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Volumn 12, Issue 5, 2011, Pages 2853-2890

Conformationally constrained histidines in the design of peptidomimetics: Strategies for the χ-space control

Author keywords

space; Alkyl substitution; Amino acids; Conformation; Histidine; Stereoselective synthesis

Indexed keywords

1 (4 IMIDAZOLYL)ALKYL CHLORIDE; 1 AMINO 2 (4 IMIDAZOLYL)CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; 2 ACETAMIDO 3 [IMIDAZOL 4(5)YL ACRYLIC]ACID; 2 ALKYL 2 (4 IMIDAZOLYLMETHYL)ACETOACETIC ACID; 4,5,6,7 TETRAHYDRO 1H IMIDAZO[4,5 C]PYRIDINE 6 CARBOXYLIC ACID; ALPHA AMINO 1,2,3 TRIAZOLE 4 PROPIONIC ACID; ALPHA BENZAMIDO 1,2,3 TRIAZOLE 4 PROPIONIC ACID; ALPHA HYDROGEN; ALPHABETA DEHYDROHISTIDINE; AZA HISTIDINE; AZLACTONE; BETA HYDROGEN; BETA METHYLHISTIDINE DERIVATIVE; BETA2 HOMO HISTIDINE; DIETHYL ACETAMIDOMALONATE; HISTIDINE DERIVATIVE; HOMO HISTIDINE; HYDROGEN; IMIDAZOLE 5 METHANOL; IMIDAZOLYLGLYCINE; N TOSYL ACETOXYMETHYLIMIDAZOLE; N TRITYL 4 CYANOMETHYLIMIDAZOLE; NOR HISTIDINE; PEPTIDOMIMETIC AGENT; PILOCARPINE DERIVATIVE; SPINACINE DERIVATIVE; UNCLASSIFIED DRUG; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; HISTIDINE;

EID: 79957810027     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms12052853     Document Type: Article
Times cited : (38)

References (93)
  • 3
    • 37049095671 scopus 로고
    • Cyclodepsitripeptides. Synthesis, Crystal Structure and Molecular Conformations of cyclo(-L-2-Hydroxyisovaleryl-L-prolyl-L-prolyl-) and cyclo(-D-2-Hydroxyisovaleryl-L-prolyl-L-prolyl-)
    • Pinnen, F.; Zanotti, G.; Lucente, G.; Cerrini, S.; Fedeli, W.; Gavuzzo, E. Cyclodepsitripeptides. Synthesis, Crystal Structure and Molecular Conformations of cyclo(-L-2-Hydroxyisovaleryl-L-prolyl-L-prolyl-) and cyclo(-D-2-Hydroxyisovaleryl-L-prolyl-L-prolyl-). J. Chem. Soc. Perkin Trans. II 1985, 12, 1931-1937.
    • (1985) J. Chem. Soc. Perkin Trans , vol.2 , Issue.12 , pp. 1931-1937
    • Pinnen, F.1    Zanotti, G.2    Lucente, G.3    Cerrini, S.4    Fedeli, W.5    Gavuzzo, E.6
  • 6
    • 0027626855 scopus 로고
    • Conformational and topographical considerations in the design of biologically active peptides
    • Hruby, V.J. Conformational and topographical considerations in the design of biologically active peptides. Biopolymers 1993, 33, 1073-1082.
    • (1993) Biopolymers , vol.33 , pp. 1073-1082
    • Hruby, V.J.1
  • 7
    • 0013612864 scopus 로고
    • Hodges, R.S., Wieland, T., Karger, S., Eds.; Karger: Basel, Switzerland
    • Hruby, V.J. Peptides: Chemistry, Structure and Biology; Hodges, R.S., Wieland, T., Karger, S., Eds.; Karger: Basel, Switzerland, 1995; pp. 207-220.
    • (1995) Peptides: Chemistry, Structure and Biology , pp. 207-220
    • Hruby, V.J.1
  • 8
    • 0034716521 scopus 로고    scopus 로고
    • First stereoselective synthesis of an optically pure β-substituted histidine: (2S,3S)-β-methylhistidine
    • Wang, S.; Tang, X.; Hruby, V.J. First stereoselective synthesis of an optically pure β-substituted histidine: (2S,3S)-β-methylhistidine. Tetrahedron Lett. 2000, 41, 1307-1310.
    • (2000) Tetrahedron Lett , vol.41 , pp. 1307-1310
    • Wang, S.1    Tang, X.2    Hruby, V.J.3
  • 9
    • 0000254274 scopus 로고
    • Release of vasopressin from the rat hypothalamo-neurohypophysial system by angiotensin-(1-7) heptapeptide
    • Schiavone, M.T.; Santos, R.A.; Brosnihan, K.B.; Khosla, M.C.; Ferrario, C.M. Release of vasopressin from the rat hypothalamo-neurohypophysial system by angiotensin-(1-7) heptapeptide. Proc. Natl. Acad. Sci. USA 1988, 85, 4095-4098.
    • (1988) Proc. Natl. Acad. Sci. USA , vol.85 , pp. 4095-4098
    • Schiavone, M.T.1    Santos, R.A.2    Brosnihan, K.B.3    Khosla, M.C.4    Ferrario, C.M.5
  • 10
    • 0021209195 scopus 로고
    • Characterization of cDNA for precursore of human luteinizing hormone releasing hormone
    • Seeburg, P.H.; Adelman, J.P. Characterization of cDNA for precursore of human luteinizing hormone releasing hormone. Nature 1984, 311, 666-668.
