This strategy has been already applied for the preparation of 1,4-fused ring β-lactams. See for examples:. Barrett A.G., Baugh S.P.D., Braddock D.C., Flack K., Gibson V.C., Giles M.R., Marshall E.L., Procopiou P.A., White A.J.P., and Williams D.J. J. Org. Chem. 63 (1998) 7893
Tarling C.A., Holmes A.B., Markwell R.E., and Pearson N.D. J. Chem. Soc. Perkin Trans. 1 (1999) 1695
Barrett A.G., Ahmed M., Baker S.P., Baugh S.P.D., Braddock D.C., Procopiou P.A., White A.J.P., and Williams D.J. J. Org. Chem. 65 (2000) 3716
Desroy N., Robert-Peillard F., Toueg J., Hénaut C., Duboc R., Rager M.-N., Savignac M., and Genêt J.-P. Synthesis 16 (2004) 2665
For HLE (human leucocyte elastase) inhibitors, see for examples:. Burnett D.A. Curr. Med. Chem. 11 (2004) 1873
Macchia B., Gentili D., Macchia M., Mamone F., Martinelli A., Orlandini E., Rossello A., Cercignani G., Pierotti R., Allegretti M., Asti C., and Caselli G. Eur. J. Med. Chem. 35 (2000) 53
Finke P.E., Shah S.K., Fletcher D.S., Ashe K.M., Maycock A.L., Osinga D.G., Underwood D.J., Weston H., Davies P., and Doherty J.B. J. Med. Chem. 38 (1995) 2449
Underwood D.J., Green B.G., Chabin R., Mills S., Doherty J.B., Finke P.E., Mc Coss M., Shah S.K., Burgey C.S., Dickinson T.A., Griffin P.R., Lee T.E., Swiderek K.M., Covey T., Westler W.M., and Knight W.B. Biochemistry 34 (1995) 14344
Shah S.K., Dorn Jr. C.P., Finke P.E., Hale J.J., Hagmann W.K., Brause K.A., Chandler G.O., Kissinger A.L., Ashe B.M., Weston H., Knight W.B., Maycock A.L., Dellea P.S., Fletcher D.S., Hand K.M., Mumford R.A., Underwood D.J., and Doherty J.B. J. Med. Chem. 35 (1992) 3745
see for examples:. Yoakim C., Ogilvie W.W., Cameron D.R., Chabot C., Guse I., Haché B., Naud J., O'Meara J.A., Plante R., and Déziel R. J. Med. Chem. 41 (1998) 2882 For HCMV (human cytomegalovirus) protease inhibitors
Déziel R., and Malenfant E. Bioorg. Med. Chem. Lett. 8 (1998) 1437
Bonneau P.R., Hasani F., Plouffe C., Malenfant E., LaPlante S.R., Guse I., Ogilvie W.W., Plante R., Davidson W.C., Hopkins J.L., Morelock M.G., Cordingley M.G., and Déziel R. J. Am. Chem. Soc. 121 (1999) 2965
For PSA (prostate specific antigen) inhibitors, see for examples:. Adlington R.M., Baldwin J.E., Chen B., Cooper S.L., Mc Coull W., and Pritchard G.J. Bioorg. Med. Chem. Lett. 7 (1997) 1689
Adlington R.M., Baldwin J.E., Becker G.W., Chen B., Chen L., Cooper S.L., Hermann R.B., Mc Coull W., Mc Nulty A.N., Neubauer B.L., and Pritchard G.J. J. Med. Chem. 44 (2001) 1491
For human chymase inhibitors, see for example:. Aoyama Y., Uenaka M., Kii M., Tanaka M., Konoike T., Hayasaki-Kajiwara Y., Noya N., and Nokajima M. Bioorg. Med. Chem. 9 (2001) 3065
Corey E.J., and Venkateswarlu A. J. Am. Chem. Soc. 94 (1972) 6190
Murakami M., Aoki T., and Nagata W. Heterocycles 30 (1990) 567
Ahn Y.M., Yang K., and Georg G.I. Org. Lett. 3 (2001) 1411
Wagner A., Flaig R., Dittrich B., Schmidt H., Koritsanszky T., and Luger P. Chem. Eur. J. 10 (2004) 2977
Dapporto P., Paoli P., Rossi P., Altamura M., and Perrotta E. Struct. Chem. 10 (1999) 311
Lopez R., Menendez M.I., Diaz N., Suarez D., Campomanes P., Ardura D., and Sordo T.L. Curr. Org. Chem. 10 (2006) 805 and references cited therein
Pitarch J., Ruiz-Lopez M.F., Pascual-Ahuir J.L., Silla E., and Tunon I. J. Phys. Chem. B. 101 (1997) 3581
Olmstead W.N., and Brauman J.I. J. Am. Chem. Soc. 99 (1977) 4219
Frau J., Donoso J., Munoz F., and Garcia Blanco F. Helv. Chim. Acta 80 (1997) 739
Massova I., and Kollman P.A. J. Phys. Chem. B. 103 (1999) 8628
Page M.I. Adv. Phys. Org. Chem. 23 (1987) 165
Page M.I. Acc. Chem. Res. 17 (1984) 144
Tsang W.I., Ahmed N., Hemming K., and Page M.I. Can. J. Chem. 83 (2005) 1432
Pitarch J., Ruiz-Lopez M.F., Silla E., Pascual-Ahuir J.L., and Tunon I. J. Am. Chem. Soc. 120 (1998) 2146
Dive G., Dehareng D., and Peeters D. Int. J. Quant. Chem. 58 (1996) 85
Gérard S., Galleni M., Dive G., and Marchand-Brynaert J. Bioorg. Med. Chem. 12 (2004) 129 and references cited therein
Dive G., and Dehareng D. Int. J. Quant. Chem. 73 (1999) 161
The reactive species have been calculated at the Hartree-Fock level as the sum of the energies of the isolated partners, and not as a pre-complex moving toward the transition state. Accordingly, the sum of entropies of isolated partners is significantly more higher than the entropy of an intermediate complex and this leads to an over-estimation of the free energy differences.
