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Journal of Organic Chemistry

Volumn 67, Issue 5, 2002, Pages 1536-1547

Serine and threonine β-lactones: A new class of hepatitis A virus 3C cysteine proteinase inhibitors

(4) Lall, Manjinder S a Ramtohul, Yeeman K a James, Michael N G b,c Vederas, John C a,c

a UNIVERSITY OF ALBERTA (Canada)

b UNIVERSITY OF ALBERTA (Canada)

c Chaires de recherche du Canada (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

VIRAL REPLICATION;

CHEMICAL BONDS; DRUG DOSAGE; ENZYME INHIBITION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL); VIRUSES;

ENZYMES;

AZETIDINONE DERIVATIVE; BETA LACTAM; CYCLOBUTANONE DERIVATIVE; CYSTEINE PROTEINASE INHIBITOR; HOMOSERINE GAMMA LACTONE; LACTONE DERIVATIVE; OXETANE DERIVATIVE; SERINE BETA LACTONE; THREONINE BETA LACTONE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATITIS A VIRUS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

CYCLIZATION; CYSTEINE ENDOPEPTIDASES; CYSTEINE PROTEINASE INHIBITORS; ESCHERICHIA COLI; FATTY ACIDS, UNSATURATED; HEPATOVIRUS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; SERINE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THREONINE; VIRAL PROTEINS;

EID: 0037040706 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0109016 Document Type: Article

Times cited : (105)

References (87)

1
- 0029286961
- (1995) J. Lab. Clin. Med. , vol.125 , pp. 433-441
- Roose, J.P.¹ Van Noorden, C.J.F.²

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

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

4
- 0034628448
- (2000) J. Med. Chem. , vol.43 , pp. 305-341
- Leung, D.¹ Abbenante, G.² Fairlie, D.P.³

5
- 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

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

7
- 0004006373
- Von der Helm, K.; Korant, B.; Eds.; Springer: Heiderlberg
- (1999) Proteinases as Targets for Therapy
- Bergmann, E.M.¹ James, M.N.G.²

8
- 0001872996
- (1996) Perspect. Drug Discov. Des. , vol.6 , pp. 64-86
- Gorbalenya, A.E.¹ Snijder, E.J.²

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

10
- 0028851295
- (1995) J. Virology , vol.69 , pp. 1727-1733
- Schultheiss, T.¹ Sommergruber, W.² Kusov, Y.³ Gauss-Müller, V.⁴

11
- 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

12
- 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

13
- 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

14
- 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

15
- 0028328469
- (1994) Nature , vol.369 , pp. 72-76
- Allaire, M.¹ Chernaia, M.M.² Malcolm, B.A.³ James, M.N.G.⁴

16
- 0029016492
- (1995) Biochemistry , vol.34 , pp. 8172-8174
- 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

17
- 14444269890
- (1998) J. Med. Chem. , vol.41 , pp. 2786-2805
- Webber, S.E.¹ Okano, K.² Little, T.L.³ Reich, S.H.⁴ Xin, Y.⁵ Fuhrman, S.A.⁶ Matthews, D.A.⁷ Love, R.A.⁸ Hendrickson, T.F.⁹ Patick, A.K.¹⁰ Meador III, J.W.¹¹ Ferre, R.A.¹² Brown, E.L.¹³ Ford, C.E.¹⁴ Binford, S.L.¹⁵ Worland, S.T.¹⁶

18
- 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

19
- 0025677291
- (1990) Tetrahedron Lett. , vol.31 , pp. 7277-7280
- Skiles, J.W.¹ McNeil, D.²

20
- 12644306888
- (1996) J. Med. Chem. , vol.39 , pp. 5072-5082
- Webber, S.E.¹ Tikhe, J.² Worland, S.T.³ Fuhrman, S.A.⁴ Hendrickson, T.F.⁵ Matthews, D.A.⁶ Love, R.A.⁷ Patick, A.K.⁸ Meador, J.W.⁹ Ferre, R.A.¹⁰ Brown, E.L.¹¹ DeLisle, D.A.¹² Ford, C.E.¹³ Binford, S.L.¹⁴

21
- 0031968180
- (1998) Antimicrob. Agents Chemother. , vol.42 , pp. 916-920
- Wang, Q.M.¹ Johnson, R.B.² Jungheim, L.N.³ Cohen, J.D.⁴ Villarreal, E.C.⁵

22
- 14444272282
- (1998) J. Med. Chem. , vol.41 , pp. 2806-2818
- Dragovich, P.S.¹ Webber, S.E.² Babine, R.E.³ Fuhrman, S.A.⁴ Patick, A.K.⁵ Matthews, D.A.⁶ Lee, C.A.⁷ Reich, S.H.⁸ Prins, T.J.⁹ Marakovits, J.T.¹⁰ Littlefield, E.S.¹¹ Zhuo, R.¹² Tikhe, J.¹³ Ford, C.E.¹⁴ Wallace, M.B.¹⁵ Meador III, J.W.¹⁶ Ferre, R.A.¹⁷ Brown, E.L.¹⁸ Binford, S.L.¹⁹ Harr, J.E.V.²⁰ DeLisle, D.M.²¹ Worland, S.T.²² more..