    • (1984) Nature , vol.311 , pp. 666-668
    • Seeburg, P.H.1    Adelman, J.P.2
  • 12
    • 0016260535 scopus 로고
    • Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological system
    • Sundberg, R.J.; Martin, R.B. Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological system. Chem. Rev. 1974, 74, 471-517.
    • (1974) Chem. Rev , vol.74 , pp. 471-517
    • Sundberg, R.J.1    Martin, R.B.2
  • 13
    • 0003505419 scopus 로고    scopus 로고
    • In Compendium of Chemical Terminology
    • 2nd ed.; Blackwell Scientific Publications: Oxford, UK
    • McNaught, A.D.; Wilkinson, A. In Compendium of Chemical Terminology: IUPAC Reccomandations, 2nd ed.; Blackwell Scientific Publications: Oxford, UK, 1997; p. 43.
    • (1997) IUPAC Reccomandations , pp. 43
    • McNaught, A.D.1    Wilkinson, A.2
  • 14
    • 14044258481 scopus 로고    scopus 로고
    • Peptides containing 4-amino-1,2-dithiolane-4-carboxylic acid (Adt): Conformation of Boc-Adt-Adt-NHMe and NH...S interactions
    • Morera, E.; Nalli, M.; Mollica, A.; Paradisi, M.P.; Aschi, M.; Gavuzzo, E.; Mazza, F.; Lucente, G. Peptides containing 4-amino-1,2-dithiolane-4-carboxylic acid (Adt): Conformation of Boc-Adt-Adt-NHMe and NH...S interactions. J. Pept. Sci. 2005, 11, 104-112.
    • (2005) J. Pept. Sci , vol.11 , pp. 104-112
    • Morera, E.1    Nalli, M.2    Mollica, A.3    Paradisi, M.P.4    Aschi, M.5    Gavuzzo, E.6    Mazza, F.7    Lucente, G.8
  • 15
    • 84855994462 scopus 로고
    • The preparation of DL-α-methylhistidine dihydrochloride
    • Robinson, B.; Shepherd, D.M. The preparation of DL-α-methylhistidine dihydrochloride. J. Chem. Soc. 1961, 503-508.
    • (1961) J. Chem. Soc , pp. 503-508
    • Robinson, B.1    Shepherd, D.M.2
  • 16
    • 0038655728 scopus 로고
    • C-Alkylation with quaternary ammonium salts. A new approach to the synthesis of compounds containing the β-indolemethylene group
    • Snyder, H.R.; Smith, C.W.; Curtius, W.; Stewart, J.M. C-Alkylation with quaternary ammonium salts. A new approach to the synthesis of compounds containing the β-indolemethylene group. J. Am. Chem. Soc. 1944, 66, 200-204.
    • (1944) J. Am. Chem. Soc , vol.66 , pp. 200-204
    • Snyder, H.R.1    Smith, C.W.2    Curtius, W.3    Stewart, J.M.4
  • 17
    • 85171969389 scopus 로고
    • A new synthesis of imidazole derivatives
    • Weidenhagen, R.; Harrmann, R. A new synthesis of imidazole derivatives. Chem. Ber. 1935, 68, 1953-1961.
    • (1935) Chem. Ber , vol.68 , pp. 1953-1961
    • Weidenhagen, R.1    Harrmann, R.A.2
  • 18
    • 33947447077 scopus 로고
    • Studies on imidazole compounds. I. 4-Methylimidazole and related compounds
    • Turner, R.A.; Huebner, C.F.; Scholz, C.R. Studies on imidazole compounds. I. 4-Methylimidazole and related compounds. J. Am. Chem. Soc. 1949, 71, 2801-2803.
    • (1949) J. Am. Chem. Soc , vol.71 , pp. 2801-2803
    • Turner, R.A.1    Huebner, C.F.2    Scholz, C.R.3
  • 19
    • 85162674246 scopus 로고
    • The imine residue
    • Schmidt, K.F. The imine residue. Chem. Ber. 1924, 57, 704-706.
    • (1924) Chem. Ber , vol.57 , pp. 704-706
    • Schmidt, K.F.1
  • 20
    • 84856015952 scopus 로고
    • α-alkyl histidines
    • U.S. Patent 3
    • Sletzinger, M.; Pfister, K. α-alkyl histidines. U.S. Patent 3,169, 971, 1965.
    • (1965) , vol.3 , Issue.169 , pp. 971
    • Sletzinger, M.1    Pfister, K.2
  • 22
    • 84973065254 scopus 로고
    • Synthesis of α-methylhistidine by catalytic phase-transfer alkylations
    • O'Donnell, M.J.; Rusterholz, D.B. Synthesis of α-methylhistidine by catalytic phase-transfer alkylations. Synt. Commun. 1989, 19, 1157-1165.
    • (1989) Synt. Commun , vol.19 , pp. 1157-1165
    • O'Donnell, M.J.1    Rusterholz, D.B.2
  • 23
    • 0016190247 scopus 로고
    • Synthesis of amino acids and related compounds. 8. Improved synthesis of DL-histidine
    • Matsumoto, K.; Miyahara, T.; Suzuki, M.; Miyoshi, M. Synthesis of amino acids and related compounds. 8. Improved synthesis of DL-histidine. Agric. Biol. Chem. 1974, 38, 1097-1115.
