Toluene-4-sulfonamide

ID: ALA574

Chembl Id: CHEMBL574

Cas Number: 70-55-3

PubChem CID: 6269

Product Number: T102876

Max Phase: Phase

Molecular Formula: C7H9NO2S

Molecular Weight: 171.22

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: P-methylbenzenesulfonamide | P-toluenesulfonamide | P-toluenesulfonylamide | P-tosylamide | Para-toluenesulfonamide | Paratoulene sulfonamide | Toluenesulfonamide, p- | NSC-9908 | P-TOLUENESULFONAMIDE|4-Methylbenzenesulfonamide|70-55-3|4-Toluenesulfonamide|Tosylamide|p-Tosylamide|Toluene-4-sulfonamide|para-Toluenesulfonamide|Benzenesulfonamide, 4-methyl-|p-Tolylsulfonamide|4-methylbenzene-1-sulfonamide|p-Methylbenzenesulfonamide|p-Toluenesulfonylamide|Tolylsulfonamide|Toluene-4-sulphonamide|p-ToShow More

Canonical SMILES:  Cc1ccc(S(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C7H9NO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)

Standard InChI Key:  LMYRWZFENFIFIT-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

CA2 Tclin Carbonic anhydrase (122 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA1 Tclin Carbonic anhydrase I (13240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Tclin Carbonic anhydrase II (17698 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA7 Tclin Carbonic anhydrase VII (2318 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA12 Tclin Carbonic anhydrase XII (6231 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA5A Tclin Carbonic anhydrase VA (1168 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA5B Tclin Carbonic anhydrase VB (957 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA6 Tclin Carbonic anhydrase VI (993 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA9 Tclin Carbonic anhydrase IX (8255 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA3 Tclin Carbonic anhydrase III (753 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP9 Tchem Matrix metalloproteinase 9 (6779 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP8 Tchem Matrix metalloproteinase 8 (1942 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP2 Tchem Matrix metalloproteinase-2 (6627 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SN12C (47755 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-N (28205 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHN (49357 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H23 (49055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UO-31 (46270 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HOP-92 (41141 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-539 (44845 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-5 (47095 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Malme-3M (44254 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A498 (42825 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-3 (48710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MOLT-4 (49676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI/ADR-RES (33767 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HOP-62 (47048 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-251 (51189 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-5 (45555 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-8 (47708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNB-19 (46794 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SR (39847 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TK-10 (45540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW-620 (52400 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H522 (44358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KM12 (47707 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
M14 (47487 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H322M (45589 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPMI-8226 (44974 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LOX IMVI (44321 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BT-549 (31254 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-2 (46422 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCC 2998 (41480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-15 (51914 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EKVX (44102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T47D (39041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-62 (47335 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-435 (38290 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IGROV-1 (47897 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-295 (48000 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
786-0 (47912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hs-578T (29457 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-257 (46019 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H226 (44470 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RXF 393 (41971 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
COLO 205 (50209 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AHR Tclin Aryl hydrocarbon receptor (1071 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TNF Tclin TNF-alpha (1897 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFE2L2 Tchem Nuclear factor erythroid 2-related factor 2 (95332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
QPCT Tchem Glutaminyl-peptide cyclotransferase (1121 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

CA2 Carbonic anhydrase II (205 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Carbonic anhydrase (170 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ca13 Carbonic anhydrase XIII (322 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
cynT Carbonic anhydrase 1 (82 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCE103 Carbonic anhydrase (85 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ca15 Carbonic anhydrase 15 (173 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
mtcA1 Uncharacterized protein Rv1284/MT1322 (182 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCE103 Carbonic anhydrase (253 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA Alpha carbonic anhydrase (93 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
mtcA2 Carbonic anhydrase (65 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Carbonic anhydrase (39 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Carbonic anhydrase (56 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPO2 Tyrosinase (3884 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
lef Anthrax lethal factor (7585 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nos2 Nitric oxide synthase, inducible (3573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Astrosclerin-3 (80 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAN2 Carbonic anhydrase 2 (140 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Malassezia furfur (70 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Malassezia pachydermatis (160 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCE103 Carbonic anhydrase (137 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ca1 Delta carbonic anhydrase (40 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
1272966 AGAP002992-PA (40 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Carbonate dehydratase (40 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Carbonic anhydrase, alpha family (44 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 171.22Molecular Weight (Monoisotopic): 171.0354AlogP: 0.64#Rotatable Bonds: 1
Polar Surface Area: 60.16Molecular Species: NEUTRALHBA: 2HBD: 1
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 10.46CX Basic pKa: CX LogP: 1.09CX LogD: 1.09
Aromatic Rings: 1Heavy Atoms: 11QED Weighted: 0.67Np Likeness Score: -1.60

