메뉴 건너뛰기




Volumn 52, Issue 16, 1996, Pages 5983-5988

A N-nitrosochloroethyl-cephalosporin carbamate prodrug for antibody-directed enzyme prodrug therapy (ADEPT)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAMASE; CEPHEM DERIVATIVE; CHLOROETHYLNITROSOUREA DERIVATIVE; NITROSO DERIVATIVE; PRODRUG;

EID: 0030012284     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00228-1     Document Type: Article
Times cited : (14)

References (31)
  • 1
    • 0023619243 scopus 로고
    • Bagshawe, K.D. Br. J. Cancer, 1987, 56, 531. Recent reviews include: Bagshawe, K.D.;. Sharma, S.K; Springer, C.J.; Rogers, G.T. Annals of Oncology, 1994, 5, 879; Jungheim, L.N.; Shepherd, T.A. Chem. Rev., 1994, 94, 1553.
    • (1987) Br. J. Cancer , vol.56 , pp. 531
    • Bagshawe, K.D.1
  • 3
    • 0345678344 scopus 로고
    • Bagshawe, K.D. Br. J. Cancer, 1987, 56, 531. Recent reviews include: Bagshawe, K.D.;. Sharma, S.K; Springer, C.J.; Rogers, G.T. Annals of Oncology, 1994, 5, 879; Jungheim, L.N.; Shepherd, T.A. Chem. Rev., 1994, 94, 1553.
    • (1994) Chem. Rev. , vol.94 , pp. 1553
    • Jungheim, L.N.1    Shepherd, T.A.2
  • 5
    • 0028793511 scopus 로고
    • Recent studies include: Hay, M.P.; Wilson, W.R.; Denny, W.A. Bioorg. Med. Chem. Lett., 1995, 5, 2829; Leenders, R.G.G.; Gerrits, K.A.A.; Ruijtenbeek, R.; Scheeren, H.W.; Haisma, H.J.; Boven, E. Tetrahedron Lett., 1995, 36, 1701.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2829
    • Hay, M.P.1    Wilson, W.R.2    Denny, W.A.3
  • 7
    • 85030195670 scopus 로고    scopus 로고
    • Eur. Pat. 90303681.2. (1990)
    • Eaton, M.A.W.; Pratt. A.J.; Alexander, R.P. Eur. Pat. 90303681.2. (1990); Shepherd, T.A.; Jungheim, L.N.; Meyer, D.L.; Starling, J.J. Bioorg. Med. Chem. Lett., 1991, 1, 21; Meyer, D.L.; Jungheim, L.N.; Law, K.L.; Mikolajczyk, S.D.; Shepherd, T.A.; Mackenson, D.G.; Briggs, S.L.; Starling, J.J. Cancer Res., 1993, 53, 3956; Goshorn, S.C.; Svensson, H.P.; Kerr, D.E.; Somerville, J.E.; Senter, P.D.; Fell, H.P. Cancer Res., 1993, 53, 2123; Vrudhula, V.M.; Svensson, H.P.; Senter, P.D. J. Med. Chem., 1995, 38, 1380.
    • Eaton, M.A.W.1    Pratt, A.J.2    Alexander, R.P.3
  • 8
    • 0025864963 scopus 로고
    • Eaton, M.A.W.; Pratt. A.J.; Alexander, R.P. Eur. Pat. 90303681.2. (1990); Shepherd, T.A.; Jungheim, L.N.; Meyer, D.L.; Starling, J.J. Bioorg. Med. Chem. Lett., 1991, 1, 21; Meyer, D.L.; Jungheim, L.N.; Law, K.L.; Mikolajczyk, S.D.; Shepherd, T.A.; Mackenson, D.G.; Briggs, S.L.; Starling, J.J. Cancer Res., 1993, 53, 3956; Goshorn, S.C.; Svensson, H.P.; Kerr, D.E.; Somerville, J.E.; Senter, P.D.; Fell, H.P. Cancer Res., 1993, 53, 2123; Vrudhula, V.M.; Svensson, H.P.; Senter, P.D. J. Med. Chem., 1995, 38, 1380.
