17260-71-8

Usage

Uses

Used in Chemical Synthesis:
3-CHLOROBENZENESULFONAMIDE is used as a chemical intermediate for the synthesis of various compounds. Its reactivity with other chemicals allows for the creation of a wide range of products with different applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-CHLOROBENZENESULFONAMIDE is used as a building block for the development of new drugs. Its unique structure and reactivity make it a valuable component in the synthesis of various medicinal compounds.
Used in Laboratory Research:
3-CHLOROBENZENESULFONAMIDE is also utilized in laboratory research as a reagent for various chemical reactions. Its ability to react with different chemicals, such as 1-chloro-4-isocyanato-benzene, enables the preparation of complex molecules like C13H10Cl2N2O3S, which can be further studied for their potential applications.
For example, the result for 3-CHLOROBENZENESULFONAMIDE is:

InChI:InChI=1/C6H6ClNO2S/c7-5-2-1-3-6(4-5)11(8,9)10/h1-4H,(H2,8,9,10)

Upstream product

• 2888-06-4 3-chlorophenylsulfonyl chloride 
• 68984-05-4 3-chlorobenzenesulfonyl isocyanate 
• 71-43-2 benzene 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 24344-58-9 tributyl(3-chlorophenyl)stannane 
• 1336-21-6 ammonium hydroxide 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 456-39-3 3-chlorobenzenediazonium tetrafluoroborate 
• 2037-31-2 3-chlorophenylthiol 
• 20677-52-5 3-chlorobenzenesulphonic acid 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 19876-01-8 N-butyl-N'-(3-chloro-benzenesulfonyl)-urea 
• 102607-88-5 3-Chloro-N-([(4-chlorophenyl)amino]carbonyl)-benzenesulfonamide 
• 189076-97-9 3-Chloro-N-(2,2-dimethyl-propionyl)-benzenesulfonamide 
• 125002-83-7 methyl N'-cyano-N-[(3-chlorophenyl)sulfonyl]imidothiocarbamate 
• 847728-12-5 5-chloro-N-{(1S)-1-[4-({[(3-chlorophenyl)sulfonyl]amino}carbonyl)phenyl]ethyl}-2-(3-fluorophenoxy)nicotinamide 
• 364038-74-4 3-Chloro-N-(6,7-dimethoxyquinazolin-4-yl)benzenesulphonamide 
• 441054-36-0 N-t-butoxycarbonyl-3-chlorobenzenesulfonamide 
• 1057256-45-7 3-Chloro-N-[2-(1H-indol-4-yloxy)-acetyl] benzenesulfonamide 
• 1048660-70-3 2-bromo-N-[(3-chlorophenyl)sulfonyl]acetamide 
• 1159836-03-9 5-(4-chlorophenyl)-N-(3-chlorophenylsulfonyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 1057257-33-6 C₂₈H₂₁ClN₂O₄S 
• 1221895-75-5 C₂₂H₁₇Cl₂N₃O₃S 

Relevant academic research and scientific papers

Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent N-Sulfinyl- O-(tert-butyl)hydroxylamine, t-BuONSO

Sulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents and a novel sulfinylamine reagent, t-BuONSO. A variety of (hetero)aryl and alkyl Grignard and organolithium reagents perform well in the reaction, providing primary sulfonamides in good to excellent yields in a convenient one-step process.

Aryl uracil compound or agriculturally acceptable salt and preparation method thereof and herbicide composition

The invention provides an aryl uracil compound represented by a formula I (shown in the description) or agriculturally acceptable salt thereof. According to the formula I, R1 and R2 are independentlyselected from hydrogen, amino, C1-C4 alkyl or C1-C4 alkyl halide; X and Y are independently selected from hydrogen, halogen, nitryl, cyan, C1-C4 alkyl or substituted C1-C4 alkyl; R3 is selected from hydrogen, cyan or C1-C4 alkyl; and R4 is selected from cyan, nitryl, substituted or unsubstituted phenyl, substituted or unsubstituted five-membered or six-membered aromatic heterocyclic radical or a substituent group represented by a formula II (shown in the description), wherein R5 is selected from halogen, R6 and R7 are independently selected from hydrogen, halogen, C1-C4 alkyl or C1-C4 alkyl halide. The compound has the characteristics of wide weed control spectrum and high herbicidal activity. The invention further provides a preparation method of the aryl uracil compound or the agriculturally acceptable salt of the aryl uracil compound and a herbicide composition.

Rational Design, synthesis and biological evaluation of novel triazole derivatives as potent and selective PRMT5 inhibitors with antitumor activity

Protein arginine methyltransferase 5 (PRMT5) is responsible for the mono-methylation and symmetric dimethylation of arginine, and its expression level and methyl transferring activity have been demonstrated to have a close relationship with tumorigenesis, development and poor clinical outcomes of human cancers. Two PRMT5 small molecule inhibitors (GSK3326595 and JNJ-64619178) have been put forward into clinical trials. Here, we describe the design, synthesis and biological evaluation of a series of novel, potent and selective PRMT5 inhibitors with antiproliferative activity against Z-138 mantle cell lymphoma cell line. Among them, compound C_4 exhibited the highest potency with enzymatic and cellular level IC50 values of 0.72 and 2.6 μM, respectively, and displayed more than 270-fold selectivity toward PRMT5 over several other isoenzymes (PRMT1, PRMT4 and PRMT6). Besides, C_4 demonstrated obvious cell apoptotic effect while reduced the cellular symmetric arginine dimethylation levels of SmD3 protein. The potency, small size, and synthetic accessibility of this compound class provide promising hit scaffold for medicinal chemists to further explore this series of PRMT5 inhibitors.

