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Journal of Organic Chemistry

Volumn 67, Issue 10, 2002, Pages 3169-3178

Synthesis and evaluation of keto-glutamine analogues as inhibitors of hepatitis A virus 3C proteinase

(3) Ramtohul, Yeeman K a James, Michael N G a Vederas, John C a

a UNIVERSITY OF ALBERTA (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

INFECTIVITY;

ENZYME INHIBITION; HYDROGEN BONDS; SYNTHESIS (CHEMICAL); TOPOLOGY; VIRUSES;

ENZYMES;

AZETIDINONE DERIVATIVE; CATHEPSIN K; CYSTEINE PROTEINASE; DITHIOTHREITOL; GLUTAMINE DERIVATIVE; N,N DIMETHYL 4 (ACETYLLEUCYLALANYLALANYL)AMINO 5 OXO 6 (2,3 DIHYDROPHTHALAZINE 1,4 DIONE)HEXANAMIDE; PHTHALAZINE DERIVATIVE; UNCLASSIFIED DRUG; 3C PROTEASE, VIRAL; ACETYL LEUCYL ALANYL ALANYL OH; ACETYL-LEUCYL-ALANYL-ALANYL-OH; CATHEPSIN; CYSTEINE PROTEINASE INHIBITOR; DRUG DERIVATIVE; GLUTAMINE; OLIGOPEPTIDE; VIRUS PROTEIN;

ARTICLE; COMPETITIVE INHIBITION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME LOCALIZATION; HEPATITIS A VIRUS; HYDROGEN BOND; IC 50; INHIBITION KINETICS; MOLECULAR RECOGNITION; PROTEIN SYNTHESIS; BINDING SITE; CHEMICAL STRUCTURE; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BINDING SITES; CATHEPSINS; CRYSTALLOGRAPHY, X-RAY; CYSTEINE ENDOPEPTIDASES; CYSTEINE PROTEINASE INHIBITORS; GLUTAMINE; HEPATITIS A VIRUS; HYDROGEN BONDING; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OLIGOPEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.; VIRAL PROTEINS;

EID: 0037123412 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0157831 Document Type: Article

Times cited : (75)

References (55)

1
- 0343433408
- (1997) Chem. Rev. , vol.97 , pp. 133-171
- Otto, H.-H.¹ Schirmeister, T.²

2
- 0034628448
- (2000) J. Med. Chem. , vol.43 , pp. 305-341
- Leung, D.¹ Abbenante, G.² Fairlie, D.P.³

3
- 0000705825
- (1999) Bioorg. Med. Chem. , vol.7 , pp. 571
- Thompson, S.K.¹

4
- 0004250845
- Fields, B. N.; Knipe, D. M.; Howley, P. M.; Channock, R. M.; Melnick, J. L.; Monath, T. P.; Roizmann, B. E.; Strauss S. E.; Eds.; Lippincott-Raven Publishers: Philadelphia
- (1996) Fields Virology
- Hollinger, F.B.¹ Ticehurst, J.R.²

5
- 0031934426
- (1998) Epidemiol. Infect. , vol.120 , pp. 55-59
- Pebody, R.G.¹ Leino, T.² Ruuutu, P.³ Kinnunen, L.⁴ Davidkin, I.⁵ Nohynek, H.⁶ Leinikki, P.⁷

6
- 0004006373
- Von der Helm, K., Korant, B. Eds.; Springer: Heiderlberg
- (1999) Proteases as Targets for Therapy
- Bergmann, E.M.¹ James, M.N.G.²

7
- 0001872996
- (1996) Perspect. Drug Discov. Des. , vol.6 , pp. 64-86
- Gorbalenya, A.E.¹ Snijder, E.J.²

8
- 0004250845
- Fields, B. N.; Knipe, D. M.; Howley, P. M.; Channock R. M.; Melnick, J. L.; Monath, T. P.; Roizmann, B. E.; Strauss, S. E.; Eds.; Lippincott-Raven Publishers: Philadelphia
- (1996) Fields Virology
- Rueckert, R.R.¹

9
- 0029086385
- (1995) Protein Sci. , vol.4 , pp. 1439-1445
- Malcolm, B.A.¹

10
- 0023947898
- (1988) Annu. Rev. Biochem. , vol.57 , pp. 701-754
- Krausslich, H.G.¹ Wimmer, E.²

11
- 0001920201
- (1996) Perspect. in Drug Discov. Des. , vol.6 , pp. 47-63
- Rasnick, D.¹

12
- 0031047974
- (1997) J. Virol. , vol.71 , pp. 2436-2448
- Bergmann, E.M.¹ Mosimann, S.C.² Chernaia, M.M.³ Malcolm, B.A.⁴ James, M.N.G.⁵

13
- 0033527893
- (1999) Virology , vol.265 , pp. 153-163
- Bergmann, E.M.¹ Cherney, M.M.² McKendrick, J.³ Frormann, S.⁴ Luo, C.⁵ Malcolm, B.A.⁶ Vederas, J.C.⁷ James, M.N.G.⁸

