-
2
-
-
0029656226
-
-
For some examples of a,a-difluorophosphonates as inhibitors of enzymes other than FTP's, see: Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996,51,177.
-
(1996)
Tetrahedron
, vol.51
, pp. 177
-
-
Halazy, S.1
Ehrhard, A.2
Eggenspiller, A.3
Berges-Gross, V.4
Danzin, C.5
-
3
-
-
37049109325
-
-
Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Ferkln Trans, l 1984, 1119.
-
(1984)
J. Chem. Soc., Ferkln Trans
, vol.50
, pp. 1119
-
-
Blackburn, G.M.1
Kent, D.E.2
Kolkmann, F.3
-
4
-
-
0025916164
-
-
Hebel, D.; Kirk, K. L.; Kinjo, J.; Kovacs, T.; Lesiak, K.; Baizarini, J.; De Clercq, E.; Torrence, P. F. Bioorg. Med. Chem. Lett. 1991, l, 357.
-
(1991)
Med. Chem. Lett.
, vol.50
, pp. 357
-
-
Hebel, D.1
Kirk, K.L.2
Kinjo, J.3
Kovacs, T.4
Lesiak, K.5
Baizarini, J.6
De Clercq, E.7
Bioorg, T.P.F.8
-
5
-
-
0028077830
-
-
(a) Burke, T. R.; Kole, H. K.; Roller, P. P. Biochem. Biophys. Res. Commun. 1994, 204, 129.
-
(1994)
Biochem. Biophys. Res. Commun.
, vol.204
, pp. 129
-
-
Burke, T.R.1
Kole, H.K.2
Roller, P.P.3
-
6
-
-
0028785789
-
-
(b) Chen, L.; Wu, L.; Otaka, A.; Smyth, M. S.; Roller, P. R.; Burke, T. R.; den Hertog, J.; Zhang, Z.-Y. Biochem. Biophys. Res. Commun. 1995, 216, 976.
-
(1995)
Biochem. Biophys. Res. Commun.
, vol.216
, pp. 976
-
-
Chen, L.1
Wu, L.2
Otaka, A.3
Smyth, M.S.4
Roller, P.R.5
Burke, T.R.6
Den Hertog, J.7
Zhang, Z.-Y.8
-
7
-
-
0028882428
-
-
(a) Kole, K. H.; Smyth, M. S.; RUSS, P. L.; Burke, T. R. Biochem. J. 1995,311,1025.
-
(1995)
Biochem. J.
, vol.311
, pp. 1025
-
-
Kole, K.H.1
Smyth, M.S.2
Russ, P.L.3
Burke, T.R.4
-
8
-
-
0010330478
-
-
in press.
-
(b) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Wang, Q.; Ramachandran, C.; Huang, H. Bioorg. Med. Chem., in press.
-
Bioorg. Med. Chem.
-
-
Taylor, S.D.1
Kotoris, C.C.2
Dinaut, A.N.3
Wang, Q.4
Ramachandran, C.5
Huang, H.6
-
9
-
-
0032539505
-
-
Wang, Q.; Huang, Z.; Ramachandran, C.; Dinaut, A. N.; Taylor, S. D. Bioorg. Med. Chem. Lett. 1998, 8, 345.
-
(1998)
Bioorg. Med. Chem. Lett.
, vol.8
, pp. 345
-
-
Wang, Q.1
Huang, Z.2
Ramachandran, C.3
Dinaut, A.N.4
Taylor, S.D.5
-
10
-
-
0032567871
-
-
(a) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Chen, M.-J. Tetrahedron 1998, 54,1691.
-
(1998)
Tetrahedron
, pp. 1691
-
-
Taylor, S.D.1
Kotoris, C.C.2
Dinaut, A.N.3
Chen, M.-J.4
-
11
-
-
0030569370
-
-
(b) Taylor, S. D.; Dinaut, A. N.; Thadani, A. T.; Huang, Z. Tetrahedron Lett. 1996, 37, 8089.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 8089
-
-
Taylor, S.D.1
Dinaut, A.N.2
Thadani, A.T.3
Huang, Z.4
-
12
-
-
17544391511
-
-
Stankovic, C. J.; Surendram, N.; Lunney, E. A.; Plummer, M. S.; Para, K. S.; Shahripour, A.; Fergus, J. H.; Marks, J. S.; Herrera, R.; Hubbell, S. E.; Humblet, C.; Saltiel, A. R.; Stewart, B. H.; Sawyer, T. K. Bioorg. Med. Chem. Lett. 1997, 7, 1909.
