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14949-00-9 | 1,3,4-Thiadiazole-2-sulfonamide, 5-amino-
CAS No: 14949-00-9 Catalog No: AG001LRR MDL No:MFCD03425417
Product Description
Catalog Number:
AG001LRR
Chemical Name:
1,3,4-Thiadiazole-2-sulfonamide, 5-amino-
CAS Number:
14949-00-9
Molecular Formula:
C2H4N4O2S2
Molecular Weight:
180.2088
MDL Number:
MFCD03425417
IUPAC Name:
5-amino-1,3,4-thiadiazole-2-sulfonamide
InChI:
InChI=1S/C2H4N4O2S2/c3-1-5-6-2(9-1)10(4,7)8/h(H2,3,5)(H2,4,7,8)
InChI Key:
VGMVBPQOACUDRU-UHFFFAOYSA-N
SMILES:
Nc1nnc(s1)S(=O)(=O)N
UNII:
F687N81LIZ
NSC Number:
22979
Properties
Complexity:
208
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
179.978g/mol
Formal Charge:
0
Heavy Atom Count:
10
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
180.2g/mol
Monoisotopic Mass:
179.978g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
149A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.9
Literature
| Title | Journal |
|---|---|
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| 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 |
| Cloning, characterization and sulfonamide inhibition studies of an α-carbonic anhydrase from the living fossil sponge Astrosclera willeyana. | Bioorganic & medicinal chemistry 20120215 |
| Inhibition studies of the β-carbonic anhydrases from the bacterial pathogen Salmonella enterica serovar Typhimurium with sulfonamides and sulfamates. | Bioorganic & medicinal chemistry 20110815 |
| Synthesis of 5-amino-1,3,4-thiadiazole-2-sulphonamide derivatives and their inhibition effects on human carbonic anhydrase isozymes. | Journal of enzyme inhibition and medicinal chemistry 20110401 |
| Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site. | Bioorganic & medicinal chemistry 20110215 |
| A new β-carbonic anhydrase from Brucella suis, its cloning, characterization, and inhibition with sulfonamides and sulfamates, leading to impaired pathogen growth. | Bioorganic & medicinal chemistry 20110201 |
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| Acetazolamide-based fungal chitinase inhibitors. | Bioorganic & medicinal chemistry 20101201 |
| Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide. | European journal of medicinal chemistry 20101101 |
| Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors. | Bioorganic & medicinal chemistry letters 20100801 |
| Mutation of Phe91 to Asn in human carbonic anhydrase I unexpectedly enhanced both catalytic activity and affinity for sulfonamide inhibitors. | Bioorganic & medicinal chemistry 20100801 |
| Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis. | Journal of medicinal chemistry 20100311 |
| Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c. | Bioorganic & medicinal chemistry letters 20091201 |
| Simultaneous determination of epinephrine, uric acid and xanthine in the presence of ascorbic acid using an ultrathin polymer film of 5-amino-1,3,4-thiadiazole-2-thiol modified electrode. | Analytica chimica acta 20090804 |
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| Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis. | Journal of medicinal chemistry 20090514 |
| Effects of new 5-amino-1,3,4-thiadiazole-2-sulfonamide derivatives on human carbonic anhydrase isozymes. | Bioorganic & medicinal chemistry 20090501 |
| Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate. | Journal of medicinal chemistry 20090423 |
| Carbonic anhydrase inhibitors. Biphenylsulfonamides with inhibitory action towards the transmembrane, tumor-associated isozymes IX possess cytotoxic activity against human colon, lung and breast cancer cell lines. | Journal of enzyme inhibition and medicinal chemistry 20090401 |
| Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates. | Bioorganic & medicinal chemistry 20090201 |
| Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: synthesis and investigation of inhibitory effects. | Journal of enzyme inhibition and medicinal chemistry 20081201 |
| Carbonic anhydrase inhibitors. Interaction of 2-N,N-dimethylamino-1,3,4-thiadiazole-5-methanesulfonamide with 12 mammalian isoforms: kinetic and X-ray crystallographic studies. | Bioorganic & medicinal chemistry letters 20080201 |
| Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. | Bioorganic & medicinal chemistry 20071201 |
| Design, synthesis, and docking studies of new 1,3,4-thiadiazole-2-thione derivatives with carbonic anhydrase inhibitory activity. | Bioorganic & medicinal chemistry 20071115 |
| Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from Helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors. | Bioorganic & medicinal chemistry letters 20070701 |
| Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. | Journal of medicinal chemistry 20070125 |
| Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of 5-amino-1,3,4-thiadiazole-2-sulfonamide and 5-(4-amino-3-chloro-5-fluorophenylsulfonamido)-1,3,4-thiadiazole-2-sulfonamide to human isoform II. | Bioorganic & medicinal chemistry letters 20061215 |
| Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori. | Bioorganic & medicinal chemistry letters 20060415 |
| QSAR study on topically acting sulfonamides incorporating GABA moieties: a molecular connectivity approach. | Bioorganic & medicinal chemistry letters 20060401 |
| 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. | Journal of medicinal chemistry 20060323 |
| Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. | Journal of medicinal chemistry 20051201 |
| Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides. | Bioorganic & medicinal chemistry letters 20050901 |
| Carbonic anhydrase inhibitors. Inhibition of red blood cell ostrich (Struthio camelus) carbonic anhydrase with a series of aromatic and heterocyclic sulfonamides. | Journal of enzyme inhibition and medicinal chemistry 20050801 |
| Carbonic anhydrase inhibitors. Inhibition of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II, and IX with a series of 1,3,4-thiadiazole- and 1,2,4-triazole-thiols. | Bioorganic & medicinal chemistry letters 20050502 |
| Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? | Bioorganic & medicinal chemistry letters 20050215 |
| Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. | Bioorganic & medicinal chemistry letters 20050215 |
| Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. | Bioorganic & medicinal chemistry letters 20050215 |
| Carbonic anhydrase inhibitors. Novel sulfanilamide/acetazolamide derivatives obtained by the tail approach and their interaction with the cytosolic isozymes I and II, and the tumor-associated isozyme IX. | Bioorganic & medicinal chemistry letters 20050117 |
| Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides. | Bioorganic & medicinal chemistry letters 20040621 |
| Carbonic anhydrase inhibitors: Schiff's bases of aromatic and heterocyclic sulfonamides and their metal complexes. | Journal of enzyme inhibition and medicinal chemistry 20040601 |
| Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives. | Journal of medicinal chemistry 20030522 |
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| Bile acid derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide as new carbonic anhydrase inhibitors: synthesis and investigation of inhibition effects. | Bioorganic & medicinal chemistry 20020801 |
| 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 |
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