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Volumn 2, Issue 1, 2000, Pages 48-65

Solid-phase synthesis of phenolic steroids: From optimization studies to a convenient procedure for combinatorial synthesis of biologically relevant estradiol derivatives

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ESTRADIOL; PHENOL DERIVATIVE; PLANT RESIN; STEROID;

EID: 0033651549     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9900504     Document Type: Article
Times cited : (29)

References (75)
  • 1
    • 0028243847 scopus 로고
    • Applications of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries
    • Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. Applications of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries. J. Med. Chem. 1994, 37, 1233-1251.
    • (1994) J. Med. Chem. , vol.37 , pp. 1233-1251
    • Gallop, M.A.1    Barrett, R.W.2    Dower, W.J.3    Fodor, S.P.A.4    Gordon, E.M.5
  • 2
    • 0028318863 scopus 로고
    • Applications of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and future directions
    • Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. Applications of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and future directions. J. Med. Chem. 1994, 37, 1385-1401.
    • (1994) J. Med. Chem. , vol.37 , pp. 1385-1401
    • Gordon, E.M.1    Barrett, R.W.2    Dower, W.J.3    Fodor, S.P.A.4    Gallop, M.A.5
  • 3
    • 0000951871 scopus 로고
    • Combinatorial Chemistry
    • Lowe, G. Combinatorial Chemistry. Chem. Soc. Rev. 1995, 309-317.
    • (1995) Chem. Soc. Rev. , pp. 309-317
    • Lowe, G.1
  • 4
    • 0029065615 scopus 로고
    • Combinatorial synthesis: The design of compound libraries and their application to drug discovery
    • Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Combinatorial synthesis: the design of compound libraries and their application to drug discovery. Tetrahedron 1995, 51, 8135-8173.
    • (1995) Tetrahedron , vol.51 , pp. 8135-8173
    • Terrett, N.K.1    Gardner, M.2    Gordon, D.W.3    Kobylecki, R.J.4    Steele, J.5
  • 5
    • 0031109859 scopus 로고    scopus 로고
    • Discovery of enzyme inhibitors through combinatorial chemistry
    • Dolle, R. E. Discovery of enzyme inhibitors through combinatorial chemistry. Mol. Diversity 1996, 2, 223-236.
    • (1996) Mol. Diversity , vol.2 , pp. 223-236
    • Dolle, R.E.1
  • 9
    • 0032600590 scopus 로고    scopus 로고
    • Parallel personal comments on "classical" papers in combinatorial chemistry
    • Lebl, M. Parallel personal comments on "classical" papers in combinatorial chemistry. J. Comb. Chem. 1999, 1, 1-22.
    • (1999) J. Comb. Chem. , vol.1 , pp. 1-22
    • Lebl, M.1
  • 10
    • 0000577984 scopus 로고    scopus 로고
    • The "one-bead-one-compound" combinatorial library method
    • Lam, K. S.; Lebl, M.; Krchňák, V. The "one-bead-one-compound" combinatorial library method. Chem. Rev. 1997, 97, 411-448.
    • (1997) Chem. Rev. , vol.97 , pp. 411-448
    • Lam, K.S.1    Lebl, M.2    Krchňák, V.3
  • 11
    • 2842561522 scopus 로고    scopus 로고
    • Design, synthesis, evaluation of small molecule libraries
    • Ellman, J. A. Design, synthesis, evaluation of small molecule libraries. Acc. Chem. Res. 1996, 29, 132-143.
    • (1996) Acc. Chem. Res. , vol.29 , pp. 132-143
    • Ellman, J.A.1
  • 13
    • 0014694677 scopus 로고
    • Binding of estrogen receptor to estradiol immobilized on insoluble resins
    • Vonderhaar, B.; Mueller, G. C. Binding of estrogen receptor to estradiol immobilized on insoluble resins. Biochim. Biophys. Acta 1969, 176, 626-631.
    • (1969) Biochim. Biophys. Acta , vol.176 , pp. 626-631
    • Vonderhaar, B.1    Mueller, G.C.2
  • 15
    • 37049094373 scopus 로고
    • Preparation of a polymer-supported diol and its use in isolating aldehydes and ketones from mixtures and as a protecting group for aldehydes and ketones
    • Hodge, P.; Waterhouse, J. Preparation of a polymer-supported diol and its use in isolating aldehydes and ketones from mixtures and as a protecting group for aldehydes and ketones. J. Chem. Soc., Perkin Trans, 1 1983, 2319-2323.
