-
4
-
-
33544454880
-
-
note
-
The CAS Registry No. for terrazole is 25-931-59.
-
-
-
-
5
-
-
0026730087
-
-
(a) Unangst, P. C.; Shrum, G. P.; Connor, D. T.; Dyer, R. D.; Schrier, D. J. J. Med. Chem. 1992, 35, 3691-3698.
-
(1992)
J. Med. Chem.
, vol.35
, pp. 3691-3698
-
-
Unangst, P.C.1
Shrum, G.P.2
Connor, D.T.3
Dyer, R.D.4
Schrier, D.J.5
-
6
-
-
0033535606
-
-
(b) Song, Y.; Connor, D. T.; Sercel, A. D.; Sorenson, R. J.; Doubleday: R.; Unangst, P. C.; Roth, B. D.; Beylin, V. G.; Gilbertsen, R. B.; Chan, K.; Schrier, D. J.; Guglietta, A.; Bornemeier, D. A.; Dyer, R. D. J. Med. Chem. 1999, 42, 1161-1169.
-
(1999)
J. Med. Chem.
, vol.42
, pp. 1161-1169
-
-
Song, Y.1
Connor, D.T.2
Sercel, A.D.3
Sorenson, R.J.4
Doubleday, R.5
Unangst, P.C.6
Roth, B.D.7
Beylin, V.G.8
Gilbertsen, R.B.9
Chan, K.10
Schrier, D.J.11
Guglietta, A.12
Bornemeier, D.A.13
Dyer, R.D.14
-
7
-
-
0027932589
-
-
Smith, C. W.; Chakrabarti, J. K.; Williamson, W. R. N. Bioorg. Med. Chem. Lett. 1994, 4, 1673-1678.
-
(1994)
Bioorg. Med. Chem. Lett.
, vol.4
, pp. 1673-1678
-
-
Smith, C.W.1
Chakrabarti, J.K.2
Williamson, W.R.N.3
-
9
-
-
0035282632
-
-
(a) van Muijlwijk-Koezen, J. E.; Timmerman, H.; Vollinga, R. C.; Frijtag von Drabbe Kunzel, J.; de Groote, M.; Visser, S.; Ijzerman, A. P. J. Med. Chem. 2001, 44, 749-762.
-
(2001)
J. Med. Chem.
, vol.44
, pp. 749-762
-
-
Van Muijlwijk-Koezen, J.E.1
Timmerman, H.2
Vollinga, R.C.3
Frijtag Von Drabbe Kunzel, J.4
De Groote, M.5
Visser, S.6
Ijzerman, A.P.7
-
10
-
-
1642499664
-
-
(b) van den Nieuwendijk, A. M.; Pietra, D.; Heitman, L.; Göblyös, A.; Ijzerman, A. P. J. Med. Chem. 2004, 47, 663-672.
-
(2004)
J. Med. Chem.
, vol.47
, pp. 663-672
-
-
Van Den Nieuwendijk, A.M.1
Pietra, D.2
Heitman, L.3
Göblyös, A.4
Ijzerman, A.P.5
-
11
-
-
13944279479
-
-
(c) Göblyös, A.; de Vries, H.; Brussee, J.; Ijzerman, A. P. J. Med. Chem. 2005, 48, 1145-1151.
-
(2005)
J. Med. Chem.
, vol.48
, pp. 1145-1151
-
-
Göblyös, A.1
De Vries, H.2
Brussee, J.3
Ijzerman, A.P.4
-
12
-
-
0017907626
-
-
Antonio, Y.; Camargo, C.; Galeazzi, E.; Iriarte, J.; Guzman, M.; Muchowski, J. M.; Gerrity, K.; Liu, F.; Miller, L. M.; Strosberg, A. M. J. Med. Chem. 1978, 21, 123-126.
-
(1978)
J. Med. Chem.
, vol.21
, pp. 123-126
-
-
Antonio, Y.1
Camargo, C.2
Galeazzi, E.3
Iriarte, J.4
Guzman, M.5
Muchowski, J.M.6
Gerrity, K.7
Liu, F.8
Miller, L.M.9
Strosberg, A.M.10
-
13
-
-
0025328674
-
-
MacLeod, A. M.; Baker, R.; Freedman, S. B.; Patel, S.; Merchant, K. J.; Ros, M.; Saunders J. J. Med. Chem. 1990, 33, 2052-2059.
