Holloway et al.
3. Yoshida M., Hedberg C., Kaiser M., Waldmann H. (2009) Trace-
less solid phase synthesis of natural product inspired cis-1,2-de-
hydrodecalins. Chem Commun (Camb);20:2926–2928.
4. Grabowski K., Schneider G. (2007) Properties and architecture
of drugs and natural products revisited. Curr Chem Biol;1:115–
127.
22. Bagwell C.L., Moloney M.G., Thompson A.L. (2008) On the anti-
biotic activity of oxazolomycin. Bioorg Med Chem Lett;18:4081–
4086.
23. Bagwell C.L., Moloney M.G., Yaqoob M. (2010) Oxazolomycins:
lead structures for novel antibiotics by click hybridisation. Bioorg
Med Chem Lett;20:2090–2094.
5. Gullo V.P., McAlpine J., Lam K.S., Baker D., Petersen F. (2006)
Drug discovery from natural products. J Ind Microbiol Biotech-
nol;33:523–531.
6. Rouhi A.M. (2003) The case for natural products research. Chem
Eng News;81:77–91.
7. Breinbauer R.B., Vetter I.R., Waldmann H. (2002) From protein
domains to drug candidates – Natural products as guiding prin-
ciples in the design and synthesis of compound libraries. Angew
Chem Int Ed Engl;41:2878.
8. Ganesan A. (2004) Natural products as a hunting ground for
combinatorial chemistry. Curr Opin Biotechnol;15:584–590.
9. Njardarson J.T., Gaul C., Shan D., Huang X.-Y., Danishefsky S.J.
(2004) Discovery of potent cell migration inhibitors through total
synthesis: lessons from structure-activity studies of (+)-migrasta-
tin. J Am Chem Soc;126:1038–1040.
10. vonNussbaum F., Brands M., Hinzen B., Weigand S., Habich D.
(2006) Antibacterial natural products in medicinal chemistry-exo-
dus or revival? Angew Chem Int Ed;45:5072–5129.
11. O'Shea R., Moser H.E. (2008) Physicochemical properties of anti-
bacterial compounds: implications for drug discovery. J Med
Chem;51:2871–2878.
12. Quinn R.J., Carroll A.R., Pham N.B., Baron P., Palframan M.E.,
Suraweera L., Pierens G.K., Muresan S. (2008) Developing a
drug-like natural product library. J Nat Prod;71:464–468.
13. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. (2001)
Experimental and computational approaches to estimate solubil-
ity and permeability in drug discovery and development settings.
Adv Drug Deliv Rev;46:3–26.
24. Rees D.C., Congreve M., Murray C.W., Carr R. (2004) Fragment-
based lead discovery. Nat Rev Drug Discov;3:660–672.
25. Congreve M., Carr R., Murray C., Jhoti H. (2003) A 'rule of three'
for fragment-based lead discovery? Drug Discov Today;8:876–877.
26. Feher M., Schmidt J.M. (2003) Property distributions: differences
between drugs, natural products, and molecules from combina-
torial chemistry. J Chem Inf Comput Sci;43:218–227.
27. Payne D.J., Gwynn M.N., Holmes D.J., Pompliano D.L. (2007)
Drugs for bad bugs: confronting the challenges of antibacterial
discovery. Nat Rev Drug Discov;6:29–40.
28. Seebach D., Sting A.R., Hoffmann M. (1996) Self-regeneration of
stereocenters (SRS) – applications, limitations, and abandonment
of a synthetic principle. Angew Chem Int Ed Engl;35:2708–2748.
29. Zimmer H., Hillstrom W.W., Schmidt J.C., Seemuth P.D., Vogelli
R. (1978) Substituted gamma-lactones 28. 3-(phenylmethylene)-
2,4(3h,5h)-furandiones. J Org Chem;43:1541.
30. Henning H.-G., Gelbin A. (1993) Advances in tetramic acid chem-
istry. Adv Heterocycl Chem;57:139.