References

1. Jorgensen WL, Duffy EM..  (2000)  Prediction of drug solubility from Monte Carlo simulations.,  10  (11): [PMID:10866370] [10.1016/s0960-894x(00)00172-4]
2. Avila LZ, Chu YH, Blossey EC, Whitesides GM..  (1993)  Use of affinity capillary electrophoresis to determine kinetic and equilibrium constants for binding of arylsulfonamides to bovine carbonic anhydrase.,  36  (1): [PMID:8421278] [10.1021/jm00053a016]
3. Amat L, Carbó-Dorca R, Ponec R..  (1999)  Simple linear QSAR models based on quantum similarity measures.,  42  (25): [PMID:10602702] [10.1021/jm9910728]
4. Menziani MC, De Benedetti PG, Gago F, Richards WG..  (1989)  The binding of benzenesulfonamides to carbonic anhydrase enzyme. A molecular mechanics study and quantitative structure-activity relationships.,  32  (5): [PMID:2709382] [10.1021/jm00125a005]
5. Khadikar PV, Sharma V, Karmarkar S, Supuran CT..  (2005)  Novel use of chemical shift in NMR as molecular descriptor: a first report on modeling carbonic anhydrase inhibitory activity and related parameters.,  15  (4): [PMID:15686889] [10.1016/j.bmcl.2004.12.057]
6. Vullo D, Voipio J, Innocenti A, Rivera C, Ranki H, Scozzafava A, Kaila K, Supuran CT..  (2005)  Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides.,  15  (4): [PMID:15686895] [10.1016/j.bmcl.2004.12.052]
7. Khadikar PV, Sharma V, Karmarkar S, Supuran CT..  (2005)  QSAR studies on benzene sulfonamide carbonic anhydrase inhibitors: need of hydrophobic parameter for topological modeling of binding constants of sulfonamides to human CA-II.,  15  (4): [PMID:15686888] [10.1016/j.bmcl.2004.12.056]
8. Vullo D, Innocenti A, Nishimori I, Pastorek J, Scozzafava A, Pastoreková S, Supuran CT..  (2005)  Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs?,  15  (4): [PMID:15686894] [10.1016/j.bmcl.2004.12.053]
9. Innocenti A, Antel J, Wurl M, Scozzafava A, Supuran CT..  (2004)  Carbonic anhydrase inhibitors: inhibition of human cytosolic isozyme II and mitochondrial isozyme V with a series of benzene sulfonamide derivatives.,  14  (22): [PMID:15482952] [10.1016/j.bmcl.2004.07.085]
10. Jaiswal M, Khadikar PV, Supuran CT..  (2004)  Topological modeling of lipophilicity, diuretic activity, and carbonic inhibition activity of benzene sulfonamides: a molecular connectivity approach.,  14  (22): [PMID:15482943] [10.1016/j.bmcl.2004.08.051]
11. Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT..  (2005)  Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors.,  48  (24): [PMID:16302824] [10.1021/jm050483n]
12. Nishimori I, Minakuchi T, Morimoto K, Sano S, Onishi S, Takeuchi H, Vullo D, Scozzafava A, Supuran CT..  (2006)  Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs.,  49  (6): [PMID:16539401] [10.1021/jm0512600]
13. Nishimori I, Vullo D, Minakuchi T, Morimoto K, Onishi S, Scozzafava A, Supuran CT..  (2006)  Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori.,  16  (8): [PMID:16459077] [10.1016/j.bmcl.2006.01.044]
14. Nishimori I, Minakuchi T, Onishi S, Vullo D, Scozzafava A, Supuran CT..  (2007)  Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors.,  50  (2): [PMID:17228881] [10.1021/jm0612057]
15. Nishimori I, Minakuchi T, Kohsaki T, Onishi S, Takeuchi H, Vullo D, Scozzafava A, Supuran CT..  (2007)  Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from Helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors.,  17  (13): [PMID:17482815] [10.1016/j.bmcl.2007.04.063]
16. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT..  (2007)  Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides.,  15  (23): [PMID:17826101] [10.1016/j.bmc.2007.08.037]
17. Reynolds CH, Tounge BA, Bembenek SD..  (2008)  Ligand binding efficiency: trends, physical basis, and implications.,  51  (8): [PMID:18380424] [10.1021/jm701255b]
18. Isik S, Kockar F, Aydin M, Arslan O, Guler OO, Innocenti A, Scozzafava A, Supuran CT..  (2009)  Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates.,  17  (3): [PMID:19124253] [10.1016/j.bmc.2008.12.035]
19. Hilvo M, Salzano AM, Innocenti A, Kulomaa MS, Scozzafava A, Scaloni A, Parkkila S, Supuran CT..  (2009)  Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV.,  52  (3): [PMID:19193158] [10.1021/jm801267c]
