메뉴 건너뛰기




Volumn 70, Issue 11, 2005, Pages 763-769

A concise method for the preparation of deuterium-labeled cortisone: Synthesis of [6,7-2H]cortisone

Author keywords

11 HSD; 6,7 2H Cortisone; Cortisol; Cortisone; Deuterium label

Indexed keywords

17ALPHA,20:20,21 BISMETHYLENEDIOXYPREGNA 4,6 DIENE 3,11 DIONE; 17ALPHA,21 DIHYDROXYPREGNA 4,6 DIENE 3,11,20 TRION 21 ACETATE; 17ALPHA,21 DIHYDROXYPREGNA 4,6 DIENE 3,11,20 TRIONE; [6,7 2 H 2] 17ALPHA,20:20,21 BISMETHYLENEDIOXYPREGN 4 ENE 3,11 DIONE; [6,7 2 H 2] 17ALPHA,21 DIHYDROXYPREGN 4 ENE 3,11,20 TRIONE; [6,7 H 2] CORTISONE; ACETIC ACID DERIVATIVE; ALKADIENE; CORTISONE; CORTISONE ACETATE; CORTISONE DERIVATIVE; DEUTERIUM; DIENONE ACETATE; SOLVENT; UNCLASSIFIED DRUG;

EID: 23844539772     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.04.006     Document Type: Article
Times cited : (4)

