Synthesis of caged 2,3,3a,7a-tetrahydro-3,6-methanobenzofuran-7(6H)-ones: Evaluating the minimum structure for apoptosis induction by gambogic acid

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 8, 2008, Pages 4233-4241

  Kuemmerle, Jared ^a   Jiang, Songchun ^a   Tseng, Ben ^a   Kasibhatla, Shailaja ^a   Drewe, John ^a   Cai, Sui Xiong ^a  

^a EpiCept Corporation   (United States)

Author keywords

2,3,3a,7a Tetrahydro 3,6 methanobenzofuran 7(6H) ones; Apoptosis inducer; Cell growth inhibition; Claisen Diels Alder reaction cascade; Gambogic acid; Potential anti cancer drugs

Indexed keywords

1,3A,4,11A TETRAHYDRO 1 (2 PROPENYL) 3H 1,4A METHANO 10H FURO[3,4 B]XANTHENE 10,12 DIONE; 1,3A,4,11A TETRAHYDRO 3,3 DIMETHYL 1 (3 METHYL 2 BUTENYL) 3H 1,4A METHANO 10H FURO[3,4 B]XANTHENE 10,12 DIONE; 2 PHENYLCHROMENE 4 ONE; 2,3,3A,7A TETRAHYDRO 3,6 METHANOBENZOFURAN 7(6H) ONE DERIVATIVE; 3,3A,4,5 TETRAHYDRO 1 (2 PROPENYL) 1,5 METHANO 1H,7H FURO[3,4 D]XANTHENE 7,13 DIONE; 3,3A,4,5 TETRAHYDRO 3,3 DIMETHYL 1 (3 METHYL 2 BUTENYL) 1,5 METHANO 1H,7H FURO[3,4 D]XANTHENE 7,13 DIONE; 3,3A,4,5,6,6A HEXAHYDRO 1 (2 PROPENYL) 1,5 METHANO 1H,7H FURO[3,4 D]XANTHENE 7,13 DIONE; 4 BENZOYL 2,3,3A,7A TETRAHYDRO 3A,6,7 TRI(2 PROPENYL) 3,6 METHANOBENZOFURAN 7(6H) ONE; 5 BENZOYL 2,3,3A,7A TETRAHYDRO 3A,6,7A TRI(2 PROPENYL) 3,6 METHANOBENZOFURAN 7(6H) ONE; 5A,6,8A,9 TETRAHYDRO 8,8 DIMETHYL 6 (3 METHYL 2 BUTENYL) 2 PHENYL 8H 6,9A METHANO 4H FURO[3,4 G] 1 BENZOPYRAN 4,10 DIONE; 6,7,7A,8 TETRAHYDRO 8,8 DIMETHYL 10 (3 METHYL 2 BUTENYL) 2 PHENYL 6,10 METHANO 4H,10H FURO[3,4 I] 1 BENZOPYRAN 4,11 DIONE; ANTINEOPLASTIC AGENT; BENZOPHENONE; CHROMENE DERIVATIVE; GAMBOGIC ACID; UNCLASSIFIED DRUG; XANTHONE 4 ACETIC ACID;

APOPTOSIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL GROWTH; CONTROLLED STUDY; DIELS ALDER REACTION; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

APOPTOSIS; BENZOFURANS; CASPASES; CELL LINE, TUMOR; ENZYME ACTIVATION; HUMANS; HYDROGEN; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; XANTHONES;

ALNUS;

EID: 42149140804     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.084     Document Type: Article

References (37)