23
- 0032474754
- (1998) J. Med. Chem. , vol.41 , pp. 2579-2587
- Kong, J.¹ Venkatraman, S.² Furness, K.³ Nimkar, S.⁴ Shepherd, T.A.⁵ Wang, Q.M.⁶ Aub́, J.⁷ Hanzlik, R.P.⁸

24
- 0033535596
- (1999) J. Med. Chem. , vol.42 , pp. 1213-1214
- Dragovich, P.S.¹ Prins, T.J.² Zhuo, R.³ Webber, S.E.⁴ Marakovits, J.T.⁵ Fuhrman, S.A.⁶ Patick, A.K.⁷ Matthews, D.A.⁸ Lee, C.A.⁹ Ford, C.E.¹⁰ Burke, B.J.¹¹ Rejto, P.A.¹² Hendrickson, T.F.¹³ Tuntland, T.¹⁴ Brown, E.L.¹⁵ Meador III, J.W.¹⁶ Ferre, R.A.¹⁷ Harr, J.E.V.¹⁸ Worland, S.T.¹⁹

25
- 37049089837
- (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 1081-1082
- Sham, H.L.¹ Rosenbrook, W.² Karl, W.³ Betebenner, D.A.⁴ Wideburg, N.E.⁵ Saldivar, A.⁶ Plattner, J.J.⁷ Norbeck, D.W.⁸

26
- 0001627578
- (1998) Int. J. Mass Spectrom. , vol.176 , pp. 113-124
- McKendrick, J.E.¹ Frormann, S.² Luo, C.³ Semchuk, P.⁴ Vederas, J.C.⁵ Malcolm, B.A.⁶

27
- 0033593862
- (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 577-580
- Venkatraman, S.¹ Kong, J.² Nimkar, S.³ Wang, Q.M.⁴ Aubé, J.⁵ Hanzlik, R.P.⁶

28
- 0032986993
- (1999) Bioorg. Med. Chem. , vol.7 , pp. 607-619
- Huang, Y.¹ Malcolm, B.A.² Vederas, J.C.³

29
- 0033601364
- (1999) J. Org. Chem. , vol.64 , pp. 9538-9546
- Hill, R.D.¹ Vederas, J.C.²

30
- 77955455980
- (1995) Org. Prep. Proc. Int. , vol.27 , pp. 305-346
- Lowe, C.¹ Vederas, J.C.²

31
- 0029119647
- (1995) Synthesis , vol.7 , pp. 729-744
- Pommier, A.¹ Pons, J.M.²

32
- 0033591141
- (1999) Tetrahedron , vol.55 , pp. 6403-6434
- Yang, H.W.¹ Romo, D.²

33
- 0033022744
- (1999) Chem. Pharm. Bull. , vol.47 , pp. 1-10
- Corey, E.J.¹ Li, W.D.Z.²

34
- 0033104464
- (1999) Tetrahedron , vol.55 , pp. 3305-3316
- Corey, E.J.¹ Li, W.D.Z.² Nagamitsu, T.³ Fenteany, G.⁴

35
- 0034685889
- (2000) J. Biol. Chem. , vol.275 , pp. 14831-14837
- Kisselev, A.F.¹ Songyang, Z.² Goldberg, A.L.³

36
- 0035799898
- (2001) Org. Lett. , vol.3 , pp. 1395-1397
- Crane, S.N.¹ Corey, E.J.²

37
- 0031679829
- (1998) Bioorg. Med. Chem. , vol.6 , pp. 1255-1272
- Romo, D.¹ Harrison, P.H.M.² Jenkins, S.I.³ Riddoch, R.W.⁴ Park, K.⁵ Yang, H.W.⁶ Zhao, C.⁷ Wright, G.D.⁸

38
- 0025279341
- (1990) Biochem. Biophys. Res. Commun. , vol.169 , pp. 610-616
- Mayer, R.J.¹ Louis-Flamberg, P.² Elliott, J.D.³ Fisher, M.⁴ Leber, J.⁵

