Design and synthesis of diketopiperazine and acyclic analogs related to the caprazamycins and liposidomycins as potential antibacterial agents

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 1, 2008, Pages 428-436

  Hirano, Shinpei ^a   Ichikawa, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Antibacterial; Caprazamycin; MraY; Translocase I

Indexed keywords

ALKYL GROUP; ANTIINFECTIVE AGENT; CAPRAZAMYCIN DERIVATIVE; GLYCINE DERIVATIVE; LIPOSIDOMYCIN DERIVATIVE; O PALMITOYL DEXTRO SERYLAMIDE; O PALMITOYLDIKETOPIPERAZINE; O PALMITOYLSERYLAMIDE; PIPERAZINEDIONE; RIBOSE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CORYNEBACTERIUM; CORYNEBACTERIUM BOVIS; DRUG DESIGN; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; LIPOPHILICITY; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; AZEPINES; DIKETOPIPERAZINES; DRUG DESIGN; LIPIDS; MICROBIAL SENSITIVITY TESTS; NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP; URIDINE;

EID: 38049092920     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.09.022     Document Type: Article

References (33)

1. Meka V.G., Pillai S.K., Sakoulas G., Wennersten C., Venkataraman L., DeGirolami P.C., Eliopoulos G.M., Moellering Jr. R.C., and Gold H.S. J. Infect. Dis. Drug Targets 190 (2004) 311-317
2. Igarashi M., Nakagawa N., Doi N., Hattori S., Naganawa H., and Hamada M. J. Antibiot. 56 (2003) 580-583
3. Takeuchi, T.; Igarashi, M.; Naganawa, H. JP P2003-12687A, 2003.
4. Isono K., Uramoto M., Kusakabe H., Kimura K., Izaki K., Nelson C.C., and McCloskey J.A. J. Antibiot. 38 (1985) 1617-1621
5. Kimura K., Ikeda Y., Kagami S., Yoshihama M., Suzuki K., Osada H., and Isono K. J. Antibiot. 51 (1998) 1099-1104
6. Ubukata M., Kimura K., Isono K., Nelson C.C., Gregson J.M., and McCloskey J.A. J. Org. Chem. 57 (1992) 6392-6403
7. Kimura K., Ikeda Y., Kagami S., Yoshihama M., Ubukata M., Esumi Y., Osada H., and Isono K. J. Antibiot. 51 (1998) 647-654
8. Kimura K., Kagami S., Ikeda Y., Takahashi H., Yoshihama M., Kusakabe H., Osada H., and Isono K. J. Antibiot. 124 (1998) 10260-10261
9. McDonald L.A., Barbieri L.R., Carter G.T., Lenoy E., Lotvin J., Petersen P.J., Siegel M.M., Singh G., and Williamson R.T. J. Am. Chem. Soc 124 (2002) 10260-10261
10. Ochi, K.; Ezaki, M.; Iwani, M.; Komori, T.; Kohsaka, M. EP-333177, 1989.
11. Yoshida, Y.; Yamanaka, H.; Sakane, K. JP H05-78385, 1993.
12. Boyle D.S., and Donachie W.D. J. Bacteriol. 180 (1998) 6429-6432
13. Bugg T.D.H., Lloyd A.J., and Roper D.I. J. Infect. Dis. Drug Targets 6 (2006) 85-106
14. Kimura K., and Bugg T.D.H. Nat. Prod. Rep. 20 (2003) 252-273
15. Ichikawa S., and Matsuda A. Expert Opin. Ther. Patents 17 (2007) 487-498
16. Dini C. Curr. Top. Med. Chem. 5 (2005) 1221-1236
17. Hyland S.A., and Anderson M.S. Anal. Biochem. 317 (2003) 156-164
18. Zawadzke L.E., Wu P., Cook L., Fan L., Casperson M., Kishinani M., Calambur D.S., Hofstead J., and Padmanabha R. Anal. Biochem. 314 (2003) 243-252
19. Stachyra T., Dini C., Ferrari P., Bouhss A., van Heijenoort J., Mengin-Lecreulx D., Blanot D., Biton J., and Belller D.L. Antimicrob. Agents Chemother. 48 (2004) 897-907
20. Yamashita A., Norton E., Petersen P.J., Rasmussen B.A., Singh G., Yang Y., Mansour T.S., and Ho D.M. Bioorg. Med. Chem. Lett. 13 (2003) 3345-3350
21. Sarabia F., and Martin-Ortiz L. Tetrahedron 61 (2005) 11850-11865
22. Yamashita A., Norton E.B., Williamson R.T., Ho D.M., Sinishtaj S., and Mansour T.S. Org. Lett. 5 (2003) 3305-3308
23. Dini C., Collette P., Drochon N., Guillot J.C., Lemoine G., Mauvais P., and Aszodi J. Bioorg. Med. Chem. Lett. 10 (2000) 1839-1843
24. Dini C., Drochon N., Guillot J.C., Mauvais P., Walter P., and Aszodi J. Bioorg. Med. Chem. Lett. 11 (2001) 533-536
25. Dini C., Drochon N., Feteanu S., Guillot J.C., Peixoto C., and Aszodi J. Bioorg. Med. Chem. Lett. 11 (2001) 529-531
26. Dini C., Didier-Laurent S., Drochon N., Fereanu S., Guillot J.C., Monti F., Uridat E., Zhang J., and Aszodi J. Bioorg. Med. Chem. Lett. 12 (2002) 1209-1213
27. For example:. Besada P., Mamedova L., Thomas C.J., Costanzi S., and Jacobson K.A. Org. Biomol. Chem. 3 (2005) 2016-2025
28. Fischer P.M. J. Pept. Sci. 9 (2003) 9-35
29. Szardenings A.K., Harris D., Lam S., Shi L., Tien D., Wang Y., Patel D.V., Navre M., and Campbell D.A. J. Med. Chem. 41 (1998) 2194-2200
30. Pons J.-F., Fauchere J.-L., Lamaty F., Molla A., and Lazaro R. Eur. J. Org. Chem. (1998) 853-859
31. Hirano S., Ichikawa S., and Matsuda A. Angew. Chem., Int. Ed. 44 (2005) 1854-1856
32. Hirano S., Ichikawa S., and Matsuda A. Tetrahedron 63 (2007) 2798-2804
33. Li H., Jiang X., Ye Y., Fan C., Romoff T., and Goodman M. Org. Lett. 1 (1999) 91-94