    • (1974) Agric. Biol. Chem , vol.38 , pp. 1097-1115
    • Matsumoto, K.1    Miyahara, T.2    Suzuki, M.3    Miyoshi, M.4
  • 24
    • 0017687534 scopus 로고
    • Attempted inhibition of histidine decarboxylase with β-alkyl analogs of histidine
    • Kelley, J.L.; Miller, C.A.; McLean, E.W. Attempted inhibition of histidine decarboxylase with β-alkyl analogs of histidine. J. Med. Chem. 1977, 20, 721-723.
    • (1977) J. Med. Chem , vol.20 , pp. 721-723
    • Kelley, J.L.1    Miller, C.A.2    McLean, E.W.3
  • 25
    • 0041159141 scopus 로고
    • Use of Et acetamidomalonate in the synthesis of amino acids. Preparation of dl-histidine, dl-phenilalanine and dl-leucine
    • Albertson, N.F.; Archer, S. Use of Et acetamidomalonate in the synthesis of amino acids. Preparation of dl-histidine, dl-phenilalanine and dl-leucine. J. Am. Chem. Soc. 1945, 67, 308-310.
    • (1945) J. Am. Chem. Soc , vol.67 , pp. 308-310
    • Albertson, N.F.1    Archer, S.2
  • 26
    • 0022490196 scopus 로고
    • Asymmetric glycine enolate aldol reactions: Synthesis of cyclosporin's unusual amino acid, MeBmt
    • Evans, D.A.; Weber, A.E. Asymmetric glycine enolate aldol reactions: Synthesis of cyclosporin's unusual amino acid, MeBmt. J. Am. Chem. Soc. 1986, 108, 6757-6761.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 6757-6761
    • Evans, D.A.1    Weber, A.E.2
  • 27
    • 0342581678 scopus 로고
    • Derivatives of glyoxaline-4(or 5)-formaldehyde and glyoxaline-4(or 5)-carboxylic acid. A new synthesis of histidine
    • Pyman, F.L. Derivatives of glyoxaline-4(or 5)-formaldehyde and glyoxaline-4(or 5)-carboxylic acid. A new synthesis of histidine. J. Chem. Soc. 1916, 109, 186-202.
    • (1916) J. Chem. Soc , vol.109 , pp. 186-202
    • Pyman, F.L.1
  • 28
    • 14644388072 scopus 로고    scopus 로고
    • Novel β-(imidazol-4-yl)-β-amino acids: Solid-phase synthesis and study of their inhibitory activity against geranylgeranyl protein transferase type I
    • Saha, A.K.; End, D.W. Novel β-(imidazol-4-yl)-β-amino acids: Solid-phase synthesis and study of their inhibitory activity against geranylgeranyl protein transferase type I. Biorg. Med. Chem. Lett. 2005, 15, 1713-1719.
    • (2005) Biorg. Med. Chem. Lett , vol.15 , pp. 1713-1719
    • Saha, A.K.1    End, D.W.2
  • 29
    • 0025818883 scopus 로고
    • Asymmetric synthesis of R-β-amino butanoic acid and S-β-tyrosine: Homochiral lithium amide equivalents for Michael additions to α,β-unsaturated esters
    • Davies, S.G.; Ichihara, O. Asymmetric synthesis of R-β-amino butanoic acid and S-β-tyrosine: Homochiral lithium amide equivalents for Michael additions to α,β-unsaturated esters. Tetrahedron: Asimmetry 1991, 2, 183-186.
    • (1991) Tetrahedron: Asimmetry , vol.2 , pp. 183-186
    • Davies, S.G.1    Ichihara, O.2
  • 30
    • 0017669320 scopus 로고
    • Potential histidine decarboxylase inhibitors. I. α- and β-substituted histidine analogues
    • De Graw, J.I.; Engstrom, J.; Ellis, M.; Johnson, H.L. Potential histidine decarboxylase inhibitors. I. α- and β-substituted histidine analogues. J. Med. Chem. 1977, 20, 1671-1674.
    • (1977) J. Med. Chem , vol.20 , pp. 1671-1674
    • de Graw, J.I.1    Engstrom, J.2    Ellis, M.3    Johnson, H.L.4
  • 32
    • 33947475233 scopus 로고
    • Potential growth antagonists. I. Hydantoins and di-substituted glycine
    • Goodson, L.H.; Honigberg, I.L.; Lehman, J.J.; Burton, W.H. Potential growth antagonists. I. Hydantoins and di-substituted glycine. J. Org. Chem. 1960, 25, 1920-1924.
    • (1960) J. Org. Chem , vol.25 , pp. 1920-1924
    • Goodson, L.H.1    Honigberg, I.L.2    Lehman, J.J.3    Burton, W.H.4
  • 33
    • 84937424396 scopus 로고
    • Formation of isoquinoline derivatives by the action of methylal on phenylethylamine, phenylalanine and tyrosine
    • Pictet, A.; Spengler T. Formation of isoquinoline derivatives by the action of methylal on phenylethylamine, phenylalanine and tyrosine. Ber. Dtsch. Chem. Ges. 1911, 44, 2030-2036.