1. Reed J.C., and Tomaselli K.J. Curr. Opin. Biotechnol. 11 (2000) 586-592
2. Kim R., Tanabe K., Uchida Y., Emi M., Inoue H., and Toge T. Cancer Chemother. Pharmacol. 50 (2002) 343-352
3. Thornberry N.A. Chem. Biol. 5 (1998) R97-R103
4. Reed J.C. J. Clin. Oncol. 17 (1999) 2941-2953
5. Fesik S.W. Nat. Rev. Cancer 5 (2005) 876-885
6. van Delft M.F., Wei A.H., Mason K.D., Vandenberg C.J., Chen L., Czabotar P.E., Willis S.N., Scott C.L., Day C.L., Cory S., Adams J.M., Roberts A.W., and Huang D.C. Cancer Cell 10 (2006) 389-399
7. Hardcastle I.R., Ahmed S.U., Atkins H., Farnie G., Golding B.T., Griffin R.J., Guyenne S., Hutton C., Kallblad P., Kemp S.J., Kitching M.S., Newell D.R., Norbedo S., Northen J.S., Reid R.J., Saravanan K., Willems H.M.G., and Lunec J. J. Med. Chem. 49 (2006) 6209-6221
8. Ding K., Lu Y., Nikolovska-Coleska Z., Wang G., Qiu S., Shangary S., Gao W., Qin D., Stuckey J., Krajewski K., Roller P.P., and Wang S. J. Med. Chem. 49 (2006) 3432-3435
9. Chen J., Nikolovska-Coleska Z., Wang G., Qiu S., and Wang S. Bioorg. Med. Chem. Lett. 16 (2006) 5805-5808
10. Li L., Thomas R.M., Suzuki H., De Brabander J.K., Wang X., and Harran P.G. Science 305 (2004) 1471-1474
11. Cai S.X., Zhang H.Z., Guastella J., Drewe J., Yang W., and Weber E. Bioorg. Med. Chem. Lett. 11 (2001) 39-42
12. Zhang H.Z., Kasibhatla S., Guastella J., Drewe J., Tseng B., and Cai S.X. Bioconjug. Chem. 14 (2003) 458-463
13. Kemnitzer W., Drewe J., Jiang S., Zhang H., Wang Y., Zhao J., Jia S., Herich J., Labrecque D., Storer R., Meerovitch K., Bouffard D., Rej R., Denis R., Blais C., Lamothe S., Attardo G., Gourdeau H., Tseng B., Kasibhatla S., and Cai S.X. J. Med. Chem. 47 (2004) 6299-6310
14. Zhang H.Z., Kasibhatla S., Kuemmerle J., Kemnitzer W., Oliis-Mason K., Qui L., Crogran-Grundy C., Tseng B., Drewe J., and Cai S.X. J. Med. Chem. 48 (2005) 5215-5223
15. Jessen K., English N., Wang J., Qui L., Brand R., Maliartchouk S., Drewe J., Kuemmerle J., Zhang H.Z., Gehlsen K., Tseng B., Cai S.X., and Kasibhatla S. Mol. Cancer Ther. 4 (2005) 761-771
16. Cai S.X., Drewe J., and Kasibhatla S. Curr. Med. Chem. 13 (2006) 2627-2644
17. Zhang H.Z., Kasibhatla S., Wang Y., Herich J., Guastella J., Tseng B., Drewe J., and Cai S.X. Bioorg. Med. Chem. 12 (2004) 309-317
18. Kasibhatla S., Jessen K., Maliartchouk S., Wang J., English N., Drewe J., Qui L., Archer S., Ponce A., Sirisoma N., Jiang S., Zhang H.Z., Gehlsen K., Cai S.X., Green D.R., and Tseng B. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 12095-12100
19. Pandey M.K., Sung B., Ahn K.S., Kunnumakkara A.B., Chaturvedi M.M., and Aggarwal B.B. Blood 110 (2007) 3517-3525
20. Yang Y., Yang L., You Q.D., Nie F.F., Gu H.Y., Zhao L., Wang X.T., and Guo Q.L. Cancer Lett. 256 (2007) 259-266
21. Qin Y., Meng L., Hu C., Duan W., Zuo Z., Lin L., Zhang X., and Ding J. Mol. Cancer Ther. 6 (2007) 2429-2440
22. Lu N., Yang Y., You Q.D., Ling Y., Gao Y., Gu H.Y., Zhao L., Wang X.T., and Guo Q.L. Cancer Lett. 258 (2007) 80-89
23. Abbas S., Bhoumik A., Dahl R., Vasile S., Krajewski S., Cosford N.D., and Ronai Z.A. Clin. Cancer Res. 13 (2007) 6769-6778
24. Tao Z., Zhou Y., Lu J., Duan W., Qin Y., He X., Lin L., and Ding J. Cancer Biol. Ther. 6 (2007) 691-696
25. Jang S.W., Okada M., Sayeed I., Xiao G., Stein D., Jin P., and Ye K. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 16329-16334
26. Weakley T.J.R., Cai S.X., Zhang H.Z., and Keana J.F.W. J. Chem. Crystallogr. 31 (2001) 501-505
27. Ollis W.D., Ramsay M.V.J., Sutherland I.O., and Mongkolsuk S. Tetrahedron 21 (1965) 1453-1470
28. Xu Y.J., Yip S.C., Kosela S., Fitri E., Hana M., Goh S.H., and Sim K.Y. Org. Lett. 2 (2000) 3945-3948
29. Thoison O., Fahy J., Dumontet V., Chiaroni A., Riche C., Tri M.V., and Sevenet T. J. Nat. Prod. 63 (2000) 441-446
30. Nicolaou K.C., and Li J. Angew. Chem. Int. Ed. 40 (2001) 4264-4268
31. Tisdale E.J., Slobodov I., and Theodorakis E.A. Org. Biomol. Chem. 1 (2003) 4418-4422
32. Batova A., Lam T., Wascholowski V., Yu A.L., Giannis A., and Theodorakis E.A. Org. Biomol. Chem. 5 (2007) 494-500
33. Nicolaou K.C., Edmonds D.J., and Bulger P.G. Angew. Chem. Int. Ed. Engl. 45 (2006) 7134-7186
34. Tisdale E.J., Slobodov I., and Theodorakis E.A. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 12030-12035
35. Kasibhatla, S.; Cai, S.X.; Tseng, B.; Jessen, K.; Maliartchouk, S.; English, N.; Jiang, S.; Sirisoma, N.; Zhang, H. Z.; Kuemmerle, J. International patent application, WO04094647, 2004.
36. Cai S.X., Nguyen B., Jia S., Herich J., Guastella J., Reddy S., Tseng B., Drewe J., and Kasibhatla S. J. Med. Chem. 46 (2003) 2474-2481
37. Sirisoma N., Kasibhatla S., Nguyen B., Pervin A., Wang Y., Claassen G., Tseng B., Drewe J., and Cai S.X. Bioorg, Med. Chem. 14 (2006) 7761-7773