13909-63-2

Usage

InChI:InChI=1/C14H14N2O3S/c1-11-7-9-13(10-8-11)20(18,19)16-14(17)15-12-5-3-2-4-6-12/h2-10H,1H3,(H2,15,16,17)

Upstream product

• 101280-86-8 N-acetyl-N-phenyl-N'-(toluene-4-sulfonyl)-urea 
• 103-71-9 phenyl isocyanate 
• 70-55-3 toluene-4-sulfonamide 
• 4083-64-1 Tosyl isocyanate 
• 62-53-3 aniline 
• 64-77-7 N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide 
• 18522-92-4 sodium p-toluenesulfonamide 
• 102-07-8 bis(diphenyl)urea 
• 101359-08-4 N-tosyltriphenylbismuthimine 
• 98-59-9 p-toluenesulfonyl chloride 
• 165334-40-7 N-trimethylsilyl-N'-phenylurea 
• 65-85-0 benzoic acid 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 933-00-6 p-methylbenzenesulfenyl chloride 

Relevant academic research and scientific papers

Hydroamination and Hydrophosphination of Isocyanates/Isothiocyanates under Catalyst-Free Conditions

Symmetrical and unsymmetrical N,N’-disubstituted as well as trisubstituted ureas/thioureas by the hydroamination of isocyanates/isothiocyanates, and various phosphathioureas by the hydrophosphination of isothiocyanates have been synthesized in good to excellent yields under catalyst-free and mild conditions. This protocol is also applicable for the efficient synthesis of chiral ureas and thioureas and common herbicides, such as fenuron and monuron.

Catalyst-free solventless synthesis of polysubstituted urea Method for preparing thioureas and chiral ureas and thiourea compounds

The invention discloses a method for synthesizing polysubstituted urea, thiourea and chiral urea and thiourea compounds without catalyst without solvent, and the method comprises A contact reaction of an amine compound with a structure shown B as shown first in a non-catalyst and a solventless condition to prepare a polysubstituted urea or thiourea compound with a structure as shown C. R1 And R2 Each independently selected from a hydrocarbyl or substituted hydrocarbyl group, R3 The method is selected from H, hydrocarbyl or substituted hydrocarbyl, X is S or o. The method solves the defect that a catalyst and/or a solvent need to be used in the synthesis of urea and thiourea compounds in the prior art.

Implication of sulfonylurea derivatives as prospective inhibitors of human carbonic anhydrase II

Selective carbonic anhydrase (CA) inhibitors have gained a lot of importance owing to the implication of specific isoforms of CA in certain diseases like glaucoma, leukemia, cystic fibrosis, and epilepsy. A novel class of sulfonylurea derivatives was synthesized from corresponding sulfonyl chlorides and amines. Compounds with different pendant moieties in the sulfonylurea derivatives show significant interactions with human carbonic anhydrase II (CAII). In vitro evaluation of the sulfonylurea derivatives revealed that three compounds possess admirable inhibitory activity against CAII. Compounds containing methyl (G2), isopropyl (G4) and o-tosyl (G5) groups displayed IC50 (109-137 μm) for CAII. Fluorescence binding and cytotoxicity studies revealed that these compounds are showing good binding affinity (18-34 μM) to CAII and non- toxic to human cells. Further, molecular docking studies of G2, G4 and G5 with CAII showed that these compounds fit nicely in the active site of CAII. Molecular dynamics simulation studies of these compounds complexed with CAII showed that essential interactions were maintained up to 50 ns of simulation. These results indicate the promising nature of the sulfonylurea scaffold towards CAII inhibition and opens scope of hit to-lead optimization for discovery of effective drugs against CAII-associated disorders.

