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Volumn 58, Issue 12, 2002, Pages 2423-2433

Synthesis, hydrolysis, biochemical and theoretical evaluation of 1,4-bis(alkoxycarbonyl)azetidin-2-ones as potential elastase inhibitors

(5) Gérard, Stéphane a Dive, Georges b Clamot, Brigitte a Touillaux, Roland a Marchand Brynaert, Jacqueline a

a UNIVERSITÉ CATHOLIQUE DE LOUVAIN (Belgium)

b UNIVERSITY OF LIÈGE (Belgium)

Author keywords

lactam; Ab initio calculation; Elastase; Serine protease inhibition

Indexed keywords

AZETIDINONE DERIVATIVE; BENZYLOXYCARBONYL; CARBONYL DERIVATIVE; ELASTASE INHIBITOR; ESTER; PANCREATIC ELASTASE; PHENETHYLOXYCARBONYL; SERINE PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; URETHAN;

AB INITIO CALCULATION; ARTICLE; CHEMICAL ANALYSIS; DRUG HYDROLYSIS; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOISOMERISM;

SUIDAE;

EID: 0037128464 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4020(02)00112-6 Document Type: Article

Times cited : (31)

References (67)

1
- 0026463583
- (1992) Bioorg. Med. Chem. Lett. , vol.2 , pp. 1323
- Pratt, R.F.¹

2
- 0025364110
- (1990) J. Enzyme Inhibitor , vol.3 , pp. 249
- Demuth, H.-V.¹

3
- 77956934215
- Academic: New York
- (1990) The Enzymes , vol.19 , pp. 213-282
- Ator, M.A.¹ Ortiz de Montellano, P.R.²

4
- 0000722843
- (1997) Acc. Chem. Res. , vol.30 , pp. 162
- Massova, I.¹ Mobashery, S.²

5
- 0032555436
- (1998) Chem. Commun. , pp. 1609
- Page, M.I.¹ Laws, A.P.²

6
- 0033082703
- (1999) Nat. Prod. Rep. , vol.16 , pp. 1
- Matagne, A.¹ Dubus, A.² Galleni, M.³ Frère, J.-M.⁴

7
- 0032032930
- (1998) Biochem. J. , vol.330 , pp. 581
- Matagne, A.¹ Lamotte-Brasseur, J.² Frère, J.-M.³

8
- 0008620061
- (1994) Biotechnol. Genetic Engng. Rev. , vol.12 , pp. 149
- Lamotte-Brasseur, J.¹ Knox, J.² Kelly, J.A.³ Charlier, P.⁴ Fonzé, E.⁵ Dideberg, O.⁶ Frère, J.-M.⁷

9
- 0032767857
- (1999) Exp. Opin. Theor. Patents , vol.9 , pp. 869
- Skiles, J.W.¹ Jeng, A.Y.²

10
- 0032930510
- (1999) J. R. Soc. Med. , vol.92 , Issue.SUPPL. 37 , pp. 23
- Balfour-Lynn, I.M.¹

11
- 15444357089
- (1998) J. Med. Chem. , vol.41 , pp. 2461
- Cregge, R.J.¹ Durham, S.L.² Farr, R.A.³ Gallion, S.L.⁴ Hare, C.M.⁵ Hoffman, R.V.⁶ Janusz, M.J.⁷ Kim, H.-O.⁸ Koehl, J.R.⁹ Mehdi, S.¹⁰ Metz, W.A.¹¹ Peet, N.P.¹² Pelton, J.P.¹³ Schreuder, H.A.¹⁴ Sunder, S.¹⁵ Tardif, C.¹⁶

12
- 0026466858
- (1992) J. Med. Chem. , vol.35 , pp. 4297
- Rai, R.¹ Katzenellenbogen, J.A.²

13
- 0030591867
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2941
- Hlasta, D.J.¹ Court, J.J.² Desai, R.C.³ Talomie, T.G.⁴ Shen, J.A.⁵

14
- 0034598349
- (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 27
- Kerrigan, J.E.¹ Walters, M.C.² Forrester, K.J.³ Crowder, J.B.⁴ Christopher, L.J.⁵

15
- 0033919340
- (2000) Bioorg. Med. Chem. , vol.8 , pp. 1713
- He, S.¹ Kuang, R.² Venkataraman, R.³ Tu, J.⁴ Truong, T.M.⁵ Chan, H.-K.⁶ Groutas, W.C.⁷

