X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners

Molecules

Volumn 4, Issue 12, 1999, Pages 338-352

  Milić, Dragana R ^a,b   Kapor, Agneš ^c   Markov, Borislava ^c   Ribar, Bela ^c   Strümpel, Marianne ^d   Juranić, Zorica ^e   Gašić, Miroslav J ^a,b   Šolaja, Bogdan A ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c UNIVERSITY OF NOVI SAD   (Serbia)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

^e INSTITUTE FOR ONCOLOGY AND RADIOLOGY OF SERBIA   (Serbia)

Author keywords

Antitumor activity; Epoxyquinol; Quinol; Steroids; X ray crystallography

Indexed keywords

10BETA HYDROXY 4BETA,5BETA EPOXYESTR 1 EN 3,17 DIONE; ESTRANE DERIVATIVE; HYDROXYL GROUP; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ATOM; CELL LINE; CELL STRAIN; CONFORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LEUKEMIA CELL; MOLECULE; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0000703525     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/41200338     Document Type: Article

References (22)

1. 2 symmetric diol derived from pbenzoquinone: synthesis of (+)- and (-)-Bromoxone. J.Org. Chem. 1995, 60, 6674-6675; Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. M. Manumycin A: Synthesis of the (+)-Enantiomer and Revision of Stereochemical Assignment. J. Org. Chem. 1998, 63, 3526-3527; Wipf, P.; Kim, Y. Synthesis of the Antitumor Antibiotic LL-C10037α. J. Org. Chem. 1994, 59, 3518-3519.
2. 2 symmetric diol derived from pbenzoquinone: synthesis of (+)- and (-)-Bromoxone. J.Org. Chem. 1995, 60, 6674-6675; Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. M. Manumycin A: Synthesis of the (+)-Enantiomer and Revision of Stereochemical Assignment. J. Org. Chem. 1998, 63, 3526-3527; Wipf, P.; Kim, Y. Synthesis of the Antitumor Antibiotic LL-C10037α. J. Org. Chem. 1994, 59, 3518-3519.
3. 2 symmetric diol derived from pbenzoquinone: synthesis of (+)- and (-)-Bromoxone. J.Org. Chem. 1995, 60, 6674-6675; Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. M. Manumycin A: Synthesis of the (+)-Enantiomer and Revision of Stereochemical Assignment. J. Org. Chem. 1998, 63, 3526-3527; Wipf, P.; Kim, Y. Synthesis of the Antitumor Antibiotic LL-C10037α. J. Org. Chem. 1994, 59, 3518-3519.
4. 2 symmetric diol derived from pbenzoquinone: synthesis of (+)- and (-)-Bromoxone. J.Org. Chem. 1995, 60, 6674-6675; Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. M. Manumycin A: Synthesis of the (+)-Enantiomer and Revision of Stereochemical Assignment. J. Org. Chem. 1998, 63, 3526-3527; Wipf, P.; Kim, Y. Synthesis of the Antitumor Antibiotic LL-C10037α. J. Org. Chem. 1994, 59, 3518-3519.
5. Results of further transformations of epoxyquinol 3 and quinol 2 will be published elsewhere.
6. a) Balci, M.; Sütbeyaz, Y.; Seçen, H. Conduritols and Related Compounds. Tetrahedron 1990, 46, 3715-3742; b) Angyal, S. J. The Inositols. Q. Rev. Chem. Soc. 1957, 11, 212-226.
7. a) Balci, M.; Sütbeyaz, Y.; Seçen, H. Conduritols and Related Compounds. Tetrahedron 1990, 46, 3715-3742; b) Angyal, S. J. The Inositols. Q. Rev. Chem. Soc. 1957, 11, 212-226.
8. Šolaja, B. A.; Milić, D. R.; Gašić, M. J. A Novel m-CPBA Oxidation: p-Quinols and Epoxyquinols from Phenols. Tetrahedron Lett. 1996, 37, 3765-3768.