    • (1911) Ber. Dtsch. Chem. Ges , vol.44 , pp. 2030-2036
    • Pictet, A.1    Spengler, T.2
  • 34
    • 0001625508 scopus 로고
    • The Pictet-Spengler of tetrahydroisoquinolines and related compounds
    • Whaley, W.M.; Govindachari, T.R. The Pictet-Spengler of tetrahydroisoquinolines and related compounds. Org. React. 1951, 6, 151-190.
    • (1951) Org. React , vol.6 , pp. 151-190
    • Whaley, W.M.1    Govindachari, T.R.2
  • 35
    • 0026550526 scopus 로고
    • A facile synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxyilic acid, a conformationally constrained tyrosine analog
    • Verschueren, K.; Toth, G.; Tourwe, D.; Lelb, M.; van Binst, G.; Hruby, V.J. A facile synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxyilic acid, a conformationally constrained tyrosine analog. Synthesis 1992, 458-460.
    • (1992) Synthesis , pp. 458-460
    • Verschueren, K.1    Toth, G.2    Tourwe, D.3    Lelb, M.4    van Binst, G.5    Hruby, V.J.6
  • 36
    • 0023776001 scopus 로고
    • Acylphenylalanines and related compounds. A new class of oral hypoglycemic agents
    • Shinkai, H.; Toi, K.; Kumashiro, I.; Seto, Y.; Fukuma, M.; Dan, K.; Toyoshima, S. N-acylphenylalanines and related compounds. A new class of oral hypoglycemic agents. J. Med. Chem. 1988, 31, 2092-2097.
    • (1988) J. Med. Chem , vol.31 , pp. 2092-2097
    • Shinkai, H.1    Toi, K.2    Kumashiro, I.3    Seto, Y.4    Fukuma, M.5    Dan, K.6    Toyoshima, S.N.7
  • 37
    • 0020534264 scopus 로고
    • Studies on angiotensin-converting enzyme inhibitors. I. Syntheses and angiotensin-converting enzyme inhibitory activity of 2-(3-mercaptopropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives
    • Hayashi, K.; Ozaki, Y.; Nunami, K.; Uchida, T.; Kato, J.; Kinashi, K.; Yoneda, N. Studies on angiotensin-converting enzyme inhibitors. I. Syntheses and angiotensin-converting enzyme inhibitory activity of 2-(3-mercaptopropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives. Chem. Pharm. Bull. 1983, 31, 570-576.
    • (1983) Chem. Pharm. Bull , vol.31 , pp. 570-576
    • Hayashi, K.1    Ozaki, Y.2    Nunami, K.3    Uchida, T.4    Kato, J.5    Kinashi, K.6    Yoneda, N.7
  • 38
    • 37049089861 scopus 로고
    • Binary and ternary copper (II) complexes of Nτ- and Nπ- methyl-L-histidine in aqueous solution
    • Remelli, M.; Munerato, C.; Pulidori, F. Binary and ternary copper (II) complexes of Nτ- and Nπ- methyl-L-histidine in aqueous solution. J. Chem. Soc. Dalton Trans. 1994, 14, 2049-2056.
    • (1994) J. Chem. Soc. Dalton Trans , vol.14 , pp. 2049-2056
    • Remelli, M.1    Munerato, C.2    Pulidori, F.3
  • 39
    • 0000424787 scopus 로고
    • Binary and ternary copper (II) complexes of L-spinacine in aqueous solution
    • Remelli, M.; Rossi, S.; Guerrini, R.; Pulidori, F. Binary and ternary copper (II) complexes of L-spinacine in aqueous solution. Ann. Chim. 1995, 85, 503-518.
    • (1995) Ann. Chim , vol.85 , pp. 503-518
    • Remelli, M.1    Rossi, S.2    Guerrini, R.3    Pulidori, F.4
  • 41
    • 0039383524 scopus 로고
    • Synthetic alkaloids from tyrosine, tryptophane and histidine
    • Wellisch, J. Synthetic alkaloids from tyrosine, tryptophane and histidine. Biochem. Z. 1913, 49, 173-194.
    • (1913) Biochem. Z , vol.49 , pp. 173-194
    • Wellisch, J.1
  • 42
    • 0025973810 scopus 로고
    • 4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acids (Spinacines)
    • Klutchko, S.; Hodges, J.C.; Blankley, C.J.; Colbry, N.L. 4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acids (Spinacines). J. Heterocycl. Chem. 1991, 28, 97-108.
    • (1991) J. Heterocycl. Chem , vol.28 , pp. 97-108
    • Klutchko, S.1    Hodges, J.C.2    Blankley, C.J.3    Colbry, N.L.4
  • 43
    • 0006344903 scopus 로고    scopus 로고
    • Synthesis of spinacine and spinacine derivatives: Crystal and molecular structures of NΠ-hydroxy-methyl spinacine and Nα-methyl spinaceamine
    • Remelli, M.; Pulidori, F.; Guerrini, R.; Bertolasi, V. Synthesis of spinacine and spinacine derivatives: Crystal and molecular structures of NΠ-hydroxy-methyl spinacine and Nα-methyl spinaceamine. J. Chem. Crystallogr. 1997, 27, 507-513.
    • (1997) J. Chem. Crystallogr , vol.27 , pp. 507-513
    • Remelli, M.1    Pulidori, F.2    Guerrini, R.3    Bertolasi, V.4
  • 46
    • 0039383522 scopus 로고
    • Crystal and molecular structure of the amino acid spinacine dihydrate [4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrate] Gazz
    • Andreetti, G.D.; Cavalca, L.; Sgarabotto, P. Crystal and molecular structure of the amino acid spinacine dihydrate [4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid dihydrate] Gazz. Chim. Ital. 1971, 101, 625-634.