39
- 0026517225
- (1992) FEBS Lett. , vol.299 , pp. 111-115
- Lüthi-Peng, Q.¹ Märki, H.P.² Hadvàry, P.³

40
- 0025911832
- (1991) J. Biol. Chem. , vol.266 , pp. 2021-2027
- Hadvàry, P.¹ Sidler, W.² Meister, W.³ Vetter, W.⁴ Wolfer, H.⁵

41
- 33748591880
- and references therein
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1373-1382
- Kocienski, P.J.¹ Pelotier, B.² Pons, J.-M.³ Prideaux, H.⁴

42
- 0033972194
- (2000) Synlett , pp. 107-109
- Parsons, P.J.¹ Cowell, J.K.²

43
- 0002558905
- (1991) Org. Synth. , vol.70 , pp. 1-9
- Pansare, S.V.¹ Huyer, G.² Arnold, L.D.³ Vederas, J.C.⁴

44
- 0001933783
- (1991) Org. Synth. , vol.70 , pp. 10-17
- Pansare, S.V.¹ Arnold, L.D.² Vederas, J.C.³

45
- 0022354620
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 7105-7109
- Arnold, L.D.¹ Kalantar, T.H.² Vederas, J.C.³

46
- 33845280741
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 2237-2241
- Arnold, L.D.¹ May, R.G.² Vederas, J.C.³

47
- 0001014188
- (1999) Org. Lett. , vol.1 , pp. 803-806
- Lall, M.S.¹ Karvellas, C.² Vederas, J.C.³

48
- 0026646534
- (1992) Biochemistry , vol.31 , pp. 7862-7869
- Jewell, D.A.¹ Swietnicki, W.² Dunn, B.M.³ Malcolm, B.A.⁴

49
- 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

50
- 0003518480
- John Wiley & Sons: New York
- (1975) Enzyme Kinetics , pp. 100-125
- Segel, I.H.¹

51
- 73649151319
- (1962) J. Biol. Chem. , vol.237 , pp. 3245-3249
- Kitz, R.¹ Wilson, I.B.²

52
- 0003803058
- Springer-Verlag: Berlin
- (1994) The Practice of Peptide Synthesis , pp. 129-130
- Bodanszky, M.¹ Bodanszky, A.²

53
- 2042533101
- note

54
- 4444366051
- (1997) J. Chem. Soc., Perkin Trans. 2 , pp. 1929-1938
- Aldridge, D.C.¹ Nicholson, S.² Taylor, P.J.³

55
- 0001622883
- (1959) Tetrahedron , vol.6 , pp. 253-267
- Huisgen, R.¹ Ott, H.²

56
- 0033594929
- (1999) Biochemistry , vol.38 , pp. 7969-7977
- Jhoti, H.¹ Cleasby, A.² Reid, S.³ Thomas, P.J.⁴ Weir, M.⁵ Wonacott, A.⁶

57
- 0032541734
- (1998) Tetrahedron Lett. , vol.39 , pp. 6979-6982
- Kelly, H.A.¹ Bolton, R.² Brown, S.A.³ Coote, S.J.⁴ Dowle, M.⁵ Dyer, U.⁶ Finch, H.⁷ Golding, D.⁸ Lowdon, A.⁹ McLaren, J.¹⁰ Montana, J.G.¹¹ Owen, M.R.¹² Pegg, N.A.¹³ Ross, B.C.¹⁴ Thomas, R.¹⁵ Walker, D.A.¹⁶

58
- 0032510762
- (1998) Biochemistry , vol.37 , pp. 6752-6759
- Mitchell, A.E.¹ Zheng, J.² Hammock, B.D.³ Lo Bello, M.⁴ Jones, A.D.⁵

59
- 0001147898
- (1962) J. Org. Chem. , vol.27 , pp. 739-741
- Vaughan, W.R.¹ Baumann, J.B.²

60
- 0000361703
- (1989) J. Am. Chem. Soc. , vol.111 , Issue.1 , pp. 1057-1063
- Schwab, J.M.¹ Ray, T.² Ho, C.-K.³

61
- 0029981008
- (1996) Tetrahedron Lett. , vol.37 , pp. 4237-4240
- Sliedregt, K.M.¹ Schouten, A.² Kroon, J.³ Liskamp, R.M.J.⁴

62
- 2042462989
- note

63
- 84984399310
- (1990) Chem. Ber. , vol.123 , pp. 2413-2428
- Amberg, W.¹ Seebach, D.²

