Development of novel steroid sulfatase inhibitors: I. Synthesis and biological evaluation of biphenyl-4-O-sulfamates

Journal of Steroid Biochemistry and Molecular Biology

Volumn 87, Issue 2-3, 2003, Pages 141-148

  Okada, Makoto ^a   Nakagawa, Takayoshi ^a   Iwashita, Shigeki ^a   Takegawa, Shigehiro ^a   Fujii, Tomohito ^a   Koizumi, Naoyuki ^a  

^a Grelan Pharmaceutical Co Ltd   (Japan)

Author keywords

Biphenyl; Inhibitor; Steroid; Sulfamate; Sulfatase

Indexed keywords

(4 O SULFAMOYL) N TETRADECANOYLBENZYLAMINE; 2' CYANO 4' NITROBIPHENYL 4 O SULFAMATE; 2' CYANOBIPHENYL 4 O SULFAMATE; 2' METHYLBIPHENYL 4 O SULFAMATE; 2' NITROBIPHENYL 4 O SULFAMATE; 2' TRIFLUOROMETHYLBIPHENYL 4 O SULFAMATE; 2',4' DICYANOBIPHENYL 4 O SULFAMATE; 2'4' DICYANOBIPHENYL 4 O SULFAMATE; 3' NITROBIPHENYL 4 O SULFAMATE; 4' BROMOBIPHENYL 4 O SULFAMATE; 4' CHLOROBIPHENYL 4 O SULFAMATE; 4' CYANOBIPHENYL 4 O SULFAMATE; 4' METHOXYBIPHENYL 4 O SULFAMATE; 4' NITROBIPHENYL 4 O SULFAMATE; 4' TRIFLUOROMETHYLBIPHENYL 4 O SULFAMATE; BENZYLAMINE DERIVATIVE; BIPHENYL 4 O SULFAMATE; BIPHENYL 4,4' O,O' DISULFAMATE; BIPHENYL DERIVATIVE; ESTROGEN RECEPTOR ALPHA; STEROID; STERYL SULFATASE; TZS 8478; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG ACTIVITY; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; ESTROGEN ACTIVITY; FEMALE; HUMAN; HUMAN CELL; IN VITRO STUDY; LIVER; NONHUMAN; OVARIECTOMY; RAT; UTERUS GROWTH;

EID: 0348110622     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2003.07.005     Document Type: Article

References (19)

1. Pasqualini J.R., Chetrite G., Blacker C., Feinstein M.C., Delalonde L., Talbi M., Maloche C. Concentrations of estrone, estradiol, and estrone sulfate and evaluation of sulfatase and aromatase activities in pre- and postmenopausal breast cancer patients. J. Clin. Endocrinol. Metab. 81:1996;1460-1464.
2. Tilson-Mallett N., Santner S.J., Feil P.D., Santen R.J. Biological significance of aromatase activity in human breast tumors. J. Clin. Endocrinol. Metab. 57:1983;1125-1128.
3. Santner S.J., Feil P.D., Santen R.J. In situ estrogen production via the estrone sulfatase pathway in breast tumors: relative importance versus the aromatase pathway. J. Clin. Endocrinol. Metab. 59:1984;29-33.
4. Howarth N.M., Purohit A., Reed M.J., Potter B.V.L. Estrone sulfamates: potent inhibitors of estrone sulfatase with therapeutic potential. J. Med. Chem. 37:1994;219-221.
5. Li P.K., Chu G.H., Guo J., Peters A., Selcer K.W. Development of potent non-estrogenic estrone sulfatase inhibitors. Steroids. 63:1998;425-432.
6. Ciobanu L.C., Boivin R.P., Luu-The V., Labrie F., Poirier D. Potent inhibition of steroid sulfatase activity by 3-O-sulfamate 17α-benzyl (or 4′-tert-butylbenzyl)-estra-1,3,5(10)-trienes: combination of two substituents at positions C3 and C17α of estradiol. J. Med. Chem. 42:1999;2280-2286.
7. Kolli A., Chu G.H., Rhodes M.E., Inoue K., Selcer K.W., Li P.K. Development of (p-O-sulfamoyl)-N-alkanoyl-phenylalkyl amines as non-steroidal estrone sulfatase inhibitors. J. Steroid Biochem. Mol. Biol. 68:1999;31-40.
8. Billich A., Nussbaumer P., Lehr P. Stimulation of MCF-7 breast cancer cell proliferation by estrone sulfate and dehydroepiandrosterone sulfate: inhibition by novel non-steroidal steroid sulfatase inhibitors. J. Steroid Biochem. Mol. Biol. 73:2000;225-235.
9. Malini B., Purohit A., Ganeshapillai D., Woo L.W.L., Potter B.V.L., Reed M.J. Inhibition of steroid sulphatase activity by tricyclic coumarin sulphamates. J. Steroid Biochem. Mol. Biol. 75:2000;253-258.
10. Ahmed S., James K., Owen C.P. Design, synthesis and biochemical evaluation of AC ring mimics as novel inhibitors of the enzyme estrone sulfatase (ES). J. Steroid Biochem. Mol. Biol. 82:2002;425-435.
11. Elger W., Schwarz S., Hedden A., Reddersen G., Schneider B. Sulfamates of various estrogens are prodrugs with increased systemic and reduced hepatic estrogenicity at oral application. J. Steroid Biochem. Mol. Biol. 55:1995;396-403.
12. Hatanaka Y., Goda K., Okahara Y. Highly selective cross-coupling reactions of aryl(halo)silanes with aryl halides: a general and practical route to functionalized biaryls. Tetrahedron. 50:1994;8301-8316.
13. Badone D., Baroni M., Cardamone R., Ielmini A., Guzzi U. Highly efficient palladium-catalyzed boronic acid coupling reactions in water: scope and limitations. J. Org. Chem. 62:1997;7170-7173.
14. Miyaura N., Yanagi T., Suzuki A. The palladium-catalyzed cross-coupling reaction of phenylboronic acid with haloarenes in the presence of bases. Synth. Commun. 11:1981;513-519.
15. Appel R., Berger G. Uber das hydrazidosulfamide (on hydrazidosulfanamide) . Chem. Ber. 91:1958;1339-1341.
16. Duncan L.J., Purohit A., Howarth N.M., Potter B.V.L., Reed M.J. Inhibition of estrone sulfatase activity by estrone-3-methylthiophosphonate: a potential therapeutic agent in breast cancer. Cancer Res. 53:1993;298-303.
17. Purohit A., Williams G.J., Roberts C.J., Potter B.V.L., Reed M.J. In vivo inhibition of oestrone sulphatase and dehydroepiandrosterone sulphatase by oestrone-3-O-sulphamate. Int. J. Cancer. 63:1995;106-111.
18. Obourn J.D., Koszewski N.J., Notides A.C. Hormone- and DNA-binding mechanisms of the recombinant human estrogen receptor. Biochemistry. 32:1993;6229-6236.
19. Woo L.W.L., Howarth N.M., Purohit A., Hejaz H.A.M., Reed M.J., Potter B.V.L. Steroidal and nonsteroidal sulfamates as potent inhibitors of steroid sulfatase. J. Med. Chem. 41:1998;1068-1083.