    • (1991) Bioorg. Med. Chem. Lett. , vol.1 , pp. 21
    • Shepherd, T.A.1    Jungheim, L.N.2    Meyer, D.L.3    Starling, J.J.4
  • 9
    • 0027220125 scopus 로고
    • Eaton, M.A.W.; Pratt. A.J.; Alexander, R.P. Eur. Pat. 90303681.2. (1990); Shepherd, T.A.; Jungheim, L.N.; Meyer, D.L.; Starling, J.J. Bioorg. Med. Chem. Lett., 1991, 1, 21; Meyer, D.L.; Jungheim, L.N.; Law, K.L.; Mikolajczyk, S.D.; Shepherd, T.A.; Mackenson, D.G.; Briggs, S.L.; Starling, J.J. Cancer Res., 1993, 53, 3956; Goshorn, S.C.; Svensson, H.P.; Kerr, D.E.; Somerville, J.E.; Senter, P.D.; Fell, H.P. Cancer Res., 1993, 53, 2123; Vrudhula, V.M.; Svensson, H.P.; Senter, P.D. J. Med. Chem., 1995, 38, 1380.
    • (1993) Cancer Res. , vol.53 , pp. 3956
    • Meyer, D.L.1    Jungheim, L.N.2    Law, K.L.3    Mikolajczyk, S.D.4    Shepherd, T.A.5    Mackenson, D.G.6    Briggs, S.L.7    Starling, J.J.8
  • 10
    • 0027157591 scopus 로고
    • Eaton, M.A.W.; Pratt. A.J.; Alexander, R.P. Eur. Pat. 90303681.2. (1990); Shepherd, T.A.; Jungheim, L.N.; Meyer, D.L.; Starling, J.J. Bioorg. Med. Chem. Lett., 1991, 1, 21; Meyer, D.L.; Jungheim, L.N.; Law, K.L.; Mikolajczyk, S.D.; Shepherd, T.A.; Mackenson, D.G.; Briggs, S.L.; Starling, J.J. Cancer Res., 1993, 53, 3956; Goshorn, S.C.; Svensson, H.P.; Kerr, D.E.; Somerville, J.E.; Senter, P.D.; Fell, H.P. Cancer Res., 1993, 53, 2123; Vrudhula, V.M.; Svensson, H.P.; Senter, P.D. J. Med. Chem., 1995, 38, 1380.
    • (1993) Cancer Res. , vol.53 , pp. 2123
    • Goshorn, S.C.1    Svensson, H.P.2    Kerr, D.E.3    Somerville, J.E.4    Senter, P.D.5    Fell, H.P.6
  • 11
    • 0028939031 scopus 로고
    • Eaton, M.A.W.; Pratt. A.J.; Alexander, R.P. Eur. Pat. 90303681.2. (1990); Shepherd, T.A.; Jungheim, L.N.; Meyer, D.L.; Starling, J.J. Bioorg. Med. Chem. Lett., 1991, 1, 21; Meyer, D.L.; Jungheim, L.N.; Law, K.L.; Mikolajczyk, S.D.; Shepherd, T.A.; Mackenson, D.G.; Briggs, S.L.; Starling, J.J. Cancer Res., 1993, 53, 3956; Goshorn, S.C.; Svensson, H.P.; Kerr, D.E.; Somerville, J.E.; Senter, P.D.; Fell, H.P. Cancer Res., 1993, 53, 2123; Vrudhula, V.M.; Svensson, H.P.; Senter, P.D. J. Med. Chem., 1995, 38, 1380.