64
- 84989446814
- (1994) Chem. Ber. , vol.127 , pp. 565-579
- Gautschi, M.¹ Schweizer, W.B.² Seebach, D.³

65
- 0001718485
- (1998) Helv. Chim. Acta , vol.81 , pp. 603-631
- Murer, P.¹ Seebach, D.²

66
- 2042486841
- note

67
- 0003137834
- (1991) Heterocycles , vol.32 , pp. 245-251
- Box, V.G.S.¹ Marinovic, N.² Yiannikouros, G.P.³

68
- 0025073109
- (1990) Tetrahedron Lett. , vol.31 , pp. 1023-1026
- Lee, E.¹ Jung, K.W.² Kim, Y.S.³

69
- 0032572879
- (1998) Tetrahedron Lett. , vol.39 , pp. 6381-6382
- Balaji, B.S.¹ Chanda, B.M.²

70
- 15644380718
- (1998) J. Med. Chem. , vol.41 , pp. 2882-2891
- Yoakim, C.¹ Ogilive, W.W.² Cameron, D.R.³ Chabot, C.⁴ Guse, I.⁵ Hache, B.⁶ Naud, J.⁷ O'Meara, J.A.⁸ Plante, R.⁹ Deziel, R.¹⁰

71
- 0032474569
- (1998) Bioorg Med. Chem. Lett. , vol.8 , pp. 1437-1442
- Deziel, R.¹ Malenfant, E.²

72
- 0021128554
- (1984) Bull. Soc. Chim. Belg. , vol.93 , pp. 571-578
- Hanessian, S.¹ Sahoo, S.² Couture, C.³ Wyss, H.⁴

73
- 0032554725
- (1998) Bioorg Med. Chem. Lett. , vol.8 , pp. 977-978
- Dollinger, L.M.¹ Howell, A.R.²

74
- 0033578699
- and references therein
- (1999) J. Org. Chem. , vol.64 , pp. 7074-7080
- Dollinger, L.M.¹ Ndalaka, A.J.² Hashemzadeh, M.³ Wang, G.⁴ Wang, Y.⁵ Martinez, I.⁶ Arcari, J.T.⁷ Galluzzo, D.J.⁸ Howell, A.R.⁹

75
- 0002960798
- (1998) Eur. J. Org. Chem. , pp. 729-733
- Bisel, P.¹ Breitling, E.² Frahm, W.³

76
- 0031932202
- (1998) Synth. Commun. , vol.3 , pp. 403-408
- Sengupta, S.¹ Das, D.²

77
- 0000709206
- (1994) Chem. Rev. , vol.94 , pp. 1091-1160
- Ye, T.¹ McKervey, M.A.²

78
- 0001121776
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 2277-2280
- Wang, J.¹ Hou, Y.² Wu, P.³

79
- 0029046842
- (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 1287-1292
- Kim, D.H.¹ Ryoo, J.J.²

80
- 0032479233
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1676-1679
- Corey, E.J.¹ Li, W.² Nagamitsu, T.³

81
- 0029993963
- (1996) J. Org. Chem. , vol.61 , pp. 2613-2623
- Witter, D.J.¹ Vederas, J.C.²

82
- 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 Jungheim, L.N.⁶

83
- 0002012936
- Schneider, C. H., Eberle, A. N., Eds.; Escom: Leiden Netherlands
- (1993) Peptides 1992: Proceedings of the 22nd European Peptide Symposium , pp. 936-937
- Pennington, M.W.¹ Zaydenberg, I.² Byrnes, M.E.³ De Chastonay, J.⁴ Malcolm, B.A.⁵ Swietnicki, W.⁶ Farmerie, W.G.⁷ Scarborough, P.E.⁸ Dunn, B.M.⁹

84
- 0003828322
- John Wiley and Sons: New York
- (1961) Chemistry of the Amino Acids , pp. 891-895
- Greenstein, J.P.¹ Winitz, M.²

85
- 0000215053
- (1954) J. Am. Chem. Soc. , vol.76 , pp. 2884-2887
- Moore, J.A.¹ Dice, J.R.² Nicolaides, E.D.³ Westland, R.D.⁴ Wittle, E.L.⁵

86
- 0001010190
- (1997) J. Org. Chem. , vol.62 , Issue.2 , pp. 7364-7375
- Anderson, P.G.¹ Guijarro, D.² Tanner, D.³

87
- 0021377133
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 1095-1098
- Maurer, P.J.¹ Takahata, H.² Rapoport, H.³

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