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Journal of Organic Chemistry

Volumn 67, Issue 10, 2002, Pages 3387-3397

Design and synthesis of a novel class of constrained tricyclic pyrrolizidinone carboxylic acids as carbapenem mimics

(3) Hanessian, Stephen a Buckle, Ronald a Bayrakdarian, Malken a

a UNIVERSITÉ DE MONTRÉAL (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL STRAINS;

ALKYLATION; BACTERIOLOGY; SYNTHESIS (CHEMICAL);

CARBOXYLIC ACIDS;

3 ACETOXY 5BETA METHANOHEXAHYDROPYRROLIZIDIN 2 ONE 8 CARBOXYLIC ACID; 3 AZIDO 5BETA METHANOHEXAHYDROPYRROLIZIDIN 2 ONE 8 CARBOXYLIC ACID; 3 PHENYLACETAMIDE 5BETA METHANOHEXAHYDROPYRROLIZIDIN 2 ONE 8 CARBOXYLIC ACID; 4BETA METHANOHEXAHYDROPYRROLIZIDIN 2 ONE 8 CARBOXYLIC ACID; ANTIBIOTIC AGENT; BETA LACTAM ANTIBIOTIC; BETA LACTAMASE; CARBAPENEM DERIVATIVE; CEFTAZIDIME; PYRROLIDINE DERIVATIVE; TRICYCLIC PYRROLIZIDINONE CARBOXYLIC ACID; UNCLASSIFIED DRUG; POLYCYCLIC AROMATIC HYDROCARBON; PYRROLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THIN LAYER CHROMATOGRAPHY; X RAY CRYSTALLOGRAPHY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; MOLECULAR MIMICRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CARBAPENEMS; CATALYSIS; CEFTAZIDIME; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; PYRROLES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T;

EID: 0037123423 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0111715 Document Type: Article

Times cited : (29)

References (72)

1
- 0031946506
- (1998) Curr. Med. Chem. , vol.5 , pp. 101
- Setti, E.L.¹ Micetich, R.G.²

2
- 0029796373
- (1996) J. Med. Chem. , vol.39 , pp. 3853
- Chu, D.T.W.¹ Plattner, J.J.² Katz, L.³

3
- 0030028910
- (1996) Tetrahedron , vol.52 , pp. 331
- Berko, A.H.¹

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

5
- 0004015248
- VCH: New York
- (1993) The Organic Chemistry of β-Lactams
- Georg, G.J.¹

6
- 0003737979
- Sutcliffe, J., Georgeopapadakou, N. H., Eds.; Chapman and Hall: New York
- (1992) Emerging Targets in Antibacterial and Antifungal Chemotherapy
- Neuhaus, F.C.¹ Georgeopapadakou, N.H.²

7
- 0031950203
- (1998) Curr. Pharm. Des. , vol.4 , pp. 133
- Black, M.T.¹ Bruton, G.²

8
- 0030923633
- (1997) Drug Int. , vol.22 , pp. 271
- Setti, E.L.¹ Quattrocchio, L.² Micetich, R.G.³

9
- 0006041986
- (1987) Pure Appl. Chem. , vol.59 , pp. 475
- Brown, A.G.¹

10
- 0018640473
- (1979) J. Med. Chem. , vol.22 , pp. 1435
- Leanza, W.J.¹ Wildonger, K.J.² Miller, T.W.³ Christensen, B.G.⁴

11
- 0019168718
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 6161
- Salzmann, T.N.¹ Ratcliffe, R.W.² Christensen, B.G.³

12
- 0034597574
- (2000) J. Med. Chem. , vol.43 , pp. 4328
- Imming, P.¹ Klar, B.² Dir, D.³

13
- 0032555436
- (1998) J. Chem. Soc., Chem. Commun. , pp. 1609
- Page, M.I.¹ Laws, A.P.²

14
- 0020307051
- (1982) J. Antibiot. , vol.35 , pp. 1729
- Takasuka, M.¹ Nishikawa, J.² Tori, K.³

15
- 0006119741
- (1967) Antibiotics , vol.1 , pp. 706
- Strominger, J.L.¹

16
- 0004278888
- Clark, H. T., Johnson, J. R., Robinson, R., Eds.; Princeton Unviersity Press: Princeton, NJ
- (1949) The Chemistry of Penicillin , pp. 443
- Woodward, R.B.¹

17
- 0018233237
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 8214
- Ernest, J.¹ Gosteli, J.² Greengrass, L.W.³ Holick, W.⁴ Jackman, D.E.⁵ Pfaendler, H.R.⁶ Woodward, R.B.⁷

18
- 0019167827
- (1980) J. Antibiot. , vol.33 , pp. 453
- Franceschi, G.¹ Foglio, M.² Arcamone, F.³

19
- 0000972544
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 6138
- Afonso, A.¹ Hon, F.² Weinstein, J.³ Ganguly, A.K.⁴ McPhail, A.T.⁵