    • (1995) J. Med. Chem. , vol.38 , pp. 1380
    • Vrudhula, V.M.1    Svensson, H.P.2    Senter, P.D.3
  • 14
    • 0022618178 scopus 로고
    • See e.g. Mobashery, S.; Lerner, S.A.; Johnston, M. J. Am. Chem. Soc., 1986, 108, 1685; Brown, R.F.; Kinnick, M.D.; Morin, J.M.; Vasileff, R.T.; Counter, F.T.; Davidson, E.O.; Ensminger, P.W.;. Eudaly, J.A; Kasher, J.S.; Katner, A.S.; Koehler, R.E.; Kurtz, K.D.; Lindstrom, T.D.; Lunn, W.H.W.; Preston, D.A.; Turner, J.L.; Webber, J.A.; Wright, W.E.; Zimmerman, K.M. J. Med. Chem., 1990, 33, 2114; Albrecht, H.A.; Beskid, G.; Chan, K.K.; Christenson, J.G.; Cleeland, R.; Deitcher, K.H.; Georgopapadakou, N.H.; Keith, D.D.; Pruess, D.L.; Sepinwell, J.; Specian, A.C.; Then, R.L.; Weigele, M.; West, F.; Yang, R. J. Med. Chem., 1990, 33, 77.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 1685
    • Mobashery, S.1    Lerner, S.A.2    Johnston, M.3
  • 17
    • 0025897111 scopus 로고
    • Alexander, R.P.; Beeley, N.R.A.; O'Driscoll, M.; O'Neill, F.P.; Millican, T.A.; Pratt, A.J.; Willenbrock, F.M. Tetrahedron Lett., 1991, 32, 3269; Jungheim, L.N.; Shepherd, T.A.; Meyer, D.L. J. Org, Chem., 1992, 57, 2334; Jungheim, L.N.; Shepherd, T.A.; Kling, J.K. Heterocycles, 1993, 35, 339; Meyer, D.L.; Law, K.L.; Payne, J.K.; Mikolajczyk, S.D.; Zarrinmayeh, H.; Jungheim, L.N.; King, J.K.; Shepherd, T.A.; Starling, J.J. Bioconjugate Chem., 1995, 6, 440; Svensson, H.P.;. Vrudhula, V.M; Emswiler, J.E.; MacMaster, J.F.; Cosand, W.L.; Senter, P.D.; Wallace, P.M. Cancer Res., 1995, 55, 2357; Rodrigues, M.L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B.K. Chemistry: and Biology, 1995, 2, 223; Hudyma, T.W.; Bush, K.; Colson, K.L.; Firestone, R. A.; King, H.D. Bioorg. Med. Chem. Lett., 1993, 3, 323; Hanessian, S.; Wang, J.C. Can. J. Chem., 1993, 71, 896.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3269
    • Alexander, R.P.1    Beeley, N.R.A.2    O'Driscoll, M.3    O'Neill, F.P.4    Millican, T.A.5    Pratt, A.J.6    Willenbrock, F.M.7
  • 18
    • 0026562808 scopus 로고
    • Alexander, R.P.; Beeley, N.R.A.; O'Driscoll, M.; O'Neill, F.P.; Millican, T.A.; Pratt, A.J.; Willenbrock, F.M. Tetrahedron Lett., 1991, 32, 3269; Jungheim, L.N.; Shepherd, T.A.; Meyer, D.L. J. Org, Chem., 1992, 57, 2334; Jungheim, L.N.; Shepherd, T.A.; Kling, J.K. Heterocycles, 1993, 35, 339; Meyer, D.L.; Law, K.L.; Payne, J.K.; Mikolajczyk, S.D.; Zarrinmayeh, H.; Jungheim, L.N.; King, J.K.; Shepherd, T.A.; Starling, J.J. Bioconjugate Chem., 1995, 6, 440; Svensson, H.P.;. Vrudhula, V.M; Emswiler, J.E.; MacMaster, J.F.; Cosand, W.L.; Senter, P.D.; Wallace, P.M. Cancer Res., 1995, 55, 2357; Rodrigues, M.L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B.K. Chemistry: and Biology, 1995, 2, 223; Hudyma, T.W.; Bush, K.; Colson, K.L.; Firestone, R. A.; King, H.D. Bioorg. Med. Chem. Lett., 1993, 3, 323; Hanessian, S.; Wang, J.C. Can. J. Chem., 1993, 71, 896.