14
- 0028235532
- (1994) Cell , vol.77 , pp. 761-771
- Matthews, D.A.¹ Smith, W.W.² Ferre, R.A.³ Condon, B.⁴ Budahazi, G.⁵ Sisson, W.⁶ Villafranca, J.E.⁷ Janson, C.A.⁸ McElroy, H.E.⁹ Gribskov, C.L.¹⁰ Worland, S.¹¹

15
- 13044300859
- (1999) Proc. Natl. Acad. Sci. U.S.A. , vol.96 , pp. 11000-11007
- Matthews, D.A.¹ Dragovich, P.S.² Webber, S.E.³ Fuhrman, S.A.⁴ Patick, A.K.⁵ Zalman, L.S.⁶ Hendrickson, T.F.⁷ Love, R.A.⁸ Prins, T.J.⁹ Marakovits, J.T.¹⁰ Zhou, R.¹¹ Tikhe, J.¹² Ford, C.E.¹³ Meador, J.W.¹⁴ Ferre, R.A.¹⁵ Brown, E.L.¹⁶ Binford, S.L.¹⁷ Brothers, M.A.¹⁸ DeLisle, D.M.¹⁹ Worland, S.T.²⁰ more..

16
- 0031567786
- (1997) J. Mol. Biol. , vol.273 , pp. 1032-1047
- Mosimann, S.C.¹ Cherney, M.M.² Sia, S.³ Plotch, S.⁴ James, M.N.G.⁵

17
- 0014211618
- (1967) Biochem. Biophys. Res. Commun. , vol.27 , pp. 157-162
- Schechter, I.¹ Berger, A.²

18
- 0029016492
- (1995) Biochemistry , vol.34 , pp. 8172-8179
- Malcolm, B.A.¹ Lowe, C.² Shechosky, S.³ Mckay, R.T.⁴ Yang, C.C.⁵ Shah, V.J.⁶ Simon, R.J.⁷ Vederas, J.C.⁸ Santi, D.V.⁹

19
- 0030922322
- (1997) Bioorg. Med. Chem. , vol.5 , pp. 797-807
- Morris, T.S.¹ Frormann, S.² Shechosky, S.³ Lowe, C.⁴ Lall, M.S.⁵ Gauss-Müller, V.⁶ Purcell, R.H.⁷ Emerson, S.U.⁸ Vederas, J.C.⁹ Malcolm, B.A.¹⁰

20
- 0001627578
- (1998) Int. J. Mass. Spectrom. , vol.176 , pp. 113-124
- McKendrick, J.E.¹ Frormann, S.² Luo, C.³ Semchuck, P.⁴ Vederas, J.C.⁵ Malcolm, B.A.⁶

21
- 0032986993
- (1999) Bioorg. Med. Chem. , vol.7 , pp. 607-619
- Huang, Y.¹ Malcolm, B.A.² Vederas, J.C.³

22
- 0033601364
- (1999) J. Org. Chem. , vol.64 , pp. 9538-9546
- Hill, R.D.¹ Vederas, J.C.²

23
- 0001014188
- (1999) Org. Lett. , vol.1 , pp. 803-806
- Lall, M.S.¹ Karvellas, C.² Vederas, J.C.³

24
- 0030716360
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 11351-11352
- Yamashita, D.S.¹ Smith, W.W.² Zhao, B.³ Janson, C.A.⁴ Tomaszek, T.A.⁵ Bossard, M.J.⁶ Levy, M.A.⁷ Oh, H.-J.⁸ Carr, T.J.⁹ Thompson, S.K.¹⁰ Ijames, C.F.¹¹ Carr, S.A.¹² McQueney, M.¹³ D'Alesio, K.J.¹⁴ Amegadzie, B.Y.¹⁵ Hanning, C.R.¹⁶ Abdel-Meguid, S.¹⁷ DesJardais, R.L.¹⁸ Gleason, J.G.¹⁹ Veber, D.F.²⁰ more..

25
- 0032505149
- (1998) J. Med. Chem. , vol.41 , pp. 3563-3567
- Marquis, R.W.¹ Yamashita, D.S.² Ru, Y.³ LoCastro, S.M.⁴ Oh, H.-J.⁵ Erhard, K.F.⁶ DesJardais, R.L.⁷ Head, M.S.⁸ Smith, W.W.⁹ Zhao, B.¹⁰ Janson, C.A.¹¹ Abdel-Meguid, S.S.¹² Tomaszek, T.A.¹³ Levy, M.A.¹⁴ Veber, D.F.¹⁵

26
- 0033029816
- (1999) Bioorg. Med. Chem. , vol.7 , pp. 581-588
- Marquis, R.W.¹ Ru, Y.² Yamashita, D.S.³ Oh, H.-J.⁴ Yen, J.⁵ Thompson, S.K.⁶ Carr, T.J.⁷ Levy, M.A.⁸ Tomaszek, T.A.⁹ Ijames, C.F.¹⁰ Smith, W.W.¹¹ Zhao, B.¹² Janson, C.A.¹³ Abdel-Meguid, S.S.¹⁴ D́Alesio, K.J.¹⁵ McQueney, M.S.¹⁶ Veber, D.F.¹⁷

