H. Mitchell, and V.S. Iyer J. Am. Chem. Soc. 118 1996 722
24. F.M. Piller, and P. Knochel Org. Lett. 11 2009 445
25. S. Dapperheld, M. Feldhues, H. Litterer, F. Sistig, and P. Wegener Synthesis 1990 403
26. J.W. Hull Jr., D.R. Romer, D.E. Podhorez, M.L. Ash, and C.H. Brady Beilstein J. Org. Chem. 3 2007 23
27. To insure absence of any regioisomer, we recommend the bidistillation of dibromide 4 and purification of alcohol 5. Should any regioisomer be present, we have found the desired aldehyde 6 to be chromatographically separable at this stage (please see Supplementary data section).
28. D.W. Slocum, and P.L. Gierer Chem. Commun. 7 1971 305
29. B. Roth, E. Aig, B.S. Rauckman, J.Z. Strelitz, A.P. Phillips, R. Ferone, S.R. Bushby, and C.W. Sigel J. Med. Chem. 24 1981 933