    • (1992) J. Org, Chem. , vol.57 , pp. 2334
    • Jungheim, L.N.1    Shepherd, T.A.2    Meyer, D.L.3
  • 19
    • 0000814098 scopus 로고
    • Alexander, R.P.; Beeley, N.R.A.; O'Driscoll, M.; O'Neill, F.P.; Millican, T.A.; Pratt, A.J.; Willenbrock, F.M. Tetrahedron Lett., 1991, 32, 3269; Jungheim, L.N.; Shepherd, T.A.; Meyer, D.L. J. Org, Chem., 1992, 57, 2334; Jungheim, L.N.; Shepherd, T.A.; Kling, J.K. Heterocycles, 1993, 35, 339; Meyer, D.L.; Law, K.L.; Payne, J.K.; Mikolajczyk, S.D.; Zarrinmayeh, H.; Jungheim, L.N.; King, J.K.; Shepherd, T.A.; Starling, J.J. Bioconjugate Chem., 1995, 6, 440; Svensson, H.P.;. Vrudhula, V.M; Emswiler, J.E.; MacMaster, J.F.; Cosand, W.L.; Senter, P.D.; Wallace, P.M. Cancer Res., 1995, 55, 2357; Rodrigues, M.L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B.K. Chemistry: and Biology, 1995, 2, 223; Hudyma, T.W.; Bush, K.; Colson, K.L.; Firestone, R. A.; King, H.D. Bioorg. Med. Chem. Lett., 1993, 3, 323; Hanessian, S.; Wang, J.C. Can. J. Chem., 1993, 71, 896.
    • (1993) Heterocycles , vol.35 , pp. 339
    • Jungheim, L.N.1    Shepherd, T.A.2    Kling, J.K.3
  • 20
    • 0029328639 scopus 로고
    • Alexander, R.P.; Beeley, N.R.A.; O'Driscoll, M.; O'Neill, F.P.; Millican, T.A.; Pratt, A.J.; Willenbrock, F.M. Tetrahedron Lett., 1991, 32, 3269; Jungheim, L.N.; Shepherd, T.A.; Meyer, D.L. J. Org, Chem., 1992, 57, 2334; Jungheim, L.N.; Shepherd, T.A.; Kling, J.K. Heterocycles, 1993, 35, 339; Meyer, D.L.; Law, K.L.; Payne, J.K.; Mikolajczyk, S.D.; Zarrinmayeh, H.; Jungheim, L.N.; King, J.K.; Shepherd, T.A.; Starling, J.J. Bioconjugate Chem., 1995, 6, 440; Svensson, H.P.;. Vrudhula, V.M; Emswiler, J.E.; MacMaster, J.F.; Cosand, W.L.; Senter, P.D.; Wallace, P.M. Cancer Res., 1995, 55, 2357; Rodrigues, M.L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B.K. Chemistry: and Biology, 1995, 2, 223; Hudyma, T.W.; Bush, K.; Colson, K.L.; Firestone, R. A.; King, H.D. Bioorg. Med. Chem. Lett., 1993, 3, 323; Hanessian, S.; Wang, J.C. Can. J. Chem., 1993, 71, 896.
