55854-46-1

Usage

Chemical Properties

light yellow crystalline low melting solid

InChI:InChI=1/C4H2BrClO2S2/c5-3-1-2-4(9-3)10(6,7)8/h1-2H

Upstream product

• 1003-09-4 2-bromothiophene 
• 3141-27-3 2,5-dibromothiophen 

Downstream Products

• 55854-43-8 5-bromo-N-phenylthiophene-2-sulfonamide 
• 53595-65-6 5-bromo-thiophene-2-sulfonamide 
• 199281-07-7 5-Bromo-thiophene-2-sulfonic acid [2-(3-{[((E)-6,6-dimethyl-hept-2-en-4-ynyl)-ethyl-amino]-methyl}-phenoxy)-ethyl]-methyl-amide 
• 874957-10-5 5-bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-thiophenesulfonamide 
• 864961-42-2 5-bromothiophene-2-sulfonic acid [2-(4-fluorophenyl)ethyl]amide 
• 640269-95-0 5-bromothiophene-2-sulfonic acid {3-[4-(2-ethyl-5-methyl-2H-pyrazol-3-yl)piperidin-1-yl]-1-phenylpropyl}amide hydrochloride 
• 641999-90-8 1-(5-bromo-thiophene-2-sulfonyl)-4-methyl-piperazine 
• 948990-60-1 [4-(5-bromo-thiophene-2-sulfonyl)-3-methyl-piperazin-1-yl]-phenyl-methanone 
• 948990-68-9 [(R)-4-(5-bromo-thiophene-2-sulfonyl)-3-methyl-piperazin-1-yl]-phenyl-methanone 
• 1155860-41-5 C₁₇H₁₇BrCl₂N₂O₃S₂ 
• 286932-39-6 5-bromothiophene-2-sulphonic acid tert-butylamide 

Relevant academic research and scientific papers

2-AMINO-N-(AMINO-OXO-ARYL-LAMBDA6-SULFANYLIDENE)ACETAMIDE COMPOUNDS AND THEIR THERAPEUTIC USE

The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain 2-amino-N-(amino-oxo-aryl-λ6- sulfanylidene)acetamide compounds (referred to herein as ANASIA compounds) that, inter alia, inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase (aaRS) (e.g., bacterial leucyl-tRNA synthetase, LeuRS). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase; to treat disorders that are ameliorated by the inhibition (e.g., selective inhibition) of bacterial aminoacyl-tRNA synthetase; to treat bacterial infections; etc.

Hetaryl Bromides Bearing the SO2F Group – Versatile Substrates for Palladium-Catalyzed C–C Coupling Reactions

Synthesis of novel five- and six-membered heteroaromatic sulfonyl fluorides bearing bromine atom at various positions of the heterocyclic ring is described. The synthetic utility of these compounds is demonstrated by the Suzuki, Stille, and Negishi cross-

New methods for the synthesis of 4H-dithieno[3,2-b:2′,3′-d]pyrrole

Various alternative methods for the synthesis of 4H-dithieno[3,2-b:2′,3′-d]pyrrole (DTP) starting from commercially available bromothiophene precursors are presented. Crucial steps involve the Cadogan reaction, Ullmann-type C─N couplings, or Buchwald-Hartwig–type aminations to build up the central pyrrole ring of DTP, respectively. The use of ammonia surrogates afforded the fused target heteroacene in overall yields of 33% to 63%, and the corresponding methods are applicable on large scale.

Mtb PKNA/PKNB Dual Inhibition Provides Selectivity Advantages for Inhibitor Design to Minimize Host Kinase Interactions

Drug resistant tuberculosis (TB) infections are on the rise and antibiotics that inhibit Mycobacterium tuberculosis through a novel mechanism could be an important component of evolving TB therapy. Protein kinase A (PknA) and protein kinase B (PknB) are both essential serine-threonine kinases in M. tuberculosis. Given the extensive knowledge base in kinase inhibition, these enzymes present an interesting opportunity for antimycobacterial drug discovery. This study focused on targeting both PknA and PknB while improving the selectivity window over related mammalian kinases. Compounds achieved potent inhibition (Ki ≈ 5 nM) of both PknA and PknB. A binding pocket unique to mycobacterial kinases was identified. Substitutions that filled this pocket resulted in a 100-fold differential against a broad selection of mammalian kinases. Reducing lipophilicity improved antimycobacterial activity with the most potent compounds achieving minimum inhibitory concentrations ranging from 3 to 5 μM (1-2 μg/mL) against the H37Ra isolate of M. tuberculosis.

Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate

A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides.

Direct acyl substitution of carboxylic acids: A chemoselective o- to N-acyl migration in the traceless staudinger ligation

A chlorophosphite-modified, Staudinger-like acylation of azides involving a highly chemoselective, direct nucleophilic acyl substitution of carboxylic acids is described. The reaction provides the corresponding amides with analytical purity in 32-97 % yield after a simple aqueous workup without the need for a pre-activation step. The use of chlorophosphites as dual carboxylic acid-azide activating agents enables the formation of acyl C-N bonds in the presence of a wide range of nucleophilic and electrophilic functional groups, including amines, alcohols, amides, aldehydes, and ketones. The coupling of carboxylic acids and azides for the formation of alkyl amides, sulfonyl amides, lactams, and dipeptides is described. Copyright

Development of an acyl sulfonamide anti-proliferative agent, ly573636 ? na

The synthesis of 5-bromo-thiophene-2-sulfonic acid 2,4-dichlo- robenzoylamide sodium salt on multikilogram scale is described. The initial clinical supplies were made using carbonyl diimidazole to converge the two fragments. A more efficient acid chloride process has been developed, which also provides better control of impurities and color throughout the synthesis.

Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides

A series of arene and heteroarene sulfonamides were prepared in one vessel from aryl and heteroaryl bromides via conversion into the corresponding Grignard reagents using either magnesium or isopropylmagnesium chloride and subsequent reaction with sulfur dioxide, sulfuryl chloride, and an amine.

Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin

Biphenylsulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, bicyclic or tricyclic carbon or heterocyclic ring biphenylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.

N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin

Thienyl-, furyl- and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.