New cyclic peptides via ring-closing metathesis reactions and their anti-bacterial activities

Tetrahedron

Volumn 64, Issue 49, 2008, Pages 11270-11290

  Boyle, Timothy P ^a   Bremner, John B ^a   Coates, Jonathan ^b   Deadman, John ^b   Keller, Paul A ^a   Pyne, Stephen G ^a   Rhodes, David I ^b  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b Avexa Ltd   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

13 ACETAMIDO 10 (4 AMINOBUTYL) 8,11 DIAZA 7 METHOXYCARBONYL 2 OXA 9,12 DIOXO 1(1,4)PHENYL ENACYCLOTETRADECAPHANE 4 ENE; 13 ACETAMIDO 8,11 10 (3 [{2,2,5,7,8 PENTAMETHYL 3,4 DIHYDRO 2H 6 CHROMENYLSULFONYL} GUANIDINO]PROPYL) 7 METHOXYCARBONYL 2 OXA 9,12 DIOXO 1(1,4)PHENYLENACYCLOTETRADECAPHANE 4 ENE; 13 ACETAMIDO 8,11 DIAZA 10 (3 [AMINO{IMINO}METHYLAMINO]PROPYL) 7 METHOXYCARBONYL 2 OXA 9,12 DIOXO 1(1,4)PHENYLENACYCLOTETRADECAPHANE 4 ENE; 13 ACETAMIDO 8,11 DIAZA 10 (3 [GUANIDINO]PROPYL) 7 METHOXYCARBONYL 2 OXA 9,12 DIOXO 1(1,4)PHENYLENACYCLOTETRADECAPHANE 4 ENE; 13 ACETAMIDO 8,11 DIAZA 10 (3 [{2,2,5,7,8 PENTAMETHYL 3,4 DIHYDRO 2H 6 CHROMENYLSULFONYL}GUANIDINO] PROPYL) 7 METHOXYCARBONYL 2 OXA 9,12 DIOXO 1(1,4) PHENYLENACYCLOTETRADECAPHANE 4 ENE; 13 ACETAMIDO 8,11 DIAZA 10 (3 IMINO [{2,2,5,7,8 PENTAMETHYL 3,4 DIHYDRO 2H 6 CHRONEMYLSULFONYL} GUANIDINO]PROPYL) 7 METHOXYCARBONYL 2 OXA 9,12 DIOXO 1(1,4)PHENYLENACYCLOTETRADECAPHANE 4 ENE; 13 ACETAMIDO 8,11 DIAZA 10 (3[{2,2,5,7,8 PENTAMETHYL 3,4 DIHYDRO 2H 6 CHROMENYLSULFONYL}GUANIDINO] PROPYL) 7 METHOXYCARBONYL 2 OXA 9,12 DIOXO 1(1,4) PHENYLENACYCLOTETRADECAPHANE 4 ENE; 13 ACETAMIDO 8,11 DIAZA 10 (4 [TERT BUTOXYCARBOXAMIDO]BUTYL) 7 METHOXYCARBONYL 2 OXA 9,12 DIOXO 1(1,4)PHENYLENACYCLOTETRADECAPHANE 4 ENE; 13 ACETAMIDO 8,11 DIAZA 10 (4 [TERT BUTOXYCARBOZAMIDO]BUTYL) 7 METHOXYCARBONYL 2 OXA 9,12 DIOXO 1(1,4)PHENYLENACYCLOTETRADECAPHANE 4 ENE; 2 ACETAMIDO 3 (4 ALLYLOXYPHENYL) PROPANOATE; 2 ACETAMIDO 3 (4 ALLYLOXYPHENYL)PROPANOATE; 2 ACETAMIDO 3 (4 ALLYLOXYPHENYL)PROPANOIC ACID; 2 ACETAMIDO 3 (4 HYDROXYPHENYL)PROPANOATE; 2 ALLYL 3 AZA 5 (9H 9 FLUORENYLMETHYL OXYCARBOXAMIDO) 8 (GUANIDINO) 4 OXOOCTANOATE; 2 ALLYL 3 AZA 5 (9H 9 FLUORENYLMETHYLOXYCARBOXAMIDO) 8 [(2,2,5,7,8 PENTAMETHYL 3,4 DIHYDRO 2H 6 CHROME NYLSULFONYL)GUANIDINO] 4 OXOOCTANOATE; 2 ALLYL 3 AZA 5 (9H 9 FLUORENYLMETHYLOXYCARBOXAMIDO) 8 [(2,2,5,7,8 PENTAMETHYL 3,4 DIHYDRO 2H 6 CHROMENYLSULFONYL)GUANIDINO] 4 OXOOCTANOATE; 2 ALLYL 3 AZA 9 (TERT BUTOXYCARBOXAMIDO) 5 (9H 9 FLUORENYLMETHYLOXYCARBOXAMIDO) 4 OXONONANOATE; 2 ALLYL 3 AZA 9 (TERT BUTOXYCARBOXAMIDO) 5 (9H 9 FLUOROMETHYLOXYCARBOXAMIDO) 4 OXONONANOATE; 2 ALLYL 5 AMINO 3 AZA 8 [(2,2,5,7,8 PENTAMETHYL 3,4 DIHYDRO 2H 6 CHROMENYLSULFONYL)GUANIDINO] 4 OXOOCTANOATE; 2 ALLYL 5 AMINO 3 AZA 8 [(2,2,5,7,8 PENTAMETHYL 3,4 DUHYDRO 2H 6 CHROMENYLSULFONYL)GUANIDINO] 4 OXOOCTANOATE; 2 ALLYL 5 AMINO 3 AZA 9 (TERT BUTOXYCARBOXAMIDO) 4 OXONANOATE; 2 ALLYL 5 AMINO 3 AZA 9 (TERT BUTOXYCARBOXAMIDO) 4 OXONONANOATE; 2 ALLYL 8 (4 ALLYLOXYBENZYL) 3,6,9 TRIAZA 5 (4 [TERT BUTOXYCARBOXAMIDO]BUTYL) 4,7,10 TRIOXOUNDECANOATE; 2 ALLYL 8 (4 ALLYLOXYBENZYL) 3,6,9 TRIAZA 5 ([{2,2,5,7,8 PENTAMETHYL 3,4 DIHYDRO 2H 6 CHROMENYLSULFONYL} GUANIDINO]PROPYL) 4,7,10 TRIOXOUNDECANOATE; 2 ALLYL 8 (4 ALLYLOXYPHENYL) 5 (4 AMINOBUTYL) 3,6,9 TRIAZA 4,7,10 TRIOXOUNDECANOATE; 2 AMINO (4 HYDROXYPHENYL) 2 PROPANOATE; 2 AMINO 4 PENTENOATE; CYCLOPEPTIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; STAPHYLOCOCCUS AUREUS;

