-
1
-
-
34547272503
-
-
For recent reviews, see: a
-
For recent reviews, see: a) J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249-1262;
-
(2007)
Chem. Soc. Rev
, vol.36
, pp. 1249-1262
-
-
Moses, J.E.1
Moorhouse, A.D.2
-
4
-
-
35348874833
-
-
d) J. F. Lutz, Angew. Chem. 2007, 119, 1036-1043;
-
(2007)
Angew. Chem
, vol.119
, pp. 1036-1043
-
-
Lutz, J.F.1
-
5
-
-
34247237682
-
-
Angew. Chem. Int. Ed. 2007, 46, 1018-1025;
-
(2007)
Chem. Int. Ed
, vol.46
, pp. 1018-1025
-
-
Angew1
-
7
-
-
0348109450
-
-
In 1,4-substituted triazoles, the carbon atom at the 4-position and the C-H bond can act as an electrophilic site and a hydrogen-bond donor, respectively, whereas the pyridine-type lone pair of electrons on the nitrogen atom at the 3-position serves as a hydrogen-bond-acceptor element. The overall dipolar moment of the triazole system is larger than that of the amide bond, and its hydrogen-bond donor and acceptor properties are therefore more marked that those of an amide bond. The larger dipole moment may compensate for the increased distance between the substituents relative to the distance between substituents on a Z amide bond 3.9 versus 5.0 Å, 1d] Although this geometrical mismatch does not exist in 1,5-substituted derivatives, the degree to which they mimic an E amide bond is undermined somewhat by the poor electrophilicity of the pyrrole-like nitrogen atom relative to that of a carbonyl carbon atom. For a discussion, see, H. C. Kolb, K. B. Sharp
-
[1d] Although this geometrical mismatch does not exist in 1,5-substituted derivatives, the degree to which they mimic an E amide bond is undermined somewhat by the poor electrophilicity of the pyrrole-like nitrogen atom relative to that of a carbonyl carbon atom. For a discussion, see : H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 24, 1128-1137. (Chemical Equation Presented)
-
-
-
-
8
-
-
22144498399
-
-
A. Brik, J. Alexandratos, Y.-C. Lin, J. H. Elder, A. J. Olson, A. Wlodawer, D. S. Goodsell, C.-H. Wong, ChemBioChem 2005, 6, 1167-1169.
-
(2005)
ChemBioChem
, vol.6
, pp. 1167-1169
-
-
Brik, A.1
Alexandratos, J.2
Lin, Y.-C.3
Elder, J.H.4
Olson, A.J.5
Wlodawer, A.6
Goodsell, D.S.7
Wong, C.-H.8
-
9
-
-
33846916151
-
-
T. Lee, M. Cho, S. Y. Ko, H.-J. Youn, D. J. Baek, W.-J. Cho, C.-Y. Kang, S. Kim, J. Med. Chem. 2007, 50, 585-589;
-
(2007)
J. Med. Chem
, vol.50
, pp. 585-589
-
-
Lee, T.1
Cho, M.2
Ko, S.Y.3
Youn, H.-J.4
Baek, D.J.5
Cho, W.-J.6
Kang, C.-Y.7
Kim, S.8
-
10
-
-
34447515534
-
-
for a related study involving a cellular endpoint induction of apoptosis, see
-
for a related study involving a cellular endpoint (induction of apoptosis), see: S. Kim, M. Cho, T. Lee, S. Lee, H.-Y. Min, S. Kook, Bioorg. Med. Chem. Lett. 2007, 17, 4584-4587.
-
(2007)
Bioorg. Med. Chem. Lett
, vol.17
, pp. 4584-4587
-
-
Kim, S.1
Cho, M.2
Lee, T.3
Lee, S.4
Min, H.-Y.5
Kook, S.6
-
11
-
-
37349096869
-
-
For a recent review on the structure-activity relationships of capsaicinoids, see:, Eds, E. Fattorusso, O. Taglialatela-Scafati, Wiley-VCH, Weinheim
-
For a recent review on the structure-activity relationships of capsaicinoids, see: G. Appendino in Modern Alkaloids: Structure, Isolation, Synthesis and Biology (Eds.: E. Fattorusso, O. Taglialatela-Scafati), Wiley-VCH, Weinheim, 2007, pp. 75-112.
-
(2007)
Modern Alkaloids: Structure, Isolation, Synthesis and Biology
, pp. 75-112
-
-
Appendino, G.1
-
12
-
-
0027296078
-
-
C. S. J. Walpole, R. Wrigglesworth, S. Bevan, E. A. Campbell, A. Dray, I. F. James, K. J. Masdin, M. N. Perkins, J. Winter, J. Med. Chem. 1993, 36, 2373-2380.
