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Volumn 34, Issue 23, 2004, Pages 4369-4385

Preparation of 3,17- and 3,20-difluoro-derivatives of the androst-5-ene and pregn-5-ene series

Author keywords

3,17 and 3,20 difluorosteroids; Fluorodehtdroxylation; n Perfluorosulfonyl fluoride

Indexed keywords

20 FLUOROPREGNA 3,5 DIENE; 3ALPHA FLUORO 5ALPHA ANDROST 17 ONE; 3ALPHA FLUOROANDROST 5 ENE; 3ALPHA FLUOROPREGNA 5,17 DIENE; 3ALPHA,17ALPHA DIFLUOROANDROST 5 ENE; 3ALPHA,20 DIFLUOROPREGN 5 ENE; 3BETA FLUORO 5ALPHA ANDROST 17 ONE; 3BETA FLUOROANDROST 5 EN 17 ONE; 3BETA FLUOROANDROST 5,16 DIENE; 3BETA FLUOROPREGNA 5,17 DIENE; 3BETA,17ALPHA DIFLUOROANDROST 5 ENE; 3BETA,20 DIFLUOROPREGN 5 ENE; 5ALPHA ANDROST 17 ON 3ALPHA OL; 5ALPHA ANDROST 17 ON 3BETA OL; 5ALPHA ANDROST 2 EN 17 ONE; ANDROST 5 EN 17 ON 3BETA OL; ANDROSTA 3,5 DIEN 17 ONE; ANDROSTA 3,5,16 TRIENE; ANDROSTANE DERIVATIVE; ANDROSTENEDIOL; FLUORINE DERIVATIVE; PERFLUOROBUTANESULFONYL FLUORIDE; PREGNA 3,5,17 TRIENE; STEROID; UNCLASSIFIED DRUG;

EID: 10644291681     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200039449     Document Type: Article
Times cited : (7)

