Target Validation Information
TTD ID T64567
Target Name Carbonic anhydrase IX (CA-IX)
Type of Target
Clinical trial
Drug Potency against Target (2-bromophenyl)difluoromethanesulfonamide Drug Info Ki = 9280 nM [12]
(4-bromophenyl)difluoromethanesulfonamide Drug Info Ki = 7730 nM [12]
(4-sulfamoylphenylethylthioureido)fluorescein Drug Info Ki = 24 nM [20]
1,4-Dihydro-1-methyl-4-oxo-3-pyridinesulfonamide Drug Info Ki = 7.1 nM [32]
1,4-phenylene disulfamate Drug Info Ki = 61.6 nM [22]
1-(3,4-dichlorophenyl)-3-hydroxyurea Drug Info Ki = 540 nM [14]
1-acetamido-5-sulfonamidoindane Drug Info Ki = 193 nM [13]
1-Benzyl-1,4-dihydro-4-oxo-3-pyridinesulfonamide Drug Info Ki = 7.8 nM [32]
1-cyclohexylamido-5-sulfonamidoindane Drug Info Ki = 108 nM [13]
1-pentafluorophenylamido-5-sulfonamidoindane Drug Info Ki = 3.5 nM [13]
1-valproylamido-5-sulfonamidoindane Drug Info Ki = 37.5 nM [13]
2,2,2-Trifluoro-N-(4-sulfamoyl-phenyl)-acetamide Drug Info Ki = 112 nM [11]
2,2-Dimethyl-N-(4-sulfamoyl-phenyl)-propionamide Drug Info Ki = 136 nM [11]
2,4-Disulfamyltrifluoromethylaniline Drug Info Ki = 24 nM [23]
2-(4-chlorobenzyloxyamino)-N-hydroxyacetamide Drug Info Ki = 8800 nM [17]
2-(4-chlorobenzyloxyamino)-N-hydroxyhexanamide Drug Info Ki = 6900 nM [17]
2-(4-chlorobenzyloxyamino)-N-hydroxypropanamide Drug Info Ki = 9200 nM [17]
2-(benzyloxyamino)-N-hydroxy-3-methylpentanamide Drug Info Ki = 7100 nM [17]
2-(benzyloxyamino)-N-hydroxyacetamide Drug Info Ki = 6700 nM [17]
2-(benzyloxyamino)-N-hydroxyhexanamide Drug Info Ki = 7600 nM [17]
2-(N''-Acetyl-hydrazino)-benzenesulfonamide Drug Info Ki = 175 nM [6]
2-acetamido-5-sulfonamidoindane Drug Info Ki = 290 nM [13]
2-Amino-benzenesulfonamide Drug Info Ki = 33 nM [23]
2-butylamido-5-sulfonamidoindane Drug Info Ki = 3.4 nM [13]
2-cyclohexylamido-5-sulfonamidoindane Drug Info Ki = 30 nM [13]
2-ethylamido-5-sulfonamidoindane Drug Info Ki = 2015 nM [13]
2-Hydrazinocarbonyl-benzenesulfonamide Drug Info Ki = 547 nM [6]
2-hydrazinylbenzenesulfonamide Drug Info Ki = 176 nM [23]
2-Mercapto-N-(4-sulfamoyl-phenyl)-benzamide Drug Info Ki = 9.1 nM [20]
2-Morpholin-4-yl-N-(4-sulfamoyl-phenyl)-acetamide Drug Info Ki = 181 nM [3]
2-nonylamido-5-sulfonamidoindane Drug Info Ki = 3.7 nM [13]
2-oxo-2H-chromene-3-carboxylic acid Drug Info Ki = 6500 nM [27]
2-oxo-2H-thiochromene-3-carboxylic acid Drug Info Ki = 6200 nM [27]
2-pentafluorophenylamido-5-sulfonamidoindane Drug Info Ki = 33 nM [13]
2-propylamido-5-sulfonamidoindane Drug Info Ki = 2320 nM [13]
2-Sulfamoyl-benzoic acid methyl ester Drug Info Ki = 680 nM [6]
2-valproylamido-5-sulfonamidoindane Drug Info Ki = 282 nM [13]
3-((4-aminophenyl)diazenyl)benzenesulfonamide Drug Info Ki = 5.9 nM [26]
3-((4-hydroxyphenyl)diazenyl)benzenesulfonamide Drug Info Ki = 6.1 nM [26]
3-(3-Phenyl-ureido)-benzenesulfonamide Drug Info Ki = 14 nM [11]