-
(1997)
Bioorg. Med. Chem. Lett.
, vol.7
, pp. 1909
-
-
Stankovic, C.J.1
Surendram, N.2
Lunney, E.A.3
Plummer, M.S.4
Para, K.S.5
Shahripour, A.6
Fergus, J.H.7
Marks, J.S.8
Herrera, R.9
Hubbell, S.E.10
Humblet, C.11
Saltiel, A.R.12
Stewart, B.H.13
Sawyer, T.K.14
-
17
-
-
20444447553
-
-
(e) Bardin, V. V.; Furin, G. G.; Yakobson, G. G. Zh. Org. Khim. 1984,20, 567.
-
(1984)
Zh. Org. Khim.
, vol.20
, pp. 567
-
-
Bardin, V.V.1
Furin, G.G.2
Yakobson, G.G.3
-
18
-
-
0001299637
-
-
(f) Laurent, E.; Marquet, B.; Tardivel, R. Tetrahedron 1989, 45, 4431.
-
(1989)
Tetrahedron
, vol.45
, pp. 4431
-
-
Laurent, E.1
Marquet, B.2
Tardivel, R.3
-
19
-
-
0010114968
-
-
(a) Finnegan, W. G.; Henry, R. A.; Lofquist, R. J. Am. Chem. Soc. 1958,80,3908.
-
(1958)
J. Am. Chem. Soc.
, vol.80
, pp. 3908
-
-
Finnegan, W.G.1
Henry, R.A.2
Lofquist, R.3
-
22
-
-
0001250488
-
-
Duncia, J. V.; Pierce, M. E.; Santella, J. B. J. Org. Chem. 1991, 56, 2395.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2395
-
-
Duncia, J.V.1
Pierce, M.E.2
Santella, J.B.3
-
23
-
-
0001029493
-
-
For a review on electrophilic fluorination, see: Rozen, S. Chem. Rev. 1996, 96, 1717.
-
(1996)
Chem. Rev.
, vol.96
, pp. 1717
-
-
Rozen, S.1
-
24
-
-
1542502218
-
-
For some examples of electrophilic fluorination using NFSi, see: (a) McAtee, J. J.; Schinazi, R. F.; Liotta, D. C. J. Org. Chem. 1998, 63, 2161.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 2161
-
-
McAtee, J.J.1
Schinazi, R.F.2
Liotta, D.C.3
-
25
-
-
0030721614
-
-
(b) Ender, D.; Potthoff, M.; Raabe, G.; Runsink, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2362.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 2362
-
-
Ender, D.1
Potthoff, M.2
Raabe, G.3
Runsink, J.4
-
27
-
-
0011210489
-
-
Difierding, E.; Duthaler, R. O.; Kreiger, A.; Ruegg, G. M.; Schmit, C. Synlett 1991, 395.
-
(1991)
Synlett
, pp. 395
-
-
Difierding, E.1
Duthaler, R.O.2
Kreiger, A.3
Ruegg, G.M.4
Schmit, C.5
-
28
-
-
85034166505
-
-
8c However, we were unable to obtain any appreciable quantities of 20 in pure form using this procedure.
-
8c However, we were unable to obtain any appreciable quantities of 20 in pure form using this procedure.
-
-
-
-
29
-
-
0025755872
-
-
The tert-butyl group is commonly employed as a protecting group for tetrazoles and is removed using acid. For example, see
-
The tert-butyl group is commonly employed as a protecting group for tetrazoles and is removed using acid. For example, see: Tilley, J. W.; Danho, W.; Lovey, K.; Wagner, R.; Swistok, J.; Makofske, R.; Michaelewsky, J.; Triscari, J.; Nelson, D.; Weatherford, S. J. Med. Chem. 1991, 34, 1125.