27
- 0026646534
- (1992) Biochemistry , vol.31 , pp. 7862-7869
- Jewell, D.A.¹ Swietnicki, W.² Dunn, B.N.³ Malcolm, B.A.⁴

28
- 0025073031
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 7050-7051
- Fukuyama, T.¹ Lin, S.C.² Li, L.³

29
- 0024557406
- (1989) J. Med. Chem. , vol.32 , pp. 165-170
- Greenlee, W.J.¹ Springer, J.P.² Patchett, A.A.³

30
- 33644528891
- (1983) J. Org. Chem. , vol.48 , pp. 4155-4156
- Dess, D.B.¹ Martin, J.C.²

31
- 3042741556
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 7277-7287
- Dess, D.B.¹ Martin, J.C.²

32
- 0026578572
- (1992) Biochemistry , vol.31 , pp. 3358-3363
- Malcolm, B.A.¹ Chin, S.M.² Jewell, D.A.³ Stratton-Thomas, J.R.⁴ Thudium, K.B.⁵ Rosenberg, S.⁶

33
- 0030769558
- (1997) Antiviral Chem. Chemother. , vol.8 , pp. 303-310
- Wang, Q.M.¹ Johnson, R.B.² Cohen, J.D.³ Voy, G.T.⁴ Richardson, J.M.⁵ Junghein, L.N.⁶

34
- 0028048980
- (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 1965-1968
- Mjalli, A.M.M.¹ Chapman, K.T.² MacCoss, M.³ Thornberry, N.A.⁴ Peterson, E.P.⁵

35
- 0001627944
- (1999) J. Org. Chem. , vol.64 , pp. 5036-5041
- Kim, B.H.¹ Soo, G.C.² Hu, T.-K.³

36
- 0027986716
- (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2799
- Kim, B.H.¹ Ryu, E.J.² Chung, Y.J.³

37
- 0027763470
- (1993) Tetrahedron Lett. , vol.34 , pp. 8465-8468
- Kim, B.H.¹ Chung, Y.J.² Ryu, E.R.³

38
- 0032550656
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4610-4621
- Ding, J.¹ Fraser, M.E.² Meyer, J.H.³ Bartlett, P.A.⁴ James, M.N.G.⁵

39
- 0032550642
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4600-4609
- Meyer, J.H.¹ Bartlett, P.A.²

40
- 0032550658
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4622-4628
- Smith, W.W.¹ Bartlett, P.A.²

41
- 0032400532
- (1998) Biochemistry , vol.37 , pp. 16839-16845
- Khan, A.R.¹ Parrish, J.C.² Fraser, M.E.³ Smith, W.W.⁴ Bartlett, P.A.⁵ James, M.N.G.⁶

42
- 0003520774
- John Wiley & Sons: New York
- (1998) Spectrometric Identification of Organic Compounds, 6th ed. , pp. 96
- Silverstein, R.M.¹ Webster, F.X.²

43
- 0003722102
- W.H. Freeman and Co.: San Francisco; Chapter 5
- (1960) The Hydrogen Bond
- Pimentel, G.C.¹ McClellan, A.L.²

44
- 2142800644
- note

45
- 0000092066
- (1993) J. Org. Chem. , vol.53 , pp. 5683-5689
- Pirrung, M.C.¹ Rowley, E.G.² Holmes, C.P.³

46
- 84948259401
- (1981) Synth. Commun. , vol.11 , pp. 43-53
- Dow, R.L.¹ Kelly, R.C.² Schletter, I.³ Wierenga, W.⁴

47
- 37049075015
- (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 1951-1959
- Harris, J.M.¹ Bolessa, E.A.² Vederas, J.C.³

48
- 0003518480
- John Wiley & Sons: New York
- (1975) Enzyme Kinetics , pp. 100-125
- Segel, I.H.¹

49
- 0031932202
- (1998) Synth. Commun. , vol.3 , pp. 403-408
- Sengupta, S.¹ Das, D.²

50
- 0000709206
- (1994) Chem. Rev. , vol.94 , pp. 1091-1160
- Ye, T.¹ McKervey, M.A.²

51
- 37049088823
- (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 1945-1950
- Harris, J.M.¹ Bolessa, E.A.² Mendonca, A.J.³ Feng, S.-C.⁴ Vederas, J.C.⁵

52
- 0033606237
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4904-4905
- Merkler, D.J.¹ Glufke, U.² Ritenour-Rodgers, K.J.³ Baumgart, L.E.⁴ DeBlassio, J.L.⁵ Merkler, K.A.⁶ Vederas, J.C.⁷

53
- 0004266860
- Springer, New York, and references therein
- (1988) Peptide Chemistry , pp. 55-146
- Bodansky, M.¹

54
- 84986803804
- (1979) Org. Magn. Reson. , vol.12 , pp. 393-395
- Matsoukas, J.¹ Theodoropoulos, D.²

55
- 0018924390
- (1980) J. Med. Chem. , vol.2 , pp. 213-217
- Stahl, G.L.¹ Smith, C.W.² Walter, R.³ Tsgenidis, T.⁴ Stavropoulos, G.⁵

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