20. Minakuchi T, Nishimori I, Vullo D, Scozzafava A, Supuran CT..  (2009)  Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate.,  52  (8): [PMID:19317447] [10.1021/jm9000488]
21. Nishimori I, Minakuchi T, Vullo D, Scozzafava A, Innocenti A, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis.,  52  (9): [PMID:19338333] [10.1021/jm9003126]
22. Innocenti A, Hall RA, Schlicker C, Scozzafava A, Steegborn C, Mühlschlegel FA, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides.,  17  (13): [PMID:19450983] [10.1016/j.bmc.2009.05.002]
23. Bertucci A, Innocenti A, Zoccola D, Scozzafava A, Tambutté S, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides.,  17  (14): [PMID:19520577] [10.1016/j.bmc.2009.05.063]
24. Carta F, Maresca A, Covarrubias AS, Mowbray SL, Jones TA, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c.,  19  (23): [PMID:19846301] [10.1016/j.bmcl.2009.10.009]
25. Joseph P, Turtaut F, Ouahrani-Bettache S, Montero JL, Nishimori I, Minakuchi T, Vullo D, Scozzafava A, Köhler S, Winum JY, Supuran CT..  (2010)  Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis.,  53  (5): [PMID:20158185] [10.1021/jm901855h]
26. PubChem BioAssay data set, 
27. Munei Y, Shimamoto K, Harada M, Yoshida T, Chuman H..  (2011)  Correlation analyses on binding affinity of substituted benzenesulfonamides with carbonic anhydrase using ab initio MO calculations on their complex structures (II).,  21  (1): [PMID:21130650] [10.1016/j.bmcl.2010.11.050]
28. Bertucci A, Innocenti A, Scozzafava A, Tambutté S, Zoccola D, Supuran CT..  (2011)  Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata.,  21  (2): [PMID:21208801] [10.1016/j.bmcl.2010.11.124]
29. Jacobsen JA, Fullagar JL, Miller MT, Cohen SM..  (2011)  Identifying chelators for metalloprotein inhibitors using a fragment-based approach.,  54  (2): [PMID:21189019] [10.1021/jm101266s]
30. Joseph P, Ouahrani-Bettache S, Montero JL, Nishimori I, Minakuchi T, Vullo D, Scozzafava A, Winum JY, Köhler S, Supuran CT..  (2011)  A new β-carbonic anhydrase from Brucella suis, its cloning, characterization, and inhibition with sulfonamides and sulfamates, leading to impaired pathogen growth.,  19  (3): [PMID:21251841] [10.1016/j.bmc.2010.12.048]
31. Nishimori I, Minakuchi T, Vullo D, Scozzafava A, Supuran CT..  (2011)  Inhibition studies of the β-carbonic anhydrases from the bacterial pathogen Salmonella enterica serovar Typhimurium with sulfonamides and sulfamates.,  19  (16): [PMID:21757360] [10.1016/j.bmc.2011.06.038]
32. Ohradanova A, Vullo D, Pastorekova S, Pastorek J, Jackson DJ, Wörheide G, Supuran CT..  (2012)  Cloning, characterization and sulfonamide inhibition studies of an α-carbonic anhydrase from the living fossil sponge Astrosclera willeyana.,  20  (4): [PMID:22285172] [10.1016/j.bmc.2012.01.007]
33. PubChem BioAssay data set, 
34. Hewitson KS, Vullo D, Scozzafava A, Mastrolorenzo A, Supuran CT..  (2012)  Molecular cloning, characterization, and inhibition studies of a β-carbonic anhydrase from Malassezia globosa, a potential antidandruff target.,  55  (7): [PMID:22424239] [10.1021/jm300203r]
35. PubChem BioAssay data set, 
36. PubChem BioAssay data set, 
37. Del Prete S, Isik S, Vullo D, De Luca V, Carginale V, Scozzafava A, Supuran CT, Capasso C..  (2012)  DNA cloning, characterization, and inhibition studies of an α-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae.,  55  (23): [PMID:23181552] [10.1021/jm301611m]
38. Pan P, Vermelho AB, Capaci Rodrigues G, Scozzafava A, Tolvanen ME, Parkkila S, Capasso C, Supuran CT..  (2013)  Cloning, characterization, and sulfonamide and thiol inhibition studies of an α-carbonic anhydrase from Trypanosoma cruzi, the causative agent of Chagas disease.,  56  (4): [PMID:23391336] [10.1021/jm4000616]
39. Demirdağ R, Çomaklı V, Şentürk M, Ekinci D, İrfan Küfrevioğlu Ö, Supuran CT..  (2013)  Purification and characterization of carbonic anhydrase from sheep kidney and effects of sulfonamides on enzyme activity.,  21  (6): [PMID:22974493] [10.1016/j.bmc.2012.08.018]
40. Vullo D, Leewattanapasuk W, Mühlschlegel FA, Mastrolorenzo A, Capasso C, Supuran CT..  (2013)  Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides.,  23  (9): [PMID:23511020] [10.1016/j.bmcl.2013.02.092]
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