    • (1983) J. Chem. Soc., Perkin Trans, 1 , pp. 2319-2323
    • Hodge, P.1    Waterhouse, J.2
  • 16
    • 0000305913 scopus 로고
    • Preparation and chemical reactions of some polymer-supported steroids
    • Hodge, P.; Kemp, J.; Khoshdel, E.; Perry, G. M. Preparation and chemical reactions of some polymer-supported steroids. React. Polym. 1985, 3, 299-313.
    • (1985) React. Polym. , vol.3 , pp. 299-313
    • Hodge, P.1    Kemp, J.2    Khoshdel, E.3    Perry, G.M.4
  • 17
    • 37049100695 scopus 로고
    • Polymer-anchored organosilyl protecting group in organic synthesis
    • Chan, T.-H.; Huang, W.-Q. Polymer-anchored organosilyl protecting group in organic synthesis. J. Chem. Soc., Chem. Commun. 1985, 909-911.
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 909-911
    • Chan, T.-H.1    Huang, W.-Q.2
  • 19
    • 0028100318 scopus 로고
    • Peptidosteroidal receptors for opioid peptides. Sequence-selective binding using a synthetic receptor library
    • Boyce, R.; Li, G.; Nestler, P.; Suenaga, T.; Still, W. C. Peptidosteroidal receptors for opioid peptides. Sequence-selective binding using a synthetic receptor library. J. Am. Chem. Soc. 1994, 116, 7955-7956.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7955-7956
    • Boyce, R.1    Li, G.2    Nestler, P.3    Suenaga, T.4    Still, W.C.5
  • 20
    • 0029925955 scopus 로고    scopus 로고
    • Sequence-selective peptide binding with a peptido-A,B-trans-steroidal receptor selected from an encoded combinatorial receptor library
    • Cheng, Y.; Suenaga, T.; Still, W. C. Sequence-selective peptide binding with a peptido-A,B-trans-steroidal receptor selected from an encoded combinatorial receptor library. J. Am. Chem. Soc. 1996, 118, 1813-1814.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1813-1814
    • Cheng, Y.1    Suenaga, T.2    Still, W.C.3
  • 21
    • 0027940148 scopus 로고
    • Straightforward and general method for coupling alcohols to solid supports
    • Thompson, L. A.; Ellman, J. A. Straightforward and general method for coupling alcohols to solid supports. Tetrahedron Lett. 1994, 35, 9333-9336.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9333-9336
    • Thompson, L.A.1    Ellman, J.A.2
  • 23
    • 0031596753 scopus 로고    scopus 로고
    • A 6β-(thiaheptanamide) derivative of estradiol as inhibitor of 17β-hydroxysteroid dehydrogenase type 1
    • Poirier, D.; Dionne, P.; Auger, S. A 6β-(thiaheptanamide) derivative of estradiol as inhibitor of 17β-hydroxysteroid dehydrogenase type 1. J. Steroid Biochem. Mol. Biol. 1998, 64, 83-90.
    • (1998) J. Steroid Biochem. Mol. Biol. , vol.64 , pp. 83-90
    • Poirier, D.1    Dionne, P.2    Auger, S.3
  • 25
    • 0030571293 scopus 로고    scopus 로고
    • D-ring alkylamide derivatives of estradiol: Effect on ER-binding affinity and antiestrogenic activity
    • Poirier, D.; Mérand, Y.; Labrie, C.; Labrie, F. D-ring alkylamide derivatives of estradiol: effect on ER-binding affinity and antiestrogenic activity. Bioorg. Med. Chem. Lett. 1996, 6, 2537-2542.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2537-2542
    • Poirier, D.1    Mérand, Y.2    Labrie, C.3    Labrie, F.4
  • 26
    • 0031713373 scopus 로고    scopus 로고
    • Overview of a rational approach to design type I 17β-hydrosteroid dehydrogenase inhibitors without estrogenic activity: Chemical synthesis and biological evaluation
    • Tremblay, M. R.; Poirier, D. Overview of a rational approach to design type I 17β-hydrosteroid dehydrogenase inhibitors without estrogenic activity: chemical synthesis and biological evaluation. J. Steroid Biochem. Mol. Biol. 1998, 66, 179-191.
