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Literature summary for 3.4.24.B4 extracted from

  • Li, W.; Hu, Y.; Li, J.; Thomason, J.R.; DeVincentis, D.; Du, X.; Wu, J.; Hotchandani, R.; Rush, T.S.; Skotnicki, J.S.; Tam, S.; Chockalingam, P.S.; Morris, E.A.; Levin, J.I.
    3,4-Disubstituted benzofuran P1 MMP-13 inhibitors: optimization of selectivity and reduction of protein binding (2009), Bioorg. Med. Chem. Lett., 19, 4546-4550.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
additional information development and optimization of potent 3,4-disubstituted benzofuran P1' MMP-13 inhibitors, overview Homo sapiens
N-([4'-[([3-methyl-4-[(methylsulfonyl)amino]-1-benzofuran-2-yl]carbonyl)amino]biphenyl-4-yl]sulfonyl)-L-threonine
-
Homo sapiens
N-([4'-[([3-methyl-4-[(methylsulfonyl)amino]-1-benzofuran-2-yl]carbonyl)amino]biphenyl-4-yl]sulfonyl)-L-valine
-
Homo sapiens
N-([4'-[([4-[(1-methoxy-2-methyl-1-oxopropan-2-yl)oxy]-3-methyl-1-benzofuran-2-yl]carbonyl)amino]biphenyl-4-yl]sulfonyl)-L-valine
-
Homo sapiens
N-[(4'-[[(3,4-dimethyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4'-[[(3-methyl-4-phenoxy-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4'-[[(3-methyl-4-phenyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4'-[[(4-amino-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4'-[[(4-cyano-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4'-[[(4-ethenyl-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4'-[[(4-ethoxy-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4'-[[(4-ethyl-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4'-[[(4-hydroxy-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4'-[[(4-methoxy-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
-
Homo sapiens
N-[(4-[5-[([3-methyl-4-[(methylsulfonyl)amino]-1-benzofuran-2-yl]carbonyl)amino]pyridin-2-yl]phenyl)sulfonyl]-L-threonine replacing a backbone benzene with a pyridine and valine with threonine results in greatly reduced plasma protein binding of the compound Homo sapiens
N-[(4-[5-[([3-methyl-4-[(methylsulfonyl)amino]-1-benzofuran-2-yl]carbonyl)amino]pyridin-2-yl]phenyl)sulfonyl]-L-valine
-
Homo sapiens
N-[[4'-([[3-methyl-4-(methylamino)-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
-
Homo sapiens
N-[[4'-([[3-methyl-4-(morpholin-4-yl)-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
-
Homo sapiens
N-[[4'-([[3-methyl-4-(prop-1-yn-1-yl)-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
-
Homo sapiens
N-[[4'-([[4-(3-hydroxypropyl)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
-
Homo sapiens
N-[[4'-([[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
-
Homo sapiens
N-[[4'-([[4-(acetylamino)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
-
Homo sapiens
N-[[4'-([[4-(dimethylamino)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
-
Homo sapiens
N-[[4'-([[4-(furan-2-yl)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
-
Homo sapiens
N-[[4-(5-[[(4-cyano-3-methyl-1-benzofuran-2-yl)carbonyl]amino]pyridin-2-yl)phenyl]sulfonyl]-L-valine
-
Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
extracellular matrix
-
Homo sapiens 31012
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
type II collagen + H2O Homo sapiens
-
?
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
cartilage osteoarthritic Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
type II collagen + H2O
-
Homo sapiens ?
-
?

Synonyms

Synonyms Comment Organism
collagenase-3
-
Homo sapiens
MMP-13
-
Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000023
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(4-ethyl-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.0000037
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(4-cyano-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.0000043
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(4-amino-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.0000048
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(3,4-dimethyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.0000061
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(4-ethenyl-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.0000061
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(4-hydroxy-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.0000064
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[[4'-([[4-(furan-2-yl)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
0.0000065
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[[4'-([[4-(dimethylamino)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
0.0000071
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[[4'-([[4-(3-hydroxypropyl)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
0.0000074
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(4-ethoxy-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.000008
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[[4'-([[3-methyl-4-(methylamino)-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
0.0000095
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[[4'-([[3-methyl-4-(prop-1-yn-1-yl)-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
0.0000095
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(4-methoxy-3-methyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.000011
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[[4'-([[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
0.000013
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-([4'-[([3-methyl-4-[(methylsulfonyl)amino]-1-benzofuran-2-yl]carbonyl)amino]biphenyl-4-yl]sulfonyl)-L-valine
0.000013
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-([4'-[([3-methyl-4-[(methylsulfonyl)amino]-1-benzofuran-2-yl]carbonyl)amino]biphenyl-4-yl]sulfonyl)-L-threonine
0.000014
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[[4-(5-[[(4-cyano-3-methyl-1-benzofuran-2-yl)carbonyl]amino]pyridin-2-yl)phenyl]sulfonyl]-L-valine
0.000015
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(3-methyl-4-phenyl-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.000019
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4'-[[(3-methyl-4-phenoxy-1-benzofuran-2-yl)carbonyl]amino]biphenyl-4-yl)sulfonyl]-L-valine
0.000025
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[[4'-([[4-(acetylamino)-3-methyl-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
0.000025
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-([4'-[([4-[(1-methoxy-2-methyl-1-oxopropan-2-yl)oxy]-3-methyl-1-benzofuran-2-yl]carbonyl)amino]biphenyl-4-yl]sulfonyl)-L-valine
0.000032
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[[4'-([[3-methyl-4-(morpholin-4-yl)-1-benzofuran-2-yl]carbonyl]amino)biphenyl-4-yl]sulfonyl]-L-valine
0.000035
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4-[5-[([3-methyl-4-[(methylsulfonyl)amino]-1-benzofuran-2-yl]carbonyl)amino]pyridin-2-yl]phenyl)sulfonyl]-L-threonine
0.00004
-
pH not specified in the publication, temperature not specified in the publication Homo sapiens N-[(4-[5-[([3-methyl-4-[(methylsulfonyl)amino]-1-benzofuran-2-yl]carbonyl)amino]pyridin-2-yl]phenyl)sulfonyl]-L-valine