-
(1990)
J. Med. Chem.
, vol.33
, pp. 2052-2059
-
-
MacLeod, A.M.1
Baker, R.2
Freedman, S.B.3
Patel, S.4
Merchant, K.J.5
Ros, M.6
Saunders, J.7
-
14
-
-
0037171775
-
-
Collins, I.; Moyes, C.; Davey, W. B.; Rowley, M.; Bromidge, F. A.; Quirk, K.; Atack, J. R.; McKernan, R. M.; Thompson, S. A.; Wafford, K.; Dawson, G. R.; Pike, A.; Sohal, B.; Tsou, N. N.; Ball, R. G.; Castro, J. L. J. Med. Chem. 2002, 45, 1887-1900.
-
(2002)
J. Med. Chem.
, vol.45
, pp. 1887-1900
-
-
Collins, I.1
Moyes, C.2
Davey, W.B.3
Rowley, M.4
Bromidge, F.A.5
Quirk, K.6
Atack, J.R.7
McKernan, R.M.8
Thompson, S.A.9
Wafford, K.10
Dawson, G.R.11
Pike, A.12
Sohal, B.13
Tsou, N.N.14
Ball, R.G.15
Castro, J.L.16
-
15
-
-
77956780168
-
-
Bristol, J. A., Ed.; Academic Press: London, Chapter 34
-
Cheng, X.-M. Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press: London, 1996; Vol. 31, Chapter 34, pp 337-355; in particular p 339.
-
(1996)
Annual Reports in Medicinal Chemistry
, vol.31
, pp. 337-355
-
-
Cheng, X.-M.1
-
16
-
-
0036260967
-
-
(a) For recent reviews on cysteine proteases, see the following: Leung-Toung, R.; Li, W.; Tam, T. F.; Karimian, K. Curr. Med. Chem. 2002, 9, 979-1002.
-
(2002)
Curr. Med. Chem.
, vol.9
, pp. 979-1002
-
-
Leung-Toung, R.1
Li, W.2
Tam, T.F.3
Karimian, K.4
-
17
-
-
0036882396
-
-
(b) Powers, J. C.; Asgian, J. L.; Ekici, Ö. D.; James, K. L. Chem. Rev. 2002, 12, 4639-4750.
-
(2002)
Chem. Rev.
, vol.12
, pp. 4639-4750
-
-
Powers, J.C.1
Asgian, J.L.2
Ekici, Ö.D.3
James, K.L.4
-
19
-
-
0034618635
-
-
(d) Talanian, R. V.; Brady, K. D.; Cryns, V. L. J. Med. Chem. 2000, 43, 3351-3371.
-
(2000)
J. Med. Chem.
, vol.43
, pp. 3351-3371
-
-
Talanian, R.V.1
Brady, K.D.2
Cryns, V.L.3
-
20
-
-
0036259879
-
-
For a review on inhibitors targeting the cysteine residues of biomolecules, see the following: Scozzafava, A.; Casini, A.; Supuran, C. T. Curr. Med. Chem. 2002, 9, 1167-1185.
-
(2002)
Curr. Med. Chem.
, vol.9
, pp. 1167-1185
-
-
Scozzafava, A.1
Casini, A.2
Supuran, C.T.3
-
21
-
-
16344378692
-
-
PENCE AGM 2000 Meeting, Montebello, Quebec, Canada, June 24-26, 2000; PENCE, Inc.: Edmonton
-
Bryson, S.; Pai, E. F.; Desilets, D.; Li W.; Tam T.; Karimian K. Evidence for the formation of a disulfide bond between cysteine proteases and 1,2,4-thiadiazoles; PENCE AGM 2000 Meeting, Montebello, Quebec, Canada, June 24-26, 2000; PENCE, Inc.: Edmonton, 2000.
-
(2000)
Evidence for the Formation of a Disulfide Bond between Cysteine Proteases and 1,2,4-thiadiazoles
-
-
Bryson, S.1
Pai, E.F.2
Desilets, D.3
Li, W.4
Tam, T.5
Karimian, K.6
-
23
-
-
85010181453
-
-
(b) Hagiwara, K.; Hashimoto, S.; Shimoda, S. J. Pestic. Sci. 1992, 17, 251-259.
-
(1992)
J. Pestic. Sci.
, vol.17
, pp. 251-259
-
-
Hagiwara, K.1
Hashimoto, S.2
Shimoda, S.3
-
25
-
-
0344851547
-
-
(a) Leung-Toung, R.; Wodzinska, J.; Li, W.; Lowrie, J.; Kukreja, R.; Desilets, D.; Karimian, K.; Tam, T. F. Bioorg. Med. Chem. 2003, 11, 5529-5537.
