Substituted 2,5-diazabicyclo[4.1.0]heptanes and their application as general piperazine surrogates: synthesis and biological activity of a Ciprofloxacin analogue

Tetrahedron

Volumn 66, Issue 18, 2010, Pages 3370-3377

  Taylor, Rivka R R ^a   Twin, Heather C ^a   Wen, Wendy W ^a   Mallot, Rebecca J ^a   Lough, Alan J ^a   Gray Owen, Scott D ^a   Batey, Robert A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

2,5 Diazabicyclo 4.1.0 heptanes; Cyclopropanation; Enamide; Piperazine heterocycle analogues; Quinolone antibiotic

Indexed keywords

CIPROFLOXACIN; CIPROFLOXACIN DERIVATIVE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; SIMMONS SMITH REACTION; X RAY CRYSTALLOGRAPHY;

EID: 77950459873     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.02.046     Document Type: Article

References (61)

1. Pitt W.R., Parry D.M., Perry D.G., and Groom C.R. J. Med. Chem. 52 (2009) 2952-2963
2. Gleeson M.P. J. Med. Chem. 51 (2008) 817-834
3. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Delivery Rev. 23 (1997) 3-25
4. Keller T.H., Pichota A., and Yin Z. Curr. Opin. Chem. Biol. 10 (2006) 357-361
5. Determined by a survey of all new drugs approved by the FDA between the years 1998-2009. Accessed at http://www.accessdata.fda.gov/Scripts/cder/DrugsatFDA/index.cfm?fuseacti on=Reports.ReportsMenu.
6. De Pol S., Zorn C., Klein C.D., Zerbe O., and Reiser O. Angew. Chem., Int. Ed. 43 (2004) 511-514
7. Reichelt A., Gaul C., Frey R.R., Kennedy A., and Martin S.F. J. Org. Chem. 67 (2002) 4062-4075
8. Witiak D.T., Lee H.J., Goldman D., and Zwilling B.S. J. Med. Chem. 21 (1978) 1194-1197
9. Yang D., Ke S., Audinot V., Millan M.-J., and Langlois M. Bioorg. Med. Chem. 8 (2000) 321-327
10. Millar B.C., Jenkins T.C., Smithen C.E., and Jinks S. Radiat. Res. 101 (1985) 111-122
11. Reddy K.F., Valasinas A., Sarkar A., Basu H.S., Marton L.J., and Frydman B. J. Med. Chem. 41 (1998) 4723-4732
12. Frydman B., Blokhin A.V., Brummel S., Wilding G., Maxuitenko Y., Sarkar A., Bhattacharya S., Church D., Reddy V.K., Kink J.A., Marton L.J., Valasinas A., and Basu H.S. J. Med. Chem. 46 (2003) 4586-4600
13. 1H NMR spectroscopy. See:. Majchrzak M.W., Kotelko A., and Lambert J.B. J. Heterocycl. Chem. 20 (1983) 815-817
14. Rare examples of the 2,5-diazabicyclo[4.1.0]heptane core embedded within larger structures are also known. See:
15. Zoellinger M., Kelter G., Fiebig H.-H., and Lindel T. Bioorg. Med. Chem. Lett. 17 (2007) 346-349
16. Wai, J. S.; Vacca, J. P.; Zhuang, L.; Kim, B.; Lyle, T. A.; Wiscount, C. M.; Egbertson, M. S.; Neilson, L. A.; Embrey, M.; Fisher, T. E.; Staas, D. D. Patent WO 2005/110414 A2, 2005;
17. Williams, P. D.; Wai, J. S.; Embrey, M. W.; Staas, D. D.; Zhuang, L.; Langford, H. M. Patent WO 2005/092099 A1, 2005;
18. Wai, J. S.; Kim, B.; Fisher, T. E.; Zhuang, L.; Williams, P. D.; Lyle, T. A.; Langford, H. M.; Robinson, K. A. Patent WO 2004/024078 A2, 2004;
19. Mellor J.M., Pons B.S., and Stibbard J.H.A. J. Chem. Soc., Perkin Trans. 1 (1981) 3097-3100
20. Mellor J.M., Pons B.S., and Stibbard J.H.A. J. Chem. Soc., Chem. Commun. (1979) 761-762
21. 2-Ketopiperazine is commercially available, however, we prepared it on a multigram scale in 45% yield by treatment of ethyl chloroacetate with an excess of ethylenediamine. See:. Aspinal S.R. J. Am. Chem. Soc. 62 (1940) 1202-1204
22. Armstrong R.W., and Maurer K.W. Tetrahedron Lett. 36 (1995) 357-360
23. Song Z., Lu T., Hsung H.P., Al-Rashid Z.F., Ko C., and Tang Y. Angew. Chem., Int. Ed. 46 (2007) 4069-4072
24. Sheppeck J.E., Kar H., and Hong H. Tetrahedron Lett. 41 (2000) 5329-5333
25. Caner H., Groner E., Levy L., and Agranat I. Drug Discov. Today 9 (2004) 105-110
