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Home > Sulfanilamide > 452-35-7

452-35-7

452-35-7 | 6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE

CAS No: 452-35-7 Catalog No: AG00DEP4 MDL No:MFCD00057089

Product Description

Catalog Number:
AG00DEP4
Chemical Name:
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE
CAS Number:
452-35-7
Molecular Formula:
C9H10N2O3S2
Molecular Weight:
258.3173
MDL Number:
MFCD00057089
IUPAC Name:
6-ethoxy-1,3-benzothiazole-2-sulfonamide
InChI:
InChI=1S/C9H10N2O3S2/c1-2-14-6-3-4-7-8(5-6)15-9(11-7)16(10,12)13/h3-5H,2H2,1H3,(H2,10,12,13)
InChI Key:
OUZWUKMCLIBBOG-UHFFFAOYSA-N
SMILES:
CCOc1ccc2c(c1)sc(n2)S(=O)(=O)N
EC Number:
207-199-5
UNII:
Z52H4811WX

Properties

Complexity:
341  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
258.013g/mol
Formal Charge:
0
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
258.31g/mol
Monoisotopic Mass:
258.013g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
119A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2  

Literature

Title Journal
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Single and mixed poloxamine micelles as nanocarriers for solubilization and sustained release of ethoxzolamide for topical glaucoma therapy. Journal of the Royal Society, Interface 20120907
Methazolamide is a new hepatic insulin sensitizer that lowers blood glucose in vivo. Diabetes 20120801
Molecular cloning, characterization, and inhibition studies of a β-carbonic anhydrase from Malassezia globosa, a potential antidandruff target. Journal of medicinal chemistry 20120412
Mutation of active site residues Asn67 to Ile, Gln92 to Val and Leu204 to Ser in human carbonic anhydrase II: influences on the catalytic activity and affinity for inhibitors. Bioorganic & medicinal chemistry 20120401
Structure-activity relationships for the interaction of 5,10-dihydroindeno[1,2-b]indole derivatives with human and bovine carbonic anhydrase isoforms I, II, III, IV and VI. European journal of medicinal chemistry 20120301
Cloning, characterization and sulfonamide inhibition studies of an α-carbonic anhydrase from the living fossil sponge Astrosclera willeyana. Bioorganic & medicinal chemistry 20120215
Synthesis and carbonic anhydrase inhibitory properties of novel cyclohexanonyl bromophenol derivatives. Bioorganic & medicinal chemistry letters 20120201
Dependence of avidity on linker length for a bivalent ligand-bivalent receptor model system. Journal of the American Chemical Society 20120111
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Thermodynamics of aryl-dihydroxyphenyl-thiadiazole binding to human Hsp90. PloS one 20120101
Regulation of the cyanobacterial CO2-concentrating mechanism involves internal sensing of NADP+ and α-ketogutarate levels by transcription factor CcmR. PloS one 20120101
Carbonic anhydrase activity in Arabidopsis thaliana thylakoid membrane and fragments enriched with PSI or PSII. Photosynthesis research 20111201
Testing the limits of sensitivity in a solid-state structural investigation by combined X-ray powder diffraction, solid-state NMR, and molecular modelling. Physical chemistry chemical physics : PCCP 20111028
Photosynthetic characteristics of a multicellular green alga Volvox carteri in response to external CO2 levels possibly regulated by CCM1/CIA5 ortholog. Photosynthesis research 20110901
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Carbonate precipitates and bicarbonate secretion in the intestine of sea bass, Dicentrarchus labrax. Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20110501
Extracellular β-class carbonic anhydrase of the alkaliphilic cyanobacterium Microcoleus chthonoplastes. Journal of photochemistry and photobiology. B, Biology 20110404
Evaluation of the reproductive and developmental risks of caffeine. Birth defects research. Part B, Developmental and reproductive toxicology 20110401
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Bioinspired imprinted PHEMA-hydrogels for ocular delivery of carbonic anhydrase inhibitor drugs. Biomacromolecules 20110314
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A high throughput screen identifies chemical modulators of the laminin-induced clustering of dystroglycan and aquaporin-4 in primary astrocytes. PloS one 20110101
Treat ankylosing spondylitis with methazolamide. International journal of medical sciences 20110101
Bacterial carbonic anhydrases as drug targets: toward novel antibiotics? Frontiers in pharmacology 20110101
Transport activity of the sodium bicarbonate cotransporter NBCe1 is enhanced by different isoforms of carbonic anhydrase. PloS one 20110101
Sharpey-Schafer lecture: gas channels. Experimental physiology 20101201
Carbonic anhydrase II regulates differentiation of ameloblasts via intracellular pH-dependent JNK signaling pathway. Journal of cellular physiology 20101101
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Carbonic anhydrase inhibitors: crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mammalian isoforms I-XV. Bioorganic & medicinal chemistry letters 20100615
New hydroxypyrimidinone-containing sulfonamides as carbonic anhydrase inhibitors also acting as MMP inhibitors. Bioorganic & medicinal chemistry letters 20100615
Carbonic anhydrase inhibitors: synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with 4-substituted 3-pyridinesulfonamides. European journal of medicinal chemistry 20100601