References (27)
  • 1
    • 0035656177 scopus 로고    scopus 로고
    • Pathophysiology of modulation of local glucocorticoid levels by 11b-hydroxysteroid dehydrogenases
    • T.C. Sandeep, and B.R. Walker Pathophysiology of modulation of local glucocorticoid levels by 11b-hydroxysteroid dehydrogenases Trends Endocrinol Metab 12 2001 446 453
    • (2001) Trends Endocrinol Metab , vol.12 , pp. 446-453
    • Sandeep, T.C.1    Walker, B.R.2
  • 2
    • 33645370815 scopus 로고    scopus 로고
    • The role of 11beta-hydroxysteroid dehydrogenase in regulating glucocorticoid action
    • N.J. Goulding R.J. Flower Birkhauser Verlag Basel
    • M.B. Feinstein, and R.P. Schleimer The role of 11beta-hydroxysteroid dehydrogenase in regulating glucocorticoid action N.J. Goulding R.J. Flower Milestones in drug therapy: glucocorticoids 2001 Birkhauser Verlag Basel 147 160
    • (2001) Milestones in Drug Therapy: Glucocorticoids , pp. 147-160
    • Feinstein, M.B.1    Schleimer, R.P.2
  • 3
    • 0344217785 scopus 로고    scopus 로고
    • 11b-Hydroxysteroid dehydrogenase
    • P.M. Stewart, and Z.S. Krozowski 11b-Hydroxysteroid dehydrogenase Vitam Horm 57 1999 294 324
    • (1999) Vitam Horm , vol.57 , pp. 294-324
    • Stewart, P.M.1    Krozowski, Z.S.2
  • 4
    • 0028169395 scopus 로고
    • Human kidney 1lb-hydroxysteroid dehydrogenase is a high affinity nicotinamide adenine dinucleotide-dependent enzyme and differs from the cloned type I isoform
    • P.M. Stewart, B.M. Murray, and J.I. Mason Human kidney 1lb-hydroxysteroid dehydrogenase is a high affinity nicotinamide adenine dinucleotide-dependent enzyme and differs from the cloned type I isoform J Clin Endocrinol Metab 79 1994 480 484
    • (1994) J Clin Endocrinol Metab , vol.79 , pp. 480-484
    • Stewart, P.M.1    Murray, B.M.2    Mason, J.I.3
  • 5
    • 0033305631 scopus 로고    scopus 로고
    • Differentiation of adipose stromal cells: The roles of glucocorticoids and 11b-hydroxysteroid dehydrogenase
    • I.J. Bujalska, S. Kumar, M. Hewison, and P.M. Stewart Differentiation of adipose stromal cells: the roles of glucocorticoids and 11b-hydroxysteroid dehydrogenase Endocrinology 140 1999 3188 3196
    • (1999) Endocrinology , vol.140 , pp. 3188-3196
    • Bujalska, I.J.1    Kumar, S.2    Hewison, M.3    Stewart, P.M.4
  • 6
    • 0036547966 scopus 로고    scopus 로고
    • Cortisol 11b-hydroxysteroid dehydrogenase type 1 and central obesity
    • P.M. Stewart, and J.W. Tomlinson Cortisol 11b-hydroxysteroid dehydrogenase type 1 and central obesity Trends Endocrinol Metab 13 2002 94 96
    • (2002) Trends Endocrinol Metab , vol.13 , pp. 94-96
    • Stewart, P.M.1    Tomlinson, J.W.2
  • 7
    • 0000061019 scopus 로고
    • Introduction of deuterium into the steroid system
    • J. Fried J.A. Edwards Van Nostrand Reinhold Company New York
    • L. Tökés, and L.J. Throop Introduction of deuterium into the steroid system J. Fried J.A. Edwards Organic reactions in steroid chemistry vol. 1 1972 Van Nostrand Reinhold Company New York 145 221
    • (1972) Organic Reactions in Steroid Chemistry , vol.1 , pp. 145-221
    • Tökés, L.1    Throop, L.J.2
  • 8
    • 0025110330 scopus 로고
    • Synthetic procedures for the preparation of deuterium-labeled analogs of naturally occurring steroids
    • S.A. Wudy Synthetic procedures for the preparation of deuterium-labeled analogs of naturally occurring steroids Steroids 55 1990 463 471
    • (1990) Steroids , vol.55 , pp. 463-471
    • Wudy, S.A.1
  • 9
    • 0042737832 scopus 로고    scopus 로고
    • Syntheses of stable isotope-labeled 6b-hydroxycortisol, 6b-hydroxycortisone, and 6b-hydroxytestosterone
    • T. Furuta, A. Suzuki, M. Matsuzawa, H. Shibasaki, and Y. Kasuya Syntheses of stable isotope-labeled 6b-hydroxycortisol, 6b-hydroxycortisone, and 6b-hydroxytestosterone Steroids 68 2003 693 703 [and references cited therein]
    • (2003) Steroids , vol.68 , pp. 693-703
    • Furuta, T.1    Suzuki, A.2    Matsuzawa, M.3    Shibasaki, H.4    Kasuya, Y.5
  • 10
    • 0013692147 scopus 로고
    • The dehydrogenation of corticosteroids with chloranil
    • E.J. Agnello, and G.D. Laubach The dehydrogenation of corticosteroids with chloranil J Am Chem Soc 82 1960 4293 4299
    • (1960) J Am Chem Soc , vol.82 , pp. 4293-4299
    • Agnello, E.J.1    Laubach, G.D.2
  • 11
    • 0006311191 scopus 로고
    • Steroids derived from bile acids XVI. Preparation of 6-dehydrocortisone
    • V.R. Mattox, E.L. Woroch, G.A. Fleisher, and E.C. Kendall Steroids derived from bile acids XVI. Preparation of 6-dehydrocortisone J Biol Chem 197 1952 261 270
    • (1952) J Biol Chem , vol.197 , pp. 261-270
    • Mattox, V.R.1    Woroch, E.L.2    Fleisher, G.A.3    Kendall, E.C.4
  • 13
    • 0034012733 scopus 로고    scopus 로고
    • Synthesis of multi-labeled cortisols and cortisones with 2H and 13C for study of cortisol metabolism in humans
    • T. Furuta, N. Eguchi, A. Yokokawa, H. Shibasaki, and Y. Kasuya Synthesis of multi-labeled cortisols and cortisones with 2H and 13C for study of cortisol metabolism in humans Steroids 65 2000 180 189
    • (2000) Steroids , vol.65 , pp. 180-189
    • Furuta, T.1    Eguchi, N.2    Yokokawa, A.3    Shibasaki, H.4    Kasuya, Y.5
  • 14
