Synthesis and antibacterial activity of some binaphthyl-supported macrocycles containing a cationic amino acid

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 11, 2011, Pages 3549-3557

  Coghlan, Daniel R ^a   Bremner, John B ^a   Keller, Paul A ^a   Pyne, Stephen G ^a   David, Dorothy M ^a   Somphol, Kittiya ^a   Baylis, Dean ^b   Coates, Jonathan ^b   Deadman, John ^b   Rhodes, David I ^b   Robertson, Alan D ^c  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b Avexa Ltd   (Australia)

^c Formerly Amrad Corporation Ltd   (Australia)

Author keywords

Anti bacterial agents; Atropisomerism; Cyclic peptoids; Metathesis; S. aureus

Indexed keywords

1(3,3') 2,2' DIMETHOXY 1,1' BINAPHTHYLENA 3 ACETAMIDO 5,8 DIAZA 6 (3 GUANIDINOPROPYL) 9 METHOXYCARBONYL 4,7 DIOXOCYCLODODECAPHANE 11 ENE; 1(3,3') 2,2' DIMETHOXY 1,1' BINAPHTHYLENA 3 ACETAMIDO 5,8 DIAZA 6 [4 (TERT BUTOXYCARBONYLAMINO)BUTYL] 9 METHOXYCARBONYL 4,7 DIOXOCYCLOTRIDECAPHANE 11 ENE; 1(3,3') 2,2' DIMETHOXY 1,1' BINAPHTHYLENA 3 ACETAMIDO 5,8 DIAZA 6 [4 [[(9H FLUOREN 9 YL)METHOXY]CARBONYLAMINO]BUTYL] 9 METHOXYCARBONYL 4,7 DIOXOCYCLODODECAPHANE 11 ENE; 1(3,3') 2,2' DIMETHOXY 1,1' BINAPHTHYLENA 3 ACETAMIDO 5,8 DIAZA 9 METHOXYCARBONYL 6 [3 [3 (2,2,5,7,8 PENTAMETHYLCHROMAN 6 YLSULFONYL)GUANIDINE]PROPYL] 4,7 DIOXOCYCLODODECAPHANE 11 ENE; 1(3,3') 2,2' DIMETHOXY 1,1' BINAPHTHYLENA 3 ACETAMIDO 6 (4 AMINOBUTYL) 5,8 DIAZA 9 METHOXYCARBONYL 4,7 DIOXOCYCLOTRIDECAPHANE 11 ENE; 1(3,3') 2,2' DIMETHOXY 1,1' BINAPHTHYLENA 3 ACETAMIDO 9 (4 AMINOBUTYL) 8,11 DIAZA 12 METHOXYCARBONYL 5 METHYL 4,7,10 TRIOXOCYCLOHEXADECAPHANE 14 ENE; 2 ACETYLAMINO 3 [3 (3' ALLYL 2,2' DIMETHOXY 1,1' BINAPHTHYL)]PROPANOIC ACID; 2,2' DIMETHOXY 1,1' BINAPHTHYL; 2,2' DIMETHOXY 3 IODO 3' METHYL 1,1' BINAPHTHYL; 3 BROMOMETHYL 3' IODO 2,2' DIMETHOXY 1,1' BINAPHTHYL; 3 IODO 2,2' DIMETHOXY 3' METHYL 1,1' BINAPHTHYL; 3,3' DIIODO 2,2' DIMETHOXY 1,1' BINAPHTHYL; BINAPHTHYL DERIVATIVE; CARBOXYLIC ACID; ETHYL 2 ACETAMINO 3 [3 (2,2' DIMETHOXY 3' IODO 1,1' BINAPHTHYL)]PROPANOIC ACID; ETHYL 2 ACETYLAMINO 3 [3 (3' ALLYL 2,2' DIMETHOXY 1,1' BINAPHTHYL)]PROPANOIC ACID; ETHYL 2 AMINO 3 [3 (2,2' DIMETHOXY 3' IODO 1,1' BINAPHTHYL)]PROPANOIC ACID; ETHYL 2 AMINO 3 [3 (3' IODO 2,2' DIMETHOXY 1,1' BINAPHTHYL)]PROPANOIC ACID; ETHYL 3 [3 (3' IODO 2,2' DIMETHOXY 1,1' BINAPHTHYL)] 2 [(DIPHENYLMETHYLENE)AMINO]PROPANOIC ACIDE; MACROCYCLIC COMPOUND; METHYL 2 ALLYL 9 [2 (3' ALLYL 2,2' DIMETHOXY 1,1' BINAPHTHALEN 3 YL)] 5 [4 (TERT BUTOXYCARBONYLAMINO)BUTYL] 8 ACETAMIDO 3,6 DIAZA 4,7 DIOXONANOIC ACID; METHYL 2 ALLYL 9 [2 (3' ALLYL 2,2' DIMETHOXY 1,1' BINAPHTHALEN 3 YL)] 8 ACETAMIDO 3,6 DIAZA 4,7 DIOXO 5 [3 [3 (2,2,5,7,8 PENTAMETHYLCHROMAN 6 YLSULFONYL)GUANIDINE]PROPYL]NONANOIC ACID; METHYL 2 ALLYL 9 [2 (3' ALLYL 2,2' DIMETHOXY 1,1' BINAPHTHALEN 3 YL)] 8 ACETAMIDO 3,6 DIAZA 5 (3 GUANIDINOPROPYL) 4,7 DIOXONONANOIC ACID; METHYL 2 ALLYL 9 [2 (3' ALLYL 2,2' DIMETHOXY 1,1' BINAPHTHALEN 3 YL)] 8 ACETAMIDO 3,6 DIAZA 5 [4 [(9H FLUOREN 9 YL)METHOXYCARBONYLAMINO]BUTYL] 4,7 DIOXONONANOIC ACID; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; RING CLOSING METATHESIS; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