20
- 85010145124
- (1983) Chem. Pharm. Bull. , vol.31 , pp. 768
- Yoshida, H.¹ Hayashi, T.² Takeda, N.³ Oida, S.⁴ Ohki, E.⁵

21
- 0000629001
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 1438
- Hanessian, S.¹ Bedeschi, A.² Battistini, C.³ Mongelli, N.⁴

22
- 0022545040
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 6431
- Williams, R.M.¹ Lee, B.H.²

23
- 2142792702
- (1989) Spec. Publ. R. Soc. Chem. , vol.70 , pp. 106
- Williams, R.M.¹ Lee, B.H.² Miller, S.³ Anderson, O.P.⁴

24
- 0032527999
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 6846
- Buynak, J.D.¹ Rao, A.S.² Adam, G.³ Nidamenthy, S.D.⁴ Zhang, H.⁵

25
- 0030820238
- (1997) Angew. Chem., Int. Ed. Eng. , vol.36 , pp. 1881
- Hanessian, S.¹ Reinhold, U.² Gentile, G.³

26
- 2142851064
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 213
- Hanessian, S.¹ Reinhold, U.² Saulnier, M.³ Claridge, S.⁴

27
- 2142739882
- note

28
- 0000130893
- Lukacs, G., Ed.; Springer-Verlag: Berlin
- (1990) Recent Progress in the Chemical Synthesis of Antibiotics , vol.2 , pp. 729
- Marchand-Brynaert, J.¹ Ghosez, L.²

29
- 0020630014
- (1983) J. Chem. Soc., Chem. Commun. , pp. 250
- Baldwin, J.E.¹ Chan, M.F.² Gallacher, G.³ Monk, P.⁴ Prout, K.⁵

30
- 0001439898
- (1986) Tetrahedron , vol.42 , pp. 6551
- Baldwin, J.E.¹ Lee, E.²

31
- 0022590785
- (1986) Tetrahedron Lett. , vol.27 , pp. 3461
- Baldwin, J.E.¹ Lowe, C.² Schofield, C.J.³ Lee, E.⁴

32
- 0024333184
- (1989) Tetrahedron Lett. , vol.30 , pp. 4019
- Baldwin, J.E.¹ Freeman, R.T.² Schofield, C.³

33
- 0022613020
- (1986) Tetrahedron Lett. , vol.27 , pp. 3457
- Boyd, D.B.¹ Foster, B.J.² Hatfield, L.D.³ Hornback, W.J.⁴ Jones, N.D.⁵ Munroe, J.E.⁶ Swartzendruber, J.K.⁷

34
- 37049076881
- (1988) J. Chem. Soc., Perkin Trans. 1 , pp. 2345
- Hashigushi, S.¹ Natsugari, H.² Ochiai, M.³

35
- 0023629165
- (1987) J. Org. Chem. , vol.52 , pp. 4007
- Junghein, L.N.¹ Sigmund, S.K.²

36
- 0023078581
- (1987) Tetrahedron Lett. , vol.28 , pp. 289
- Jungheim, L.N.¹ Sigmund, S.K.² Jones, N.D.³ Swartzendruber, J.K.⁴

37
- 0024515453
- (1989) Tetrahedron Lett. , vol.30 , pp. 1889
- Jungheim, L.N.¹

38
- 0025328741
- (1990) Tetrahedron Lett. , vol.31 , pp. 2805
- Ternansky, R.J.¹ Draheim, S.F.²

39
- 0035819444
- (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 21
- Smith, P.W.¹ Wittington, A.R.² Cobley, K.N.³ Jaxa-Chamiec, A.⁴ Finch, H.⁵

40
- 0027208774
- (1993) J. Med. Chem. , vol.36 , pp. 2356
- Subasinghe, N.L.¹ Bontems, R.J.² McIntee, E.³ Mishra, R.K.⁴ Johnson, R.L.⁵

41
- 0031584913
- (1997) Tetrahedron Lett. , vol.38 , pp. 1317
- Subasinghe, N.L.¹ Khalil, E.M.² Johnson, R.L.³

42
- 0030768259
- (1997) Tetrahedron , vol.53 , pp. 12789
- Hanessian, S.¹ McNaughton-Smith, G.² Lombart, H.-G.³ Lubell, W.D.⁴

43
- 0034604670
- (2000) Tetrahedron , vol.56 , pp. 5743
- Gomez-Gallego, M.¹ Mancheno, M.J.² Sierra, M.A.³

44
- 33748659244
- (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 463
- Marchioro, C.¹ Pentassuglia, G.² Perboni, A.³ Donati, D.⁴

45
- 0030932639
- and references cited therein
- (1997) J. Org. Chem. , vol.62 , pp. 1653
- Rossi, T.¹ Marchioro, C.² Paio, A.³ Thomas, R.J.⁴ Zarantonello, P.⁵

46
- 0001526331
- (1998) Heterocycles , vol.48 , pp. 2287
- Iso, Y.¹ Nishitani, Y.²