-
(1991)
J. Med. Chem.
, vol.34
, pp. 1125
-
-
Tilley, J.W.1
Danho, W.2
Lovey, K.3
Wagner, R.4
Swistok, J.5
Makofske, R.6
Michaelewsky, J.7
Triscari, J.8
Nelson, D.9
Weatherford, S.10
-
30
-
-
0030962736
-
-
For some examples of biologically active benzylic tetrazoles, see: Bleisch, T. J.; Ornstein, P. L.; Alien, N. K.; Wright, R. A.; Lodge, D.; Schoepp, D. D. Bioorg. Med. Chem. Lett. 1997, 7, 1161.
-
(1997)
Bioorg. Med. Chem. Lett.
, vol.7
, pp. 1161
-
-
Bleisch, T.J.1
Ornstein, P.L.2
Alien, N.K.3
Wright, R.A.4
Lodge, D.5
Schoepp, D.D.6
-
31
-
-
0029560999
-
-
Kogan, T. P.; Dupre, B.; Keller, K. M.; Scott, I. L.; Bui, H.; Market, R. V.; Beck, P. J.; Vogtus, J. A.; Revelle, B. M.; Scott, D. J. Med. Chem. 1995, 38, 4976.
-
(1995)
J. Med. Chem.
, vol.38
, pp. 4976
-
-
Kogan, T.P.1
Dupre, B.2
Keller, K.M.3
Scott, I.L.4
Bui, H.5
Market, R.V.6
Beck, P.J.7
Vogtus, J.A.8
Revelle, B.M.9
Scott, D.10
-
32
-
-
0028577773
-
-
Al-Khamees, H. A.; Kandil, H. A.; El-Tahir, K. E. H.; Al-Attas, O. S.; Bayomi, S. M. Sei. Pharm. 1994, 62, 363.
-
(1994)
Sei. Pharm.
, vol.62
, pp. 363
-
-
Al-Khamees, H.A.1
Kandil, H.A.2
El-Tahir, K.E.H.3
Al-Attas, O.S.4
Bayomi, S.M.5
-
33
-
-
0026574160
-
-
Kees, K. L.; Smith, T. M.; McCaleb, M. L.; Prozialeck, D. H.; Cheeseman, R. S.; Christas, J. A.; Patt, W. C.; Steiner, K. E. J. Med. Chem. 1992,35, 944.
-
(1992)
J. Med. Chem.
, vol.35
, pp. 944
-
-
Kees, K.L.1
Smith, T.M.2
McCaleb, M.L.3
Prozialeck, D.H.4
Cheeseman, R.S.5
Christas, J.A.6
Patt, W.C.7
Steiner, K.E.8
-
34
-
-
0026758370
-
-
Ornstein, P. L.; Schoepp, D. D.; Arnold, M. B.; Augenstein, N. K.; Lodge, D.; Millar, J. P.; Chambers, J.; Campbell, J.; Paschal, J. W.; Zimmerman, D. M.; Leander, J. D. J. Med. Chem. 1992, 35, 3547.
-
(1992)
J. Med. Chem.
, vol.35
, pp. 3547
-
-
Ornstein, P.L.1
Schoepp, D.D.2
Arnold, M.B.3
Augenstein, N.K.4
Lodge, D.5
Millar, J.P.6
Chambers, J.7
Campbell, J.8
Paschal, J.W.9
Zimmerman, D.M.10
Leander, J.D.11
-
35
-
-
0025174164
-
-
Musser, J. H.; Kreft, A. F.; Bender, R. H. W.; Kubrak, D. M.; Grimes, D.; Carolson, R. P.; Hand, J. M.; Chang, J. J. Med. Chem. 1990, 33, 240.
-
(1990)
J. Med. Chem.
, vol.33
, pp. 240
-
-
Musser, J.H.1
Kreft, A.F.2
Bender, R.H.W.3
Kubrak, D.M.4
Grimes, D.5
Carolson, R.P.6
Hand, J.M.7
Chang, J.8
-
36
-
-
0025237214
-
-
Huang, F.-C.; Galemmo, R. A.; Johnson, W. H.; Poli, G. B.; Morrisette, M. M.; Mencel, J. J.; Warus, J. P.; Campbell, H. F.; NUSS, G. W.; Carnathan, G. W.; van Inwegen, R. G. J. Med. Chem. 1990,33,1194.
