메뉴 건너뛰기




Volumn 74, Issue 2, 2009, Pages 208-211

Chemical aromatization of 19-hydroxyandrosta-1,4-diene-3,17-dione with acid or alkaline: Elimination of the 19-hydroxymethyl group as formaldehyde

Author keywords

19 Hydroxyandrosta 1,4 diene 3,17 dione; Acid catalyzed reaction; Base catalyzed reaction; Chemical aromatization; Formaldehyde formation

Indexed keywords

19 HYDROXYANDROST 1,4 DIENE 3,17 DIONE; ACETIC ACID DERIVATIVE; ACETONE; ACID; ALDEHYDE; ALKADIENE; AROMATASE; ESTRONE; FLUORINE; FORMALDEHYDE; HYDROCHLORIC ACID; METHYL GROUP; NITROGEN; POTASSIUM HYDROXIDE; SILANE DERIVATIVE; SODIUM HYDROXIDE; STEROID; UNCLASSIFIED DRUG;

EID: 58549095640     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.10.011     Document Type: Article
Times cited : (2)

References (25)
  • 1
    • 0016272566 scopus 로고
    • The involvement of human placental microsomal cytochrome P-450 in aromatization
    • Thompson Jr. E.A., and Siiteri P.K. The involvement of human placental microsomal cytochrome P-450 in aromatization. J Biol Chem 249 (1974) 5373-5378
    • (1974) J Biol Chem , vol.249 , pp. 5373-5378
    • Thompson Jr., E.A.1    Siiteri, P.K.2
  • 2
    • 0023180688 scopus 로고
    • Purification and characterization of human placental aromatase cytochrome P-450
    • Kellis Jr. J., and Vickery L.E. Purification and characterization of human placental aromatase cytochrome P-450. J Biol Chem 262 (1987) 4413-4420
    • (1987) J Biol Chem , vol.262 , pp. 4413-4420
    • Kellis Jr., J.1    Vickery, L.E.2
  • 3
    • 0025872595 scopus 로고
    • Purification of human placental aromatase cytochrome P-450 with monoclonal antibody and its characterization
    • Yoshida N., and Osawa Y. Purification of human placental aromatase cytochrome P-450 with monoclonal antibody and its characterization. Biochemistry 30 (1991) 3003-3010
    • (1991) Biochemistry , vol.30 , pp. 3003-3010
    • Yoshida, N.1    Osawa, Y.2
  • 4
    • 0000636448 scopus 로고
    • Conversion of 19-hydroxy-4-androstene-3,17-dione to estrone by endocrine tissue
    • Meyer A.S. Conversion of 19-hydroxy-4-androstene-3,17-dione to estrone by endocrine tissue. Biochim Biophys Acta 17 (1995) 441-442
    • (1995) Biochim Biophys Acta , vol.17 , pp. 441-442
    • Meyer, A.S.1
  • 6
    • 0001689527 scopus 로고
    • 1H]-3β-hydroxy-androst-5-en-17-one by human placental aromatase
    • 1H]-3β-hydroxy-androst-5-en-17-one by human placental aromatase. J Am Chem Soc 108 (1986) 1847-1852
    • (1986) J Am Chem Soc , vol.108 , pp. 1847-1852
    • Caspi, E.1    Arunachalam, Y.2    Nelson, P.A.3
  • 7
    • 0020073188 scopus 로고
    • Mechanistic studies on C-19 demethylation in oestrogen biosynthesis
    • Akhtar M., Calder M.R., Corina D.L., and Wright J.N. Mechanistic studies on C-19 demethylation in oestrogen biosynthesis. Biochem J 201 (1982) 569-580
    • (1982) Biochem J , vol.201 , pp. 569-580
    • Akhtar, M.1    Calder, M.R.2    Corina, D.L.3    Wright, J.N.4
  • 9
    • 0024502595 scopus 로고
    • Dissociation of 19-hydroxy-, 19-oxo-, and aromatizing activities in human placental microsomes through the use of suicide substrate to aromatase
    • Bednarski P.J., and Nelson S.D. Dissociation of 19-hydroxy-, 19-oxo-, and aromatizing activities in human placental microsomes through the use of suicide substrate to aromatase. J Steroid Biochem 32 (1989) 309-316
    • (1989) J Steroid Biochem , vol.32 , pp. 309-316
    • Bednarski, P.J.1    Nelson, S.D.2
  • 11
    • 0025284640 scopus 로고
    • 2H]-androgens into oestrogens by human placental aromatase
    • 2H]-androgens into oestrogens by human placental aromatase. Biochem J 268 (1990) 553-561
    • (1990) Biochem J , vol.268 , pp. 553-561
    • Cole, P.A.1    Robinson, C.H.2
  • 12
    • 0027997441 scopus 로고
    • Aromatase inhibitors in the treatment of breast cancer
    • Brodie A.M.H. Aromatase inhibitors in the treatment of breast cancer. J Steroid Biochem Mol Biol 49 (1994) 281-287
    • (1994) J Steroid Biochem Mol Biol , vol.49 , pp. 281-287
    • Brodie, A.M.H.1
  • 13
    • 0034991842 scopus 로고    scopus 로고
    • Recent advances in the clinical application of aromatase inhibitors
    • Harper-Wynne C., and Dowsett M. Recent advances in the clinical application of aromatase inhibitors. J Steroid Biochem Mol Biol 76 (2001) 179-186
    • (2001) J Steroid Biochem Mol Biol , vol.76 , pp. 179-186
    • Harper-Wynne, C.1    Dowsett, M.2
  • 14
    • 0035714768 scopus 로고    scopus 로고
