4-Substituted 4-hydroxycyclohexa-2,5-dien-1-ones with selective activities against colon and renal cancer cell lines

Journal of Medicinal Chemistry

Volumn 46, Issue 4, 2003, Pages 532-541

  Wells, Geoffrey ^a   Berry, Jane M ^a   Bradshaw, Tracey D ^a   Burger, Angelika M ^b   Seaton, Angela ^a   Wang, Bo ^a   Westwell, Andrew D ^a   Stevens, Malcolm F G ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 (BENZOTHIAZOL 2 YL) 4 HYDROXY 2,5 CYCLOHEXADIEN 1 ONE; 4 HYDROXYCYCLOHEXA 2,5 DIEN 1 ONE DERIVATIVE; ANTINEOPLASTIC AGENT; HYDROXYCYCLOHEXADIENONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CENTRAL NERVOUS SYSTEM TUMOR; CHEMICAL MODIFICATION; COLON CANCER; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; KIDNEY CANCER; LEUKEMIA CELL; LUNG NON SMALL CELL CANCER; MELANOMA; NONHUMAN; OVARY CANCER; PROSTATE CANCER; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE; XENOGRAFT;

ALGORITHMS; ANIMALS; ANTINEOPLASTIC AGENTS; BENZOTHIAZOLES; COLONIC NEOPLASMS; COMPUTER SIMULATION; CYCLOHEXANES; CYCLOHEXANONES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; KIDNEY NEOPLASMS; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; TRANSPLANTATION, HETEROLOGOUS; TUMOR CELLS, CULTURED;

EID: 0037434507     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020984y     Document Type: Article

References (22)

1. Gibson, G. G.; Skett, P. Introduction to Drug Metabolism, 3rd Edition; Nelson Thornes: Cheltenham, U.K., 2001; pp 1-36.
2. Umezawa, K.; Imoto, M. Use of erbstatin as protein tyrosine kinase inhibitor. Methods Enzymol. 1991, 201, 379-385.
3. Rambas, L.; McMurray, J. S.; Budde, R. J. A. The degree of inhibition of protein tyrosine kinase activity by Tyrphostin 23 and 25 is related to their instability. Cancer Res. 1994, 54, 867-869.
4. Faaland, C. A.; Mermelstein, F. H.; Hayastin, J.; Laskin, J. D. Rapid uptake of tyrphostin into A431 human epidermoid cells is followed by delayed inhibition of epidermal growth factor (EGF) stimulated EGF receptor tyrosine kinase activity. Mol. Cell Biol. 1991, 11, 2697-2703.
5. Reddy, K. B.; Mangold, G. L.; Tandon, A. K.; Yoneda, T.; Mundy, G. R.; Zilberstein, A. Inhibition of breast cancer cell growth in vitro by a tyrosine kinase inhibitor. Cancer Res. 1992, 52, 3631-3641.
6. Wells, G.; Seaton, A.; Stevens, M. F. G. Structural studies on bioactive compounds. 32. Oxidation of tyrphostin protein tyrosine kinase inhibitors with hypervalent iodine reagents. J. Med. Chem. 2000, 43, 1550-1562.
7. Wells, G.; Bradshaw, T. D.; Diana, P.; Seaton, A.; Westwell, A. D.; Stevens, M. F. G. Antitumor benzothiazoles. 10. The synthesis and antitumor activity of benzothiazole substituted quinol derivatives. Bioorg. Med. Chem. Lett. 2000, 10, 513-515.
8. Patent application filed July 6, 2001 (U.K.).
9. Capparelli, M. P.; DeSchepper, R. E.; Swenton, J. S. Structural and solvent/electrolyte effects on the selectivity and efficiency of the anodic oxidation of para-substituted aromatic ethers. J. Org. Chem. 1987, 52, 4953-4961.
10. Livinghouse, T. Trimethylsilyl cyanide: cyanosilylation of pbenzoquinone. Org. Synth. 1981, 60, 126-132.
11. McKillop, A.; McLaren, L.; Watson, R. J.; Taylor, R. J. K.; Lewis, N. A concise synthesis of the novel antibiotic aranorosin. Tetrahedron Lett. 1993, 34, 5519-5522.
12. McKillop, A.; Perry, D. H.; Edwards, M.; Antus, S.; Farkas, L.; Nogradi, M.; Taylor, E. C. Thallium in organic synthesis. XLII. Direct oxidation of 4-substituted cyclohexa-2,5-dienones using thallium(III) nitrate. J. Org. Chem. 1976, 41, 282-287.
13. Stevens, M. F. G.; Shi, D.-F.; Castro, A. Antitumour benzothiazoles. Part 2. Formation of 2,2′-diaminobiphenyls from the decomposition of 2-(4-azidophenyl)benzazoles in trifluoromethanesulfonic acid. J. Chem. Soc., Perkin Trans. 1 1996, 83-93.
14. Boyd, M. R.; Paull, K. D. Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Dev. Res. 1995, 34, 91-104.
15. Weinstein, J. N.; Myers, T. G.; O'Connor, P. M.; Friend, S. H.; Fornace, A. J.; Kohn, K. W.; Fojo, T.; Bates, S. E.; Rubinstein, L. V.; Anderson, N. L.; Buolamwini, J. K.; van Osdol, W. W.; Monks, A. P.; Scudiero, D. A.; Sausville, E. A.; Zaharevitz, D. W.; Bunow, B.; Viswanadhan, V. N.; Johnson, G. S.; Wittes, R. E.; Paull, K. D. An information-intensive approach to the molecular pharmacology of cancer. Science 1997, 275, 343-349.
16. Kunkel, M. W.; Kirkpatrick, D. L.; Johnson, J. I.; Powis, G. Cell line-directed screening assay for inhibitors of thioredoxin reductase signalling as potential anti-cancer drugs. Anti-Cancer Drug Des. 1997, 12, 659-670.
17. Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. Manumycin A: synthesis of the (+)-enantiomer and revision of stereochemical assignment. J. Org. Chem. 1998, 63, 3526-3527.
18. Wipf, P.; Kim, Y. Synthesis of the antitumor antibiotic LL-C10037α. J. Org. Chem. 1994, 59, 3518-3519.
19. Wada, H.; Fujita, H.; Murakami, T.; Saiki, Y.; Chen, C. M. Chemical and chemotaxonomical studies of ferns. LXXIII. New flavonoids with modified B-ring from the genus Pseudophegopteris (Thelypteridacae). Chem. Pharm. Bull. 1987, 35, 4757-4762.
20. Milić, D. R.; Kapor, A.; Markov, B.; Ribar, B.; Strümpel, M.; Juranić, Z.; Gašić, M. J.; Šolaja, B. A. X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en-3,17-dione and antitumor activity of its congeners. Molecules 1999, 4, 338-352.
21. Hutchinson, I.; Chua, M.-S.; Browne, H. L.; Trapani, V.; Bradshaw, T. D.; Westwell, A. D.; Stevens, M. F. G. Antitumor benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles. J. Med. Chem. 2001, 44, 1446-1455.
22. Kashiyama, E.; Hutchinson, I.; Chua, M.-S.; Stinson, S. F.; Phillips, L. R.; Kaur, G.; Sausville, E. A.; Bradshaw, T. D.; Westwell, A. D.; Stevens, M. F. G. Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl)-benzothiazoles. J. Med. Chem. 1999, 42, 4172-4184.