Cytotoxic 1,3-diarylidene-2-tetralones and related compounds

European Journal of Medicinal Chemistry

Volumn 37, Issue 10, 2002, Pages 813-824

  Dimmock, Jonathan R ^a   Padmanilyam, Maniyan P ^a   Zello, Gordon A ^a   Wilson Quail, J ^a   Oloo, Eliud O ^a   Prisciak, Jared S ^a   Kraatz, Heinz Bernhard ^a   Cherkasov, Arten ^a   Lee, Jeremy S ^a   Allen, Theresa M ^b   Santos, Cheryl L ^b   Manavathu, Elias K ^c   De Clercq, Erik ^d   Balzarini, Jan ^d   Stables, James P ^e  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

^c WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^e NATIONAL INSTITUTE OF NEUROLOGICAL DISORDERS AND STROKE   (United States)

Author keywords

2 Tetralones; Cytotoxicity; Murine toxicity; Redox potentials

Indexed keywords

ANTINEOPLASTIC AGENT; KETONE DERIVATIVE; MELPHALAN; KETONE; POLYCYCLIC AROMATIC HYDROCARBON; STILBENE DERIVATIVE; TETRALIN DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; BIOSYNTHESIS; CELL LINE; COLON CANCER; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFECT; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA; MOUSE; NEUROTOXICITY; NONHUMAN; T LYMPHOCYTE; TUMOR CELL LINE; ANIMAL; CELL CULTURE; CHEMISTRY; DRUG SCREENING; IC 50; LEUKEMIA L 1210; LEUKEMIA P 388; OXIDATION REDUCTION REACTION; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE SUBPOPULATION; X RAY CRYSTALLOGRAPHY;

ANIMALS; ANTINEOPLASTIC AGENTS; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; KETONES; LEUKEMIA L1210; LEUKEMIA P388; MICE; OXIDATION-REDUCTION; POLYCYCLIC HYDROCARBONS, AROMATIC; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; T-LYMPHOCYTE SUBSETS; TETRAHYDRONAPHTHALENES; TUMOR CELLS, CULTURED;

EID: 0036809108     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(02)01402-2     Document Type: Article

References (36)

1. Dimmock J.R., Kumar P., Nazarali A.J., Motoganahalli N.L., Kowalchuk T.P., Beazely M.A., Quail J.W., Oloo E.O., Allen T.M., Szydlowski J., De Clercq E., Balzarini J. Eur. J. Med. Chem. 35:2000;967-977.
2. Dimmock J.R., Padmanilayam M.P., Puthucode R.N., Nazarali A.J., Motaganahalli N.L., Zello G.A., Quail J.W., Oloo E.O., Kraatz H.-B., Prisciak J.S., Allen T.M., Santos C.L., Balzarini J., De Clercq E., Manavathu E.K. J. Med. Chem. 44:2001;586-593.
3. Baluja A., Municio A.M., Vega S. Chem. Ind. 1964;2053-2054.
4. H. Singh, V.K. Kapoor, Medicinal and Pharmaceutical Chemistry, Vallabh Prakashan, Delhi, India, 1996, p. 522.
5. Petit G.R., Singh S.B., Boyd M.R., Hamel E., Petit R.K., Schmidt J.M., Hogan F. J. Med. Chem. 38:1995;1666-1672.
6. Mitchell J.B., Russo A. Br. J. Cancer (Suppl. VIII). 55:1987;96-104.
7. Tsutsui K., Komuro C., Ono K., Nishidai T., Shibamoto Y., Takahashi M., Abe M. Int. J. Radiat. Oncol. Biol. Phys. 12:1986;1183-1186.
8. Craig P.N. J. Med. Chem. 14:1971;680-684.
9. Topliss J.G. J. Med. Chem. 20:1977;463-469.
10. H. Singh, V.K. Kapoor, Medicinal and Pharmaceutical Chemistry, Vallabh Prakashan, Delhi, 1996, p. 519.
11. Connors T.A. Gorrod J.W., Drug Toxicity. 1979;175 Taylor and Francis Ltd, London.
12. Heytler P.G. Erecińska M., Wilson D.F., Inhibitors of Mitochondrial Functions. 1981;202-205 Pergamon Press, Oxford.
13. Jia Z., Quail J.W., Arora V.K., Dimmock J.R. Acta Crystallogr., Sect. C. 45:1989;285-289.
14. Jia Z., Quail J.W., Dimmock J.R. Acta Crystallogr., Sect. C. 46:1990;2467-2468.
15. Topliss J.G. J. Med. Chem. 15:1992;1006-1011.
16. Dimmock J.R., Kandepu N.M., Hetherington M., Quail J.W., Pugazhenthi U., Sudom A.M., Chamankhah M., Rose P., Pass E., Allen T.M., Halleran S., Szydlowski J., Mutus B., Tannous M., Manavathu E.K., Myers T.G., De Clercq E., Balzarini J. J. Med. Chem. 41:1998;1014-1026.
17. C.K. Johnson, ORTEP II. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA, 1976.
18. Laarhoven W.H., Nivard R.J.F., Havinga E. Experientia. 17:1961;214-215.
19. Adamson D.W., Barrett P.A., Billingshurst J.W., Green A.F., Jones T.S.G. Nature. 168:1951;204-205.
20. Albert A. Selective Toxicity. 7th ed. 1985;514 Chapman and Hall, London.
21. Vashishtha S.C., Allen T.M., Halleran S., Szydlowski J., Santos C.L., De Clercq E., Balzarini J., Dimmock J.R. Pharmazie. 56:2001;390-393.
22. Greenspan E.M., Bruckner H.W. Greenspan E.M., Clinical Cancer Chemotherapy. 1975;37 Raven Press, New York.
23. Remers W.A. Delgado J.N., Remers W.A., Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry. 10th ed. 1998;367 Lippincott-Raven, Philadelphia.
24. Gabe E.J., LePage Y., Charland J.-P., White P.S. J. Appl. Crystallogr. 22:1989;384-387.
25. G.M. Sheldrick, SHELXL-97. Programme for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
26. International Tables for X-ray Crystallography, vol. IV, Kynoch Press, Birmingham, UK, 1974.
27. a Prediction for Organic Acids and Bases, Chapman and Hall, London, 1981, pp. 109-112, 114.
28. Taft R.W. Jr. Newman M.S., Steric Effects in Organic Chemistry. 1956;591 John Wiley and Sons, Inc, New York.
29. Hansch C., Leo A.J. Substituent Constants for Correlation Analysis in Chemistry and Biology. 1979;49-50 John Wiley and Sons, New York.
30. Phillips O.A., Nelson L.A., Knaus E.E., Allen T.M., Fathi-Afshar R. Drug Des. Deliv. 4:1989;121-127.
31. Balzarini J., De Clercq E., Mertes M.P., Shugar D., Torrence P.F. Biochem. Pharmacol. 31:1982;3673-3682.
32. Boyd M.R., Paull K.D. Drug Dev. Res. 34:1995;91-109.
33. Morgan A.R., Lee J.S., Pulleyblank D.E., Murray N.L., Evans D.E. Nucl. Acids Res. 7:1979;547-569.
34. Manavathu E.K., Vashishtha S.C., Alangaden G.J., Dimmock J.R. Can. J. Microbiol. 44:1998;74-79.
35. Stables J.P., Kupferberg H.J. Avanzini G., Tanganelli P., Avoli M., Molecular and Cellular Targets for Antiepileptic Drugs. 1997;191-198 John Libbey and Company Ltd, London.
36. Dunham M.S., Miya T.A. J. Am. Pharm. Ass. Sci. Ed. 46:1957;208-209.