    • (1971) Chim. Ital , vol.101 , pp. 625-634
    • Andreetti, G.D.1    Cavalca, L.2    Sgarabotto, P.3
  • 47
    • 0000823903 scopus 로고
    • The crystal structure of imidazole at 103 K by neutron diffraction
    • McMullan, R.K.; Epstein, J.; Ruble, J.R.; Craven, B.M. The crystal structure of imidazole at 103 K by neutron diffraction. Acta Crystallogr. 1979, B35, 688-691.
    • (1979) Acta Crystallogr , vol.B35 , pp. 688-691
    • McMullan, R.K.1    Epstein, J.2    Ruble, J.R.3    Craven, B.M.4
  • 48
    • 0000283622 scopus 로고
    • The crystal structure of the monoclinic form of L-Histidine
    • Madden, J.L.; McGandy, E.L.; Seeman, N.C. The crystal structure of the monoclinic form of L-Histidine. Acta Crystallogr. 1972, B28, 2377-2382.
    • (1972) Acta Crystallogr , vol.B28 , pp. 2377-2382
    • Madden, J.L.1    McGandy, E.L.2    Seeman, N.C.3
  • 49
    • 1842692143 scopus 로고
    • General definition of ring puckering coordinates
    • Cremer, D.; Pople, J.A. General definition of ring puckering coordinates. J. Am. Chem. Soc. 1975, 97, 1354-1358.
    • (1975) J. Am. Chem. Soc , vol.97 , pp. 1354-1358
    • Cremer, D.1    Pople, J.A.2
  • 50
    • 84906441301 scopus 로고
    • Ring asymmetry parameters from out-of plane atomic displacements
    • Nardelli, M. Ring asymmetry parameters from out-of plane atomic displacements. Acta Crystallogr. 1983, C39, 1141-1142.
    • (1983) Acta Crystallogr , vol.C39 , pp. 1141-1142
    • Nardelli, M.1
  • 51
    • 0033555780 scopus 로고    scopus 로고
    • Towards control of χ-space: Conformationally constrained analogues of Phe, Tyr, Trp and His
    • Gibson, S.E.; Guillo, N.; Tozer, M.J. Towards control of χ-space: Conformationally constrained analogues of Phe, Tyr, Trp and His. Tetrahedron 1999, 55, 585-615.
    • (1999) Tetrahedron , vol.55 , pp. 585-615
    • Gibson, S.E.1    Guillo, N.2    Tozer, M.J.3
  • 52
    • 0013945205 scopus 로고
    • 1-Amino-2-(4-imidazolyl)cyclopropanecarboxylic acid
    • Pages, R.A.; Burger, A. 1-Amino-2-(4-imidazolyl)cyclopropanecarboxylic acid. J. Med. Chem. 1966, 9, 766-768.
    • (1966) J. Med. Chem , vol.9 , pp. 766-768
    • Pages, R.A.1    Burger, A.2
  • 53
    • 0011811110 scopus 로고
    • 2-Phenyl-4-arylidene-5-oxazolones
    • Awad, W.I.; Fateen, A.K.; Zayed, M.A. 2-Phenyl-4-arylidene-5-oxazolones. Tetrahedron 1964, 20, 891-896.
    • (1964) Tetrahedron , vol.20 , pp. 891-896
    • Awad, W.I.1    Fateen, A.K.2    Zayed, M.A.3
  • 54
    • 49749202725 scopus 로고
    • Reactivity of unsaturated centers in heterocycles and chalcones towards diazoalkanes
    • Mustafa, A.; Asker, W.; Harhash, A.H.; Fleifel, A.M. Reactivity of unsaturated centers in heterocycles and chalcones towards diazoalkanes. Tetrahedron 1965, 21, 2215-2229.
    • (1965) Tetrahedron , vol.21 , pp. 2215-2229
    • Mustafa, A.1    Asker, W.2    Harhash, A.H.3    Fleifel, A.M.4
  • 55
    • 0028359111 scopus 로고
    • A stereocontrolled synthesis of β-hydroxyphenylalanine and β-hydroxytyrosine derivatives
    • Easton, C.J.; Hutton, C.A.; Roslet, P.D.; Tiekink, E.R.T. A stereocontrolled synthesis of β-hydroxyphenylalanine and β-hydroxytyrosine derivatives. Tetrahedron 1994, 50, 7327-7340.
    • (1994) Tetrahedron , vol.50 , pp. 7327-7340
    • Easton, C.J.1    Hutton, C.A.2    Roslet, P.D.3    Tiekink, E.R.T.4
  • 56
    • 0025066805 scopus 로고
    • Synthesis of homochiral hydroxyl-α-amino acid derivatives
    • Easton, C.J.; Hutton, C.A.; Tan, E.W.; Tiekink, E.R.T. Synthesis of homochiral hydroxyl-α-amino acid derivatives. Tetrahedron Lett. 1990, 31, 7059-7062.
    • (1990) Tetrahedron Lett , vol.31 , pp. 7059-7062
    • Easton, C.J.1    Hutton, C.A.2    Tan, E.W.3    Tiekink, E.R.T.4
  • 57
    • 0030814093 scopus 로고    scopus 로고
    • Substituent effects in the stereoconvergent synthesis of β-hydroxyphenylalanine derivatives
    • Hutton, C.A. Substituent effects in the stereoconvergent synthesis of β-hydroxyphenylalanine derivatives. Tetrahedron Lett. 1997, 38, 5899-5902.