Page M.I. The mechanism of reactions of β-lactams. [Chapter 4]. In: Page M.I. (Ed). The Chemistry of β-Lactams (1992), Blackie Academic and Professional, London 129-147
Matagne A., Lamotte-Brasseur J., and Frère J.M. Biochem. J. 330 (1998) 581
Frère J.M., Nguyen-Distèche M., Coyette J., and Joris B. Mode of action: interaction with the penicillin binding proteins. [Chapter 5]. In: Page M.I. (Ed). The Chemistry of β-Lactams (1992), Blackie Academic and Professional, London 148-197
Finke P.E., Ashe B.M., Knight W.B., Maycock A.L., Navia M.A., Shah S.K., Thompson K.R., Underwood D.J., Weston H., Zimmerman M., and Doherty J.B. J. Med. Chem. 33 (1990) 2522
Enright M.C., Robinson D.A., Randle G., Feil E.J., Grundmann H., and Spratt B.G. Proc. Nat. Acad. Sci. USA 99 (2002) 7687
Lim D., and Strynadka N.C. Nat. Struct. Biol. 9 (2002) 870
Sauvage E., Kerff F., Fonzé E., Herman R., Schoot B., Marquette J.-P., Taburet Y., Prevost D., Dumas J., Leonard G., Stefanic P., Coyette J., and Charlier P. Cell. Mol. Life Sci. 59 (2002) 1223
Dessen A., Mouz N., Gordon E., Hopkins J., and Dideberg O. J. Biol. Chem. 276 (2001) 45106
Carapito R., Chesnel L., Vernet T., and Zapun A. J. Biol. Chem. 281 (2005) 1771
Pernot L., Chesnel L., Le Gouellec A., Croizé J., Vernet T., Dideberg O., and Dessen A. J. Biol. Chem. 279 (2004) 16463
Kurazono M., Ida T., Yamada K., Hirai Y., Maruyama T., Shitara E., and Yonezawa M. Antimicrob. Agents Chemother. 48 (2004) 2831
Sader H.S., Fritsche T.R., Kaniga K., Ge Y., and Jones R.N. Antimicrob. Agents Chemother. 49 (2005) 3501
Plantan I., Selic L., Mesar T., Anderluh P.S., Oblak M., Prezelj A., Hesse L., Andrejasic M., Vilar M., Turk D., Kocijan A., Prevec T., Vilfan G., Kocjan D., Copar A., Urleb U., and Solmajer T. J. Med. Chem. 50 (2007) 4113
Waley S.G. β-Lactamase: mechanism of action. [Chapter 6]. In: Page M.I. (Ed). The Chemistry of β-Lactams (1992), Blackie Academic and Professional, London 198-228
Pratt R.F. β-Lactamase: inhibition. [Chapter 7]. In: Page M.I. (Ed). The Chemistry of β-Lactams (1992), Blackie Academic and Professional, London 229-271
Spek A.L. PLATON, Molecular Geometry Program (1998), University of Utrecht, The Netherlands
Sheldrick G.M. SHELXS97 and SHELXL97: Program for the Solution and Refinement of Crystal Structures (1997), University of Göttingen, Germany
Becke A.D. J. Chem. Phys. 98 (1993) 5648
Hehre W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 56 (1972) 2257
Dive G., Dehareng D., and Ghuysen J.M. Theor. Chim. Acta 85 (1993) 409
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Inc., Wallingford, CT