-
(1990)
J. Med. Chem.
, pp. 1194
-
-
Huang, F.-C.1
Galemmo, R.A.2
Johnson, W.H.3
Poli, G.B.4
Morrisette, M.M.5
Mencel, J.J.6
Warus, J.P.7
Campbell, H.F.8
Nuss, G.W.9
Carnathan, G.W.10
Van Inwegen, R.G.11
-
37
-
-
0025091123
-
-
See also ref 13.
-
Gapinski, D. M.; Mallet, B. E.; Froelich, L. L.; Jackson, W. T. J. Med. Chem. 1990, 33, 2798. See also ref 13.
-
(1990)
J. Med. Chem.
, vol.33
, pp. 2798
-
-
Gapinski, D.M.1
Mallet, B.E.2
Froelich, L.L.3
Jackson, W.T.4
-
38
-
-
0028070371
-
-
Liotta, A. S.; Kole, H. K.; Fales, H. M.; Roth, J.; Bernier, M. J. Biol. Chem. 1994,269, 22996.
-
(1994)
J. Biol. Chem.
, vol.269
, pp. 22996
-
-
Liotta, A.S.1
Kole, H.K.2
Fales, H.M.3
Roth, J.4
Bernier, M.5
-
39
-
-
0032526549
-
-
Desmarais, S.; Jia, Z.; Ramachandran, R. Arch. Kochern. Biophys. 1998, 354, 225.
-
(1998)
Arch. Kochern. Biophys.
, vol.354
, pp. 225
-
-
Desmarais, S.1
Jia, Z.2
Ramachandran, R.3
-
40
-
-
85034185792
-
-
Sulfonates are completely ionized at physiological pH. Thus, any increase in inhibitor potency of a,a-difluorosulfonates compared to their nonfluorinated or sulfate counterparts would have to be a result of a direct interaction of the fluorines with residues in the enzyme active site, as. appears to be the case with the a-difluorinated phosphonates and PTP's.
-
Sulfonates are completely ionized at physiological pH. Thus, any increase in inhibitor potency of a,a-difluorosulfonates compared to their nonfluorinated or sulfate counterparts would have to be a result of a direct interaction of the fluorines with residues in the enzyme active site, as. appears to be the case with the a-difluorinated phosphonates and PTP's.
-
-
-
-
41
-
-
0031045478
-
-
For examples, see: (a) Selcer, K. W.; Hegde, P. V.; Li, P.-K. Cancer Res. 1997, 57, 702.
-
(1997)
Cancer Res.
, vol.57
, pp. 702
-
-
Selcer, K.W.1
Hegde, P.V.2
Li, P.-K.3
-
42
-
-
0031027933
-
-
(b) Anderson, C.; Freeman, J.; Lucas, L. H.; Parley, M.; Dalhoumi, H.; Widlanski, T. S. Biochemistry 1997,36, 2586.
-
(1997)
Biochemistry
, vol.36
, pp. 2586
-
-
Anderson, C.1
Freeman, J.2
Lucas, L.H.3
Parley, M.4
Dalhoumi, H.5
Widlanski, T.S.6
-
43
-
-
0030999931
-
-
Howarth, N. M.; Purolit, A.; Reed, M. J.; Potter, B. V. L. Steroids 1997,62,346.
-
(1997)
Steroids
, pp. 346
-
-
Howarth, N.M.1
Purolit, A.2
Reed, M.J.3
Potter, B.V.L.4
-
44
-
-
0028948089
-
-
Li, P. K.; Pillai, R.; Dibbelt, L. Steroids 1995, 60, 299.
-
(1995)
Steroids
, vol.60
, pp. 299
-
-
Li, P.K.1
Pillai, R.2
Dibbelt, L.3
-
49
-
-
85034172626
-
-
In conclusion, we have demonstrated that benzylic α,αdifluoronitriles, -tetrazoles, and -sulfonates can be prepared by electrophilic fluorination of benzylic carbanions
-
18a-d some of which are estrone sulfonates in which the labile S-O bond in the substrate is replaced by a méthylène unit.18d Conversion of these compounds to the α,α-difluorosulfonate derivatives may provide a means of increasing the potency of these compounds.
-
-
-
|