    • (1997) Tetrahedron Lett , vol.38 , pp. 5899-5902
    • Hutton, C.A.1
  • 58
    • 1842473732 scopus 로고    scopus 로고
    • Strategic use of amino acid N-substituents to limit α-carbon-centered radical formation and consequent loss of stereochemical integrity
    • Croft, A.K.; Easton, C.J.; Kociuba, K.; Radom, L. Strategic use of amino acid N-substituents to limit α-carbon-centered radical formation and consequent loss of stereochemical integrity. Tetrahedron: Asymmetry 2003, 14, 2919-2126.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2126-2919
    • Croft, A.K.1    Easton, C.J.2    Kociuba, K.3    Radom, L.4
  • 59
    • 33750484982 scopus 로고    scopus 로고
    • Expedient synthesis of threo-β-hydroxy-α-amino acid derivatives: Phenylalanine, Tyrosine, Histidine and Tryptophan
    • Crich, D.; Banerjee, A. Expedient synthesis of threo-β-hydroxy-α-amino acid derivatives: Phenylalanine, Tyrosine, Histidine and Tryptophan. J. Org. Chem. 2006, 71, 7106-7109.
    • (2006) J. Org. Chem , vol.71 , pp. 7106-7109
    • Crich, D.1    Banerjee, A.2
  • 60
    • 0028882557 scopus 로고
    • Synthesis of L-(+)-Ergothioneine
    • Xu, J.; Yadan, J.C. Synthesis of L-(+)-Ergothioneine. J. Org. Chem. 1995, 60, 6296-6301.
    • (1995) J. Org. Chem , vol.60 , pp. 6296-6301
    • Xu, J.1    Yadan, J.C.2
  • 61
    • 0018813081 scopus 로고
    • Studies of enzyme-mediated reactions. Part 13. Stereochemical course of the formation of histamine by decarboxylation of (2S)-histidine with enzymes from Clostridium welchii and Lactobacillus 30a
    • Battersby, A.R.; Nicoletti, M.; Staunton, J.; Vleggaar, R. Studies of enzyme-mediated reactions. Part 13. Stereochemical course of the formation of histamine by decarboxylation of (2S)-histidine with enzymes from Clostridium welchii and Lactobacillus 30a. J. Chem. Soc. Perkin I. 1980, 43-51.
    • (1980) J. Chem. Soc. Perkin , vol.1 , pp. 43-51
    • Battersby, A.R.1    Nicoletti, M.2    Staunton, J.3    Vleggaar, R.4
  • 63
    • 0028798592 scopus 로고
    • Escherichia Coli imidazoleglycerol phosphate dehydratase: Spectroscopic characterization of the enzymic product and the steric course of the reaction
    • Parker, A.R.; Moore, J.A.; Schwab, J.M.; Jo Davisson, V. Escherichia Coli imidazoleglycerol phosphate dehydratase: Spectroscopic characterization of the enzymic product and the steric course of the reaction. J. Am. Chem. Soc. 1995, 117, 10605-10613.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 10605-10613
    • Parker, A.R.1    Moore, J.A.2    Schwab, J.M.3    Jo, D.V.4
  • 66
  • 67
    • 0032860443 scopus 로고    scopus 로고
    • Imidazole-containing amino acids as selective inhibitors of nitric Oxide synthase
    • Lee, Y.; Martasek, P.; Roman, L.J.; Masters, B.S.S.; Silverman, R.B. Imidazole-containing amino acids as selective inhibitors of nitric Oxide synthase. Biorg. Med. Chem. 1999, 7, 1941-1951.
    • (1999) Biorg. Med. Chem , vol.7 , pp. 1941-1951
    • Lee, Y.1    Martasek, P.2    Roman, L.J.3    Masters, B.S.S.4    Silverman, R.B.5
  • 68
    • 0034615707 scopus 로고    scopus 로고
    • Synthesis of (+)-Homo-histidine
    • Pirrung, M.C.; Pei, T.J. Synthesis of (+)-Homo-histidine. J. Org. Chem. 2000, 65, 2229-2230.
    • (2000) J. Org. Chem , vol.65 , pp. 2229-2230
    • Pirrung, M.C.1    Pei, T.J.2
  • 69
    • 0025970208 scopus 로고
    • Fadrozole hydrochloride: A potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent desease
    • Browne, L.J.; Gude, C.; Rodriguez, H.; Steele, R.E.; Bhatnager, A. Fadrozole hydrochloride: A potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent desease. J. Med. Chem. 1991, 34, 725-736.
    • (1991) J. Med. Chem , vol.34 , pp. 725-736
    • Browne, L.J.1    Gude, C.2    Rodriguez, H.3    Steele, R.E.4    Bhatnager, A.5
  • 71
    • 0014666770 scopus 로고
    • Structure-taste relationships of some dipeptides
    • Mazur, R.H.; Schlatter, J.M.; Goldkamp, A.H. Structure-taste relationships of some dipeptides. J. Am. Chem. Soc. 1969, 91, 2684-2691.