    • (1995) Bioconjugate Chem. , vol.6 , pp. 440
    • Meyer, D.L.1    Law, K.L.2    Payne, J.K.3    Mikolajczyk, S.D.4    Zarrinmayeh, H.5    Jungheim, L.N.6    King, J.K.7    Shepherd, T.A.8    Starling, J.J.9
  • 21
    • 0029019242 scopus 로고
    • Alexander, R.P.; Beeley, N.R.A.; O'Driscoll, M.; O'Neill, F.P.; Millican, T.A.; Pratt, A.J.; Willenbrock, F.M. Tetrahedron Lett., 1991, 32, 3269; Jungheim, L.N.; Shepherd, T.A.; Meyer, D.L. J. Org, Chem., 1992, 57, 2334; Jungheim, L.N.; Shepherd, T.A.; Kling, J.K. Heterocycles, 1993, 35, 339; Meyer, D.L.; Law, K.L.; Payne, J.K.; Mikolajczyk, S.D.; Zarrinmayeh, H.; Jungheim, L.N.; King, J.K.; Shepherd, T.A.; Starling, J.J. Bioconjugate Chem., 1995, 6, 440; Svensson, H.P.;. Vrudhula, V.M; Emswiler, J.E.; MacMaster, J.F.; Cosand, W.L.; Senter, P.D.; Wallace, P.M. Cancer Res., 1995, 55, 2357; Rodrigues, M.L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B.K. Chemistry: and Biology, 1995, 2, 223; Hudyma, T.W.; Bush, K.; Colson, K.L.; Firestone, R. A.; King, H.D. Bioorg. Med. Chem. Lett., 1993, 3, 323; Hanessian, S.; Wang, J.C. Can. J. Chem., 1993, 71, 896.
    • (1995) Cancer Res. , vol.55 , pp. 2357
    • Svensson, H.P.1    Vrudhula, V.M.2    Emswiler, J.E.3    MacMaster, J.F.4    Cosand, W.L.5    Senter, P.D.6    Wallace, P.M.7
  • 22
    • 0029279040 scopus 로고
    • Alexander, R.P.; Beeley, N.R.A.; O'Driscoll, M.; O'Neill, F.P.; Millican, T.A.; Pratt, A.J.; Willenbrock, F.M. Tetrahedron Lett., 1991, 32, 3269; Jungheim, L.N.; Shepherd, T.A.; Meyer, D.L. J. Org, Chem., 1992, 57, 2334; Jungheim, L.N.; Shepherd, T.A.; Kling, J.K. Heterocycles, 1993, 35, 339; Meyer, D.L.; Law, K.L.; Payne, J.K.; Mikolajczyk, S.D.; Zarrinmayeh, H.; Jungheim, L.N.; King, J.K.; Shepherd, T.A.; Starling, J.J. Bioconjugate Chem., 1995, 6, 440; Svensson, H.P.;. Vrudhula, V.M; Emswiler, J.E.; MacMaster, J.F.; Cosand, W.L.; Senter, P.D.; Wallace, P.M. Cancer Res., 1995, 55, 2357; Rodrigues, M.L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B.K. Chemistry: and Biology, 1995, 2, 223; Hudyma, T.W.; Bush, K.; Colson, K.L.; Firestone, R. A.; King, H.D. Bioorg. Med. Chem. Lett., 1993, 3, 323; Hanessian, S.; Wang, J.C. Can. J. Chem., 1993, 71, 896.
