Synthesis of carbazole-linked cyclic and acyclic peptoids with antibacterial activity

Tetrahedron

Volumn 59, Issue 44, 2003, Pages 8741-8755

  Bremner, John B ^a   Coates, Jonathan A ^b   Keller, Paul A ^a   Pyne, Stephen G ^a   Witchard, Helen M ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b Zenyth Therapeutics Limited Australia   (Australia)

Author keywords

Antibacterial; Carbazole; Cyclic peptide; Ring closing metathesis

Indexed keywords

6 ACETAMIDO 8,11 DIAZA 9 (3 GUANIDINOPROPYL) 12 METHOXYCARBONYL 7,10 DIOXO[12](4,17)CARBAZOLO 14 PHENE; 6 ACETAMIDO 8,11 DIAZA 9 (3 GUANIDINOPROPYL) 12 METHOXYCARBONYL 7,10 DIOXO[12](4,17)CARBAZOLOPHANE; 6 ACETAMIDO 8,11 DIAZA 9 [3 (GUANIDINO)PROPYL] 12 METHOXYCARBONYL 7,10 DIOXO[12](4,17)CARBAZOLOPHANE; 6 ACETAMIDO 8,11 DIAZA 9 [3 (GUANIDINO)PROPYL] 12 METHOXYCARBONYL 7,10 DIOXO[12](4,7)CARBAZOLO 14 PHENE; 6 ACETAMIDO 9 (4 AMINOBUTYL) 8,11 DIAZA 1 TERT BUTOXYCARBONYL 12 METHOXYCARBONYL 7,10 DIOXO[12](4,17)CARBAZOLO 14 PHENE; 6 ACETAMIDO 9 (4 AMINOBUTYL) 8,11 DIAZA 12 METHOXYCARBONYL 7,10 DIOXO[12](4,17)CARBAZOLO 14 PHENE; 6 ACETAMIDO 9 (4 AMINOBUTYL) 8,11 DIAZA 12 METHOXYCARBONYL 7,10 DIOXO[12](4,17)CARBAZOLOPHANE; 8 ACETAMIDO 3,6 DIAZA 5 (3 GUANIDINOPROPYL) 4,7 DIOXO 2 PROPYL 9 (6 PROPYL 9H CARBAZOL 3 YL)NONANOATE; CARBAZOLE DERIVATIVE; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; RING CLOSING METATHESIS; STAPHYLOCOCCUS AUREUS;

STAPHYLOCOCCUS; STAPHYLOCOCCUS AUREUS;

EID: 0141961826     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.034     Document Type: Article

References (24)

1. Uttley A.H.C., Collins C.H., Naidoo J., George R.C. Lancet. 1:1988;57.
2. (a) Pegues D.A., Pegues C.F., Hibberd P.L., Ford D.S., Hooper D.C. J. Clin. Microbiol. 35:1997;1565
3. (b) Elsner H.A., Sobottka I., Feucht H.H., Harps E., Haun C., Mack D., Ganschow R., Laufs R., Kaulfers P.M. Int. J. Hyg. Environ. Health. 203:2000;147.
4. (a) Ariza J., Pujol M., Cabo J., Pena C., Fernandez N., Linares J., Ayats J., Gudiol F. Lancet. 353:1999;1587
5. (b) Smith T.L., Pearson M.L., Wilcox K.R., Cruz C., Lancaster M.V., Robinson-Dunn B., Tenover F.C., Zervos M.J., Band J.D., White E., Jarvis W.R.N. Engng J. Med. 340:1999;493
6. (c) CDC Report Morbidity and Mortality Weekly Report, 2002, 51, 902.
7. Tsiodras S., Gold H.S., Sakoulas G., Eliopoulos G.M., Wennersten C., Venkataraman L., Moellering R.C. Jr., Ferraro M.J. Lancet. 358:2001;207.
8. Gonzales R.D., Schreckenberger P.C., Graham M.B., Kelkar S., DenBesten K., Quinn J.P. Lancet. 357:2001;1179.
9. Arthur M., Courvalin P. Antimicrob. Agents Chemother. 37:1993;1563.
10. Williams D.H., Bardsley B. Angew. Chem. Int. Ed. 38:1999;1172.
11. Bremner J.B., Coates J.A., Coghlan D.R., David D.M., Keller P.A., Pyne S.G. New J. Chem. 26:2002;1549.
12. Bremner J.B., Coates J.A., Keller P.A., Pyne S.G., Witchard H.M. Synlett. 2002;219.
13. Yamamoto H. J. Org. Chem. 32:1967;3693.
14. Hayakawa K., Yasukouchi T., Kanematsu K. Tetrahedron Lett. 27:1986;1837.
15. Lygo B. Tetrahedron Lett. 40:1999;1389.
16. Lenna M.R., Morton H.E. Tetrahedron Lett. 34:1993;4485.
17. Krapcho A.P., Weimaster J.F. J. Org. Chem. 45:1980;4105.
18. Cummins C.H. Tetrahedron Lett. 35:1994;857.
19. Corey E.J., Narasaka K., Shibasaki M. J. Am. Chem. Soc. 98:1976;6417.
20. (a) Schwab P., Grubbs R.H., Ziller J.W. J. Am. Chem. Soc. 118:1996;100.
21. (b) For examples of ring-closing metathesis of peptoid-based systems with newer generation catalysts, see: Blackwell H.E., Sadowsky J.D., Howard R.J., Sampson J.N., Chao J.A., Steinmetz W.E., O'Leary D.J., Grubbs R.H. J. Org. Chem. 66:2001;5291.
22. For a review of Grubbs' metathesis reactions, see Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2036.
23. (a) Crews P., Rodríguez J., Jaspars M. Organic Structure Analysis. 1998;Oxford University, Oxford. pp 78
24. (b) Dominique R., Das S.K., Roy R. Chem. Commun. 1998;2437-2438.