-
(1993)
J. Med. Chem
, vol.36
, pp. 2373-2380
-
-
Walpole, C.S.J.1
Wrigglesworth, R.2
Bevan, S.3
Campbell, E.A.4
Dray, A.5
James, I.F.6
Masdin, K.J.7
Perkins, M.N.8
Winter, J.9
-
13
-
-
0030777012
-
-
M. J. Caterina, M. A. Schumacher, M. Tominaga, F. T. A. Rosen, J. D. Levine, D. Julius, Nature 1997, 389, 816-824.
-
(1997)
Nature
, vol.389
, pp. 816-824
-
-
Caterina, M.J.1
Schumacher, M.A.2
Tominaga, M.3
Rosen, F.T.A.4
Levine, J.D.5
Julius, D.6
-
14
-
-
19944430452
-
-
a) G. Appendino, L. De Petrocellis, M. Trevisani, A. Minassi, N. Daddario, A. Schiano Moriello, D. Mazzieri, A. Ligresti, B. Campi, G. Fontana. C. Pinna, P. Geppetti, V. Di Marzo, J. Pharmacol. Exp. Ther. 2004, 312, 561-570;
-
(2004)
J. Pharmacol. Exp. Ther
, vol.312
, pp. 561-570
-
-
Appendino, G.1
De Petrocellis, L.2
Trevisani, M.3
Minassi, A.4
Daddario, N.5
Schiano Moriello, A.6
Mazzieri, D.7
Ligresti, A.8
Campi, B.9
Fontana, G.10
Pinna, C.11
Geppetti, P.12
Di Marzo, V.13
-
15
-
-
30644474973
-
-
b) G. Appendino, M. G. Cascio, S. Bacchiega, A. Schiano Moriello, A. Minassi, A. Thomas, R. Ross, R. Pertwee, L. De Petrocellis, V. Di Marzo, FEBS Lett. 2006, 580, 568-574.
-
(2006)
FEBS Lett
, vol.580
, pp. 568-574
-
-
Appendino, G.1
Cascio, M.G.2
Bacchiega, S.3
Schiano Moriello, A.4
Minassi, A.5
Thomas, A.6
Ross, R.7
Pertwee, R.8
De Petrocellis, L.9
Di Marzo, V.10
-
16
-
-
0037348385
-
-
C. A. Reilly, W. J. Ehlardt, D. A. Jackson, P. Kulanthaivel, A. E. Mutlib, R. Espina, D. E. Moody, D. J. Crouch, G. S. Yost, Chem. Res. Toxicol. 2003, 16, 336-349.
-
(2003)
Chem. Res. Toxicol
, vol.16
, pp. 336-349
-
-
Reilly, C.A.1
Ehlardt, W.J.2
Jackson, D.A.3
Kulanthaivel, P.4
Mutlib, A.E.5
Espina, R.6
Moody, D.E.7
Crouch, D.J.8
Yost, G.S.9
-
17
-
-
0029619205
-
-
[5]
-
[5]
-
-
-
-
18
-
-
22244474357
-
-
G. Appendino, N. Daddario, A. Minassi, A. Schiano Morello, L. De Petrocellis, V. Di Marzo, J. Med. Chem. 2005, 48, 4663-4669.
-
(2005)
J. Med. Chem
, vol.48
, pp. 4663-4669
-
-
Appendino, G.1
Daddario, N.2
Minassi, A.3
Schiano Morello, A.4
De Petrocellis, L.5
Di Marzo, V.6
-
19
-
-
28044465418
-
-
L. Zhang, X. Chen, P. Xue, H. H. Y. Sun, I. D. Williams, K. B. Sharpless. V. V. Fokin, G. Jia, J. Am. Chem. Soc. 2005, 127, 15998-15999.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 15998-15999
-
-
Zhang, L.1
Chen, X.2
Xue, P.3
Sun, H.H.Y.4
Williams, I.D.5
Sharpless, K.B.6
Fokin, V.V.7
Jia, G.8
-
20
-
-
2442642767
-
-
TRP channels are sensitive to metal inhibition, and the dye ruthenium red is a general inhibitor of this type of channel (A. Szallasi, G. Appendino, J. Med. Chem. 2004, 47, 2717-2723).
-
TRP channels are sensitive to metal inhibition, and the dye ruthenium red is a general inhibitor of this type of channel (A. Szallasi, G. Appendino, J. Med. Chem. 2004, 47, 2717-2723).
-
-
-
-
21
-
-
33846551684
-
-
In previous studies involving metathesis reactions, we observed that capsaicinoids strongly retain metal impurities.[19] The final products were therefore purified carefully by crystallization and preparative HPLC, and examined for inorganic contaminants by atomic spectroscopy. A copper or ruthenium content of less than 3 ppm was found. Furthermore. 4a showed the same activity against the three endpoints investigated (TRPV1, CB1, and CB2) regardless of whether it had been obtained under Cu I or RuII catalysis. Despite the presence of the same potential copper impurity, iodine-induced reversal of activity was observed, as expected, for 4b. Taken together, these observations make it unlikely that transition-metal contaminants have affected the bioactivity data. For recent examples of the mediation of the activity of proteins within the endocannabinoid system by spurious metal impurities, see: S. Vandevoorde, K. O. Jonsson, G. Labar
-
II catalysis. Despite the presence of the same potential copper impurity, iodine-induced reversal of activity was observed, as expected, for 4b. Taken together, these observations make it unlikely that transition-metal contaminants have affected the bioactivity data. For recent examples of the mediation of the activity of proteins within the endocannabinoid system by spurious metal impurities, see: S. Vandevoorde, K. O. Jonsson, G. Labar, E. Persson, D. M. Lambert, C. J. Fowler, Br. J. Pharmacol. 2007, 150, 186-191;
-
-
-
-
22
-
-
33845880380
-
-
J. K. Makara, M. Mor, D. Fegley, S. I. Szabó, S. Kathuria, G. Astarita, A. Duranti, A. Tontini, G. Tarzia, S. Rivara, T. T. Freund, D. Piomelli, Nat. Neurosci. 2007, 10, 134.