    • (1998) J. Steroid Biochem. Mol. Biol. , vol.66 , pp. 179-191
    • Tremblay, M.R.1    Poirier, D.2
  • 27
    • 0028027142 scopus 로고
    • 16α-Propyl derivatives of estradiol as inhibitors of 17β-hydroxysteroid dehydrogenase type 1
    • Sam, K. M.; Boivin, R. P.; Auger, S.; Poirier, D. 16α-Propyl derivatives of estradiol as inhibitors of 17β-hydroxysteroid dehydrogenase type 1. Bioorg. Med. Chem. Lett. 1994, 4, 2129-2132.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2129-2132
    • Sam, K.M.1    Boivin, R.P.2    Auger, S.3    Poirier, D.4
  • 28
    • 0031841053 scopus 로고    scopus 로고
    • C16 and C17 derivatives of estradiol as inhibitors of 17β-hydroxysteroid dehydrogenase type 1: Chemical synthesis and structure-activity relationships
    • Sam, K. M.; Boivin, R. P.; Tremblay, M. R.; Auger, S.; Poirier, D. C16 and C17 derivatives of estradiol as inhibitors of 17β-hydroxysteroid dehydrogenase type 1: chemical synthesis and structure-activity relationships. Drug Des. Discovery 1998, 15, 157-180.
    • (1998) Drug Des. Discovery , vol.15 , pp. 157-180
    • Sam, K.M.1    Boivin, R.P.2    Tremblay, M.R.3    Auger, S.4    Poirier, D.5
  • 29
    • 0032555172 scopus 로고    scopus 로고
    • 17α-Alkyl-or 17α-substituted benzyl-17β-estradiols: A new family of estrone-sulfatase inhibitors
    • Poirier, D.; Boivin, R. P. 17α-Alkyl-or 17α-substituted benzyl-17β-estradiols: a new family of estrone-sulfatase inhibitors. Bioorg. Med. Chem. Lett. 1998, 8, 1891-1896.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1891-1896
    • Poirier, D.1    Boivin, R.P.2
  • 30
    • 0032589988 scopus 로고    scopus 로고
    • 17α-alkan (or alkyn) amide derivatives of estradiol as inhibitors of steroid-sulfatase activity
    • Boivin, R. P.; Labrie, F.; Poirier, D. 17α-alkan (or alkyn) amide derivatives of estradiol as inhibitors of steroid-sulfatase activity. Steroids 1999, 64, 825-833.
    • (1999) Steroids , vol.64 , pp. 825-833
    • Boivin, R.P.1    Labrie, F.2    Poirier, D.3
  • 31
    • 0033578075 scopus 로고    scopus 로고
    • 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
    • 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. 1999, 42, 2280-2287.
    • (1999) J. Med. Chem. , vol.42 , pp. 2280-2287
    • Ciobanu, L.C.1    Boivin, R.P.2    Luu-The, V.3    Labrie, F.4    Poirier, D.5
  • 32
    • 0029998812 scopus 로고    scopus 로고
    • 17β-Hydroxysteroid dehydrogenase: Inhibitors and inhibitor design
    • Penning, T. M. 17β-Hydroxysteroid dehydrogenase: inhibitors and inhibitor design. Endocr.-related cancer 1996, 3, 41-56.
    • (1996) Endocr.-related Cancer , vol.3 , pp. 41-56
    • Penning, T.M.1
  • 35
    • 0033547988 scopus 로고    scopus 로고
    • Solid-phase synthesis of phenolic steroids: Towards combinatorial libraries of estradiol derivatives
    • Tremblay, M. R.; Poirier, D. Solid-phase synthesis of phenolic steroids: towards combinatorial libraries of estradiol derivatives. Tetrahedron Lett. 1999, 40, 1277-1280.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1277-1280
    • Tremblay, M.R.1    Poirier, D.2
  • 36
    • 0033523617 scopus 로고    scopus 로고
    • Parallel solid-phase synthesis of a model library of 7α-alkylamide estradiol derivatives as potential estrogen receptor antagonists
    • Tremblay, M. R.; Simard, J.; Poirier, D. Parallel solid-phase synthesis of a model library of 7α-alkylamide estradiol derivatives as potential estrogen receptor antagonists. Bioorg. Med. Chem. Lett. 1999, 9, 2827-2832.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 2827-2832
    • Tremblay, M.R.1    Simard, J.2    Poirier, D.3
  • 37
    • 0023156403 scopus 로고
    • A short, stereoselective route to 16α-(substituted-alkyl)-estradiol derivatives
    • Fevig, T. L.; Katzenellenbogen, J. A. A short, stereoselective route to 16α-(substituted-alkyl)-estradiol derivatives. J. Org. Chem. 1987, 52, 247-251.