References (35)
  • 1
    • 0011879122 scopus 로고    scopus 로고
    • Practical synthesis of enantiopure fluoroatnino acids of biological interest by asymmetric aldol reactions
    • Ojima, I., McCarthy, J.R., Welch, J.T., Eds.; American Chemical Society Symposium Series: Washington, DC
    • (a) Aoloshonok, V. Practical synthesis of enantiopure fluoroatnino acids of biological interest by asymmetric aldol reactions. In Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J.R., Welch, J.T., Eds.; American Chemical Society Symposium Series: Washington, DC, 1996; Vol. 639, 26-41;
    • (1996) Biomedical Frontiers of Fluorine Chemistry , vol.639 , pp. 26-41
    • Aoloshonok, V.1
  • 3
    • 0023237559 scopus 로고
    • Advances in the preparation of biologically active organofluorine compounds
    • (a) Welch, J.T. Advances in the preparation of biologically active organofluorine compounds. Tetrahedron 1987, 43, 3123;
    • (1987) Tetrahedron , vol.43 , pp. 3123
    • Welch, J.T.1
  • 4
    • 34247143283 scopus 로고
    • Preparation and properties of chiral fluoroorganic compounds
    • (b) Bravo, P.; Resnati, G. Preparation and properties of chiral fluoroorganic compounds. Terahedron: Asymmetry 1990, 1, 661.
    • (1990) Terahedron: Asymmetry , vol.1 , pp. 661
    • Bravo, P.1    Resnati, G.2
  • 5
    • 1542534457 scopus 로고
    • Recent advances in the selective formation of the C-F bond
    • Wilkinson, J.A. Recent advances in the selective formation of the C-F bond. Chem. Rev. 1992 (92), 505.
    • (1992) Chem. Rev. , Issue.92 , pp. 505
    • Wilkinson, J.A.1
  • 6
    • 0011981781 scopus 로고
    • Metabolites derived from mevalonate: Isoprenoids
    • Oxford University Press: Oxford, 2nd Ed.
    • Mann, J.E. Metabolites derived from mevalonate: isoprenoids. In Secondary Metabolish; Oxford University Press: Oxford, 2nd Ed., 1987; 95-171.
    • (1987) Secondary Metabolish , pp. 95-171
    • Mann, J.E.1
  • 8
    • 0000420715 scopus 로고
    • Fluorination with diehtylaminosulfur trifluoride and related aminofluorosulfanes
    • (a) Hudlicky, M. Fluorination with diehtylaminosulfur trifluoride and related aminofluorosulfanes. Org. React. 1988, 35, 513;
    • (1988) Org. React. , vol.35 , pp. 513
    • Hudlicky, M.1
  • 10
    • 0009819307 scopus 로고
    • Steroids. 240. Reaction of steroidal alcohol with 2-chloro-1,1,2- trifluorothylamine
    • (c) Knox, L.H.; Velarde, E.; Berger, S.; Cuadriello, D.; Cross, A.D. Steroids. 240. Reaction of steroidal alcohol with 2-chloro-1,1,2- trifluorothylamine. J. Org. Chem. 1964, 29, 2187.
    • (1964) J. Org. Chem. , vol.29 , pp. 2187
    • Knox, L.H.1    Velarde, E.2    Berger, S.3    Cuadriello, D.4    Cross, A.D.5
  • 11
    • 0009819140 scopus 로고
    • A new method for the preparation of fluorosteroids
    • (a) Ayer, D.E. A new method for the preparation of fluorosteroids. Tetrahedron Lett. 1962, 23, 1065;
    • (1962) Tetrahedron Lett. , vol.23 , pp. 1065
    • Ayer, D.E.1
  • 12
    • 0009857050 scopus 로고
    • Flourinated steroids - Synthesis of 3α-fluoro-17-β-acetoxy- estr-5(10)-ene
    • (b) Borgna, J.-L.; Mousseron-Canet, M. Flourinated steroids - synthesis of 3α-fluoro-17-β-acetoxy-estr-5(10)-ene. Bull. Soc. Chim. Fr. 1970; 2218.
    • (1970) Bull. Soc. Chim. Fr. , pp. 2218
    • Borgna, J.-L.1    Mousseron-Canet, M.2
  • 13
    • 37049045394 scopus 로고
    • Use of aprotic solvents for nucleophilic substitution reactions at C(3) and C(17) in steroids
    • (a) Henbest, H.B.; Jackson, W.R. Use of aprotic solvents for nucleophilic substitution reactions at C(3) and C(17) in steroids. J. Chem. Soc. 1962, 954;
    • (1962) J. Chem. Soc. , pp. 954
    • Henbest, H.B.1    Jackson, W.R.2
  • 14
    • 33845378182 scopus 로고
    • 1H-NMR analyses, shielding mechanism, coupling constants, and conformations in steroids bearing halogen, hydroxy, oxo groups, and double-bonds
    • 1H-NMR analyses, shielding mechanism, coupling constants, and conformations in steroids bearing halogen, hydroxy, oxo groups, and double-bonds. J. Am. Chem. Soc. 1985, 707, 7027;
    • (1985) J. Am. Chem. Soc. , vol.707 , pp. 7027
    • Schneider, H.-J.1    Buchheit, U.2    Becker, N.3    Schmidt, G.4    Siehl, U.5
  • 15
    • 0025251173 scopus 로고
    • 11-β-methoxy-substituted, 11-β-ethyl-substituted and 17-α-ethynyl-substituted 16-α-fluoroestradiols-based imaging agents with enhanced uptake efficiency and selectivity