9. Milić, D. R.; Gašić, M. J.; Muster, W.; Csanádi, J. J.; Šolaja, B. A. The Synthesis and Biological Evaluation of A-ring Substituted Steroidal p-Quinones. Tetrahedron 1997, 53, 14073-14084.
10. Quinol 2 was treated with Katsuki-Sharpless reagent to give the epoxyquinol 3 (97% yield of (1:1)- mixture of two regioisomers; 20% overall yield in three phases from starting estrone) the structure of which was proposed on the basis of the known mechanism of the reaction. See: Adam, W.; Lupon, P. Quinol Epoxides from p-Cresol and Estrone by Photooxigenation and Titanium( IV)- or Vanadium(V)-Catalysed Oxygen Transfer. Chem. Ber. 1988, 121, 21-25.
11. Cremer, D.; Pople, J.A. A General Definition of Ring Puckering Coordinates. J. Am. Chem. Soc. 1975, 97, 1354-1358.
12. Kálmán, A.; Czugler, M.; Simon, K. In Molecular Structure and Biological Activity; Griffin, J.F., Duax, W.L., Eds.; Elsevier Biomedical: New York, 1982; pp 367-376.
13. Milić D.R.; Šolaja B.A.; Došen-Mićovid Lj.; Ribar, B.; Kapor, A.; Sladić D.; Gašić M.J. Structure and reactivity of steroidal quinones. J. Serb. Chem. Soc. 1997, 62, 755-768.
14. Quinol 4 and epoxyquinol 5 were tested in National Cancer Institute, Bethesda, U.S.A. as part of NCI developmental therapeutics program. For detailed synthetic procedure and spectroscopic data of 4 and 5 see refs. 4 and 9.
15. Sheldrick, G.M. SHELXS86 Program for Solution of Crystal Structure; University of Göttingen: Germany, 1985.
16. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M.C.; Polidori, G.; Camalli, M. SIR92-a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. 1994, 27, 435-436.
17. Sheldrick, G.M. SHELXL93 Program for Refinement of Crystal Structure; University of Göttingen: Germany, 1993.
18. Párkányi, L. RING, Program for Conformational Analysis; Budapest, Hungary, 1979.
19. Johnoson, C.K.; Burnett, M.N.; Farrugia, L.J. ORTEP III Version 1.0.2 University of Glasgow; Great Britain, 1997.
20. a) Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immunol. Methods 1983, 65, 55-56; b) Ohno, M.; Abe, T. Rapid colorimetric assays for the quantification of leukemia inhibitory factor (LIF) and interleukin-6 (IL-6). J. Immunol. Methods 1991, 145, 199-203; c) Juranić, Z.; Radulović, S.; Joksimović, J.; Juranić I. The Mechanism of 8-CI-cAMP Action. J. Exp. Clin. Cancer Res. 1998, 17, 269-275.
21. a) Mosmann, T. Rapid .colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immunol. Methods 1983, 65, 55-56; b) Ohno, M.; Abe, T. Rapid colorimetric assays for the quantification of leukemia inhibitory factor (LIF) and interleukin-6 (IL-6). J. Immunol. Methods 1991, 145, 199-203; c) Juranić, Z.; Radulović, S.; Joksimović, J.; Juranić I. The Mechanism of 8-CI-cAMP Action. J. Exp. Clin. Cancer Res. 1998, 17, 269-275.
22. a) Mosmann, T. Rapid .colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, J. Immunol. Methods 1983, 65, 55-56; b) Ohno, M.; Abe, T. Rapid colorimetric assays for the quantification of leukemia inhibitory factor (LIF) and interleukin-6 (IL-6). J. Immunol. Methods 1991, 145, 199-203; c) Juranić, Z.; Radulović, S.; Joksimović, J.; Juranić I. The Mechanism of 8-CI-cAMP Action. J. Exp. Clin. Cancer Res. 1998, 17, 269-275.