3-(4'-Hydroxyphenyl)diazenylbenzenesulfonamide Drug Info Ki = 6 nM [26]
3-Amino-benzenesulfonamide Drug Info Ki = 238 nM [10]
3-bromophenyl-difluoromethanesulfonamide Drug Info Ki = 1495 nM [12]
3-Chloro-4-hydrazino-benzenesulfonamide Drug Info Ki = 149 nM [6]
3-Fluoro-4-hydrazino-benzenesulfonamide Drug Info Ki = 136 nM [6]
3-mercapto-N-(4-sulfamoyl-phenyl)-propionamide Drug Info Ki = 65 nM [15]
4,4'-thiodipyridine-3-sulfonamide Drug Info Ki = 47.3 nM [30]
4-((4-hydroxyphenyl)diazenyl)benzenesulfonamide Drug Info Ki = 6.4 nM [26]
4-(2-AMINOETHYL)BENZENESULFONAMIDE Drug Info Ki = 33 nM [9]
4-(2-aminopyrimidin-4-ylamino)benzenesulfonamide Drug Info Ki = 16 nM [23]
4-(2-Hydroxy-ethyl)-benzenesulfonamide Drug Info Ki = 22 nM [23]
4-(2-Methyl-8-quinolinoxy)-3-pyridinesulfonamide Drug Info Ki = 313 nM [30]
4-(2-Propynylthio)pyridine-3-sulfonamide Drug Info Ki = 6.3 nM [30]
4-(4'-N-Methylphenyl)diazenylbenzenesulfonamide Drug Info Ki = 4.9 nM [26]
4-(4-Cyanophenoxy)-3-pyridinesulfonamide Drug Info Ki = 7.2 nM [30]
4-(4-Fluorophenoxy)-3-pyridinesulfonamide Drug Info Ki = 7.9 nM [30]
4-(5-Methyl-2-pirazolino)-3-pyridinesulfonamide Drug Info Ki = 7.8 nM [30]
4-(Allylamino)-3-pyridinesulfonamide Drug Info Ki = 12 nM [30]
4-(Carbamolymethylthio)pyridine-3-sulfonamide Drug Info Ki = 11.8 nM [30]
4-(Cyanomethylthio)pyridine-3-sulfonamide Drug Info Ki = 11.7 nM [30]
4-(hydroxymethyl)benzenesulfonamide Drug Info Ki = 21 nM [23]
4-(Methylhydrazino)-3-pyridinesulfonamide Drug Info Ki = 15.8 nM [30]
4-(N-Oxide-2-pyridylthio)pyridine-3-sulfonamide Drug Info Ki = 7.5 nM [30]
4-(Quinolinoxy)-3-pyridinesulfonamide Drug Info Ki = 9.1 nM [30]
4-Amino-3-bromo-benzenesulfonamide Drug Info Ki = 269 nM [23]
4-Amino-3-chloro-benzenesulfonamide Drug Info Ki = 264 nM [23]
4-Amino-3-fluoro-benzenesulfonamide Drug Info Ki = 245 nM [23]
4-Amino-3-iodo-benzenesulfonamide Drug Info Ki = 285 nM [23]
4-amino-6-chlorobenzene-1,3-disulfonamide Drug Info Ki = 39 nM [23]
4-amino-N-(4-sulfamoylbenzyl)benzenesulfonamide Drug Info Ki = 31 nM [23]
4-azidobenzenesulfonamide Drug Info Ki = 105 nM [24]
4-Benzenesulfonylamino-benzenesulfonamide Drug Info Ki = 52 nM [11]
4-Benzythiopyridine-3-sulfonamide Drug Info Ki = 30.4 nM [30]
4-Ethoxy-3-pyridinesulfonamide Drug Info Ki = 300 nM [30]
4-ethynyl benzene sulfonamide Drug Info Ki = 8.1 nM [19]
4-fluoro-N-(4-sulfamoylbenzyl)benzenesulfonamide Drug Info Ki = 290 nM [22]
4-Hydrazino-3-pyridinesulfonamide Drug Info Ki = 4.9 nM [30]
4-Hydrazino-benzenesulfonamide Drug Info Ki = 294 nM [23]
4-Methanesulfonylamino-benzenesulfonamide Drug Info Ki = 113 nM [11]
4-Methoxy-3-pyridinesulfonamide Drug Info Ki = 5.7 nM [30]
4-methylphenyl-difluoromethanesulfonamide Drug Info Ki = 250 nM [12]
4-Methylthiopyridine-3-sulfonamide Drug Info Ki = 47 nM [30]
4-nitrophenyl-difluoromethanesulfonamide Drug Info Ki = 2420 nM [12]