-
(2003)
Bioorg. Med. Chem.
, vol.11
, pp. 5529-5537
-
-
Leung-Toung, R.1
Wodzinska, J.2
Li, W.3
Lowrie, J.4
Kukreja, R.5
Desilets, D.6
Karimian, K.7
Tam, T.F.8
-
26
-
-
33544458305
-
-
W00190095, 2001
-
(b) Karimian, K.; Tam, T. F.; Leung-Toung, R. C. S. H.; Li, W.; Bryson, S.; Wodzinska, J. M. W00190095, 2001.
-
-
-
Karimian, K.1
Tam, T.F.2
Leung-Toung, R.C.S.H.3
Li, W.4
Bryson, S.5
Wodzinska, J.M.6
-
27
-
-
0035656107
-
-
Marrano, C.; de Macedo, P.; Gagnon, P.; Lapierre, D.; Gravel, C.; Keillor, J. W. Bioorg. Med. Chem. 2001, 9, 3231-3241.
-
(2001)
Bioorg. Med. Chem.
, vol.9
, pp. 3231-3241
-
-
Marrano, C.1
De Macedo, P.2
Gagnon, P.3
Lapierre, D.4
Gravel, C.5
Keillor, J.W.6
-
28
-
-
17144386944
-
-
(a) Leung-Toung, R.; Tam, T. F.; Wodzinska, M. J.; Zhao, Y.; Lowrie, J.; Simpson, D. C.; Karimian, K.; Spino, M. J. Med. Chem. 2005, 48, 2266-2269.
-
(2005)
J. Med. Chem.
, vol.48
, pp. 2266-2269
-
-
Leung-Toung, R.1
Tam, T.F.2
Wodzinska, M.J.3
Zhao, Y.4
Lowrie, J.5
Simpson, D.C.6
Karimian, K.7
Spino, M.8
-
29
-
-
33544466576
-
-
US patent application 20030225007A1, 2003
-
(b) Tam, T. F.; Karimian, K.; Leung-Toung, R. C. S. H.; Zhao, Y.; Wodzinska, J. M.; Li, W.; Lowrie, J. N. US patent application 20030225007A1, 2003.
-
-
-
Tam, T.F.1
Karimian, K.2
Leung-Toung, R.C.S.H.3
Zhao, Y.4
Wodzinska, J.M.5
Li, W.6
Lowrie, J.N.7
-
30
-
-
16344390004
-
-
(a) Tam, F. T.; Leung-Toung, R.; Li, W.; Spino, M.; Karimian, K. Mini-Rev. Med. Chem. 2005, 5, 367-379.
-
(2005)
Mini-Rev. Med. Chem.
, vol.5
, pp. 367-379
-
-
Tam, F.T.1
Leung-Toung, R.2
Li, W.3
Spino, M.4
Karimian, K.5
-
31
-
-
0009088679
-
-
(b) Tam, T.; Li, W.; Leung-Toung, R.; Karimian, K. IDrugs 2000, 3, 1064-1074.
-
(2000)
IDrugs
, vol.3
, pp. 1064-1074
-
-
Tam, T.1
Li, W.2
Leung-Toung, R.3
Karimian, K.4
-
32
-
-
33544467577
-
-
US patent 5,677,302, 1997
-
(c) Karimian, K.; Tam, T. F.; Desilets, D.; Lee, S.; Cappelletto, T.; Li, W. US patent 5,677,302, 1997.
-
-
-
Karimian, K.1
Tam, T.F.2
Desilets, D.3
Lee, S.4
Cappelletto, T.5
Li, W.6
-
33
-
-
37049094493
-
-
Haugwitz, R. D.; Toeplitz, B.; Gougoudas, J. Z. J. Chem. Soc., Chem. Commun. 1977, 736-737.
-
(1977)
J. Chem. Soc., Chem. Commun.
, pp. 736-737
-
-
Haugwitz, R.D.1
Toeplitz, B.2
Gougoudas, J.Z.3
-
37
-
-
0010207748
-
-
Pentimalli, L.; Milani, G.; Biavati, F. Gazz. Chim. Ital. 1977, 107, 1-5.
-
(1977)
Gazz. Chim. Ital.
