Unexpected oxidation of a substituted benzo(a)phenazine: oxidative cleavage of a double bond and formation of a macrolactone

[1]  W. Denny,et al.  Novel angular benzophenazines: dual topoisomerase I and topoisomerase II inhibitors as potential anticancer agents. , 2002, Journal of medicinal chemistry.

[2]  M. Garland,et al.  Preparation and cytotoxicity toward cancer cells of mono(arylimino) derivatives of beta-lapachone. , 2001, Journal of medicinal chemistry.

[3]  U. Nubbemeyer.  Planar Chirality − Synthesis and Transformations of 8‐ to 10‐Membered Heterocycles Bearing (E)‐Olefins , 2001 .

[4]  K. Bastow,et al.  Novel mechanisms of DNA topoisomerase II inhibition by pyranonaphthoquinone derivatives—eleutherin, α lapachone, and β lapachone∗ , 2000 .

[5]  A. V. Pinto,et al.  Fluorescent symmetric phenazines from naphthoquinones. 3. Steady-state spectroscopy and solvent effect of seven phenazine derivatives: structure-photophysics correlations , 2000 .

[6]  A. Pardee,et al.  Potent inhibition of tumor survival in vivo by beta-lapachone plus taxol: combining drugs imposes different artificial checkpoints. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[7]  Louis J. Farrugia,et al.  WinGX suite for small-molecule single-crystal crystallography , 1999 .

[8]  G. Burton,et al.  Preparation and NMR characterization of new substituted benzo[a]phenazines , 1998 .

[9]  Louis J. Farrugia,et al.  ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) , 1997 .

[10]  A. Liu,et al.  Induction of DNA topoisomerase II-mediated DNA cleavage by beta-lapachone and related naphthoquinones. , 1997, Cancer research.

[11]  Robert M. Sweet,et al.  Macromolecular Crystallography: Part A , 1997 .

[12]  G. Wilding,et al.  Beta-lapachone-mediated apoptosis in human promyelocytic leukemia (HL-60) and human prostate cancer cells: a p53-independent response. , 1995, Cancer research.

[13]  A. Pardee,et al.  beta-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. , 1993, The Journal of biological chemistry.

[14]  F. Einstein,et al.  Structure of 3,4,5,6,7,8-hexahydro-1-methyl-1H-2-benzoxecine-3,8-dione , 1991 .

[15]  W. Denny,et al.  Potential antitumor agents. 51. Synthesis and antitumor activity of substituted phenazine-1-carboxamides. , 1987, Journal of medicinal chemistry.

[16]  R. Murray.  Mechanism of ozonolysis , 1968 .

[17]  I. Borowitz,et al.  Synthesis of 6-oxononanolides, 6- and 7-oxodecanolides and 7-oxoundecanolide via enamine reactions , 1968 .

[18]  Samuel C. Hooker.  C.—The constitution of lapachol and its derivatives. Part II. The azines of the lapachol group , 1893 .