    • (1987) J. Org. Chem. , vol.52 , pp. 247-251
    • Fevig, T.L.1    Katzenellenbogen, J.A.2
  • 40
    • 20744456789 scopus 로고
    • Solid phase peptide synthesis. The synthesis of a tetrapeptide
    • Merrifield, R. B. Solid phase peptide synthesis. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963, 85, 2149-2154.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2149-2154
    • Merrifield, R.B.1
  • 41
    • 33947291827 scopus 로고
    • Solid-phase synthesis of oligosaccharides. I. Preparation of the solid support. Poly[p-(1-propen-3-ol-1-yl)-styrene]
    • Fréchet, J. M.; Schuerch, C. Solid-phase synthesis of oligosaccharides. I. Preparation of the solid support. Poly[p-(1-propen-3-ol-1-yl)-styrene]. J. Am. Chem. Soc. 1971, 93, 492-496.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 492-496
    • Fréchet, J.M.1    Schuerch, C.2
  • 42
    • 0000299442 scopus 로고
    • 13C NMR to monitor solid-phase peptide synthesis
    • 13C NMR to monitor solid-phase peptide synthesis. Tetrahedron 1984, 40, 4141-4152.
    • (1984) Tetrahedron , vol.40 , pp. 4141-4152
    • Giralt, E.1    Rizo, J.2    Pedroso, E.3
  • 45
    • 0020667176 scopus 로고
    • Sn1 and Sn2 mechanisms for the deprotection of synthetic peptides by hydrogen fluoride
    • Tam, J. P.; Heath, W. F.; Merrifield, R. B. Sn1 and Sn2 mechanisms for the deprotection of synthetic peptides by hydrogen fluoride. Int. J. Pept. Protein Res. 1983, 21, 57-65.
    • (1983) Int. J. Pept. Protein Res. , vol.21 , pp. 57-65
    • Tam, J.P.1    Heath, W.F.2    Merrifield, R.B.3
  • 46
    • 0017402736 scopus 로고
    • Hydrogenation of protected leucine enkephalin from a resin during solid-phase synthesis
    • Jones, D. A. Hydrogenation of protected leucine enkephalin from a resin during solid-phase synthesis. Tetrahedron Lett. 1977, 33, 2853-2856.
    • (1977) Tetrahedron Lett. , vol.33 , pp. 2853-2856
    • Jones, D.A.1
  • 47
    • 0001603231 scopus 로고
    • Hydrogenation in solid-phase peptide synthesis. I. Removal of product from the resin
    • Schlatter, J. M.; Mazur, R. H. Hydrogenation in solid-phase peptide synthesis. I. Removal of product from the resin. Tetrahedron Lett. 1977, 33, 2851-2852.
    • (1977) Tetrahedron Lett. , vol.33 , pp. 2851-2852
    • Schlatter, J.M.1    Mazur, R.H.2
  • 48
    • 0018121446 scopus 로고
    • Catalytic transfer hydrogenation in solid-phase peptide synthesis: Synthesis of bradykinin
    • Khan, S. A.; Sivanandaiah, K. M. Catalytic transfer hydrogenation in solid-phase peptide synthesis: synthesis of bradykinin. Synthesis 1978, 750-751.