16
- 0035132213
- (2001) Eur. J. Org. Chem. , vol.1 , pp. 141
- Cabaret, D.¹ Garcia Gonzales, M.² Wakselman, M.³ Adediran, S.A.⁴ Pratt, R.F.⁵

17
- 0034095633
- (2000) Bioorg. Med. Chem. , vol.8 , pp. 1489
- Pochet, L.¹ Doucet, C.² Dive, G.³ Wouters, J.⁴ Masereel, B.⁵ Reboux-Ravaux, M.⁶ Pirotte, B.⁷

18
- 0028899156
- (1995) Curr. Med. Chem. , vol.1 , pp. 441
- Mascaretti, O.A.¹ Boschetti, C.E.² Danelon, G.O.³ Mata, E.G.⁴ Roveri, O.A.⁵

19
- 0034725923
- (2000) Tetrahedron , vol.56 , pp. 5719
- Bulychev, A.¹ Bellettini, J.R.² O'Brien, M.³ Crocker, P.J.⁴ Samama, J.-P.⁵ Miller, M.J.⁶ Mobashery, S.⁷

20
- 0034725875
- (2000) Tetrahedron , vol.56 , pp. 5729
- Wilmouth, R.C.¹ Ly, Y.-H.² Wright, P.A.³ Claridge, T.D.W.⁴ Aplin, R.T.⁵ Schofield, C.J.⁶

21
- 0004030275
- Blackie Academic & Professional: London
- (1992) The Chemistry of β-lactams
- Page, M.I.¹

22
- 0024987599
- (1990) Tetrahedron , vol.46 , pp. 2255
- Firestone, R.A.¹ Barker, P.L.² Pisano, J.M.³ Ashe, B.M.⁴ Dahlgren, M.E.⁵

23
- 0028282060
- (1994) Med. Res. Rev. , vol.14 , pp. 127
- Edwards, P.D.¹ Bernstein, P.R.²

24
- 0027410572
- (1993) J. Med. Chem. , vol.36 , pp. 771
- Hagmann, W.K.¹ Kissinger, A.L.² Shah, S.K.³ Finke, P.E.⁴ Dorn, C.P.⁵ Brause, K.A.⁶ Ashe, B.M.⁷ Weston, H.⁸ Maycock, A.L.⁹ Knight, W.B.¹⁰ Dellea, P.S.¹¹ Fletcher, D.S.¹² Hand, K.M.¹³ Osinga, D.¹⁴ Davies, P.¹⁵ Doherty, J.B.¹⁶

25
- 0028800117
- (1995) Biochemistry , vol.34 , pp. 14331
- Green, B.G.¹ Chabin, R.² Mills, S.³ Underwood, D.J.⁴ Shah, S.K.⁵ Kuo, D.⁶ Gale, P.⁷ Maycock, A.L.⁸ Liesch, J.⁹ Burgey, C.S.¹⁰ Doherty, J.B.¹¹ Dorn, C.P.¹² Finke, P.E.¹³ Hagmann, W.K.¹⁴ Hale, J.J.¹⁵ MacCoss, M.¹⁶ Westler, W.M.¹⁷ Knight, W.B.¹⁸

26
- 0030175241
- (1996) J. Mol. Graphics , vol.14 , pp. 158
- Vergely, I.¹ Laugâa, P.² Reboud-Ravaux, M.³

27
- 0032535644
- (1998) Biochemistry , vol.37 , pp. 17506
- Wilmouth, R.C.¹ Westwood, N.J.² Anderson, K.³ Brownlee, W.⁴ Claridge, T.D.W.⁵ Clifton, I.J.⁶ Pritchard, G.J.⁷ Aplin, R.T.⁸ Schofield, C.J.⁹

28
- 0035938401
- (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 1065
- Clemente, A.¹ Domingos, A.² Grancho, A.P.³ Iley, J.⁴ Moreira, R.⁵ Neres, J.⁶ Palma, N.⁷ Santana, A.B.⁸ Valente, E.⁹

29
- 0033550261
- (1999) Tetrahedron , vol.55 , pp. 13301
- Beauve, C.¹ Bouchet, M.² Touillaux, R.³ Fastrez, J.⁴ Marchand-Brynaert, J.⁵