4-[2-(3-Phenyl-ureido)-ethyl]-benzenesulfonamide Drug Info Ki = 18 nM [11]
5-Amino-[1,3,4]thiadiazole-2-thiol Drug Info Ki = 9300 nM [7]
6-(aminomethyl)-2H-chromen-2-one Drug Info Ki = 8400 nM [27]
6-(hydroxymethyl)-2H-chromen-2-one Drug Info Ki = 8400 nM [27]
6-Acetyl-7-ethoxy-2H-chromen-2-one Drug Info Ki = 7400 nM [36]
6-Acetyl-7-hydroxy-2H-chromen-2-one Drug Info Ki = 8030 nM [36]
6-acetyl-7-methoxy-2H-chromen-2-one Drug Info Ki = 7800 nM [36]
6-acetyl-7-propoxy-2H-chromen-2-one Drug Info Ki = 7580 nM [36]
6-Hydroxy-benzothiazole-2-sulfonic acid amide Drug Info Ki = 14 nM [23]
6-methoxy-2-oxo-2H-chromene-3-carboxylic acid Drug Info Ki = 5700 nM [27]
6-methyl-2-oxo-2H-chromene-3-carboxylic acid Drug Info Ki = 48 nM [27]
7-(benzyloxy)-2H-chromen-2-one Drug Info Ki = 4300 nM [27]
7-butoxy-2H-chromen-2-one Drug Info Ki = 4900 nM [27]
7-ethoxy-8-propionyl-2H-chromen-2-one Drug Info Ki = 46.7 nM [36]
7-hydroxy-6-propionyl-2H-chromen-2-one Drug Info Ki = 8015 nM [36]
7-hydroxy-8-propionyl-2H-chromen-2-one Drug Info Ki = 58.2 nM [36]
7-hydroxycoumarin Drug Info Ki = 482 nM [36]
7-methoxy-2-oxo-2H-chromene-4-carboxylic acid Drug Info Ki = 4100 nM [27]
7-methoxy-8-propionyl-2H-chromen-2-one Drug Info Ki = 37.8 nM [36]
7-phenethoxy-2H-chromen-2-one Drug Info Ki = 5800 nM [27]
7-propoxy-2H-chromen-2-one Drug Info Ki = 8100 nM [27]
8-acetyl-7-(benzyloxy)-2H-chromen-2-one Drug Info Ki = 72.3 nM [36]
8-acetyl-7-butoxy-2H-chromen-2-one Drug Info Ki = 61.2 nM [36]
8-acetyl-7-ethoxy-2H-chromen-2-one Drug Info Ki = 70.8 nM [36]
8-Acetyl-7-hydroxy-2H-chromen-2-one Drug Info Ki = 73 nM [36]
8-acetyl-7-methoxy-2H-chromen-2-one Drug Info Ki = 78.3 nM [36]
8-acetyl-7-propoxy-2H-chromen-2-one Drug Info Ki = 56.7 nM [36]
8-methoxy-2-oxo-2H-chromene-3-carboxylic acid Drug Info Ki = 5400 nM [27]
8-Propionyl-7-propoxy-2H-chromen-2-one Drug Info Ki = 50.2 nM [36]
ACETYLSULFANILAMIDE Drug Info Ki = 135 nM [11]
Aminobenzolamide derivative Drug Info Ki = 4.6 nM [2]
Azide Drug Info Ki = 5000 nM [1]
BENZOLAMIDE Drug Info Ki = 47 nM [23]
BICARBONATE Drug Info Ki = 8600 nM [4]
Carzenide Drug Info Ki = 26 nM [23]
CATECHIN Drug Info Ki = 5030 nM [35]
CL-5343 Drug Info Ki = 41 nM [34]
COUMARIN Drug Info Ki = 9100 nM [27]
Coumate Drug Info Ki = 34 nM [21]
Curcumin Drug Info Ki = 4050 nM [35]
Decane-1,10-diyl disulfamate Drug Info Ki = 7 nM [25]
Decyl sulfamate Drug Info Ki = 23.1 nM [25]
ELLAGIC ACID Drug Info Ki = 9370 nM [28]
ETHOXYCOUMARIN Drug Info Ki = 9600 nM [27]
Ethyl 7-methoxy-2-oxo-2H-chromene-3-carboxylate Drug Info Ki = 9400 nM [27]
FERULIC ACID Drug Info Ki = 9870 nM [28]
GALLICACID Drug Info Ki = 6990 nM [28]
HERNIARIN Drug Info Ki = 9800 nM [27]
Hexane-1,6-diamine Drug Info Ki = 410 nM [33]
HYDROSULFIDE Drug Info Ki = 7000 nM [1]
INDISULAM Drug Info Ki = 24 nM [32]
MMI270 Drug Info Ki = 7800 nM [17]
