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Literature summary extracted from

  • Doiron, J.; Boudreau, L.H.; Picot, N.; Villebonet, B.; Surette, M.E.; Touaibia, M.
    Synthesis and 5-lipoxygenase inhibitory activity of new cinnamoyl and caffeoyl clusters (2009), Bioorg. Med. Chem. Lett., 19, 1118-1121.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.13.11.34 drug development caffeoyl clusters are good lead compounds in the design and synthesis of more potent 5-lipoxygenase inhibitors Homo sapiens

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.13.11.34 HEK 293 cells stably transfected with a pcDNA3.1 vector expressing 5-lipoxygenase Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.34 (2E,2'E)-(1,1'-(2,2-bis((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate) potent inhibition by 92% Homo sapiens
1.13.11.34 (2E,2'E)-(1,1'-(2,2-bis((4-(cinnamoyloxymethyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-phenylacrylate) shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety Homo sapiens
1.13.11.34 (2E,2'E)-(1,1'-(2-((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate) potent inhibition by 91% Homo sapiens
1.13.11.34 (2E,2'E)-(1,1'-(2-((4-(cinnamoyloxymethyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-phenylacrylate) shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety Homo sapiens
1.13.11.34 (2E,2'E)-2,2'-(4,4'-(2,2-bis(((1-(2-((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)propane-1,3-diyl)bis(oxy)bis(methylene)bis(1H-1,2,3-triazole-4,1-diyl))bis(ethane-2,1-diyl) bis(3-(3,4-dihydroxyphenyl)acrylate)
-
 Homo sapiens
1.13.11.34 (2E,2'E)-2,2'-(4,4'-(2,2-bis(((1-(2-(cinnamoyloxy)ethyl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)propane-1,3-diyl)bis(oxy)bis(methylene)bis(1H-1,2,3-triazole-4,1-diyl))bis(ethane-2,1-diyl) bis(3-phenylacrylate) shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety Homo sapiens
1.13.11.34 2-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
 Homo sapiens
1.13.11.34 caffeic acid
-
 Homo sapiens
1.13.11.34 [1-(2-[[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
 Homo sapiens
1.13.11.34 [1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
-
 Homo sapiens
1.13.11.34 [1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-phenylprop-2-enoate shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety Homo sapiens
1.13.11.34 [1-(3-[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2-[(3-[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2,2-bis[[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propoxy)methyl]-2-[[4-([[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate incorporation of additional caffeoyl units in hexamer results in less potent inhibition Homo sapiens
1.13.11.34 [1-(3-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2-[(3-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]-2,2-bis[[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propoxy)methyl]-2-[[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]methyl]propyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-phenylprop-2-enoate shows less inhibitory activity than the corresponding clusters bearing the caffeic acid moiety Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
1.13.11.34 Homo sapiens
-
-
-

Synonyms

EC Number Synonyms Comment Organism
1.13.11.34 5-lipoxygenase
-
 Homo sapiens
1.13.11.34 5-LO
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.13.11.34 0.00066
-
-
 Homo sapiens (2E,2'E)-(1,1'-(2,2-bis((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
1.13.11.34 0.00068
-
-
 Homo sapiens 2-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
1.13.11.34 0.00068
-
 per number of caffeic acid moieties Homo sapiens 2-[4-([[(2E)-3-phenylprop-2-enoyl]oxy]methyl)-1H-1,2,3-triazol-1-yl]ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
1.13.11.34 0.00074
-
-
 Homo sapiens [1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
1.13.11.34 0.00079
-
-
 Homo sapiens (2E,2'E)-(1,1'-(2-((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
1.13.11.34 0.00148
-
 per number of caffeic acid moieties Homo sapiens [1-(2-[[(2E)-3-phenylprop-2-enoyl]oxy]ethyl)-1H-1,2,3-triazol-4-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
1.13.11.34 0.00237
-
 per number of caffeic acid moieties Homo sapiens (2E,2'E)-(1,1'-(2-((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-(hydroxymethyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
1.13.11.34 0.00246
-
 per number of caffeic acid moieties Homo sapiens (2E,2'E)-(1,1'-(2,2-bis((4-(((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)propane-1,3-diyl)bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene) bis(3-(3,4-dihydroxyphenyl)acrylate)
1.13.11.34 0.025
-
-
 Homo sapiens caffeic acid