메뉴 건너뛰기




Volumn 45, Issue 24, 2002, Pages 5303-5310

Design, synthesis, and tripeptidyl peptidase II inhibitory activity of a novel series of (S)-2,3-dihydro-2-(4-alkyl-1H-imidazol-2-yl)-1H-indoles

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 AMINO 1 OXOBUTYL) N BUTYL 2,3 DIHYDRO 1H INDOLE 2 CARBOXAMIDE; INDOLE DERIVATIVE; PEPTIDASE II INHIBITOR; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

EID: 0037153232     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0202831     Document Type: Article
Times cited : (20)

References (22)
  • 4
    • 0032907895 scopus 로고    scopus 로고
    • Pharmacological treatment of obesity: Therapeutic strategies
    • Kordik, C. P.; Reitz, A. B. Pharmacological treatment of obesity: Therapeutic strategies. J. Med. Chem. 1999, 42, 181-201.
    • (1999) J. Med. Chem. , vol.42 , pp. 181-201
    • Kordik, C.P.1    Reitz, A.B.2
  • 7
    • 0011903267 scopus 로고    scopus 로고
    • Tripeptidylpeptidase inhibitors, methods of synthesis, and use of inhibitors in treatment of gastrointestinal and mental disorders. Patent WO 9635805 A2, November 14, 1996
    • Rose, C.; Vargas, F.; Bourgeat, P.; Schwartz, J.-C.; Bishop, P. B.; Bambal, R. B.; Ganellin, C. R.; Leblond, B.; Moore, A. N. J.; Chan, S.; Zhao, L. Tripeptidylpeptidase inhibitors, methods of synthesis, and use of inhibitors in treatment of gastrointestinal and mental disorders. Patent WO 9635805 A2, November 14, 1996.
    • Rose, C.1    Vargas, F.2    Bourgeat, P.3    Schwartz, J.-C.4    Bishop, P.B.5    Bambal, R.B.6    Ganellin, C.R.7    Leblond, B.8    Moore, A.N.J.9    Chan, S.10    Zhao, L.11
  • 8
    • 0011872889 scopus 로고    scopus 로고
    • Preparation of new 1-(2-aminobutyryl)-indoline-2-carboxylic acid amides as tripeptidyl peptidase inhibitors. Patent WO 9933801 A1, July 8, 1999
    • Schwartz, J.-C.; Rose, C.; Vargas, F.; Ganellin, C. R.; Zhao, L.; Samad, S.; Chen, Y. Preparation of new 1-(2-aminobutyryl)-indoline-2-carboxylic acid amides as tripeptidyl peptidase inhibitors. Patent WO 9933801 A1, July 8, 1999.
    • Schwartz, J.-C.1    Rose, C.2    Vargas, F.3    Ganellin, C.R.4    Zhao, L.5    Samad, S.6    Chen, Y.7
  • 9
    • 0011910107 scopus 로고    scopus 로고
    • note
    • We ran the stability study in a Fisher versa-bath at a constant temperature of 38 °C at pH 7.0 (0.05 M potassium phosphate mono-basic-sodium hydroxide buffer solution; Fisher SB108-500). The percentage of degradation was measured by HPLC (monitoring area percent at 214 and 254 nm on a HP series 1050 HPLC instrument).
  • 10
    • 0030576302 scopus 로고    scopus 로고
    • Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere
    • (a) Chen, J. J.; Zhang, Y.; Hammond, S.; Dewdney, N.; Ho, T.; Lin, X.; Browner, M. F.; Castelhano, A. L. Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere. Bioorg. Med. Chem. Lett. 1996, 6 (13), 1601-1606.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , Issue.13 , pp. 1601-1606
    • Chen, J.J.1    Zhang, Y.2    Hammond, S.3    Dewdney, N.4    Ho, T.5    Lin, X.6    Browner, M.F.7    Castelhano, A.L.8
  • 12
    • 0027324641 scopus 로고
    • Peptide azoles: A new class of biologically-active dipeptide mimetics
    • (c) Gordon, T.; Hansen, P.; Morgan, B.; Singh, J.; Baizman, E.; Ward, S. Peptide azoles: A new class of biologically-active dipeptide mimetics. Biomed. Chem. Lett. 1993, 3 (5), 915-920.
    • (1993) Biomed. Chem. Lett. , vol.3 , Issue.5 , pp. 915-920
    • Gordon, T.1    Hansen, P.2    Morgan, B.3    Singh, J.4    Baizman, E.5    Ward, S.6
  • 14
    • 0023643147 scopus 로고
    • The high-resolution X-ray crystal structure of the complex formed between subtilisin Carlsberg and eglin c, an elastase inhibitor from the leech Hirudo medicinalis. Structural analysis, subtilisin structure and interface geometry