AMINO ACIDS; ANTI-BACTERIAL AGENTS; CATIONS; MACROCYCLIC COMPOUNDS; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS); STAPHYLOCOCCUS AUREUS;

EID: 79957471147     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.04.013     Document Type: Article

References (26)

1. P. Nordmann, T. Naas, N. Fortineau, and L. Poirel Curr. Opin. Microbiol. 10 2007 436
2. H.W. Boucher, G.H. Talbot, J.S. Bradley, J.E. Edwards, D. Gilbert, L.B. Rice, M. Scheld, B. Spellberg, and J. Bartlett Clin. Infect. Dis. 48 2009 1
3. G.L. French Int. J. Antimicrob. Agents Suppl. 3 2010 S3
4. G.D. Wright, and A.D. Sutherland Trends Mol. Med. 13 2007 260
5. D.P. Levine South. Med. J. 101 2008 284
6. D.M. Sievert, J.T. Rudrik, J.B. Patel, L.C. McDonald, M.J. Wilkins, and J.C. Hageman Clin. Infect. Dis. 46 2008 668
7. D. Kahne, C. Leimkuhler, W. Lu, and C. Walsh Chem. Rev. 105 2005 425
8. S.J. Projan, and P.A. Bradford Curr. Opin. Microbiol. 10 2007 441
9. J. Lu, O. Yoshida, S. Hayashi, and H. Arimoto Chem. Commun. 2007 251
10. N. Srinivas, K. Moehle, K. Abou-Hadeed, D. Obrecht, and J.A. Robinson Org. Biomol. Chem. 5 2007 3100
11. J.B. Bremner, J.A. Coates, D.R. Coghlan, D.M. David, P.A. Keller, and S.G. Pyne New J. Chem. 26 2002 1549
12. J.B. Bremner, J.A. Coates, P.A. Keller, S.G. Pyne, and H.M. Witchard Tetrahedron 59 2003 8741
13. J.B. Bremner, J.A. Coates, P.A. Keller, S.G. Pyne, and H.M. Witchard Synlett 2002 219
14. V.S. Au, J.B. Bremner, J. Coates, P.A. Keller, and S.G. Pyne Tetrahedron 62 2006 9373
15. T.P. Boyle, J.B. Bremner, J. Coates, J. Deadman, P.A. Keller, S.G. Pyne, and D.I. Rhodes Tetrahedron 64 2008 11270
16. J.B. Bremner, P.A. Keller, S.G. Pyne, A.D. Robertson, B.W. Skelton, A.H. White, and H.M. Witchard Aust. J. Chem. 53 2000 535
17. 1H NMR analysis. The macrocyclic free amines were also judged to be homogenous by TLC analysis and the subsequent salts were recrystallised.
18. We also attempted the stereoselective alkylation of the (S)-bromide 5 using the Seebach chiral imidazolidinone auxiliary, see D. Seebach, A.R. Sting, and M. Hoffmann Angew. Chem., Int. Ed. 35 1996 2708 In our hands, it gave modest yields of the desired alkylated product (∼50%) with subsequent hydrolysis being slow and not producing the required amino acid intermediate, but instead an unwanted amide
19. 13C NMR was not productive in the assignment of structure.
20. 1H NMR spectra were notably broad but were consistent with the assigned structures. Hence, a greater emphasis was placed on MS and in particular, HRMS, for elucidation of structure.
21. The synthesis of compounds 15, 20 and 1, were described previously, see Ref. 9.
22. For examples of typical procedures used, see Ref. 9 and Bremner, J. B.; Pyne, S. G.; Keller, P. A.; Coghlan, D. R.; Garas, A.; Witchard, H. M.; Boyle, T. P.; Coates, J. A. WO 03/002545 A1, Patent, Peptoid Compounds, AU2002/00850 2003.
23. The E/Z mixture arises from the RCM reaction and the ratio is unknown due to the lack of resolution of the NMR spectra (see Ref. 18).
24. A. Garas, J.B. Bremner, J. Coates, J. Deadman, P.A. Keller, S.G. Pyne, and D.I. Rhodes Bioorg. Med. Chem. Lett. 19 2009 3010
25. J.B. Bremner, P.A. Keller, S.G. Pyne, T.P. Boyle, Z. Brkic, D.M. David, A. Garas, J. Morgan, M. Robertson, K. Somphol, P. Ambrose, S. Bhavnani, T.R. Fritsche, D.J. Biedenbach, R.N. Jones, M.H. Miller, R.W. Buckheit Jr., K.M. Watson, D. Baylis, J.A. Coates, J. Deadman, D. Jeevarajah, A. McCracken, and D.I. Rhodes Angew. Chem., Int. Ed. 49 2010 537
26. The presence of diastereomers and rotamers accounts for the excess peaks appearing in the NMR spectra.