    • (c) Pomper, M.G.; Van Brocklin, H.; Thieme, A.M.; Thomas, D.R.; et al. 11-β-methoxy-substituted, 11-β-ethyl-substituted and 17-α-ethynyl-substituted 16-α-fluoroestradiols-based imaging agents with enhanced uptake efficiency and selectivity. J. Med. Chem. 1990, 33, 3143-3155.
    • (1990) J. Med. Chem. , vol.33 , pp. 3143-3155
    • Pomper, M.G.1    Van Brocklin, H.2    Thieme, A.M.3    Thomas, D.R.4
  • 17
    • 34648824568 scopus 로고
    • Anionic activation in polymer supported reactions 2. Stereochemical studies on the introduction of fluorine at chiral centers and in biologically significant molecules
    • Colonna, S.; Re, A.; Gelbard, G.; Cesarotti, E. Anionic activation in polymer supported reactions 2. Stereochemical studies on the introduction of fluorine at chiral centers and in biologically significant molecules. J. Chem. Soc. Perkin Trans. I 1979, 2248.
    • (1979) J. Chem. Soc. Perkin Trans. I , pp. 2248
    • Colonna, S.1    Re, A.2    Gelbard, G.3    Cesarotti, E.4
  • 18
    • 0028938150 scopus 로고
    • A facile conversion of primary or secondary alcohols with n-perfluorobutanesulfonyl fluoride/1,8-diazabicyclo[5.4.0]undec-7-ene into their corresponding fluorides
    • (a) Bennua-Skalmowski, B.; Vorbrüggen, H. A facile conversion of primary or secondary alcohols with n-perfluorobutanesulfonyl fluoride/1,8-diazabicyclo[5.4.0]undec-7-ene into their corresponding fluorides. Tetrahedron Lett. 1995, 36, 2611;
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2611
    • Bennua-Skalmowski, B.1    Vorbrüggen, H.2
  • 19
    • 0036326040 scopus 로고    scopus 로고
    • Preparation of 3-α-fluoro- and 3-β-fluoroderivatives of 5-α-androst-16-enes and androsta-5,16-dienes
    • (b) Marson, C.M.; Decreau, R.A.; Smith, K.E. Preparation of 3-α-fluoro- and 3-β-fluoroderivatives of 5-α-androst-16-enes and androsta-5,16-dienes. Synth. Commun. 2002, 32, 2125.
    • (2002) Synth. Commun. , vol.32 , pp. 2125
    • Marson, C.M.1    Decreau, R.A.2    Smith, K.E.3
  • 20
    • 0027743482 scopus 로고
    • 2-Fluorinated and 4-fluorinated 16-α-[I-125]iodoestarndiol derivatives synthesis and effect on estrogen-receptor binding and receptor binding mediated target tissue uptake
    • (a) Ali, H.; Rousseau, J.; Gantchev, T.G.; vanLier, J.E. 2-Fluorinated and 4-fluorinated 16-α-[I-125]iodoestarndiol derivatives synthesis and effect on estrogen-receptor binding and receptor binding mediated target tissue uptake. J. Med. Chem. 1993, 36, 4255;
    • (1993) J. Med. Chem. , vol.36 , pp. 4255
    • Ali, H.1    Rousseau, J.2    Gantchev, T.G.3    VanLier, J.E.4
  • 21
    • 10644224602 scopus 로고
    • Bromo-derivatives, chloroderivatives, and amino derivatives of 5α-androstan and 5α-estrane
    • (b) Cowell, B.D.; Davis, A.K.; Mathieson, D.W.; Nicklin, P.D. Bromo-derivatives, chloroderivatives, and amino derivatives of 5α-androstan and 5α-estrane. J. Chem. Soc. Perkin 1, 1974, 7, 505.
    • (1974) J. Chem. Soc. Perkin 1 , vol.7 , pp. 505
    • Cowell, B.D.1    Davis, A.K.2    Mathieson, D.W.3    Nicklin, P.D.4
  • 22
    • 0016393722 scopus 로고
    • Detection of 5-α-androst-16-en-3-α-ol in human male auxiliary sweat
    • (a) Brooksband, B.W.L.; Brown, R.; Gustafsson, J.-A. Detection of 5-α-androst-16-en-3-α-ol in human male auxiliary sweat. Experientia 1974, 30, 864;
    • (1974) Experientia , vol.30 , pp. 864
    • Brooksband, B.W.L.1    Brown, R.2    Gustafsson, J.-A.3
  • 23
    • 0017142275 scopus 로고
    • Biosynthesis of steroid sulfates by the boar testes
    • (b) Gasparini, F.J.; Hochberg, R.B.; Lieberman, S. Biosynthesis of steroid sulfates by the boar testes. Biochemistry 1976, 75, 3969;
    • (1976) Biochemistry , vol.75 , pp. 3969
    • Gasparini, F.J.1    Hochberg, R.B.2    Lieberman, S.3
  • 24
    • 0028230553 scopus 로고
    • Comparison of 16-androstene steroid concentartions in sterile apocrine sweat and axillary secretions: Interconversions of 16-androstenes by the axillary microflora and a mechanism for axillary odour production in man?
    • (c) Gower, D.B.; Holland, K.T.; Mallet, A.I.; Remue, P.J.; Watkins, W.J. Comparison of 16-androstene steroid concentartions in sterile apocrine sweat and axillary secretions: interconversions of 16-androstenes by the axillary microflora and a mechanism for axillary odour production in man?. J. Steroid Biochem. Molec. Biol. 1994, 48, 409;