    • (1969) J. Am. Chem. Soc , vol.91 , pp. 2684-2691
    • Mazur, R.H.1    Schlatter, J.M.2    Goldkamp, A.H.3
  • 72
    • 0025328904 scopus 로고
    • High-Potency Dipeptide Sweeteners. 2. L-Aspartylfuryl-, Thienyl-, and Imidazolylglycine Esters
    • Janusz, J.M.; Young, P.A.; Blum, R.B.; Riley, C.M. High-Potency Dipeptide Sweeteners. 2. L-Aspartylfuryl-, Thienyl-, and Imidazolylglycine Esters. J. Med. Chem. 1990, 33, 1676-1682.
    • (1990) J. Med. Chem , vol.33 , pp. 1676-1682
    • Janusz, J.M.1    Young, P.A.2    Blum, R.B.3    Riley, C.M.4
  • 73
    • 0017189536 scopus 로고
    • Studies on polypeptides. Part XIX. Synthesis and enzymic activity of an RNase S' analog in which the 4-imidazolylglycyl residue takes the position and the role of histidine-12
    • van Batenburg, O.D.; Kerling, K.E.T.; Havinga, E. Studies on polypeptides. Part XIX. Synthesis and enzymic activity of an RNase S' analog in which the 4-imidazolylglycyl residue takes the position and the role of histidine-12. FEBS Lett. 1976, 68, 228-230.
    • (1976) FEBS Lett , vol.68 , pp. 228-230
    • van Batenburg, O.D.1    Kerling, K.E.T.2    Havinga, E.3
  • 75
    • 0022501372 scopus 로고
    • Semisynthetic β-lactam antibiotics. I. Synthesis and and antibacterial activity of 7β-[2-aryl-2-(aminoacetamido)acetamido]cephalosporins
    • Furukawa, M.; Arimoto, M.; Nakamura, S.; Ejima, A.; Higashi, O.; Tagawa, H. Semisynthetic β-lactam antibiotics. I. Synthesis and and antibacterial activity of 7β-[2-aryl-2-(aminoacetamido)acetamido]cephalosporins. J. Antibiot. 1986, 9, 1225-1235.
    • (1986) J. Antibiot , vol.9 , pp. 1225-1235
    • Furukawa, M.1    Arimoto, M.2    Nakamura, S.3    Ejima, A.4    Higashi, O.5    Tagawa, H.6
  • 76
    • 77950182231 scopus 로고    scopus 로고
    • Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system x_c over the vesicular glutamate transporter
    • Etoga, J.L.G.; Ahmed, S.K.; Patel, S.; Bridges, R.J.; Thompson, C.M. Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system x_c over the vesicular glutamate transporter. Bioorg. Med. Chem. Lett. 2010, 20, 2680-2683.
    • (2010) Bioorg. Med. Chem. Lett , vol.20 , pp. 2680-2683
    • Etoga, J.L.G.1    Ahmed, S.K.2    Patel, S.3    Bridges, R.J.4    Thompson, C.M.5
  • 77
    • 24344434030 scopus 로고    scopus 로고
    • Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics
    • Chruma, J.J.; Liu, L.; Zhou, W.; Breslow, R. Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics. Bioorg. Med. Chem. 2005, 13, 5873-5883.
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 5873-5883
    • Chruma, J.J.1    Liu, L.2    Zhou, W.3    Breslow, R.4
  • 78
    • 8444253665 scopus 로고    scopus 로고
    • Convenient synthesis of melatonin analogues: 2- and 3-substituted-N-acetylindolylalkylamines
    • Nenajdenko, V.G.; Zakurdaev, E.P.; Prusov, E.V.; Balenkova, E.S. Convenient synthesis of melatonin analogues: 2- and 3-substituted-N-acetylindolylalkylamines. Tetrahedron 2004, 60, 11719-11724.
    • (2004) Tetrahedron , vol.60 , pp. 11719-11724
    • Nenajdenko, V.G.1    Zakurdaev, E.P.2    Prusov, E.V.3    Balenkova, E.S.4
  • 80
    • 11244287323 scopus 로고    scopus 로고
    • Preparation of Protected β2- and β3-Homo-cysteine, β2- and β3-Homo-histidine, and β2-Homo-serine for solid-phase Syntheses
    • Lelais, G.; Micuch, P.; Lefebvre, D.J.; Rossi, F.; Seeback, D. Preparation of Protected β2- and β3-Homo-cysteine, β2- and β3-Homo-histidine, and β2-Homo-serine for solid-phase Syntheses. D. Helv. Chim. Acta 2004, 87, 3131-3159.
    • (2004) D. Helv. Chim. Acta , vol.87 , pp. 3131-3159
    • Lelais, G.1    Micuch, P.2    Lefebvre, D.J.3    Rossi, F.4    Seeback, D.5
  • 82
    • 76449114183 scopus 로고    scopus 로고
    • Synthesis of orthogonally protected aza-histidine: Application to the synthesis of a GHK analogue
    • Roux, S.; Ligeti, M.; Buisson, D.A.; Rousseaux, B.; Cintrat, J.C. Synthesis of orthogonally protected aza-histidine: Application to the synthesis of a GHK analogue. Amino Acids 2010, 38, 279-286.