ˇ
ˇ
ˇ
31. Pirc S., Bevk D., JakÐe R., Recnik S., Golic L., Golobic A., Meden
A., Stanovnik B., Svete J. (2005) Synthesis of N-substituted
3-aminomethylidenetetramic acids. Synthesis;17:2969–2988.
32. Selic L., Stanovnik B. (2001) Dimethylamine substitution in N,N-
dimethyl enamines. Synthesis of aplysinopsin analogues and 3-
aminotetrahydrocoumarin derivatives. Tetrahedron;57:3159–3164.
33. Nolte M.J., Steyn P.S., Wessels P.L. (1980) Structural investiga-
tions of 3-acylpyrrolidine-2,4-diones by nuclear magnetic-reso-
nance spectroscopy and X-ray crystallography. J Chem Soc,
Perkin Trans 1;1980:1057–1065.
14. Royles B.J.L. (1995) Naturally-occurring tetramic acids - struc-
ture, isolation, and synthesis. Chem Rev;95:1981–2001.
15. Jeong Y.-C., Moloney M.G. (2011) Synthesis of and tautomerism
in 3-acyltetramic acids. J Org Chem;76:1342–1354.
16. Andrews M.D., Brewster A.G., Crapnell K.M., Ibbett A.J., Jones
T., Moloney M.G., Prout G., Watkin D. (1998) Regioselective Die-
ckmann cyclisations leading to enantiopure highly functionalised
tetramic acid derivatives. J Chem Soc, Perkin Trans 1;1998:223–
235.
34. Cottrell I.F., Davis P.J., Moloney M.G. (2004) Stereoselective oxy-
genation of bicyclic lactams. Tetrahedron Asymmetry;15:1239–
1242.
35. Puri A.A., Bogyo M. (2009) Using small molecules to dissect
mechanisms of microbial pathogenesis. ACS Chem Biol;4:603–
616.
36. Frearson J.A., Collie I.T. (2009) HTS and hit finding in academia
– from chemical genomics to drug discovery. Drug Discov
Today;14:1150–1158.
17. Andrews M.D., Brewster A.G., Moloney M.G. (1996) Approaches
towards the pyroglutamate skeleton of oxazolomycin. Syn-
lett;1996:612–614.
37. Ferrara P., Apostolakis J., Caflisch A. (2002) Evaluation of a fast
implicit solvent model for molecular dynamics simulations. Pro-
teins;46:24–33.
18. Andrews M.D., Brewster A., Moloney M.G. (1994) A concise
approach to functionalized, homochiral tetramic acids. Tetrahe-
dron Asymmetry;5:1477–1478.
19. Anwar M., Cowley A.R., Moloney M.G. (2010) Novel chiral pyrro-
lidinone scaffolds derived from threonine with antibacterial
activity. Tetrahedron Asymmetry;21:1758–1770.
38. Ertl P., Rohde B., Selzer P. (2000) Fast calculation of molecular
polar surface area as a sum of fragment-based contributions
and its application to the prediction of drug transport properties.
J Med Chem;43:3714–3717.
39. Ertl P. (2007) Polar surface area. In: Mannhold R., editor. Polar
Surface Area. Weinheim: Wiley-VCH; p. 111–126.
20. Anwar M., Moloney M.G. (2007) Efficient enantioselective syn-
thesis of tetramic acids and lactams from threonine. Tetrahedron
Lett;48:7259–7262.
21. Jeong Y.-C., Moloney M.G. (2009) Tetramic acids as bioactive
templates: synthesis, tautomeric and antibacterial behaviour.
Synlett;15:2487–2491.
40. Gleeson M.P. (2008) Generation of a set of simple, interpretable
ADMET rules of thumb. J Med Chem;51:817–834.
41. Price D.A., Blagg J., Jones L., Greene N., Wager T. (2009)
Physicochemical drug properties associated with in vivo toxico-
logical outcomes: a review. Expert Opin Drug Metab Toxicol;
5:921–931.
234
Chem Biol Drug Des 2011; 78: 229–235