Synthesis of diketopiperazine-based carboline homodimers and in vitro growth inhibition of human carcinomas

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 12, 2008, Pages 3522-3525

  Deveau, Amy M ^a   Costa, Nancy E ^a   Joshi, Elizabeth M ^b   Macdonald, Timothy L ^b  

^a UNIVERSITY OF NEW ENGLAND   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

Anti cancer; Carboline; Diketopiperazine; Heterocycle; Indole; Pictet Spengler; Tryprostatin; Tryptophan

Indexed keywords

CARBOLINE DERIVATIVE; ETOPOSIDE; HETEROCYCLIC COMPOUND; HOMODIMER; HYDROXYL GROUP; NITROGEN; OXYGEN; PHENOL; PIPERAZINEDIONE; TRYPTOPHAN;

ARTICLE; CANCER GROWTH; CARCINOMA CELL; CONTROLLED STUDY; CYTOTOXICITY; DRUG INHIBITION; DRUG SYNTHESIS; ENANTIOMER; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; PICTET SPENGLER REACTION; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

CARBOLINES; CARCINOMA; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DIKETOPIPERAZINES; DIMERIZATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 44649100100     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.05.022     Document Type: Article

References (41)

1. Cui C.B., Kakeya H., Okada G., Onose R., Ubukata M., Takahashi I., Isono K., and Osada H. J. Antibiot. 48 (1995) 1382
2. Wang H., Usui T., Osada H., and Ganesan A. J. Med. Chem. 43 (2000) 1577
3. Wang H., and Ganesan A. J. Org. Chem. 65 (2000) 4685
4. Wang H., and Ganesan A. Tetrahedron Lett. 38 (1997) 4327
5. Juret P., Le Talaer Y., Couette J.E., and Delozier T. Eur. J. Cancer (Oxford) Suppl. 1 (1980) 277
6. Crews C.M., and Mohan R. Cur. Opin. Chem. Biol. 4 (2000) 47
7. Schkeryantz J.M., Woo J.C.G., Siliphaivanh P., Depew K.M., and Danishefsky S.J. J. Am. Chem. Soc. 121 (1999) 11964
8. Baran P.S., Guerrero C.A., and Corey E.J. J. Am. Chem. Soc. 125 (2003) 5628
9. Boger D.L., Fink B.E., and Hedrick M.P. Bioorg. Med. Chem. Lett. 10 (2000) 1019
10. Boger D.L., Fink B.E., and Hedrick M.P. J. Am. Chem. Soc. 122 (2000) 6382
11. Yu J., Wearing X.Z., and Cook J.M. Tetrahedron Lett. 45 (2004) 3937
12. Yu J., Wearing X.Z., and Cook J.M. Tetrahedron Lett. 44 (2003) 543
13. Chen W., and Joullié M.M. Tetrahedron Lett. 39 (1998) 8401
14. Priestley N.D., Smith T.M., Shipley P.R., and Floss H.G. Bioorg. Med. Chem. 4 (1996) 1135
15. González-Vera J.A., Garci{dotless}́a-López M.T., and Herranz R. Tetrahedron 63 (2007) 9229
16. Ohba M., Natsutani I., and Sakuma T. Tetrahedron 63 (2007) 10337
17. Deveau A.M., Labroli M.A., Dieckhaus C.M., Barthen M.T., Smith K.S., and Macdonald T.L. Bioorg. Med. Chem. Lett. 11 (2001) 1251
18. Stiborová1 M., Sejbal J., Boek-Dohalská L., Aimová D., Poljaková J., Forsterová K., Rupertová M., Wiesner J., Hudeek J., Wiessler M., and Frei E. Cancer Res. 64 (2004) 8374
19. Ishikura M., Hino A., Yaginuma T., Agata I., and Katagiri N. Tetrahedron 56 (2000) 193