    • 33645347362 scopus 로고    scopus 로고
    • Bruker AXS, Inc., Madison, WI, USA.
    • Bruker. SMART 2001;v5.625:Bruker AXS, Inc., Madison, WI, USA.
    • SMART 2001;v5.625
  • 15
    • 33645365822 scopus 로고    scopus 로고
    • Bruker AXS, Inc., Madison, WI, USA.
    • Bruker. SAINT 2002;v6.36A:Bruker AXS, Inc., Madison, WI, USA.
    • SAINT 2002;v6.36A
  • 16
    • 33645363618 scopus 로고    scopus 로고
    • Bruker AXS, Inc., Madison, WI, USA.
    • Bruker. XPREP 2001;v6.12:Bruker AXS, Inc., Madison, WI, USA.
    • XPREP 2001;v6.12
  • 17
    • 33645330494 scopus 로고    scopus 로고
    • Bruker AXS, Inc., Madison, WI, USA.
    • Bruker. SADABS 2000;v2.03:Bruker AXS, Inc., Madison, WI, USA.
    • SADABS 2000;v2.03
  • 18
    • 0004150157 scopus 로고    scopus 로고
    • Bruker AXS, Inc., Madison, WI, USA.
    • Bruker. SHELXTL 2000;v6.10:Bruker AXS, Inc., Madison, WI, USA.
    • SHELXTL 2000;v6.10
  • 19
    • 0015116313 scopus 로고
    • Effect of 11-oxygen function on the steric course of reduction of steroids by homogeneous catalytic hydrogenation
    • Y.J. Abul-Hajj Effect of 11-oxygen function on the steric course of reduction of steroids by homogeneous catalytic hydrogenation Steroids 18 1971 281 287
    • (1971) Steroids , vol.18 , pp. 281-287
    • Abul-Hajj, Y.J.1
  • 20
    • 0030273659 scopus 로고    scopus 로고
    • Quantitation of cortisol and related 3-oxo-4-ene steroids in urine using gas chromatography/mass spectrometry with stable isotope-labeled internal standards
    • M. Palermo, C. Gomez-Sanchez, E. Roitman, and C.H. Shackelton Quantitation of cortisol and related 3-oxo-4-ene steroids in urine using gas chromatography/mass spectrometry with stable isotope-labeled internal standards Steroids 61 1996 583 589
    • (1996) Steroids , vol.61 , pp. 583-589
    • Palermo, M.1    Gomez-Sanchez, C.2    Roitman, E.3    Shackelton, C.H.4
  • 21
    • 0026020216 scopus 로고
    • Synthesis of a deuterium-labeled cortisol for the study of its rate of 11b-hydroxy dehydrogenation in man
    • L. Linberg, J.Z. Wang, B.H. Arison, and S. Ulick Synthesis of a deuterium-labeled cortisol for the study of its rate of 11b-hydroxy dehydrogenation in man J Steroid Biochem Mol Biol 38 1991 351 357
    • (1991) J Steroid Biochem Mol Biol , vol.38 , pp. 351-357
    • Linberg, L.1    Wang, J.Z.2    Arison, B.H.3    Ulick, S.4
  • 22
    • 33645373819 scopus 로고
    • A new method for dehydrogenation of corticosteroids
    • E.J. Agnello, and G.D. Laubach A new method for dehydrogenation of corticosteroids J Am Chem Soc 79 1957 1257 1258
    • (1957) J Am Chem Soc , vol.79 , pp. 1257-1258
    • Agnello, E.J.1    Laubach, G.D.2
  • 23
    • 0000688596 scopus 로고
    • Selective reduction of steroids by homogeneous catalytic hydrogenation
    • C. Djerassi, and J. Gutzwiller Selective reduction of steroids by homogeneous catalytic hydrogenation J Am Chem Soc 88 1966 4537 4538
    • (1966) J Am Chem Soc , vol.88 , pp. 4537-4538
    • Djerassi, C.1    Gutzwiller, J.2
  • 24
    • 0014233555 scopus 로고
    • Catalytic hydrogenation and deuteration of steroids in homogenous phase
    • W. Voelter, and C. Djerassi Catalytic hydrogenation and deuteration of steroids in homogenous phase Chem Ber 101 1968 55 68
    • (1968) Chem Ber , vol.101 , pp. 55-68
    • Voelter, W.1    Djerassi, C.2
  • 25
    • 0036753553 scopus 로고    scopus 로고
    • Determination of 11-deoxycortisol (Reichstein's compound S) in human plasma by clinical isotope dilution mass spectrometry using benchtop gas chromatography-mass selective detection
    • S.A. Wudy, M. Hartmann, and J. Homoki Determination of 11-deoxycortisol (Reichstein's compound S) in human plasma by clinical isotope dilution mass spectrometry using benchtop gas chromatography-mass selective detection Steroids 67 2002 851 857
    • (2002) Steroids , vol.67 , pp. 851-857
    • Wudy, S.A.1    Hartmann, M.2    Homoki, J.3
  • 26
    • 0015921946 scopus 로고
    • Substituent effects in carbon-13 nuclear magnetic resonance spectroscopy. Progesterone, deoxycorticosterone, corticosterone, cortisol, and related steroids
    • N.S. Bhacca, D.D. Giannini, W.S. Jankowski, and M.E. Wolff Substituent effects in carbon-13 nuclear magnetic resonance spectroscopy. Progesterone, deoxycorticosterone, corticosterone, cortisol, and related steroids J Am Chem Soc 95 1973 8421 8426
    • (1973) J Am Chem Soc , vol.95 , pp. 8421-8426
    • Bhacca, N.S.1    Giannini, D.D.2    Jankowski, W.S.3    Wolff, M.E.4
  • 27
    • 0030608826 scopus 로고    scopus 로고
    • Synthesis and characterization by 1H and 13C nuclear magnetic resonance spectroscopy of 17a-cyano, 17a-aminomethyl, and 17a-alkylamidomethyl derivatives of 5a-dihydrotestosterone and testosterone
    • E. Mappus, C. Chambon, M.R. de Ravel, C. Grenot, and C.Y. Cuilleron Synthesis and characterization by 1H and 13C nuclear magnetic resonance spectroscopy of 17a-cyano, 17a-aminomethyl, and 17a-alkylamidomethyl derivatives of 5a-dihydrotestosterone and testosterone Steroids 62 1997 603 620
    • (1997) Steroids , vol.62 , pp. 603-620
    • Mappus, E.1    Chambon, C.2    De Ravel, M.R.3    Grenot, C.4    Cuilleron, C.Y.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.