30
- 0028935827
- (1995) Bioorg. Med. Chem. , vol.3 , pp. 125
- Groutas, W.C.¹ Venkataraman, R.² Chong, L.S.³ Yoder, J.E.⁴ Epp, Y.J.⁵ Stanga, M.A.⁶ Kim, E.-H.⁷

31
- 0035106487
- (2001) Bioorg. Med. Chem. , vol.9 , pp. 637
- Vagnoni, L.M.¹ Gronostaj, M.² Kerrigan, J.E.³

32
- 0000004841
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 11787
- Vigroux, A.¹ Bergon, M.² Bergonzi, C.³ Tisnès, P.⁴

33
- 0034743811
- and references cited therein
- (2001) J. Chem. Soc., Perkin Trans. 2 , pp. 494
- Araujo, M.E.M.¹ Campelo, M.² Iley, J.³ Norberto, F.⁴

34
- 0032811725
- (1999) Eur. J. Org. Chem. , vol.6 , pp. 1441
- Beauve, C.¹ Tjoens, G.² Touillaux, R.³ Lamotte-Brasseur, J.⁴ Marchand-Brynaert, J.⁵ Fastrez, J.⁶

35
- 0025943278
- (1991) Bioorg. Med. Chem. Lett. , vol.1 , pp. 545
- Hagmann, W.K.¹ Shah, S.K.² Dorn, C.P.³ O'Grady, L.A.⁴ Hale, J.J.⁵ Finke, P.E.⁶ Thompson, K.R.⁷ Brause, K.A.⁸ Ashe, B.M.⁹ Hazel, W.¹⁰ Dahlgren, M.E.¹¹ Maycock, A.L.¹² Dellea, P.S.¹³ Hand, K.M.¹⁴ Osinga, D.G.¹⁵ Bonney, R.J.¹⁶ Davies, P.¹⁷ Fletcher, D.S.¹⁸ Doherty, J.B.¹⁹

36
- 0026668818
- (1992) Arch. Biochem. Biophys. , vol.296 , pp. 704
- Knight, W.B.¹ Chabin, R.² Green, B.³

37
- 0027405045
- (1993) Biochemistry , vol.32 , pp. 2031
- Knight, W.B.¹ Swiderek, K.M.² Sakuma, T.³ Calaycay, J.⁴ Shively, J.E.⁵ Lee, T.D.⁶ Covez, T.R.⁷ Shushan, B.⁸ Green, B.G.⁹ Chabin, R.¹⁰ Shah, S.¹¹ Mumford, R.¹² Dickinson, T.A.¹³ Griffin, P.R.¹⁴

38
- 0030687685
- (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 2973
- Westwood, N.J.¹ Claridge, T.D.W.² Edwards, P.N.³ Schofield, C.J.⁴

39
- 85045824461
- (1990) Tetrahedron , vol.46 , pp. 6585
- Firestone, R.A.¹ Barker, P.L.² Pisano, J.M.³ Ashe, B.M.⁴ Dahlgren, M.E.⁵

40
- 33748594493
- (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 2725
- Westwood, N.J.¹ Schofield, C.J.² Claridge, T.D.W.³

41
- 0019168718
- (1980) J. Am. Chem. Soc. , vol.120 , pp. 6161
- Salzman, T.N.¹ Ratcliffe, R.W.² Christensen, B.G.³ Bouffard, F.A.⁴

42
- 0025158558
- (1990) Tetrahedron , vol.46 , pp. 4733
- Baldwin, J.E.¹ Adlington, R.M.² Collins, D.W.³ Schofield, C.J.⁴

43
- 0030020114
- (1996) J. Chromatogr. A , vol.722 , pp. 221
- Abe, I.¹ Fujimoto, N.² Nishiyama, T.³ Terada, K.⁴ Nakahara, T.⁵

44
- 0028212049
- (1994) Synth. Commun. , vol.24 , pp. 745
- Garcia-Alvarez, M.¹ Lopez-Carrasquero, F.² Tort, E.³ Rodriguez-Galan, A.⁴ Munoz-Guerra, S.⁵

45
- 0024571818
- (1989) Biochemistry , vol.28 , pp. 1951
- Bode, W.¹ Meyer, E.² Powers, J.C.³