    • (1978) Synthesis , pp. 750-751
    • Khan, S.A.1    Sivanandaiah, K.M.2
  • 49
  • 50
    • 0015931593 scopus 로고
    • p-Alkoxybenzyl alcohol resin and p-Alkoxybenzyloxy-carbonylhydrazide resin for solid-phase synthesis of protected peptide fragments
    • Wang, S. S. p-Alkoxybenzyl alcohol resin and p-Alkoxybenzyloxy-carbonylhydrazide resin for solid-phase synthesis of protected peptide fragments. J. Am. Chem. Soc. 1973, 95, 1328-1333.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 1328-1333
    • Wang, S.S.1
  • 51
    • 0030590979 scopus 로고    scopus 로고
    • Stereoselective synthesis of highly functionalised pyrrolidines via 1,3-dipolar cycloaddition reactions on solid support
    • Hollinshead, S. P. Stereoselective synthesis of highly functionalised pyrrolidines via 1,3-dipolar cycloaddition reactions on solid support. Tetrahedron Lett. 1996, 37, 9157-9160.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9157-9160
    • Hollinshead, S.P.1
  • 52
    • 0029944026 scopus 로고    scopus 로고
    • Solid-phase synthesis of proline analogues via a three component 1,3-dipolar cycloaddition
    • Hamper, B. C.; Dukesherer, D. R.; South, M. S. Solid-phase synthesis of proline analogues via a three component 1,3-dipolar cycloaddition. Tetrahedron Lett. 1996, 37, 3671-3674.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3671-3674
    • Hamper, B.C.1    Dukesherer, D.R.2    South, M.S.3
  • 53
    • 0032546147 scopus 로고    scopus 로고
    • Polymer-bound p-alkoxybenzyl trichloroacetamidates: Reagents for the protection of alcohols as benzyl ethers on solid phase
    • Hanessian, S.; Xie, F. Polymer-bound p-alkoxybenzyl trichloroacetamidates: reagents for the protection of alcohols as benzyl ethers on solid phase. Tetrahedron Lett. 1998, 39, 733-736.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 733-736
    • Hanessian, S.1    Xie, F.2
  • 54
    • 0027068161 scopus 로고
    • A general and expedient method for the solid-phase synthesis of 1,4-benzodiazepine derivatives
    • Bunin, B. A.; Ellman, J. A. A general and expedient method for the solid-phase synthesis of 1,4-benzodiazepine derivatives. J. Am. Chem. Soc. 1992, 114, 10997-10998.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10997-10998
    • Bunin, B.A.1    Ellman, J.A.2
  • 55
    • 0028928237 scopus 로고
    • Solid-phase synthesis of structure diverse 1,4-benzodiazepine derivatives using the Stille coupling reaction
    • Plunkett, M. J.; Ellman, J. A. Solid-phase synthesis of structure diverse 1,4-benzodiazepine derivatives using the Stille coupling reaction. J. Am. Chem. Soc. 1995, 117, 3306-3307.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3306-3307
    • Plunkett, M.J.1    Ellman, J.A.2
  • 56
    • 0030600160 scopus 로고    scopus 로고
    • Solid-phase synthesis of 1,3-dialkyl quinazoline-2,4-diones
    • Buckman, B. O.; Mohan, R. Solid-phase synthesis of 1,3-dialkyl quinazoline-2,4-diones. Tetrahedron Lett. 1996, 37, 4439-4442.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4439-4442
    • Buckman, B.O.1    Mohan, R.2
  • 57
    • 0030607199 scopus 로고    scopus 로고
    • Heck reaction on solid support: Synthesis of indole analogues
    • Yun, W.; Mohan, R. Heck reaction on solid support: synthesis of indole analogues. Tetrahedron Lett. 1996, 37, 7189-7192.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7189-7192
    • Yun, W.1    Mohan, R.2
  • 58
    • 0343471944 scopus 로고    scopus 로고
    • A TFA-cleavable linkage for solid-phase synthesis of hydroxamic acids
    • Richter, L. S.; Desai, M. C. A TFA-cleavable linkage for solid-phase synthesis of hydroxamic acids. Tetrahedron Lett. 1997, 38, 321-322.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 321-322
    • Richter, L.S.1    Desai, M.C.2
  • 59
    • 0030873736 scopus 로고    scopus 로고
    • Nonacidic cleavage of Wang-derived ethers from solid support: Utilization of a mixed-bed scavenger for DDQ
    • Deegan, T. L.; Gooding, O. W.; Baudart, S.; Porco, J. A. Nonacidic cleavage of Wang-derived ethers from solid support: utilization of a mixed-bed scavenger for DDQ. Tetrahedron Lett. 1997, 38, 4973-4976.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 4973-4976
    • Deegan, T.L.1    Gooding, O.W.2    Baudart, S.3    Porco, J.A.4
  • 61
    • 0028968619 scopus 로고
    • Expedient method for solid-phase synthesis of aspartic acid protease inhibitors directed toward the generation of libraries
    • Kick, E. K.; Ellman, J. A. Expedient method for solid-phase synthesis of aspartic acid protease inhibitors directed toward the generation of libraries. J. Med. Chem. 1995, 38, 1427-1430.