    • (1995) Chemistry: and Biology , vol.2 , pp. 223
    • Rodrigues, M.L.1    Carter, P.2    Wirth, C.3    Mullins, S.4    Lee, A.5    Blackburn, B.K.6
  • 23
    • 0027407548 scopus 로고
    • Alexander, R.P.; Beeley, N.R.A.; O'Driscoll, M.; O'Neill, F.P.; Millican, T.A.; Pratt, A.J.; Willenbrock, F.M. Tetrahedron Lett., 1991, 32, 3269; Jungheim, L.N.; Shepherd, T.A.; Meyer, D.L. J. Org, Chem., 1992, 57, 2334; Jungheim, L.N.; Shepherd, T.A.; Kling, J.K. Heterocycles, 1993, 35, 339; Meyer, D.L.; Law, K.L.; Payne, J.K.; Mikolajczyk, S.D.; Zarrinmayeh, H.; Jungheim, L.N.; King, J.K.; Shepherd, T.A.; Starling, J.J. Bioconjugate Chem., 1995, 6, 440; Svensson, H.P.;. Vrudhula, V.M; Emswiler, J.E.; MacMaster, J.F.; Cosand, W.L.; Senter, P.D.; Wallace, P.M. Cancer Res., 1995, 55, 2357; Rodrigues, M.L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B.K. Chemistry: and Biology, 1995, 2, 223; Hudyma, T.W.; Bush, K.; Colson, K.L.; Firestone, R. A.; King, H.D. Bioorg. Med. Chem. Lett., 1993, 3, 323; Hanessian, S.; Wang, J.C. Can. J. Chem., 1993, 71, 896.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 323
    • Hudyma, T.W.1    Bush, K.2    Colson, K.L.3    Firestone, R.A.4    King, H.D.5
  • 24
    • 0027235973 scopus 로고
    • Alexander, R.P.; Beeley, N.R.A.; O'Driscoll, M.; O'Neill, F.P.; Millican, T.A.; Pratt, A.J.; Willenbrock, F.M. Tetrahedron Lett., 1991, 32, 3269; Jungheim, L.N.; Shepherd, T.A.; Meyer, D.L. J. Org, Chem., 1992, 57, 2334; Jungheim, L.N.; Shepherd, T.A.; Kling, J.K. Heterocycles, 1993, 35, 339; Meyer, D.L.; Law, K.L.; Payne, J.K.; Mikolajczyk, S.D.; Zarrinmayeh, H.; Jungheim, L.N.; King, J.K.; Shepherd, T.A.; Starling, J.J. Bioconjugate Chem., 1995, 6, 440; Svensson, H.P.;. Vrudhula, V.M; Emswiler, J.E.; MacMaster, J.F.; Cosand, W.L.; Senter, P.D.; Wallace, P.M. Cancer Res., 1995, 55, 2357; Rodrigues, M.L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B.K. Chemistry: and Biology, 1995, 2, 223; Hudyma, T.W.; Bush, K.; Colson, K.L.; Firestone, R. A.; King, H.D. Bioorg. Med. Chem. Lett., 1993, 3, 323; Hanessian, S.; Wang, J.C. Can. J. Chem., 1993, 71, 896.
    • (1993) Can. J. Chem. , vol.71 , pp. 896
    • Hanessian, S.1    Wang, J.C.2
  • 25
    • 0001737272 scopus 로고
    • Johnston, T.P.; McCaleb, G.S.; Montgomery, J.A. J. Med. Chem., 1963, 6, 669; Johnston, T.P.; McCaleb, G.S.; Montgomery, J.A. J. Med. Chem., 1966, 9, 892; Reed, D.J. Cancer Res., 1975, 35, 568.
    • (1963) J. Med. Chem. , vol.6 , pp. 669
    • Johnston, T.P.1    McCaleb, G.S.2    Montgomery, J.A.3
  • 26
    • 0013967260 scopus 로고
    • Johnston, T.P.; McCaleb, G.S.; Montgomery, J.A. J. Med. Chem., 1963, 6, 669; Johnston, T.P.; McCaleb, G.S.; Montgomery, J.A. J. Med. Chem., 1966, 9, 892; Reed, D.J. Cancer Res., 1975, 35, 568.
    • (1966) J. Med. Chem. , vol.9 , pp. 892
    • Johnston, T.P.1    McCaleb, G.S.2    Montgomery, J.A.3
  • 27
    • 0016656714 scopus 로고
    • Johnston, T.P.; McCaleb, G.S.; Montgomery, J.A. J. Med. Chem., 1963, 6, 669; Johnston, T.P.; McCaleb, G.S.; Montgomery, J.A. J. Med. Chem., 1966, 9, 892; Reed, D.J. Cancer Res., 1975, 35, 568.
    • (1975) Cancer Res. , vol.35 , pp. 568
    • Reed, D.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.