26. Bhanot S.K., Singh M., and Chatterjee N.R. Curr. Pharm. Des. 7 (2001) 311-335
27. Wise R., Andrews J.M., and Edwards L.J. Antimicrob. Agents Chemother. 23 (1983) 559-564
28. Scholar E.M., and Pratt W.B. The Antimicrobial Drugs. 2nd ed. (2000), Oxford University Press, New York, NY
29. Thornsberry C., Marsilio M.K., Jones M.E., Tomfohrde K.M., Heller B.H., Piazza G., and Sahm D.F. Drugs 58 (1999) 186-187
30. Piddock L.J.V. Antimicrob. Agents Chemother. 38 (1994) 163-169
31. Rice L.B. Am. J. Infect. Control 34 (2006) S11-S19
32. Eliopoulos G.M. Drugs 58 (1999) 23-28
33. Oliphant C.M., and Green G.M. Am. Fam. Physician 65 (2002) 455-464
34. Green S.D.R., Ilunga F., Cheesbrough J.S., Tillotson G.S., Hichens M., and Felmingham D. J. Infect. 26 (1993) 253-256
35. Karginov V.A., Robinson T.M., Riemenschneider J., Golding B., Kennedy M., Shiloach J., and Alibek K. FEMS Immunol. Med. Microbiol. 40 (2004) 71-74
36. Hooper D.C. Drugs 58 (1999) 6-10
37. Zhi C., Long Z., Manikowski A., Comstock J., Xu W., Brown N.C., Tarantino P.M., Holm K.A., Dix E.J., Wright G.E., Barnes M.H., Butler M.M., Foster K.A., LaMarr W.A., Bachand B., Bethell R., Cadilhac C., Charron S., Lamothe S., Motorina I., and Storer R. J. Med. Chem. 49 (2006) 1455-1465
38. Chu D.T.W., and Fernandes P. Antimicrob. Agents Chemother. 33 (1989) 131-135
39. Gootz T.D., and Brighty K.E. Med. Res. Rev. 16 (1996) 433-486
40. Lutsar I., McCracken G.H., and Friedland I.R. Clin. Infect. Dis. 27 (1998) 1117-1129
41. Kalkote U.R., Sathe V.T., Kharul R.K., Chavan S.P., and Ravindranathan T. Tetrahedron Lett. 37 (1996) 6785-6786
42. Hermecz I., Vasvari-Debreczy L., Podanyi B., Kereszturi G., Balogh M., Horvath A., and Varkonyi P. Heterocycles 48 (1998) 1111-1116
43. Wolfe J.P., Wagaw S., Marcoux J., and Buchwald S.L. Acc. Chem. Res. 31 (1998) 805-818
44. Sowa J.R., Simeone J.P., Hayden S., Brinkman R., Kodah J., Brice J., and Villoresi A. Chem. Ind. 89 (2003) 405-414
45. MIC was defined as the lowest concentration of compound that inhibits visible growth, and MBC was defined as the lowest concentration of compound that prevents visible growth.
46. + derivative of MS11, clinical isolate from the endocervix), N. meningitidis MC58 (clinical isolate from an invasive meningitis infection, serotype B), H. influenzae 1128 (clinical isolate from a child with otitis media).
47. Hooper D.C. Quinolone Antimicrobial Agents. 3rd ed. (2003), ASM, Washington, DC
48. Andrews J.M. J. Antimicrob. Chemother. 48 (2001) 5-16
49. Hutt A.J., and O'Grady J. J. Antimicrob. Chemother. 37 (1996) 7-32
50. Turel I., and Golobic A. Anal. Sci. 19 (2003) 329-330
51. a determination experiments. The hydrochloride salt, N-Cbz piperazine·HCl, was prepared by standard methods. Larkins H.L., and Hamilton A. Tetrahedron Lett. 27 (1986) 2721-2724
52. Perrin C.L., and Fabian M.A. Anal. Chem. 68 (1996) 2127-2134
53. See Supplementary data for a detailed procedure.
54. Hall Jr. H.K. J. Am. Chem. Soc. 79 (1957) 5441-5444
55. Roberts J.D., and Chambers V.C. J. Am. Chem. Soc. 73 (1951) 5030-5034
56. Cook A.G., Absi M.L., and Bowden V.K. J. Org. Chem. 60 (1995) 3169-3171
57. Alghasham A.A., and Nahata M.C. Ann. Pharmacother. 33 (1999) 48-60
58. Barbosa J., Barron D., Cano J., Jimenez-Lozano E., Sanz-Nebot V., and Toro I. J. Pharm. Biomed. Anal. 24 (2001) 1087-1098
59. a's relative to those in Trovafloxacin.
60. Rosenthal T.B. J. Biol. Chem. 173 (1948) 25-30
61. 2=H) were calculated as -1.48 and -1.27, respectively. C log P values for N-Cbz piperazine and 16 were calculated as 2.49 and 2.71, respectively. C log P values for Ciprofloxacin and 17 were calculated as -0.73 and -0.51, respectively (Chem. Draw Ultra 11.0.1).