    • (2010) Amino Acids , vol.38 , pp. 279-286
    • Roux, S.1    Ligeti, M.2    Buisson, D.A.3    Rousseaux, B.4    Cintrat, J.C.5
  • 83
    • 0142215403 scopus 로고    scopus 로고
    • Synthesis of a novel histidine analog and its efficient incorporation into a protein in vivo
    • Ikeda, Y.; Kawahara, S.; Taki, M.; Kuno, A.; Hasegawa, T.; Taira, K. Synthesis of a novel histidine analog and its efficient incorporation into a protein in vivo. Protein Eng. 2003, 16, 699-706.
    • (2003) Protein Eng , vol.16 , pp. 699-706
    • Ikeda, Y.1    Kawahara, S.2    Taki, M.3    Kuno, A.4    Hasegawa, T.5    Taira, K.6
  • 84
    • 0342587613 scopus 로고
    • The synthesis of triazole analogues of histamine and related compounds
    • Sheenan, J.C.; Robinson, C.A. The synthesis of triazole analogues of histamine and related compounds. J. Am. Chem. Soc. 1949, 71, 1436-1440.
    • (1949) J. Am. Chem. Soc , vol.71 , pp. 1436-1440
    • Sheenan, J.C.1    Robinson, C.A.2
  • 85
    • 0033576655 scopus 로고    scopus 로고
    • α2 Adrenoceptor Agonists as Potential Analgesic Agents. 1. (Imidazolylmethyl)oxazoles and thiazoles
    • Boyd, R.E.; Press, J.B.; Rasmussen, C.R.; Raffa, R.B. α2 Adrenoceptor Agonists as Potential Analgesic Agents. 1. (Imidazolylmethyl)oxazoles and thiazoles. J. Med. Chem. 1999, 42, 5064-5071.
    • (1999) J. Med. Chem , vol.42 , pp. 5064-5071
    • Boyd, R.E.1    Press, J.B.2    Rasmussen, C.R.3    Raffa, R.B.4
  • 88
    • 0027339691 scopus 로고
    • Solution conformations of the peptide backbone for DPDPE and its β-MePhe4-substituted analogues
    • Nikiforovich, G.V.; Prakash, O.M.; Gehrig, C.A.; Hruby, V.J. Solution conformations of the peptide backbone for DPDPE and its β-MePhe4-substituted analogues. Int. J. Peptide Prot. Res. 1993, 41, 347-361.
    • (1993) Int. J. Peptide Prot. Res , vol.41 , pp. 347-361
    • Nikiforovich, G.V.1    Prakash, O.M.2    Gehrig, C.A.3    Hruby, V.J.4
  • 89
    • 0027085885 scopus 로고
    • Main chain and side chain chiral methylated somatostatin analogs: Syntheses and conformational analyses
    • Huang, Z.; He, Y.B.; Raynor, K.; Tallent, M.; Reisine, T.; Goodman, M. Main chain and side chain chiral methylated somatostatin analogs: Syntheses and conformational analyses. J. Am. Chem. Soc. 1992, 114, 9390-9401.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 9390-9401
    • Huang, Z.1    He, Y.B.2    Raynor, K.3    Tallent, M.4    Reisine, T.5    Goodman, M.6
  • 90
    • 0026647625 scopus 로고
    • Ring substituted and other conformationally constrained tyrosine analogues of [D-Pen2, D-Pen5] enkephalin with δ opioid receptor selectivity
    • Tóth, G.; Russell, K.C.; Landis, G.; Kramer, T.H.; Fang, L.; Knapp, R.; Davis, P.; Burks, T.F.; Yamamura, H.I.; Hruby, V.J. Ring substituted and other conformationally constrained tyrosine analogues of [D-Pen2, D-Pen5] enkephalin with δ opioid receptor selectivity. J. Med. Chem. 1992, 35, 238491.
    • (1992) J. Med. Chem , vol.35 , pp. 238491
    • Tóth, G.1    Russell, K.C.2    Landis, G.3    Kramer, T.H.4    Fang, L.5    Knapp, R.6    Davis, P.7    Burks, T.F.8    Yamamura, H.I.9    Hruby, V.J.10
  • 92
    • 0027533886 scopus 로고    scopus 로고
    • The Pictet-Spengler reaction on L-Histidine. Preparation of Conformationally restricted (+)-Pilocarpine analogs
    • Sànchez, M.S.; Alberdi, L.M.T.; Rioseras, M.J.; Ferriera, M.R.; Gonzales, F.B. The Pictet-Spengler reaction on L-Histidine. Preparation of Conformationally restricted (+)-Pilocarpine analogs. Bull. Chem. Soc. Jpn. 1998, 66, 191-195.
    • (1998) Bull. Chem. Soc. Jpn , vol.66 , pp. 191-195
    • Sànchez, M.S.1    Alberdi, L.M.T.2    Rioseras, M.J.3    Ferriera, M.R.4    Gonzales, F.B.5
  • 93
    • 70349200782 scopus 로고    scopus 로고
    • The replacement of His(4) in Angiotensin IV by Conformationally residues provides highly potent and selective analogues
    • Lakaszuk, A.; Demaegdt, H.; Feytens, D.; Vanderheyden, P.; Vauquelin, G.; Tourwè, D.J. The replacement of His(4) in Angiotensin IV by Conformationally residues provides highly potent and selective analogues. J. Med. Chem. 2009, 52, 5612-5618.
    • (2009) J. Med. Chem , vol.52 , pp. 5612-5618
    • Lakaszuk, A.1    Demaegdt, H.2    Feytens, D.3    Vanderheyden, P.4    Vauquelin, G.5    Tourwè, D.J.6


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