A sulfonyl urea, sulfonamide ethyl ester preparation method of compound (by machine translation)

The description relates to a compound of formula (I) compound of the preparation method, wherein formula (II) with a compound represented by formula (III) as shown in the catalysis of palladium catalyst, under a carbon monoxide atmosphere, reacts in a solvent to obtain the compound. The invention related to the method of the reaction do not require strict-free conditions, does not need a high pressure carbon monoxide atmosphere, convenient and simple to operate, to a functional group and has very high power density and universality, the catalyst consumption is very small, the cost of reaction is very low, and can be widely used for preparing sulfonyl urea compound. R1 - SO2 - NH - CO - X (R3 )n - R2 (I) R1 - SO2 - R4 (II) HX (R3 )n - R2 (III) wherein X is O or N; n is 0 or 1; when X is when O, n=0; when X is when N, n=1; R1 Selected from aryl, heteroaryl, alkyl, alkenyl or alkynyl; R2 Selected from aryl, heteroaryl, alkyl, alkenyl or alkynyl; R3 Is selected from H, R2 , Or R3 And R2 A ring of connection; R4 For N3 Or a halogen atom; when R4 For nails halogen original, system also comprises a sodium azide. (by machine translation)

Product-Derived Bimetallic Palladium Complex Catalyzes Direct Carbonylation of Sulfonylazides

A novel product-derived bimetallic palladium complex catalyzes a sulfonylazide-transfer reaction with the σ-donor/π-acceptor ligand CO, and is advantageous given its broad substrate scope, high efficiency, and mild reaction conditions (atmospheric pressure of CO at room temperature). This methodology provides a new approach to sulfonylureas, which are present in both pharmaceuticals and agrochemicals. The synthesis of Glibenclamide on a gram scale further revealed the practical utility of this procedure. Mechanistically, the generation of a bridged bimetallic palladium species derived from the product sulfonylurea is disclosed as the crucial step for this catalytic cycle.

Design and development of sulfonylurea derivatives as zinc metalloenzyme modulators

Sulfonamide derivatives are an important class of zinc metalloenzyme inhibitors. While the sulfonylurea group is a bioisoster of sulfonamide, their effect on the modulation of metalloenzymes has never been studied. In the present work we synthesize and screen new sulfonylurea derivatives towards the zinc metalloenzymes, human Carbonic Anhydrase II (hCA II) and histone deacetylase 1 (HDAC 1). Specific sulfonylurea derivatives are found to inhibit hCA II with IC50 in the nano molar to micro molar range. Docking studies indicate the binding of the inhibitors to the mouth of the active site cavity thereby blocking access to the enzyme. Surprisingly sulfonylurea derivatives exhibit activation of HDAC 1 rather than inhibition. The activation of HDAC 1 is not uniform across the derivatives tested suggesting a specific mode that depends on structural features of the compounds. Extensive research has been performed on HDAC inhibitors due to their potential as anti-cancer agents, however relatively little has been reported in terms of HDAC activation. In this work, we present the distinctly divergent behavior of the same class of molecules namely sulfonylurea derivatives with respect to hCA II and HDAC 1 and attempt to provide an understanding of the same.

Mechanosynthesis of pharmaceutically relevant sulfonyl-(thio)ureas

We demonstrate the first application of mechanochemistry to conduct the synthesis of sulfonyl-(thio)ureas, including known anti-diabetic drugs tolbutamide, chlorpropamide and glibenclamide, in good to excellent isolated yields by either stoichiometric base-assisted or copper-catalysed coupling of sulfonamides and iso(thio)cyanates. the Partner Organisations 2014.

A convenient synthesis of sulfonylureas from carboxylic acids and sulfonamides via an in situ Curtius rearrangement

A one-pot reaction of carboxylic acids with sulfonamides to afford sulfonylureas is described.

Reaction of N-Trimethylsilyl-N′-phenylurea with Cyanuric Chloride and p-Toluenesulfonyl Chloride

Reaction of N-trimethylsilyl-N′-phenylurea with cyanuric chloride in tetrahydrofuran yields a mixture of phenylureido derivatives of sym-triazine; the major product is 2,4-bis(phenylureido)-6-chloro-1,3,5-triazine. The reaction of the same substituted urea with p-toluenesulfonyl chloride yielded N-(p-toluenesulfonyl)-N′-phenylurea.

Thermosensitive recording material

A thermosensitive recording material having a high whiteness and capable of forming clear colored images with an excellent resistance to oil and plasticizers is provided with a thermosensitive colored image-forming layer formed on a substrate sheet and comprising a substantially colorless dye precursor, a binder and a color-developing agent comprising at least one aromatic compound having, per molecule thereof, at least two functional sulfonylamino(thio)carbonylamino groups of the formula (I): wherein X is an oxygen or sulfur atom.