    • (b) Bode, W.; Papamokos, E.; Musil, D. The high-resolution X-ray crystal structure of the complex formed between subtilisin Carlsberg and eglin c, an elastase inhibitor from the leech Hirudo medicinalis. Structural analysis, subtilisin structure and interface geometry. Eur. J. Biochem. 1987, 166, 673.
    • (1987) Eur. J. Biochem. , vol.166 , pp. 673
    • Bode, W.1    Papamokos, E.2    Musil, D.3
  • 15
    • 0026568661 scopus 로고
    • Enantioselective catalytic borane reductions of achiral ketones: Synthesis and application of two chiral β-amino alcohols from (S)-2-indolinecarboxylic acid
    • Martens, J.; Dauelsberg, C.; Behnen, W.; Wallbaum, S. Enantioselective catalytic borane reductions of achiral ketones: Synthesis and application of two chiral β-amino alcohols from (S)-2-indolinecarboxylic acid. Tetrahedron: Asymmetry 1992, 3 (3), 347-50.
    • (1992) Tetrahedron: Asymmetry , vol.3 , Issue.3 , pp. 347-350
    • Martens, J.1    Dauelsberg, C.2    Behnen, W.3    Wallbaum, S.4
  • 16
    • 0011860084 scopus 로고    scopus 로고
    • Preparation and formulation of glutamylindoline carboxylates and related compounds as antihypertensives and for treatment of congestive heart failure. U.S. Patent 4,678,800, July 7, 1987
    • Stanton, J. L.; Ksander, G. M. Preparation and formulation of glutamylindoline carboxylates and related compounds as antihypertensives and for treatment of congestive heart failure. U.S. Patent 4,678,800, July 7, 1987.
    • Stanton, J.L.1    Ksander, G.M.2
  • 17
    • 0345991069 scopus 로고
    • Conversion of carboxamides to nitriles using trichloroacetyl chloride/triethylamine as a mild dehydrating agent
    • Saednya, A. Conversion of carboxamides to nitriles using trichloroacetyl chloride/triethylamine as a mild dehydrating agent. Synthesis 1985, 184-185.
    • (1985) Synthesis , pp. 184-185
    • Saednya, A.1
  • 18
    • 0011822997 scopus 로고    scopus 로고
    • note
    • Enantiomeric purity was determined using a Chiralpak AD (4.6 mm × 250 mm, 10 μm) HPLC column from Chiral Technologies (temperature, ambient; flow rate, 0.8 mL/min; mobile phase, (80% hexane)/(20% 90:10:0.05 hexane/ethanol/trifluoroacetic acid); wavelength, 254 nm).
  • 19
    • 0015915392 scopus 로고
    • Synthesis of amino acids and related compounds. 6. New convenient synthesis of α-C-acylamino acids and α-amino ketones
    • Suzuki, M.; Iwasaki, T.; Miyoshi, M.; Okumura, K.; Matsumoto, K. Synthesis of amino acids and related compounds. 6. New convenient synthesis of α-C-acylamino acids and α-amino ketones. J. Org. Chem. 1973, 38 (20), 3571-3575.
    • (1973) J. Org. Chem. , vol.38 , Issue.20 , pp. 3571-3575
    • Suzuki, M.1    Iwasaki, T.2    Miyoshi, M.3    Okumura, K.4    Matsumoto, K.5
  • 20
    • 33751498929 scopus 로고
    • tert-butyloxycarbonyl and benzyloxycarbonyl amino acid fluorides. New, stable rapid-acting acylating agents for peptide synthesis
    • Carpino, L. A.; Mansour, E.-S. M. E.; Sadat-Aalaee, D. tert-butyloxycarbonyl and benzyloxycarbonyl amino acid fluorides. New, stable rapid-acting acylating agents for peptide synthesis. J. Org. Chem. 1991, 56 (8), 2611-2614.
    • (1991) J. Org. Chem. , vol.56 , Issue.8 , pp. 2611-2614
    • Carpino, L.A.1    Mansour, E.-S.M.E.2    Sadat-Aalaee, D.3
  • 21
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 1997, 267, 727-748.
    • (1997) J. Mol. Biol. , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 22
    • 0022998836 scopus 로고
    • Purification, substrate specificity, and classification of tripeptidyl peptidase II
    • Balow, R. M.; Ragnarsson, U.; Zetterqvist, O. Purification, substrate specificity, and classification of tripeptidyl peptidase II. J. Biol. Chem. 1986, 261 (5), 2409-2417.
    • (1986) J. Biol. Chem. , vol.261 , Issue.5 , pp. 2409-2417
    • Balow, R.M.1    Ragnarsson, U.2    Zetterqvist, O.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.