Sulfonamide compound and synthesis method and application thereof

The invention discloses a synthesis method of a sulfonamide compound represented in a formula (2). According to the method, diazonium salt is used as a reaction raw material, and under the action of an inorganic nitrogen reagent, an inorganic sulfur dioxide reagent, an additive and a phosphine reagent, the diazonium salt is reacted in a solvent at 60-100 DEG C to obtain various sulfonamide compounds. According to the method inorganic salt is used as a nitrogen atom source and a sulfur dioxide source under a metal-free catalytic condition to construct the sulfonamide compound through one step,thereby avoiding the conventional multi-step synthesis of sulfonamide by condensing unstable acid chloride and amine; and the developed sulfonamide synthesis method can be further applied to the synthesis of the arthritis drug celecoxib and the psychotropic drug sulpiride.

Metal-free construction of primary sulfonamides through three diverse salts

In this report, the first metal-free construction of primary sulfonamides through a direct three-component reaction of sodium metabisulfite, sodium azide and aryldiazonium has been established. Readily available inorganic Na2S2O5 and NaN3 were applied as the sulfur dioxide surrogate and nitrogen source respectively. The widely used sulfonamide drugs Celecoxib and Sulpiride, which possess multiple heteroatoms and active hydrogen containing functional groups, are efficiently installed with -SO2NH2 groups at a late stage. Control experiments and kinetic studies demonstrated that aryl radicals, sulfonyl radicals and conjugated phosphine imine radicals are involved in this transformation.

Highly Chemoselective NH- and O-Transfer to Thiols Using Hypervalent Iodine Reagents: Synthesis of Sulfonimidates and Sulfonamides

Aryl thiols can be selectively converted to sulfonimidates or sulfonamides with three new S-X connections being made selectively in one pot. Using hypervalent iodine reagents in the presence of ammonium carbamate, NH- and O-groups are transferred under mild and practical conditions. Reducing the loading of ammonium carbamate changed the product distribution, converting the sulfonimidate to the sulfonamide. Studies into the possible intermediate species are presented, suggesting that multiple pathways may be possible via sulfinate esters, or related intermediates, with each species forming the same products.

Simple N,N-dimethyl phenylsulfonamides show potent anticonvulsant effect in two standard epilepsy models

Optimization of the previously reported benzothiazine analogue A led to the identification of compound 1, which showed anti-convulsant activity in two golden standard animal models of seizure, the MES and scPTZ models. Structure-activity relationship investigation of compound 1 revealed compounds 2, 6 and 19 as attractive anti-epileptic drug (AED) candidates with potent anticonvulsant effect in both the MES and scPTZ models. As these compounds are structurally different from existing AEDs, determination of their mechanism of actions could provide clues to understanding current therapy-resistant seizures. Moreover, these simple phenylsulfoneamide compounds could be good starting points for searching broad spectrum AEDs by such in vivo screening.

A general iodine-mediated synthesis of primary sulfonamides from thiols and aqueous ammonia

A general and efficient methodology for preparing primary sulfonamides has been developed. In the presence of iodine as the catalyst and TBHP (70% in water) as the oxidant, a wide range of primary sulfonamides were prepared from the corresponding thiols and aqueous ammonia in moderate to good yields.

Orally active aminopyridines as inhibitors of tetrameric fructose-1,6-bisphosphatase

A novel sulfonylureido pyridine series exemplified by compound 19 yielded potent inhibitors of FBPase showing significant glucose reduction and modest glycogen lowering in the acute db/db mouse model for Type-2 diabetes. Our inhibitors occupy the allosteric binding site and also extend into the dyad interface region of tetrameric FBPase.

N-Acyl arylsulfonamides as novel, reversible inhibitors of human steroid sulfatase

Steroid sulfatase (STS) is an attractive target for a range of oestrogen- and androgen-dependent diseases. In search of novel chemotypes of STS inhibitors, we had previously identified nortropinyl-arylsulfonylureas 1; however, while these compounds were good inhibitors of purified STS (lowest Ki = 76 nM), they showed only weak inhibition of STS activity in cells (lowest IC50 around 2 μM). Extended structure-activity relationship studies involving modification of the phenylacetyl side chain and replacement of the nortropine element by simpler scaffolds led to the discovery of N-acyl arylsulfonamides, more specifically N-(Boc-piperidine-4-carbonyl)- benzenesulfonamides, as STS inhibitors, some of which exhibit improved cellular potency (best IC50 = 270 nM).