10539-83-0

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 566, 1974 DOI: 10.1021/jo00918a034

Upstream product

• 49689-93-2 C₁₁H₁₈N₂O₃S 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 104-94-9 4-methoxy-aniline 
• 352275-06-0 N-(tert-butoxycarbonyl)-N'-(4-methoxyphenyl)sulfamide 

Downstream Products

• 10539-94-3 C₉H₁₁Cl₃N₂O₄S 

Relevant academic research and scientific papers

Hexafluoroisopropyl sulfamate: A useful reagent for the synthesis of sulfamates and sulfamides

Sulfamates and sulfamides are most often synthesized from alcohols and amines with sulfamoyl chloride, which is an unstable reagent. We have identified hexafluoroisopropyl sulfamate (HFIPS) as a bench-stable solid that reacts readily with a wide variety of alcohols, amines, phenols, and anilines under mild reaction conditions. The sole byproduct of the reaction is hexafluoroisopropanol (HFIP) and reaction products can often be isolated in high purity after an aqueous workup (optional) and removal of solvents by evaporation.

Convenient Synthesis of Novel N -Acylsulfonamides Containing Phosphonate Moiety

The present study describes a convenient method for the synthesis of new N-acylsulfonamides containing phosphonate moiety. The N-acylsulfonamides were prepared starting from chlorosulfonyl isocyanate (CSI) in four steps (carbamoylation, sulfamoylation, deprotection, and acylation). Trimethylphosphite has been used to introduce the phosphonate moiety into N-acylsulfonamides via Arbuzov reaction. GRAPHICAL ABSTRACT

Synthesis and antitumor evaluation of novel sulfonylcycloureas derived from nitrogen mustard

A new series of sulfonylcycloureas derivatives have been synthesized and evaluated in vitro for their antitumor activity against four cancer cell lines (A431, Jurkat, U266, and K562). These compounds were prepared by the condensation of several sulfonamides (2am) with ethyl bis(2-chloroethyl)carbamate (1a). The relative cytotoxicity of these new derivatives in comparison to chlorambucil is reported.

Synthesis and antibacterial activity of sulfonamides. SAR and DFT studies

A series of substituted sulfonamide derivatives were synthesized from chlorosulfonyl isocyanate (CSI) in tree steps (carbamoylation, sulfamoylation and deprotection). Antibacterial activity in vitro of some newly formed compounds investigated against clinical strains Gram-positive and Gram-negative: Escherichia coli and Staphylococcus aureus applying the method of dilution and minimal inhibition concentration (MIC) methods. These compounds have significant bacteriostatic activity with totalities of bacterial strains used. DFT calculations with B3LYP/6-31G(d) level have been used to analyze the electronic and geometric characteristics deduced for the stable structure of three compounds presenting conjugation between a nitrogen atom N through its lone pair and an aromatic ring next to it. The principal quantum chemical descriptors have been correlated with the antibacterial activity.

Sulfamide synthesis via Pd-catalysed cross-coupling

A novel efficient procedure for the improved synthesis of aryl-substituted sulfamides via a Pd-catalysed arylation of sulfamide is reported.

Macrocyclic compounds as inhibitors of viral replication

The embodiments provide compounds of the general formulas I-XIX, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating flaviviral infection, including hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

Carbonic anhydrase inhibitors: Inhibition of cytosolic isozymes I and II with sulfamide derivatives

A novel class of effective CAIs has been identified, starting from a very weak carbonic anhydrase inhibitor (CAI), sulfamide, whose X-ray crystal structure in the adduct with hCA II has recently been reported. A series of N,N-disubstituted- and N-substitu

Solid-phase synthesis of sulfamides

A straightforward synthesis of diversely substituted sulfamides is described. The reaction of sulfamoylating agent 1 with solid-phase bound amines to give polymer bound BOC substituted sulfamides is described. Further N-alkylation is achieved under Mitsunobu conditions. Simultaneous deprotection and cleavage of the products leads to unsymmetrically substituted sulfamides.