    • Where do selective estrogen receptor modulators (SERMs) and aromatase inhibitors (AIs) now fit into breast cancer treatment algorithms?
    • Howell A., Howell S.J., Clarke R., and Anderson E. Where do selective estrogen receptor modulators (SERMs) and aromatase inhibitors (AIs) now fit into breast cancer treatment algorithms?. J Steroid Biochem Mol Biol 79 (2001) 227-237
    • (2001) J Steroid Biochem Mol Biol , vol.79 , pp. 227-237
    • Howell, A.1    Howell, S.J.2    Clarke, R.3    Anderson, E.4
  • 15
    • 0037130287 scopus 로고    scopus 로고
    • Exemestane, a new steroidal aromatase inhibitor of clinical relevance
    • Lombardi P. Exemestane, a new steroidal aromatase inhibitor of clinical relevance. Biochim Biophys Acta 1587 (2002) 326-337
    • (2002) Biochim Biophys Acta , vol.1587 , pp. 326-337
    • Lombardi, P.1
  • 16
    • 0015594143 scopus 로고
    • Studies on the mechanism of estrogen biosynthesis. VIII. The development of inhibitors of the enzyme system in human placenta
    • Schwarzel W.C., Kruggel W.G., and Brodie H.J. Studies on the mechanism of estrogen biosynthesis. VIII. The development of inhibitors of the enzyme system in human placenta. Endocrinology 92 (1973) 866-880
    • (1973) Endocrinology , vol.92 , pp. 866-880
    • Schwarzel, W.C.1    Kruggel, W.G.2    Brodie, H.J.3
  • 17
    • 0019449456 scopus 로고
    • Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatriene-3,17-dione cause a time-dependent decrease in human placental aromatase activity
    • Covey D.F., and Hood W.F. Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatriene-3,17-dione cause a time-dependent decrease in human placental aromatase activity. Endocrinology 108 (1981) 1597-1599
    • (1981) Endocrinology , vol.108 , pp. 1597-1599
    • Covey, D.F.1    Hood, W.F.2
  • 18
    • 0031982998 scopus 로고    scopus 로고
    • Enzymic aromatization of 6-alkyl-substituted androgens, potent competitive and mechanism-based inhibitors of aromatase
    • Numazawa M., Yoshimura A., and Mariko O. Enzymic aromatization of 6-alkyl-substituted androgens, potent competitive and mechanism-based inhibitors of aromatase. Biochem J 329 (1998) 151-156
    • (1998) Biochem J , vol.329 , pp. 151-156
    • Numazawa, M.1    Yoshimura, A.2    Mariko, O.3
  • 19
    • 0142216815 scopus 로고
    • Biological aromatization of steroids
    • Ryan K.J. Biological aromatization of steroids. J Biol Chem (1958) 268-272
    • (1958) J Biol Chem , pp. 268-272
    • Ryan, K.J.1
  • 21
    • 0001828104 scopus 로고
    • Aromatase inhibitors: specific inhibitors of oestrogen biosynthesis
    • Berg D., and Plemel M. (Eds), Ellis Horwood Ltd, Chichester, United Kingdom
    • Covey D.F. Aromatase inhibitors: specific inhibitors of oestrogen biosynthesis. In: Berg D., and Plemel M. (Eds). Steroid biosynthesis inhibitors: pharmceutical and agrochemical aspects (1988), Ellis Horwood Ltd, Chichester, United Kingdom 534-571
    • (1988) Steroid biosynthesis inhibitors: pharmceutical and agrochemical aspects , pp. 534-571
    • Covey, D.F.1
  • 23
    • 0011942574 scopus 로고
    • Diene studies. III. Position of protonation of some pentadienyl carbanions
    • Bates R.B., Carnighan R.H., and Staples C.E. Diene studies. III. Position of protonation of some pentadienyl carbanions. J Am Chem Soc 85 (1963) 3032-3033
    • (1963) J Am Chem Soc , vol.85 , pp. 3032-3033
    • Bates, R.B.1    Carnighan, R.H.2    Staples, C.E.3
  • 24
    • 0034633301 scopus 로고    scopus 로고
    • High-performance liquid chromatography determination of N- and O-demethylase activities of chemicals in human liver microsomes: application of postcolumn fluorescence derivatization using nash reagent
    • Kobayashi K., Yamamoto T., Taguchi M., and Chiba K. High-performance liquid chromatography determination of N- and O-demethylase activities of chemicals in human liver microsomes: application of postcolumn fluorescence derivatization using nash reagent. Anal Biochem 284 (2000) 342-347
    • (2000) Anal Biochem , vol.284 , pp. 342-347
    • Kobayashi, K.1    Yamamoto, T.2    Taguchi, M.3    Chiba, K.4
  • 25
    • 49149146669 scopus 로고
    • Cleavage of tert-butyldimethylsilyl ethers by tetrafluoroborate salts
    • Metcalf B.W., Burkhart J.P., and Jund K. Cleavage of tert-butyldimethylsilyl ethers by tetrafluoroborate salts. Tetrahedron Lett 21 (1980) 35-36
    • (1980) Tetrahedron Lett , vol.21 , pp. 35-36
    • Metcalf, B.W.1    Burkhart, J.P.2    Jund, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.