Synthesis and antibacterial activity of O-substituted nocathiacin I derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 14, 2004, Pages 3743-3746

  Naidu, B Narasimhulu ^a   Sorenson, Margaret E ^a   Hudyma, Thomas ^a   Zheng, Xiaofan ^a   Zhang, Yunhui ^a   Bronson, Joanne J ^a   Pucci, Michael J ^a   Clark, Junius M ^a   Ueda, Yasutsugu ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Antibacterial activity; Natural product; Nocathiacin

Indexed keywords

ANTIINFECTIVE AGENT; THIAZOLE DERIVATIVE; WATER;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG SOLUBILITY; DRUG SYNTHESIS; SOLUBILIZATION; SUBSTITUTION REACTION;

ANTI-BACTERIAL AGENTS; ENTEROCOCCUS FAECALIS; MICROBIAL SENSITIVITY TESTS; PEPTIDES; SOLUBILITY; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 2942568115     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.04.102     Document Type: Article

References (19)

1. Niccolai D., Tarsi L., Thomas R. J. Chem. Commun. 1997;2333-2342
2. Chu D.T.W., Plattner J.J., Katz L. J. Med. Chem. 39:1996;3853-3874
3. Chavers L.S., Moser S.A., Benjamin W.H., Banks S.E., Steinhauer J.R., Smith A.M., Johnson C.N., Funkhouser E., Chavers L.P., Stamm A.M., Waites K.B. J. Hosp. Infect. 53:2003;159-171
4. Hiramatsu K. Lancet Infect. Dis. 1:2001;147-155
5. Li W., Leet J.E., Ax H.A., Gustavson D.R., Brown D.M., Turner L., Brown K., Clark J., Yang H., Fung-Tomc J., Lam K.S. J. Antibiot. 56:2003;226-231
6. Leet J.E., Li W., Ax H.A., Matson J.A., Huang S., Huang R., Cantone J.L., Drexler D., Dalterio R.A., Lam K.S. J. Antibiot. 56:2003;232-242
7. Sasaki T., Otani T., Matsumoto H., Unemi N., Hamada M., Takeuchi T., Hori M. J. Antibiot. 8:1998;715-721
8. Xing Y.Y., Draper D.E. Biochemistry. 35:1996;1581-1588
9. Heffron S.E., Jurnak F. Biochemistry. 39:2000;37-45
10. Ueda, Y.; Barrett, J. DenBleyker, K.; Fung-Tomc, J.; Discotto, L.; Stickle, T.; Kolek, B.; Pucci, M. Abstracts of Papers, 43rd Annual ICAAC Meeting, Chicago, IL, September 14-17, 2003; American Society for Microbiology: Washington, DC, F-1842
11. Yang, H.; Chaniewski, S.; Clark, J.; Ferraro, C.; Gali, V.; Lamb, L.; Medina, I. Abstracts of Papers, 43rd Annual ICAAC Meeting, Chicago, IL, September 14-17, 2003; American Society for Microbiology: Washington, DC, B-319
12. Regueiro-Ren A., Naidu B.N., Zheng X., Hudyma T.W., Connolly T.P., Matiskella J.D., Zhang Y., Kim O.K., Sorenson M.E., Pucci M., Clark J., Bronson J.J., Ueda Y. Bioorg. Med. Chem. Lett. 14:2004;171-175
13. Hrnciar P., Ueda Y., Huang S., Leet J.E., Bronson J.J. J. Org. Chem. 67:2002;8789-8793
14. The regiochemistry of the O-substitution is assigned using the UV absorption data. The nocathiacins with free pyridyl hydroxyl group showed bathochromic shift when the pH of solution is changed from an ambient pH to basic. Whereas nocathiacins with pyridyl hydroxyl group blocked with a substituent had no significant change in the UV absorption when the pH of the solution is changed from an ambient pH to basic. Also, see Ref. [5a] for regiochemical determination of O-alkylated nocathiacins using NMR data
15. 5 (M+H): 1620.426.; found 1620.428
16. 5 (M+H): 1515.276; found 1515.272
17. 5 (M + H): 1579.248; found 1579.245
18. 5 CFU/well and was run on microtiter plates. The volume of each well was 100 μL and the plates were inoculated at 35°C for 18 h in ambient air. The MIC was defined as the lowest drug concentration that prevented visible growth of the bacteria
19. 50s) of the drug-treated animals were determined by the Spearman-Karber nonparametric estimator method. Each experimental group consisted of 10 animals and a minimum of three different concentrations of drug was evaluated per compound