N-(4-cyanophenyl)sulfamide Drug Info Ki = 45 nM [8]
N-(4-Sulfamoyl-phenyl)-benzamide Drug Info Ki = 73 nM [11]
N-(4-Sulfamoyl-phenyl)-butyramide Drug Info Ki = 83 nM [11]
N-(4-Sulfamoyl-phenyl)-isobutyramide Drug Info Ki = 139 nM [11]
N-(4-Sulfamoyl-phenyl)-propionamide Drug Info Ki = 106 nM [11]
N-(4-sulfamoylphenylethyl)-4-sulfamoylbenzamide Drug Info Ki = 18 nM
N-(5-Mercapto-[1,3,4]thiadiazol-2-yl)-acetamide Drug Info Ki = 9500 nM [7]
N-(pentafluorophenyl)sulfamide Drug Info Ki = 19 nM [8]
N-hydroxysulfamide Drug Info Ki = 865 nM [31]
N-propynyl amidebenzenesulphonide Drug Info Ki = 113 nM [16]
N1-(2-aminoethyl)ethane-1,2-diamine Drug Info Ki = 10600 nM [33]
N1-(naphthalen-1-yl)ethane-1,2-diamine Drug Info Ki = 510 nM [33]
NSC-654077 Drug Info Ki = 653 nM [20]
Octane-1,8-diyl disulfamate Drug Info Ki = 4 nM [25]
Octyl sulfamate Drug Info Ki = 3.5 nM [25]
P-Coumaric Acid Drug Info Ki = 5330 nM [28]
P-toluenesulfonamide Drug Info Ki = 460 nM [23]
PARABEN Drug Info Ki = 3730 nM [28]
Pentane-1,5-diamine Drug Info Ki = 380 nM [33]
Pentanoic acid (4-sulfamoyl-phenyl)-amide Drug Info Ki = 79 nM [11]
PHENOL Drug Info Ki = 8800 nM [35]
PHENYLDIFLUOROMETHANESULFONAMIDE Drug Info Ki = 8500 nM [12]
PHENYLMETHANESULFONAMIDE Drug Info Ki = 9300 nM [12]
PHENYLSULFAMATE Drug Info Ki = 63 nM [12]
Prop-2-ynyl 4-sulfamoylbenzoate Drug Info Ki = 104 nM [16]
Quinoline-8-sulfonamide Drug Info Ki = 32 nM [22]
SACCHARIN Drug Info Ki = 103 nM [18]
Sodium N-methylphenylaminomethanesulfonate Drug Info Ki = 5850 nM [26]
Sodium phenylaminomethanesulfonate Drug Info Ki = 5100 nM [26]
SPERMINE Drug Info Ki = 13300 nM [33]
SULFAMATE Drug Info Ki = 9200 nM [4]
Sulfamic acid 12-sulfamoyloxy-dodecyl ester Drug Info Ki = 32.1 nM [5]
Sulfamic acid 16-sulfamoyloxy-hexadecyl ester Drug Info Ki = 525 nM [5]
Sulfamic acid 3-sulfamoyloxy-phenyl ester Drug Info Ki = 100 nM [5]
Sulfamic acid 4-sulfamoyloxy-butyl ester Drug Info Ki = 24 nM [5]
Sulfamic acid 4-sulfamoyloxymethyl-benzyl ester Drug Info Ki = 61.6 nM [5]
Sulfamic acid 6-sulfamoyloxy-hexyl ester Drug Info Ki = 13.2 nM [5]
Sulfamic acid 7-sulfamoyloxy-heptyl ester Drug Info Ki = 10.1 nM [5]
SULFAMIDE Drug Info Ki = 9600 nM [4]
Sulfamylon Drug Info Ki = 103 nM [29]
Syringic Acid Drug Info Ki = 8200 nM [28]
References
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REF 2 Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides d... Bioorg Med Chem Lett. 2004 Dec 6;14(23):5775-80.
REF 3 Carbonic anhydrase inhibitors. Novel sulfanilamide/acetazolamide derivatives obtained by the tail approach and their interaction with the cytosolic... Bioorg Med Chem Lett. 2005 Jan 17;15(2):367-72.
REF 4 Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, IV, V, and IX with anions isosteric and isoelectronic with sulfate, nitrate, and carbo... Bioorg Med Chem Lett. 2005 Feb 1;15(3):567-71.