Carbonic anhydrase inhibitors. The beta-carbonic anhydrases from the fungal pathogens Cryptococcus neoformans and Candida albicans are strongly inhibited by substituted-phenyl-1H-indole-5-sulfonamides. Bioorganic & medicinal chemistry letters 20100415
Nonenzymatic augmentation of lactate transport via monocarboxylate transporter isoform 4 by carbonic anhydrase II. The Journal of membrane biology 20100401
Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis. Journal of medicinal chemistry 20100311
Differences in transcription between free-living and CO2-activated third-stage larvae of Haemonchus contortus. BMC genomics 20100101
Alterations in osteoclast function and phenotype induced by different inhibitors of bone resorption--implications for osteoclast quality. BMC musculoskeletal disorders 20100101
Saccharomyces cerevisiae β-carbonic anhydrase: inhibition and activation studies. Current pharmaceutical design 20100101
Role of carbonic anhydrase IV in the bicarbonate-mediated activation of murine and human sperm. PloS one 20100101
Increased expression of carbonic anhydrase I in the synovium of patients with ankylosing spondylitis. BMC musculoskeletal disorders 20100101
T tubules and surface membranes provide equally effective pathways of carbonic anhydrase-facilitated lactic acid transport in skeletal muscle. PloS one 20100101
Cyclodextrins in delivery systems: Applications. Journal of pharmacy & bioallied sciences 20100101
Ocular inserts - Advancement in therapy of eye diseases. Journal of advanced pharmaceutical technology & research 20100101
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A pea mutant (costata) expressing higher activity in thylakoid membrane-bound carbonic anhydrase alters PSII downregulation mechanisms. Cell biology international 20090801
Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorganic & medicinal chemistry 20090715
Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides. Bioorganic & medicinal chemistry 20090701
Carbonic anhydrase inhibitors. Phenacetyl-, pyridylacetyl- and thienylacetyl-substituted aromatic sulfonamides act as potent and selective isoform VII inhibitors. Bioorganic & medicinal chemistry letters 20090615
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Measurement of nanomolar dissociation constants by titration calorimetry and thermal shift assay - radicicol binding to Hsp90 and ethoxzolamide binding to CAII. International journal of molecular sciences 20090601
Titration calorimetry standards and the precision of isothermal titration calorimetry data. International journal of molecular sciences 20090601
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Ligand-directed tosyl chemistry for protein labeling in vivo. Nature chemical biology 20090501
Manganese-dependent carboanhydrase activity of photosystem II proteins. Biochemistry. Biokhimiia 20090501
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QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software. Journal of enzyme inhibition and medicinal chemistry 20090401
A thiabendazole sulfonamide shows potent inhibitory activity against mammalian and nematode alpha-carbonic anhydrases. Bioorganic & medicinal chemistry letters 20090301
Design of a carbonic anhydrase IX active-site mimic to screen inhibitors for possible anticancer properties. Biochemistry 20090217
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Inhibition of aquaporin 4 by antiepileptic drugs. Bioorganic & medicinal chemistry 20090101
Label-free determination of protein-ligand binding constants using mass spectrometry and validation using surface plasmon resonance and isothermal titration calorimetry. Journal of molecular recognition : JMR 20090101
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HCO3- secretion in the esophageal submucosal glands. American journal of physiology. Gastrointestinal and liver physiology 20050401
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Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating 1,2,4-triazine moieties. Bioorganic & medicinal chemistry letters 20041101
Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides. Bioorganic & medicinal chemistry 20041015
Carbonic anhydrase inhibitors: the first on-resin screening of a 4-sulfamoylphenylthiourea library. Journal of medicinal chemistry 20041007
Roles of carbonic anhydrase in photosynthesis of Skeletonema costatum. Zhi wu sheng li yu fen zi sheng wu xue xue bao = Journal of plant physiology and molecular biology 20041001
pH microdomains in oligodendrocytes. The Journal of biological chemistry 20040827
Carbonic anhydrase isoform expression and functional role in rodent extraocular muscle. Pflugers Archiv : European journal of physiology 20040801
Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides. Bioorganic & medicinal chemistry letters 20040621
Inhibition of alpha(1E) Ca(2+) channels by carbonic anhydrase inhibitors. Journal of pharmacological sciences 20040601
Benzolamide is not a membrane-impermeant carbonic anhydrase inhibitor. Journal of enzyme inhibition and medicinal chemistry 20040601
Carbonic anhydrase inhibitors: synthesis and topical intraocular pressure lowering effects of fluorine-containing inhibitors devoid of enhanced reactivity. Journal of medicinal chemistry 20040520
Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered. Bioorganic & medicinal chemistry letters 20040503
Inhibition of 3T3-L1 adipocyte differentiation by 6-ethoxyzolamide: repressed peroxisome proliferator-activated receptor gamma mRNA and enhanced CCAAT/enhancer binding protein beta mRNA levels. Biochemical pharmacology 20040501
Carbonic anhydrase inhibitors are specific openers of skeletal muscle BK channel of K+-deficient rats. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20040401
Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. Journal of medicinal chemistry 20040226
Pdcd4 inhibits growth of tumor cells by suppression of carbonic anhydrase type II. Molecular and cellular endocrinology 20040212
Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with EMATE, a dual inhibitor of carbonic anhydrases and steroid sulfatase. Bioorganic & medicinal chemistry letters 20040105
Sodium and chloride transport in soft water and hard water acclimated zebrafish (Danio rerio). Biochimica et biophysica acta 20031230
Carbonic anhydrase inhibitors: inhibition of transmembrane, tumor-associated isozyme IX, and cytosolic isozymes I and II with aliphatic sulfamates. Journal of medicinal chemistry 20031204
Inorganic carbon limitation induces transcripts encoding components of the CO(2)-concentrating mechanism in Synechococcus sp. PCC7942 through a redox-independent pathway. Plant physiology 20031201
Bicarbonate-dependent depolarizing potentials in pyramidal cells and interneurons during epileptiform activity. The European journal of neuroscience 20030901
Carbonic anhydrase inhibitors: topically acting antiglaucoma sulfonamides incorporating esters and amides of 3- and 4-carboxybenzolamide. Bioorganic & medicinal chemistry letters 20030901
Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives. Journal of medicinal chemistry 20030522
Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors. Journal of medicinal chemistry 20030522
Spinal carbonic anhydrase contributes to nociceptive reflex enhancement by midazolam, pentobarbital, and propofol. Anesthesiology 20030401
Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorganic & medicinal chemistry letters 20030324
Carbonic anhydrase inhibitors: inhibition of cytosolic isozymes I and II with sulfamide derivatives. Bioorganic & medicinal chemistry letters 20030310
Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. Bioorganic & medicinal chemistry letters 20030310
Transepithelial sulfate transport by avian renal proximal tubule epithelium in primary culture. American journal of physiology. Regulatory, integrative and comparative physiology 20021201
Inhibition of muscle carbonic anhydrase slows the Ca(2+) transient in rat skeletal muscle fibers. American journal of physiology. Cell physiology 20021001
Proton pump activity is required for active uptake of chloride in isolated amphibian skin exposed to freshwater. Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20020801
Carbonic anhydrase inhibitors. Preparation of potent sulfonamides inhibitors incorporating bile acid tails. Bioorganic & medicinal chemistry letters 20020617
Biochemical and molecular inhibition of plastidial carbonic anhydrase reduces the incorporation of acetate into lipids in cotton embryos and tobacco cell suspensions and leaves. Plant physiology 20020401
Carbonic anhydrase inhibitors. A general approach for the preparation of water-soluble sulfonamides incorporating polyamino-polycarboxylate tails and of their metal complexes possessing long-lasting, topical intraocular pressure-lowering properties. Journal of medicinal chemistry 20020328
Potassium drives daily reversible thallus enlargement in the marine red alga Porphyra leucosticta (Rhodophyta). Planta 20020301
Inhibition of muscle carbonic anhydrase increases rise and relaxation times of twitches in rat skeletal muscle fibres. Pflugers Archiv : European journal of physiology 20020301
Role of carbon dioxide and ion transport in the formation of sub-embryonic fluid by the blastoderm of the Japanese quail. British poultry science 20020301
The catalytic properties of human carbonic anhydrase IX. Biochemical and biophysical research communications 20011102
Ionic mechanisms of GABA-induced long-term potentiation in the rat superior colliculus. Experimental brain research 20011001
Cl(-)-dependent secretory mechanisms in isolated rat bile duct epithelial units. American journal of physiology. Gastrointestinal and liver physiology 20010801
Physiological and molecular biological characterization of intracellular carbonic anhydrase from the marine diatom Phaeodactylum tricornutum. Plant physiology 20010801
A new chloroplast envelope carbonic anhydrase activity is induced during acclimation to low inorganic carbon concentrations in Chlamydomonas reinhardtii. Planta 20010601
Extracellular carbonic anhydrase activity facilitates lactic acid transport in rat skeletal muscle fibres. The Journal of physiology 20010315
Asymmetric subcellular mRNA distribution correlates with carbonic anhydrase activity in Acetabularia acetabulum. Plant physiology 20010201
Inhibition of carbonic anhydrase in the lens does not induce myopia in cynomolgus monkeys. Upsala journal of medical sciences 20010101

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