Total synthesis and biological evaluation of tambjamine K and a library of unnatural analogs

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 17, 2010, Pages 5207-5211

  Aldrich, Leslie N ^a   Stoops, Sydney L ^b   Crews, Brenda C ^b   Marnett, Lawrence J ^a,b   Lindsley, Craig W ^a,b  

^a VANDERBILT UNIVERSITY   (United States)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Cancer; Tambjamine; Total synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; MARINEOSIN A; NATURAL PRODUCT; PRODIGIOSIN; TAMBJAMINE K; TAMBJAMINE K DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL INVASION; CELL PROLIFERATION; CELL VIABILITY; CYTOTOXICITY; DIELS ALDER REACTION; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; IC 50;

CELL LINE, TUMOR; DRUG EVALUATION, PRECLINICAL; HUMANS; PYRROLES;

EID: 77955714294     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.06.154     Document Type: Article

References (21)

1. B. Carte, and D.J. Faulkner J. Org. Chem. 48 1983 2314
2. N. Lindquist, and W. Fenical Experientia 47 1991 504
3. R. Kazlauskas, J.F. Marwood, P.T. Murphy, and R.J. Wells Aust. J. Chem. 35 1982 215
4. F. Wrede, and O. Hettche Ber. Dtsch. Chem. Ges. B. 62 1929 2678
5. H.H. Wasserman, D.J. Friedland, and D.A. Morrison Tetrahedron Lett. 24 1968 641
6. B. Carte, and D.J. Faulkner J. Chem. Ecol. 12 1986 795
7. D.M. Pinkerton, M.G. Banwell, and A.C. Willis Org. Lett. 9 2007 5127
8. A.J. Blackman, and C. Li Aust. J. Chem. 47 1994 1625
9. M.S. Melvin, M.W. Calcutt, R.E. Noftle, and R.A. Manderville Chem. Res. Toxicol. 15 2002 742
10. M. Carbone, C. Irace, F. Costagliola, G. Villani, G. Calado, V. Padula, G. Cimino, J.L. Cervera, R. Santamaria, and M. Gavagnin Bioorg. Med. Chem. Lett. 20 2010 2668
11. L.N. Aldrich, E.S. Dawson, and C.W. Lindsley Org. Lett. 12 2010 1048
12. C. Boonlarppraadab, C.A. Kauffman, P.R. Jensen, and W. Fenical Org. Lett. 10 2008 5505
13. -1.
14. R.N. Daniels, B.J. Melancon, E.A. Wang, B.S. Crews, L.M. Marnett, G.A. Sulikowski, and C.W. Lindsley J. Org. Chem. 74 2009 8852
15. General method for the synthesis of tambjamine unnatural analogs (20): primary amine (0.517 mmol) was added to a stirred suspension of aldehyde 16 (30 mg, 0.103 mmol) in methanol (2.0 mL) at room temperature. 0.87 M HCl in methanol (0.6 mL) was subsequently added, and the reaction was stirred for 24 h. Reactions that had not reached completion by this time were stirred at 50 °C for an additional 24-h period. Reaction mixtures were concentrated, and crude compounds were purified by reverse phase chromatography using acetonitrile and 0.1% TFA/water to give tambjamine unnatural analogs 20 in yields ranging from 35-88%.
16. J.P. Kennedy, J.T. Brogan, and C.W. Lindsley J. Nat. Prod. 71 2008 1783
17. J.P. Kennedy, P.J. Conn, and C.W. Lindsley Bioorg. Med. Chem. Lett. 19 2009 3304
18. J.A. Lewis, N.R. Daniels, and C.W. Lindsley Org. Lett. 10 2008 4545
19. R.A. Davis, A.R. Carroll, and R.J. Quinn Aust. J. Chem. 54 2001 355
20. 2 in the air. The change in proliferation is quantified by measuring the absorbance of the dye solution at 450 nm on a microtiter plate reader.
21. 2 in the air. Then the wells were stained with 1% crystal violet in 50% methanol for 1 h and washed in PBS. The membrane was cut off, adhered to a slide with glycerol, and analyzed in 20× field via microscopy. 3-20× fields were quantified per membrane.