    • (1995) J. Med. Chem. , vol.38 , pp. 1427-1430
    • Kick, E.K.1    Ellman, J.A.2
  • 62
    • 0030694747 scopus 로고    scopus 로고
    • Solid-phase synthesis of pyrrolidines via 2-azaallyl anion cycloadditions with alkenes
    • Pearson, W. H.; Clark, R. B. Solid-phase synthesis of pyrrolidines via 2-azaallyl anion cycloadditions with alkenes. Tetrahedron Lett. 1997, 38, 7669-7672.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7669-7672
    • Pearson, W.H.1    Clark, R.B.2
  • 64
    • 0016856718 scopus 로고
    • Preparation of a new o-nitrobenzyl resin for solid-phase synthesis of t-Boc-protected peptid acids
    • Rich, D. H.; Gurwara, S. K. Preparation of a new o-nitrobenzyl resin for solid-phase synthesis of t-Boc-protected peptid acids. J. Am. Chem. Soc. 1975, 97, 1575-1579.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 1575-1579
    • Rich, D.H.1    Gurwara, S.K.2
  • 65
    • 0000886123 scopus 로고
    • A three-dimensional orthogonal protection scheme for solid-phase peptide synthesis under mild conditions
    • Barany, G.; Albericio, F. A three-dimensional orthogonal protection scheme for solid-phase peptide synthesis under mild conditions. J. Am. Chem. Soc. 1985, 107, 4936-4942.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 4936-4942
    • Barany, G.1    Albericio, F.2
  • 66
    • 0017624051 scopus 로고
    • A photolabile protecting group for the phenolic hydroxyl function of tyrosine
    • Amit, B.; Hazum, E.; Fridkin, M.; Patchornik, A. A photolabile protecting group for the phenolic hydroxyl function of tyrosine. Int. J. Pept. Protein Res. 1977, 9, 91-96.
    • (1977) Int. J. Pept. Protein Res. , vol.9 , pp. 91-96
    • Amit, B.1    Hazum, E.2    Fridkin, M.3    Patchornik, A.4
  • 69
    • 49049124890 scopus 로고
    • Réduction d'azides en amines primaires par une méthode générale utilisant la réaction de staudinger
    • Vaultier, M.; Knouzi, N.; Carrie, R. Réduction d'azides en amines primaires par une méthode générale utilisant la réaction de Staudinger. Tetrahedron Lett. 1983, 24, 763-764.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 763-764
    • Vaultier, M.1    Knouzi, N.2    Carrie, R.3
  • 71
    • 0031575797 scopus 로고    scopus 로고
    • Solid-phase synthesis of small molecule libraries using double combinatorial chemistry
    • Nielsen, J.; Jensen, F. R. Solid-phase synthesis of small molecule libraries using double combinatorial chemistry. Tetrahedron Lett. 1997, 38, 2011-2014.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 2011-2014
    • Nielsen, J.1    Jensen, F.R.2
  • 73
    • 0033534512 scopus 로고    scopus 로고
    • A simple procedure for the solid phase synthesis of unsymmetrically functionalized diamides from symmetric diacids
    • Wahhab, A.; Leban, J. A simple procedure for the solid phase synthesis of unsymmetrically functionalized diamides from symmetric diacids. Tetrahedron Lett. 1999, 40, 235-238.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 235-238
    • Wahhab, A.1    Leban, J.2
  • 74
    • 0029926720 scopus 로고    scopus 로고
    • Novel solution phase strategy for the synthesis of chemical libraries containing small organic molecules
    • Cheng, S.; Comer, D. D.; Williams, J. P.; Meyers, P. L.; Boger, D. L. Novel solution phase strategy for the synthesis of chemical libraries containing small organic molecules. J. Am. Chem. Soc. 1996, 118, 2567-2573.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2567-2573
    • Cheng, S.1    Comer, D.D.2    Williams, J.P.3    Meyers, P.L.4    Boger, D.L.5
  • 75
    • 0029011261 scopus 로고
    • Synthesis of 16-(bromoalkyl)-estradiols having inhibitory effect on human placental estradiol 17β-hydroxysteroid dehydrogenase (17β-HSD type 1)
    • Tremblay, M. R.; Auger, S.; Poirier, D. Synthesis of 16-(bromoalkyl)-estradiols having inhibitory effect on human placental estradiol 17β-hydroxysteroid dehydrogenase (17β-HSD type 1). Bioorg. Med. Chem. 1995, 3, 505-523.
    • (1995) Bioorg. Med. Chem. , vol.3 , pp. 505-523
    • Tremblay, M.R.1    Auger, S.2    Poirier, D.3


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