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Literature summary for 4.2.1.1 extracted from

  • Maresca, A.; Scozzafava, A.; Supuran, C.T.
    7,8-disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range (2010), Bioorg. Med. Chem. Lett., 20, 7255-7258.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
2-adamantylethyl 7-methoxy-2-oxo-2H-chromene-8-carboxylate
-
Homo sapiens
6-(1-hydroxy-3-methylbutyl)-7-methoxy-2H-chromen-2-one
-
Homo sapiens
6-acetyl-7-(benzyloxy)-2H-chromen-2-one
-
Homo sapiens
6-acetyl-7-adamantylethoxy-2H-chromen-2-one
-
Homo sapiens
6-acetyl-7-butoxy-2H-chromen-2-one
-
Homo sapiens
6-acetyl-7-ethoxy-2H-chromen-2-one
-
Homo sapiens
6-acetyl-7-hydroxy-2H-chromen-2-one
-
Homo sapiens
6-acetyl-7-methoxy-2H-chromen-2-one
-
Homo sapiens
6-acetyl-7-propoxy-2H-chromen-2-one
-
Homo sapiens
7-ethoxy-8-propanoyl-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-6-propanoyl-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-8-propanoyl-2H-chromen-2-one
-
Homo sapiens
7-methoxy-8-propanoyl-2H-chromen-2-one
-
Homo sapiens
8-acetyl-7-(benzyloxy)-2H-chromen-2-one
-
Homo sapiens
8-acetyl-7-butoxy-2H-chromen-2-one
-
Homo sapiens
8-acetyl-7-ethoxy-2H-chromen-2-one
-
Homo sapiens
8-acetyl-7-hydroxy-2H-chromen-2-one
-
Homo sapiens
8-acetyl-7-methoxy-2H-chromen-2-one
-
Homo sapiens
8-acetyl-7-propoxy-2H-chromen-2-one
-
Homo sapiens
8-propanoyl-7-propoxy-2H-chromen-2-one
-
Homo sapiens
coumarin
-
Homo sapiens
additional information synthesis of two series of disubstituted coumarins incorporating ether and acetyl/propionyl moieties in positions 6,7 and 7,8 of the heterocyclic ring. The compounds are very weak or ineffective as inhibitors of the housekeeping, offtarget isozymes CA I and CA II. The 6,7-disubstituted series show ineffective inhibition also for the transmembrane tumor-associated isoforms CA IX and XII, whereas the corresponding isomeric 7,8-disubstituted coumarins show nanomolar/subnanomolar inhibition of CA IX/XII, overview. No inhibition by 12 and 13 Homo sapiens
umbelliferone
-
Homo sapiens

Metals/Ions

Metals/Ions Comment Organism Structure
Zn2+ required Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
isozymes hCA I, hCA II, hCA IX, and hCA XII
-

Synonyms

Synonyms Comment Organism
carbonic anhydrase
-
Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00000098
-
8-acetyl-7-propoxy-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.000001
-
8-acetyl-7-ethoxy-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000088
-
8-acetyl-7-butoxy-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000224
-
8-acetyl-7-(benzyloxy)-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000263
-
7-methoxy-8-propanoyl-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000315
-
2-adamantylethyl 7-methoxy-2-oxo-2H-chromene-8-carboxylate inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000332
-
7-ethoxy-8-propanoyl-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000378
-
7-methoxy-8-propanoyl-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000384
-
8-propanoyl-7-propoxy-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000467
-
7-ethoxy-8-propanoyl-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000486
-
6-(1-hydroxy-3-methylbutyl)-7-methoxy-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000502
-
8-propanoyl-7-propoxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000545
-
6-(1-hydroxy-3-methylbutyl)-7-methoxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000567
-
8-acetyl-7-propoxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000582
-
7-hydroxy-8-propanoyl-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.000059
-
6-(1-hydroxy-3-methylbutyl)-7-methoxy-2H-chromen-2-one inhibition of isozyme hCA II, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000609
-
8-acetyl-7-methoxy-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000612
-
8-acetyl-7-butoxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000617
-
7-hydroxy-8-propanoyl-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000619
-
8-acetyl-7-hydroxy-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000639
-
2-adamantylethyl 7-methoxy-2-oxo-2H-chromene-8-carboxylate inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000708
-
8-acetyl-7-ethoxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000723
-
8-acetyl-7-(benzyloxy)-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.000073
-
8-acetyl-7-hydroxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.000078
-
6-(1-hydroxy-3-methylbutyl)-7-methoxy-2H-chromen-2-one inhibition of isozyme hCA I, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0000783
-
8-acetyl-7-methoxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0001
-
coumarin inhibition of isozyme hCA I, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0001
-
coumarin inhibition of isozyme hCA II, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.000482
-
umbelliferone inhibition of isozyme hCA II, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.000754
-
umbelliferone inhibition of isozyme hCA I, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0031
-
coumarin inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.00654
-
6-acetyl-7-methoxy-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0074
-
6-acetyl-7-ethoxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.00758
-
6-acetyl-7-propoxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0078
-
6-acetyl-7-methoxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.008015
-
7-hydroxy-6-propanoyl-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.00803
-
6-acetyl-7-hydroxy-2H-chromen-2-one inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0092
-
coumarin inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0584
-
umbelliferone inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.0777
-
6-acetyl-7-adamantylethoxy-2H-chromen-2-one inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication Homo sapiens
0.1
-
umbelliferone inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication Homo sapiens