BACTERIA (MICROORGANISMS); STAPHYLOCOCCUS AUREUS;

EID: 54549104576     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.031     Document Type: Article

References (25)

1. Nordmann P., Naas T., Fortineau N., and Poirel L. Curr. Opin. Microbiol. 10 (2007) 436-440
2. Neu H.C. Science 257 (1992) 1064-1072
3. Daly J.S., Eliopoulos G.M., Willey S., and Moellering Jr. R.C. Antimicrob. Agents Chemother. 32 (1988) 1341-1346
4. Tsiodras S., Gold H.S., Sakoulas G., Eliopoulos G.M., Wennersten C., Venkataraman L., Moellering R.C., and Ferraro M.J. Lancet 358 (2001) 207-208
5. Gonzales R.D., Schreckenberger P.C., Graham M.B., Kelkar S., DenBesten K., and Quinn J.P. Lancet 357 (2001) 1179
6. Levy S.B., and Marshall B. Nat. Med. (2004) S122-S129
7. Appelbaum P.C. Clin. Microbiol. Infect. 12 (2006) 16-23
8. Sievert D.M. Morb. Mortal. Wkly. Rep. 51 (2002) 565-567
9. Bremner J.B., Coates J.A., Coghlan D.R., David D.M., Keller P.A., and Pyne S.G. New J. Chem. 26 (2002) 1549-1552
10. Bremner J.B., Coates J.A., Keller P.A., Pyne S.G., and Witchard H.M. Synlett (2002) 219-222
11. Bremner J.B., Coates J.A., Keller P.A., Pyne S.G., and Witchard H.M. Tetrahedron 59 (2003) 8741-8755
12. Au V.S., Bremner J.B., Coates J.A., Keller P.A., and Pyne S.G. Tetrahedron 62 (2006) 9373-9382
13. Bremner J.B., Keller P.A., Pyne S.G., Robertson A.D., Skelton B.W., White A.H., and Witchard H.M. Aust. J. Chem. 53 (2000) 535-540
14. Deiters A., and Martin S.F. Chem. Rev. 104 (2004) 2199-2238
15. McGrady K.A.W., and Overberger C.G. Polym. J. 19 (1987) 539-555
16. 1H NMR spectrum of compounds featuring l-Lys as the cationic residue. The inclusion of HOBt resulted in no epimerization being observed. This occurred in the synthesis of cyclic peptides 11, 44 and 62-63 and their associated cyclic and acyclic precursors. The majority of our cyclic peptides (45-49) and their associated cyclic and acyclic precursors had only one epimer present. Given the final outcome of the anti-bacterial activity, we concluded that the presence of the epimer in our initial examples was unlikely to affect the activity and these were not resynthesized.
17. Luening B., Norberg T., and Tejbrant J. J. Chem. Soc., Chem. Commun. (1989) 1267-1268
18. Strom M.B., Haug B.E., Skar M.L., Stensen W., Stiberg T., and Svendsen J.S. J. Med. Chem. 46 (2003) 1567-1570
19. Hellwinkel D. Systematic Nomenclature of Organic Chemistry. 1st ed. (2001), Springer, Berlin
20. Tous G., Bush A., Tous A., and Jordan F. J. Med. Chem. 33 (1990) 1620-1634
21. Pearson A.J., and Bruhn P.R. J. Org. Chem. 56 (1991) 7092-7097
22. Meyer L., Poirier J.-M., Duhamel P., and Duhamel L. J. Org. Chem. 63 (1998) 8094-8095
23. Erickson S.D., Simon J.A., and Still W.C. J. Org. Chem. 58 (1993) 1305-1308
24. Gamet J.P., Jacquier R., and Verducci J. Tetrahedron 40 (1984) 1995-2001
25. Pirrung M.C., and Shuey S.W. J. Org. Chem. 59 (1994) 3890-3897