-
(2007)
Nat. Neurosci
, vol.10
, pp. 134
-
-
Makara, J.K.1
Mor, M.2
Fegley, D.3
Szabó, S.I.4
Kathuria, S.5
Astarita, G.6
Duranti, A.7
Tontini, A.8
Tarzia, G.9
Rivara, S.10
Freund, T.T.11
Piomelli, D.12
-
23
-
-
0033584439
-
-
1: D. Melck, T. Bisogno, L. De Petrocellis, H. Chuang, D. Julius, M. Bifulco, V. Di Marzo, Biochem. Biophys. Res. Commun, 1999, 262, 275-284.
-
1: D. Melck, T. Bisogno, L. De Petrocellis, H. Chuang, D. Julius, M. Bifulco, V. Di Marzo, Biochem. Biophys. Res. Commun, 1999, 262, 275-284.
-
-
-
-
24
-
-
34447575641
-
-
V. Di Marzo, T. Bisogno, L. De Petrocellis, Chem. Biol. 2007, 14, 741-756.
-
(2007)
Chem. Biol
, vol.14
, pp. 741-756
-
-
Di Marzo, V.1
Bisogno, T.2
De Petrocellis, L.3
-
25
-
-
31544472391
-
-
F. Pagliai, T. Pirali, E. Del Grosso, R. Di Brisco, G. C. Tron, G. Sorba, A. A. Genazzani, J. Med. Chem. 2006, 49, 467-470.
-
(2006)
J. Med. Chem
, vol.49
, pp. 467-470
-
-
Pagliai, F.1
Pirali, T.2
Del Grosso, E.3
Di Brisco, R.4
Tron, G.C.5
Sorba, G.6
Genazzani, A.A.7
-
26
-
-
0027436148
-
-
J. M. Janusz, B. L. Buckwalter, P. A. Young, T. R. LaHann, R. W. Farmer, G. B. Kasting, M. E. Loomans, G. A. Kerkaert, C. S. Maddin, E. F. Berman, R. L. Bohne, T. L. Cupps, J. R. Milstein, J. Med. Chem. 1993, 36, 2595-2604.
-
(1993)
J. Med. Chem
, vol.36
, pp. 2595-2604
-
-
Janusz, J.M.1
Buckwalter, B.L.2
Young, P.A.3
LaHann, T.R.4
Farmer, R.W.5
Kasting, G.B.6
Loomans, M.E.7
Kerkaert, G.A.8
Maddin, C.S.9
Berman, E.F.10
Bohne, R.L.11
Cupps, T.L.12
Milstein, J.R.13
-
27
-
-
33645103126
-
-
J. Lazar, D. C. Braun, A. Toth, Y. Wang, L. V. Pearce, V. A. Pavlyukovets, P. M. Blumberg, S. H. Garfield, S. Wincovitch, H. K. Choi, J. Lee, Mol. Pharmacol. 2006, 69, 1166-1173.
-
(2006)
Mol. Pharmacol
, vol.69
, pp. 1166-1173
-
-
Lazar, J.1
Braun, D.C.2
Toth, A.3
Wang, Y.4
Pearce, L.V.5
Pavlyukovets, V.A.6
Blumberg, P.M.7
Garfield, S.H.8
Wincovitch, S.9
Choi, H.K.10
Lee, J.11
-
28
-
-
0037103229
-
-
G. Appendino, A. Minassi, A. Schiano Moriello, L. DePetrocellis, V. Di Marzo, J. Med. Chem. 2002, 45, 3739-3745.
-
(2002)
J. Med. Chem
, vol.45
, pp. 3739-3745
-
-
Appendino, G.1
Minassi, A.2
Schiano Moriello, A.3
DePetrocellis, L.4
Di Marzo, V.5
-
29
-
-
33846638747
-
-
A similar observation was made for a series of phosphatidylcholine- derived bolaamphiphiles, whereby the presence of a 1,4-triazole moiety in the lipid linker was detrimental to vesicle formation: E. J. O'Neil, K. M. DiVittorio, B. D. Smith, Org. Lett. 2007, 9, 199-202.
-
A similar observation was made for a series of phosphatidylcholine- derived bolaamphiphiles, whereby the presence of a 1,4-triazole moiety in the lipid linker was detrimental to vesicle formation: E. J. O'Neil, K. M. DiVittorio, B. D. Smith, Org. Lett. 2007, 9, 199-202.
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-
-
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