20. Leteurtre F., Madalengoitia J., Orr A., Guzi T., Lehnert E., Macdonald T.L., and Pommier Y. Cancer Res. 52 (1992) 4478
21. Cline S.D., Macdonald T.L., and Osheroff N. Biochemistry 36 (1997) 13095
22. Jain H.D., Zhang C., Zhou S., Zhou H., Ma J., Liu X., Liao X., Deveau A.M., Dieckhaus C.M., Johnson M.A., Smith K.S., Macdonald T.L., Kakeya H., Osada H., and Cook J.M. Bioorg. Med. Chem. 16 (2008) 4626
23. Zhao S., Gan T., Yu P., and Cook J.M. Tetrahedron Lett. 39 (1998) 7009
24. Zhao S., Smith K.S., Deveau A.M., Dieckhaus C.M., Johnson M.A., Macdonald T.L., and Cook J.M. J. Med. Chem. 45 (2002) 1559
25. Martins M.B., and Carvalho I. Tetrahedron 63 (2007) 9923
26. Siwicka A., Wojtasiewicz K., Rosiek B., Leniewski A., Maurin J.K., and Czarnocki Z. Tetrahedron: Asymmetry 6 (2005) 975
27. Dandapani S., Lan P., Beeler A.B., Beischel S., Abbas A., Roth B.L., Porco J.A., and Panek J.S. J. Org. Chem. 71 (2006) 8934
28. During the revision of this manuscript we discovered that Panek et al. had synthesized DKP homodimer 2.31a (7% yield) as part of a program to generate DKP-based pipecolic acid scaffolds via parallel synthesis for use against G-protein coupled receptor targets. Although Panek's precedent exists the broad interest in 2.31a and related homodimers further justifies our interest in the these compounds. Notably, our yield of 83% for the dimerization step is also an improvement over Panek's previous synthesis.
29. Cox E.D., Li J., Hamaker L.K., Yu P., and Cook J.M. Chem. Comm. 21 (1996) 2477
30. Cox E.D., Hamaker L.K., Li J., Yu P., Czerwinski K.M., Deng L., Bennett D.W., Cook J.M., Watson W.H., and Krawiec M. J. Org. Chem. 62 (1997) 44
31. Cox E.D., and Cook J.M. Chem. Rev. 95 (1995) 1797
32. Boumendjel A., Nuzillard J.M., and Massiot G. Bull. Chem. Soc. Fr. 127 (1990) 645
33. Dinsmore C.J., and Beshore D.C. Tetrahedron 58 (2002) 3297
34. Fischer P.M. J. Peptide Sci. 9 (2003) 9
35. Avalos M., Babiano R., Barneto J.L., Bravo J.L., Cintas P., Jimenez J.L., and Palacios J.C. J. Org. Chem. 66 (2001) 7275
36. Robin M.B., Bovey F.A., and Basch H. Molecular and Electronic Structure of the Amide Group. In: Jacob Z. (Ed). The Chemistry of Amides (1970), John Wiley & Sons, Interscience Publishers, London 139
37. Reha D., Kabelac M., Ryjacek F., Sponer J., Sponer J.E., Elstner M., Suhai S., and Hobza P. J. Am. Chem. Soc. 124 (2002) 3366
38. Carlier P.R., Du D.M., Han Y.F., Liu J., Perola E., Williams I.D., and Pang Y.P. Angew. Chem., Int. Ed. Eng. 39 (2000) 1775
39. Shuker S.B., Hajduk P.J., Meadows R.P., and Fesik S.W. Science 274 (1996) 1531
40. Wender, P. A.; Koehler, M. F. T.; Wright, D. L.; Irie, K. Synthesis-Stuttgart 1999, Sp. Iss. SI, 1401.
41. Posner G.H., Ploypradith P., Parker M.H., O'Dowd H., Woo S.H., Northrop J., Krasavin M., Dolan P., Kensler T.W., Xie S.J., and Shapiro T.A. J. Med. Chem. 42 (1999) 4275