Halohydrin and oxime derivatives of radicicol: Synthesis and antitumor activities

Bioorganic and Medicinal Chemistry

Volumn 10, Issue 11, 2002, Pages 3445-3454

  Agatsuma, Tsutomu ^a   Ogawa, Harumi ^a   Akasaka, Kazuhito ^a   Asai, Akira ^a   Yamashita, Yoshinori ^a   Mizukami, Tamio ^a   Akinaga, Shiro ^a   Saitoh, Yutaka ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CHLOROHYDRIN; ANTINEOPLASTIC AGENT; BROMINE DERIVATIVE; BROMOHYDRIN; CHLORINE DERIVATIVE; CHLOROHYDRIN FORMATE; CHLOROHYDRIN SULFITE; OXIME DERIVATIVE; RADICICOL; RADICICOL 6 (DIMETHYLCARBAMOYLMETHYLOXIME); RADICICOL 6 (O CARBOXYMETHYLOXIME); RADICICOL 6 (O METHYLOXIME); RADICICOL 6 OXIME; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CARCINOMA; CELL PROLIFERATION; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; EPIDERMOID TUMOR; HUMAN; HUMAN CELL;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CARCINOMA, SQUAMOUS CELL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; FEMALE; HUMANS; INDICATORS AND REAGENTS; LACTONES; MACROLIDES; OXIMES; SRC-FAMILY KINASES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0036836678     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00260-2     Document Type: Article

References (33)

1. Mirrington R.N., Ritchie E., Shoppee C.W., Taylor W.C., Sternhell S. Tetrahedron Lett. 1964;365.
2. McCapra F., Scott A.I., Delmotte P., Delmotte-Plaquee J., Bhacca N.S. Tetrahedron Lett. 1964;869.
3. Delmotte P., Delmotte-Plaquee J. Nature. 171:1953;344.
4. Kwon H.J., Yoshida M., Fukui Y., Horinouchi S., Beppu T. Cancer Res. 52:1992;6926.
5. Shimada Y., Ogawa T., Sato A., Kaneko I., Tsujita Y. J. Antibiot. 48:1995;824.
6. Oikawa T., Ito H., Ashino H., Toi M., Tominaga T., Morita I., Murota S. Eur. J. Pharmacol. 241:1993;221.
7. Kwon H.J., Yoshida M., Abe K., Horinouchi S., Beppu T. Biosci. Biotech. Biochem. 56:1992;538.
8. Zhao J.-F., Nakano H., Sharma S. Oncogene. 11:1995;161.
9. Soga S., Kozawa T., Narumi H., Akinaga S., Irie K., Matsumoto K., Sharma S.V., Nakano H., Mizukami T., Hara M. J. Biol. Chem. 273:1998;822.
10. Kanda Y., Fukuyama T. J. Am. Chem. Soc. 115:1993;8451.
11. Wilchek, M.; Bayer, E. A. In Methods in Enzymology; Wilchek, M.; Bayer, E. A. Eds.; Academic: San Diego, 1990; Vol. 184, p 5.
12. Schulte T.W., Akinaga S., Murakata T., Agatsuma T., Sugimoto S., Nakano H., Lee Y.S., Simen B.B., Argon Y., Felts S., Toft D.O., Neckers L.M., Sharma S.V. Mol. Endocrinol. 13:1999;1435.
13. Sharma S.V., Agatsuma T., Nakano H. Oncogene. 16:1998;2639.
14. Schulte T.W., Akinaga S., Soga S., Sullivan W., Stensgard B., Toft D., Neckers L.M. Cell Stress Chaperones. 3:1998;100.
15. Jolly C., Morimoto R.I. J. Natl. Cancer Inst. 92:2000;1564.
16. Pratt W.B., Toft D.O. Endocr. Rev. 18:1997;306.
17. Perdew G.H. J. Biol. Chem. 263:1988;13802.
18. Blagosklonny M.V., Toretsky J., Neckers L. Oncogene. 11:1995;933.
19. Murakami Y., Mizuno S., Uehara Y. Biochem. J. 301:1994;63.
20. Chavany C., Mimnaugh E., Miller P., Bitton R., Nguyen P., Trepel J., Whitesell L., Schnur R., Moyer J.D., Neckers L. J. Biol. Chem. 271:1996;4974.
21. Hartmann F., Horak E.M., Cho C., Lupu R., Bolen J.B., Stetler-Stevenson M.A., Pfreundschuh M., Waldmann T.A., Horak I.D. Int. J. Cancer. 70:1997;221.
22. Xu Y., Lindquist S. Proc. Natl. Acad. Sci. U.S.A. 90:1993;7074.
23. Hartson S.D., Matts R.L. Biochemistry. 33:1994;8912.
24. Stancato L.F., Chow Y.-H., Hutchison K.A., Perdew G.H., Joves R., Pratt W.B. J. Biol. Chem. 268:1993;21711.
25. Stepanova L., Leng X., Parker S.B., Harper J.W. Genes Dev. 10:1996;1491.
26. Whitesell L., Mimnaugh E.G., Costa B.D., Myers C.E., Neckers L.M. Proc. Natl. Acad. Sci. U.S.A. 91:1994;8324.
27. Schnur R.C., Corman M.L., Gallaschun R.J., Cooper B.A., Dee M.F., Doty J.L., Muzzi M.L., Moyer J.D., DiOrio C.I., Barbacci E.G., Miller P.E., O'Brien A.T., Morin M.J., Foster B.A., Pollack V.A., Savage D.M., Sloan D.E., Pustilnik L.R., Moyer M.P. J. Med. Chem. 38:1995;3806
28. Schnur R.C., Corman M.L., Gallaschun R.J., Cooper B.A., Dee M.F., Doty J.L., Muzzi M.L., DiOrio C.I., Barbacci E.G., Miller P.E., Pollack V.A., Savage D.M., Sloan D.E., Pustilnik L.R., Moyer J.D., Moyer M.P. J. Med. Chem. 38:1995;3813.
29. Roe S.M., Prodromou C., O'Brien R., Labdury J.E., Piper P.W., Pearl L.H. J. Med. Chem. 42:1999;260.
30. Stebbins C.E., Russo A.A., Schneider C., Rosen N., Hartl F.U., Pavletich N.P. Cell. 89:1997;239.
31. Soga S., Neckers L.M., Schulte T.W., Shiotsu Y., Akasaka K., Narumi H., Agatsuma T., Ikuina Y., Murakata C., Tamaoki T., Akinaga S. Cancer Res. 59:1999;2931.
32. Chiosis G., Timaul M.N., Lucas B., Munster P.N., Zheng F.F., Sepp-Lorenzino L., Rosen N. Chem. Biol. 8:2001;289.
33. Armstrong A., Brackenridge I., Jackson R.F.W., Kirk J.M. Tetrahedron Lett. 29:1988;2483.