    • (1994) J. Steroid Biochem. Molec. Biol. , vol.48 , pp. 409
    • Gower, D.B.1    Holland, K.T.2    Mallet, A.I.3    Remue, P.J.4    Watkins, W.J.5
  • 25
    • 17744411641 scopus 로고    scopus 로고
    • Production of malodorous steroids from androsta-5,16-dienes and androsta-4,16-dienes by corynebacteria and other human axillary bacteria
    • (d) Decreau, R.A.; Marson, C.M.; Smith, K.E.; Behan, J. Production of malodorous steroids from androsta-5,16-dienes and androsta-4,16-dienes by corynebacteria and other human axillary bacteria. J. Steroid Biochem. Mol. Biol. 2003, 87, 327-336.
    • (2003) J. Steroid Biochem. Mol. Biol. , vol.87 , pp. 327-336
    • Decreau, R.A.1    Marson, C.M.2    Smith, K.E.3    Behan, J.4
  • 26
    • 0002269182 scopus 로고
    • Facile preparation of tetrabutylphosphonium fluoride and its HF adducts - New fluoride anion sources for selective nucleophilic fluorination
    • (a) Seto, H.; Qian, Z.H.; Yoshioka, H.; Uchibor, Y.; Umeno, M. Facile preparation of tetrabutylphosphonium fluoride and its HF adducts - new fluoride anion sources for selective nucleophilic fluorination. Chem. Lett. 1991, 7, 1185-1188;
    • (1991) Chem. Lett. , vol.7 , pp. 1185-1188
    • Seto, H.1    Qian, Z.H.2    Yoshioka, H.3    Uchibor, Y.4    Umeno, M.5
  • 27
    • 0002607513 scopus 로고
    • Convenient general preparation pf oxygenated rnonofluoro-5α- androstanes using diethylaminosulfur trifluoride
    • (b) Bird, T.G.; Fredericks, P.M.; Jones, E.R.H.; Meakins, G.D. Convenient general preparation pf oxygenated rnonofluoro-5α-androstanes using diethylaminosulfur trifluoride. J. Chem. Soc. Chem. Commun. 1979, 65.
    • (1979) J. Chem. Soc. Chem. Commun. , pp. 65
    • Bird, T.G.1    Fredericks, P.M.2    Jones, E.R.H.3    Meakins, G.D.4
  • 28
  • 30
    • 37049174452 scopus 로고
    • Experiments on the synthesis of substances related to the sterols 51. Completion of the syntheses of androgenic hormones and of the cholesterol group of sterols
    • (a) Cardwell, H.M.E.; Cornforth, J.W.; Duff, S.R.; Holtermann, H.; Robinson, R. Experiments on the synthesis of substances related to the sterols 51. Completion of the syntheses of androgenic hormones and of the cholesterol group of sterols. J. Chem. Soc. 1953, 361-384;
    • (1953) J. Chem. Soc. , pp. 361-384
    • Cardwell, H.M.E.1    Cornforth, J.W.2    Duff, S.R.3    Holtermann, H.4    Robinson, R.5
  • 32
    • 0032713322 scopus 로고    scopus 로고
    • Steroid transformations with Fusarium oxysporum var. cubense and Colletotrichum musae
    • (c) Wilson, M.R.; Gallimore, W.A.; Reese, P.B. Steroid transformations with Fusarium oxysporum var. cubense and Colletotrichum musae. Steroid 1999, 64, 834.
    • (1999) Steroid , vol.64 , pp. 834
    • Wilson, M.R.1    Gallimore, W.A.2    Reese, P.B.3
  • 33
    • 0001314965 scopus 로고
    • Palladium-catalyzed reduction of enol triflates to alkenes
    • Cacchi, S.; Morera, E.; Ortar, G. Palladium-catalyzed reduction of enol triflates to alkenes. Tetrahedron Lett. 1984, 25, 4821.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4821
    • Cacchi, S.1    Morera, E.2    Ortar, G.3
  • 34
    • 0007111366 scopus 로고
    • A convenient synthesis of 3-β-hydroxyandrost-4-en-17-1
    • (a) Ward, M.G.; Orr, J.C.; Engell, L.L. A convenient synthesis of 3-β-hydroxyandrost-4-en-17-1. J. Org. Chem. 1965, 30, 1421;
    • (1965) J. Org. Chem. , vol.30 , pp. 1421
    • Ward, M.G.1    Orr, J.C.2    Engell, L.L.3
  • 35
    • 0016660510 scopus 로고
    • Microbiological hydroxylation. 21. Hydroxylations of 3-halogeno-17-oxo- androstanes, 3-halogeno-7-oxo-androstanes, and 17-halogeno-3-oxo-androstanes by fungi Calonectria-Decora, Rhizopus-Nigricans, and Aspergillus-Ochraceus
    • (b) Jones, E.R.H.; Meakins, G.D.; Miners, J.O.; Wilkins, A.L. Microbiological hydroxylation. 21. Hydroxylations of 3-halogeno-17-oxo- androstanes, 3-halogeno-7-oxo-androstanes, and 17-halogeno-3-oxo-androstanes by fungi Calonectria-Decora, Rhizopus-Nigricans, and Aspergillus-Ochraceus. J. Chem Soc. Perkin Trans I 1975, 2308.
    • (1975) J. Chem Soc. Perkin Trans I , pp. 2308
    • Jones, E.R.H.1    Meakins, G.D.2    Miners, J.O.3    Wilkins, A.L.4


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