, vol.107
, pp. 1-5
-
-
Pentimalli, L.1
Milani, G.2
Biavati, F.3
-
38
-
-
0037472834
-
-
NAr substitution in heterocycles, see the following: (a) Chauvière, G. Bouteille, B.; Enanga, B.; de Albuquerque, C.; Croft, S. L.; Dumas, M.; Périé, J. J. Med. Chem. 2003, 46, 427-440.
-
(2003)
J. Med. Chem.
, vol.46
, pp. 427-440
-
-
Chauvière, G.1
Bouteille, B.2
Enanga, B.3
De Albuquerque, C.4
Croft, S.L.5
Dumas, M.6
Périé, J.7
-
39
-
-
0033535606
-
-
(b) Song, Y.; Connor, D. T.; Sercel, A. D.; Sorenson, R. J.; Doubleday: R.; Unangst, P. C.; Roth, B. D.; Beylin, V. G.; Gilbertsen, R. B.; Chan, K.; Schrier, D. J.; Guglietta, A.; Bornemeier, D. A.; Dyer, R. D. J. Med. Chem. 1999, 42, 1161-1169.
-
(1999)
J. Med. Chem.
, vol.42
, pp. 1161-1169
-
-
Song, Y.1
Connor, D.T.2
Sercel, A.D.3
Sorenson, R.J.4
Doubleday, R.5
Unangst, P.C.6
Roth, B.D.7
Beylin, V.G.8
Gilbertsen, R.B.9
Chan, K.10
Schrier, D.J.11
Guglietta, A.12
Bornemeier, D.A.13
Dyer, R.D.14
-
40
-
-
1242307319
-
-
(c) Zhang, Z.; Yin, Z.; Kadow, J. F.; Meanwell, N. A.; Wang, T. J. Org. Chem. 2004, 69, 1360-1363.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 1360-1363
-
-
Zhang, Z.1
Yin, Z.2
Kadow, J.F.3
Meanwell, N.A.4
Wang, T.5
-
41
-
-
0032785521
-
-
(d) Guillier, F.; Roussel, P.; Moser, H.; Kane, P.; Bradley, M. Chem. Eur. J. 1999, 5, 3450-3458.
-
(1999)
Chem. Eur. J.
, vol.5
, pp. 3450-3458
-
-
Guillier, F.1
Roussel, P.2
Moser, H.3
Kane, P.4
Bradley, M.5
-
42
-
-
4444383383
-
-
(e) Liu, J.; Janeba, Z.; Robins, M. J. Org. Lett. 2004, 6, 2917-2919.
-
(2004)
Org. Lett.
, vol.6
, pp. 2917-2919
-
-
Liu, J.1
Janeba, Z.2
Robins, M.J.3
-
43
-
-
33544469101
-
-
note
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Other isocyanates (methyl, ethyl, propyl) work equally well. However, we settled for n-butyl isocyanate because of cost and safety (higher bp) considerations and commercial availability in kilogram quantity.
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-
-
-
44
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33544473735
-
-
Noland, W. E., Ed; John Wiley & Sons, Inc.: Toronto; Collect. Vol.
-
For a preparative procedure for p-TsCN, see the following, Vrijland, M. S. A. In Organic Syntheses; Noland, W. E., Ed; John Wiley & Sons, Inc.: Toronto, 1988; Collect. Vol. VI, pp 727-730.
-
(1988)
Organic Syntheses
, vol.6
, pp. 727-730
-
-
Vrijland, M.S.A.1
-
45
-
-
33544459165
-
-
note
-
We do not have a reasonable explanation for this observation. However, we also noted that 1,3-, 1,4-, and 1,6-alkyldiamines are available reasonably cheaply in kg's quantities from commercial suppliers, but 1,5-diaminopentane is supplied in small quantities (25 g bottle) and is relatively much more expensive.
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46
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33544461759
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note
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+) and that of N2 was 10.72 (NH).
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-
48
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33544461469
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note
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Based on the experimental design (monitoring of 2-mercaptobenzimidazole), we cannot preclude the formation of an imine type intermediate like 28a or 28b in the case of 7f. However, in a different system and different conditions, the intermediates shown below were isolated (see ref 18c): (Diagram presented)
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-
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49
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33544457890
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note
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A major part of this work has been the subject of US patent 5,677,302, 1997 (ref 17b) and US patent application 20030225007A1, 2003 (ref 18c).
-
-
-
-
50
-
-
0002714675
-
-
Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 2923-2925
-
-
Still, W.C.1
Kahn, M.2
Mitra, A.3
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