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Literature summary for 3.4.24.82 extracted from

  • Noe, M.C.; Natarajan, V.; Snow, S.L.; Mitchell, P.G.; Lopresti-Morrow, L.; Reeves, L.M.; Yocum, S.A.; Carty, T.J.; Barberia, J.A.; Sweeney, F.J.; Liras, J.L.; Vaughn, M.; Hardink, J.R.; Hawkins, J.M.; Tokar, C.
    Discovery of 3,3-dimethyl-5-hydroxypipecolic hydroxamate-based inhibitors of aggrecanase and MMP-13 (2005), Bioorg. Med. Chem. Lett., 15, 2808-2811.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(2R,5R)-1-([4-[(5-fluoro-2-methylbenzyl)oxy]phenyl]sulfonyl)-N,5-dihydroxypiperidine-2-carboxamide IC50: 145 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(2,4-dichlorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 2.1 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(2-bromobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 16 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(2-chloro-4-fluorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 0.5 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(2-ethylbenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 67 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(2-isopropylbenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide 78% inhibition of enzyme activity at 500 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(2-methyl-3-fluorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 3.9 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(2-methyl-4-fluorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 2.7 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(2-methyl-5-fluorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 40 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(2-methylbenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 38 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(3-bromobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide 57% inhibition of enzyme activity at 500 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(3-methylbenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 100 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(3-methylisothiazol-4-yl)methoxy]phenyl]sulfonyl)piperidine-2-carboxamide 76% inhibition of enzyme activity at 500 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(4-bromobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide IC50: 100 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(4-methylbenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide 19% inhibition of enzyme activity at 500 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-([4-[(4-methylisothiazol-5-yl)methoxy]phenyl]sulfonyl)piperidine-2-carboxamide 55% inhibition of enzyme activity at 500 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-[[4-(2-chloropyridin-4-ylmethoxy)phenyl]sulfonyl]piperidine-2-carboxamide IC50: 18 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-[[4-(2-methylpyridin-3-ylmethoxy)phenyl]sulfonyl]piperidine-2-carboxamide IC50: 91 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-[[4-(isoquinolin-4-ylmethoxy)phenyl]sulfonyl]piperidine-2-carboxamide IC50: 100 nM Homo sapiens
(2R,5R)-N,5-dihydroxy-1-[[4-(quinolin-4-ylmethoxy)phenyl]sulfonyl]piperidine-2-carboxamide IC50: 15 nM Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
aggrecan + H2O
-
Homo sapiens fragments of aggrecan
-
?

Synonyms

Synonyms Comment Organism
aggrecanase
-
Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000005
-
IC50: 0.5 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(2-chloro-4-fluorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.0000021
-
IC50: 2.1 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(2,4-dichlorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.0000027
-
IC50: 2.7 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(2-methyl-4-fluorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.0000039
-
IC50: 3.9 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(2-methyl-3-fluorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.000015
-
IC50: 15 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-[[4-(quinolin-4-ylmethoxy)phenyl]sulfonyl]piperidine-2-carboxamide
0.000016
-
IC50: 16 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(2-bromobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.000018
-
IC50: 18 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-[[4-(2-chloropyridin-4-ylmethoxy)phenyl]sulfonyl]piperidine-2-carboxamide
0.000038
-
IC50: 38 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(2-methylbenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.00004
-
IC50: 40 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(2-methyl-5-fluorobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.000067
-
IC50: 67 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(2-ethylbenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.000091
-
IC50: 91 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-[[4-(2-methylpyridin-3-ylmethoxy)phenyl]sulfonyl]piperidine-2-carboxamide
0.0001
-
IC50: 100 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(3-methylbenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.0001
-
IC50: 100 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-([4-[(4-bromobenzyl)oxy]phenyl]sulfonyl)piperidine-2-carboxamide
0.0001
-
IC50: 100 nM Homo sapiens (2R,5R)-N,5-dihydroxy-1-[[4-(isoquinolin-4-ylmethoxy)phenyl]sulfonyl]piperidine-2-carboxamide
0.000145
-
IC50: 145 nM Homo sapiens (2R,5R)-1-([4-[(5-fluoro-2-methylbenzyl)oxy]phenyl]sulfonyl)-N,5-dihydroxypiperidine-2-carboxamide