REF 5 Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates. Bioorg Med Chem Lett. 2005 Feb 1;15(3):579-84.
REF 6 Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamide... J Med Chem. 2005 Mar 24;48(6):2121-5.
REF 7 Carbonic anhydrase inhibitors. Inhibition of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II, and IX with a series of 1,3,4-th... Bioorg Med Chem Lett. 2005 May 2;15(9):2347-52.
REF 8 Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, IX, and XII with N-hydroxy... Bioorg Med Chem Lett. 2005 May 2;15(9):2353-8.
REF 9 Carbonic anhydrase inhibitors. Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-media... J Med Chem. 2005 Jul 28;48(15):4834-41.
REF 10 Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides. Bioorg Med Chem Lett. 2005 Sep 1;15(17):3828-33.
REF 11 Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamides. Bioorg Med Chem Lett. 2005 Nov 1;15(21):4862-6.
REF 12 Carbonic anhydrase inhibitors: inhibition of the human isozymes I, II, VA, and IX with a library of substituted difluoromethanesulfonamides. Bioorg Med Chem Lett. 2005 Dec 1;15(23):5192-6.
REF 13 Indanesulfonamides as carbonic anhydrase inhibitors. Toward structure-based design of selective inhibitors of the tumor-associated isozyme CA IX. J Med Chem. 2006 May 4;49(9):2743-9.
REF 14 N-hydroxyurea--a versatile zinc binding function in the design of metalloenzyme inhibitors. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4316-20.
REF 15 Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX. J Med Chem. 2006 Sep 7;49(18):5544-51.
REF 16 A novel class of carbonic anhydrase inhibitors: glycoconjugate benzene sulfonamides prepared by "click-tailing". J Med Chem. 2006 Nov 2;49(22):6539-48.
REF 17 Carbonic anhydrase and matrix metalloproteinase inhibitors. Inhibition of human tumor-associated isozymes IX and cytosolic isozyme I and II with su... Bioorg Med Chem. 2007 Mar 15;15(6):2298-311.
REF 18 Carbonic anhydrase inhibitors: copper(II) complexes of polyamino-polycarboxylamido aromatic/heterocyclic sulfonamides are very potent inhibitors of... Bioorg Med Chem Lett. 2008 Jan 15;18(2):836-41.
REF 19 Inhibition of carbonic anhydrases with glycosyltriazole benzene sulfonamides. J Med Chem. 2008 Mar 27;51(6):1945-53.
REF 20 Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs. J Med Chem. 2008 Jun 12;51(11):3051-6.
REF 21 Carbonic anhydrase inhibitors. Interaction of the antitumor sulfamate EMD 486019 with twelve mammalian carbonic anhydrase isoforms: Kinetic and X-r... Bioorg Med Chem Lett. 2008 Aug 1;18(15):4282-6.
REF 22 Ligand-based and structure-based virtual screening to identify carbonic anhydrase IX inhibitors. Bioorg Med Chem. 2009 Jan 15;17(2):553-7.
REF 23 Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. J Med Chem. 2009 Feb 12;52(3):646-54.
REF 24 Inhibition of carbonic anhydrase isozymes with benzene sulfonamides incorporating thio, sulfinyl and sulfonyl glycoside moieties. Bioorg Med Chem Lett. 2009 Apr 15;19(8):2273-6.
REF 25 Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis-sulfamate adducts with isozymes II and IX as a platform for designing tight-bi... J Med Chem. 2009 Oct 8;52(19):5990-8.
REF 26 Carbonic anhydrase inhibitors. Diazenylbenzenesulfonamides are potent and selective inhibitors of the tumor-associated isozymes IX and XII over the... Bioorg Med Chem. 2009 Oct 15;17(20):7093-9.
REF 27 Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem. 2010 Jan 14;53(1):335-44.
REF 28 Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-2164.
REF 29 Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases. J Med Chem. 2010 Apr 8;53(7):2913-26.
REF 30 Carbonic anhydrase inhibitors: synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associa... Eur J Med Chem. 2010 Jun;45(6):2396-404.
REF 31 Carbonic anhydrase inhibitors: crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mamm... Bioorg Med Chem Lett. 2010 Jun 15;20(12):3601-5.
REF 32 Carbonic anhydrase inhibitors. Regioselective synthesis of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the... Eur J Med Chem. 2010 Sep;45(9):3656-61.
REF 33 Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J Med Chem. 2010 Aug 12;53(15):5511-22.
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REF 36 7,8-disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and X... Bioorg Med Chem Lett. 2010 Dec 15;20(24):7255-8.

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