46
- 0035105397
- (2001) Bioorg. Med. Chem. , vol.9 , pp. 647
- Odagaki, Y.¹ Ohmoto, K.² Matsuoka, S.³ Hamanaka, N.⁴ Nakai, H.⁵ Toda, M.⁶ Katsuya, Y.⁷

47
- 0029839451
- (1996) J. Org. Chem. , vol.61 , pp. 6575
- Cvetovich, R.J.¹ Chartrain, M.² Hartner Jr., F.W.³ Roberge, C.⁴ Amato, J.S.⁵ Grabowski, E.J.J.⁶

48
- 0033525476
- and references cited therein
- (1999) Tetrahedron Lett. , vol.40 , pp. 1827
- Khim, S.-K.¹ Nuss, J.M.²

49
- 85060086983
- (1993) Synlett , pp. 51
- Baldwin, J.E.¹ Adlington, R.M.² Godfrey, C.R.A.³ Gallins, D.W.⁴ Smith, M.L.⁵ Russel, A.T.⁶

50
- 0028914757
- (1995) Tetrahedron , vol.51 , pp. 4733
- Baldwin, J.E.¹ Adlington, R.M.² Russel, A.T.³ Smith, M.L.⁴

51
- 0033571278
- (1999) Angew. Chem., Int. Ed. Engl. , vol.38 , pp. 3384
- Westermann, B.¹ Walter, A.² Diedrichs, N.³

52
- 0028076811
- (1994) J. Chem. Soc., Chem. Commun. , pp. 1957
- Palomo, C.¹ Aizpurua, J.M.² Cuevas, C.³

53
- 0028877350
- (1995) Tetrahedron Lett. , vol.36 , pp. 9027
- Palomo, C.¹ Aizpurua, J.M.² Cuevas, C.³ Mielgo, A.⁴ Galarza, R.⁵

54
- 0001487950
- (1995) Pure Appl. Chem. , vol.67 , pp. 711
- Page, M.I.¹ Laws, A.P.² Slater, M.J.³ Stone, J.R.⁴

55
- 2642607033
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 2146
- Pitarch, J.¹ Ruiz-Lopez, M.F.² Silla, E.³ Pascual-Ahuir, J.-L.⁴ Tunon, I.⁵

56
- 0002037645
- (1999) J. Chem. Soc., Perkin Trans. 2 , pp. 1351
- Pitarch, J.¹ Pascual-Ahuir, J.-L.² Silla, E.³ Tunon, I.⁴ Moliner, V.⁵

57
- 0034175153
- (2000) J. Chem. Soc., Perkin Trans. 2 , pp. 761
- Pitarch, J.¹ Pascual-Ahuir, J.-L.² Silla, E.³ Tunon, I.⁴

58
- 0003103514
- (1999) Int. J. Quant. Chem. , vol.73 , pp. 161
- Dive, G.¹ Dehareng, D.²

59
- 3743087318
- (1996) Int. J. Quant. Chem. , vol.58 , pp. 85
- Dive, G.¹ Dehareng, D.² Peeters, D.³

60
- 0033533761
- (1999) J. Med. Chem. , vol.42 , pp. 4161
- Doucet, C.¹ Pochet, L.² Thierry, N.³ Pirotte, B.⁴ Delarge, J.⁵ Reboud-Ravaux, M.⁶

61
- 0008593510
- unpublished result (centre d'Ingénierie des protéines, Université of Liège, Belgium); to be published
- Vigneron, L.¹ Dive, G.²

62
- 0001602742
- (1963) Biochem. Biophys. Acta , vol.77 , pp. 676
- Baumstark, J.S.¹ Bardawill, W.A.² Sbarra, A.J.³ Hayes, N.⁴

63
- 0016363174
- (1974) Biochem. Med. , vol.11 , pp. 350
- Bieth, J.¹ Spiess, B.² Vermuth, C.G.³

64
- 84986467036
- (1980) J. Comput. Chem. , vol.1 , pp. 205
- Tatewaki, H.¹ Huzinaga, S.²

65
- 0000749814
- (1993) Theor. Chim. Acta , vol.85 , pp. 409
- Dive, G.¹ Dehareng, D.² Ghuysen, J.-M.³

66
- 36549091139
- (1984) J. Chem. Phys. , vol.80 , pp. 3265
- Frisch, M.J.¹ Pople, J.A.² Binkley, J.S.³

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