47
- 0032480942
- (1998) Tetrahedron Lett. , vol.39 , pp. 9063
- Ananda, M.¹ Hashimoto, S.²

48
- 0029961308
- (1996) J. Am Chem. Soc. , vol.118 , pp. 9884
- Hanessian, S.¹ Rozema, M.M.J.²

49
- 0030852692
- (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 1857
- Hanessian, S.¹ Griffin, A.M.² Rozema, M.J.³

50
- 0028892322
- (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2535
- Hanessian, S.¹ Rozema, M.J.² Reddy, G.B.³ Braganza, J.F.⁴

51
- 2142852553
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1657
- Hanessian, S.¹ McNaughton-Smith, C.²

52
- 49649152368
- (1971) J. Organomet. Chem. , vol.30 , pp. 151
- Seyferth, D.¹ Andrews, S.B.²

53
- 33748664603
- (1981) Tetrahedron , vol.37 , pp. 2091
- Bal, B.S.¹ Childers, W.E.² Pinnick, H.W.³

54
- 0001118419
- (1973) Acta Chem. Scand. , vol.27 , pp. 888
- Lindgren, B.O.¹ Nilsson, T.²

55
- 33847086252
- (1980) J. Org. Chem. , vol.45 , pp. 1175
- Kraus, G.A.¹ Tashner, M.J.²

56
- 0000129855
- (1988) Org. Synth. , vol.66 , pp. 203
- Vishwakarma, L.C.¹ Stringer, O.D.² Davis, F.³

57
- 0000352038
- (1984) J. Org. Chem. , vol.49 , pp. 3241
- Davis, F.A.¹ Vishwarkarma, L.C.² Billmers, J.M.³ Finn, J.⁴

58
- 2142685372
- note

59
- 33751385202
- (1993) J. Org. Chem. , vol.58 , pp. 5886
- Thompson, A.S.¹ Humphrey, G.R.² DeMarco, A.M.³ Mathre, D.J.⁴ Grabowski, E.J.J.⁵

60
- 0019252542
- (1980) J. Antibiot. , vol.33 , pp. 1388
- Nakayama, M.¹ Iwasaki, A.² Kimura, S.³ Mizoguchi, T.⁴ Tanabe, S.⁵ Murakami, A.⁶ Watanabe, I.⁷ Okuchi, M.⁸ Itoh, H.⁹ Saino, Y.¹⁰ Kobayashi, F.¹¹ Mori, T.¹²

61
- 15644378136
- (1989) Chem. Rev. , vol.89 , pp. 165
- Wong, H.W.C.¹ Hon, M.-Y.² Tse, C.-W.³ Yip, Y.-C.⁴ Tanko, J.⁵ Hudlicky, T.⁶

62
- 0022971223
- (1986) J. Org. Chem. , vol.51 , pp. 4279
- Cho, B.P.¹ Chadha, V.K.² Le Breton, G.C.³ Venton, D.L.⁴

63
- 0000125222
- (1974) J. Org. Chem. , vol.39 , pp. 259
- McMurry, J.E.¹ Melton, J.² Padgett, H.³

64
- 2142685458
- (1966) J. Org. Chem. , vol.31 , pp. 495
- Sauers, R.R.¹ Ubersax, R.W.²

65
- 0000054568
- (1995) J. Org. Chem. , vol.60 , pp. 3205
- Denmark, S.E.¹ Schmute, M.E.² Marcin, L.R.³ Thorarensen, A.⁴

66
- 2142803164
- note

67
- 0028956779
- (1995) J. Med. Chem. , vol.38 , pp. 1022
- Buynak, J.D.¹ Bachmann, B.² Khasnis, D.³ Hua, L.⁴ Nguyen, H.K.⁵ Carver, C.L.⁶

68
- 0028592697
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 10955
- Buynak, J.D.¹ Khasnis, D.² Bachmann, B.W.K.³ Lamb, G.⁴

69
- 0344175930
- (1998) J. Med. Chem. , vol.41 , pp. 3961
- Heinze-Krass, I.¹ Angehrn, P.² Charnas, R.L.³ Gubernator, K.⁴ Gutknecht, E.⁵ Hubschwerlen, C.⁶ Kami, M.⁷ Oefner, C.⁸ Page, M.G.D.⁹ Sogabe, S.¹⁰ Specklin, J.L.¹¹ Winkler, F.¹²

70
- 0032497590
- (1998) J. Med. Chem. , vol.41 , pp. 3972
- Hubschwerlen, C.¹ Angehrn, P.² Gubernator, K.³ Page, M.G.P.⁴ Specklin, J.L.⁵

71
- 0031012468
- (1997) Tetrahedron Lett. , vol.38 , pp. 167
- Belletini, J.-R.¹ Miller, M.J.²

72
- 0002714675
- (1978) J. Org. Chem. , vol.43 , pp. 2923
- Clark, W.C.¹ Kahn, M.² Mitra, A.³

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