22952-32-5

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C7H6Cl2O3S/c1-12-6-3-2-5(8)4-7(6)13(9,10)11/h2-4H,1H3

Upstream product

• 623-12-1 4-chloromethoxybenzene 
• 46170-99-4 4-chloroanisole-2-sulfonic acid 
• 106-48-9 4-chloro-phenol 
• 6470-17-3 1-amino-4-methoxybenzene-3-sulphonic acid 
• 7790-94-5 chlorosulfonic acid 

Downstream Products

• 100871-69-0 1,1'-disulfanediylbis(5-chloro-2-methoxybenzene) 
• 197959-76-5 3-(5-chloro-2-methoxyphenylsulfonyloxy)-5-methylphenol 
• 885679-19-6 1-(5-chloro-2-methoxy-benzenesulfonyl)-5-fluoro-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid methyl ester 
• 295790-36-2 C₂₁H₂₆ClN₅O₃S 
• 364067-04-9 5-chloro-2-methoxy-N-methylbenzenesulfonamide 
• 928771-94-2 methyl 1-((5-chloro-2-methoxyphenyl)sulfonyl)indoline-6-carboxylate 

Relevant academic research and scientific papers

Discovery and Structure Relationships of Salicylanilide Derivatives as Potent, Non-acidic P2X1 Receptor Antagonists

Antagonists for the ATP-gated ion channel receptor P2X1 have potential as antithrombotics and for treating hyperactive bladder and inflammation. In this study, salicylanilide derivatives were synthesized based on a screening hit. P2X1 antagonistic potency was assessed in 1321N1 astrocytoma cells stably transfected with the human P2X1 receptor by measuring inhibition of the ATP-induced calcium influx. Structure-activity relationships were analyzed, and selectivity versus other P2X receptor subtypes was assessed. The most potent compounds, N-[3,5-bis(trifluoromethyl)phenyl]-5-chloro-2-hydroxybenzamide (1, IC50 0.0192 μM) and N-[3,5-bis(trifluoromethyl)phenyl]-4-chloro-2-hydroxybenzamide (14, IC50 0.0231 μM), displayed >500-fold selectivity versus P2X2 and P2X3, and 10-fold selectivity versus P2X4 and P2X7 receptors, and inhibited collagen-induced platelet aggregation. They behaved as negative allosteric modulators, and molecular modeling studies suggested an extracellular binding site. Besides selective P2X1 antagonists, compounds with ancillary P2X4 and/or P2X7 receptor inhibition were discovered. These compounds represent the first potent, non-acidic, allosteric P2X1 receptor antagonists reported to date.

Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects

Direct fluorination of ortho-, meta- and para-substituted aromatic thiols and disulfides using elemental fluorine afforded substituted (pentafluorosulfanyl)benzenes. This work thus represents the first study of the scope and limitation of direct fluorination for the synthesis of new SF5-containing building blocks. Fluorinations in batch and flow modes were compared. A comprehensive computational study was carried out employing density functional and wave function methods to elucidate the reaction mechanism of the transformation of ArSF3 into ArSF5. Eliminating various nonradical pathways, it has been shown that the reaction proceeds by a radical mechanism, initiated by the attack of the F. on the ArSF3 moiety, propagated via an almost barrierless F2+ArSF4 .→ArSF5+F. step and terminated by the ArSF4 .+F.→ArSF5. Most of the calculated data are in very good agreement with experimental observations concerning the ortho-substituent effect on the reaction rates and yields.

Discovery of 5-((5-chloro-2-methoxyphenyl)sulfonamido)nicotinamide (SBI-425), a potent and orally bioavailable tissue-nonspecific alkaline phosphatase (TNAP) inhibitor

Tissue-nonspecific alkaline phosphatase (TNAP) is an ectoenzyme crucial for bone matrix mineralization via its ability to hydrolyze extracellular inorganic pyrophosphate (ePPi), a potent mineralization inhibitor, to phosphate (Pi). B

CHEMICAL MODULATORS OF IMMUNE CHECKPOINTS AND THERAPEUTIC USE

Compounds and pharmaceutical compositions that down-regulate immune checkpoints such as PD-1, PD-L1 and CTLA-4 are provided. Also provided are methods of treating a disease by down-regulating immune checkpoints such as PD-1, PD-L1 and CTLA-4. The methods

A novel, flexible strategy to construct privileged dibenzo[b,f][1,4,5]oxathiazepine 5,5-dioxides and their heterocyclic isosteres

Secondary o-hydroxybenzene sulfonamides have been explored as bis-electrophilic partners in a practically simple, atom-economical approach to dibenzo[b,f][1,4,5]oxathiazepine-5,5-dioxides and their heterocyclic analogs, which is an underexplored version o

Design and synthesis of new potassium channel activators derived from the ring opening of diazoxide: Study of their vasodilatory effect, stimulation of elastin synthesis and inhibitory effect on insulin release

Benzenesulfonylureas and benzenesulfonylthioureas, as well as benzenecarbonylureas and benzenecarbonylthioureas, were prepared and evaluated as myorelaxants on 30 mM KCl-precontracted rat aortic rings. The most active compounds were further examined as stimulators of elastin synthesis by vascular smooth muscle cells and as inhibitors of insulin release from pancreaticβ-cells. The drugs were also characterized for their effects on glycaemia in rats. Benzenesulfonylureas and benzenesulfonylthioureas did not display any myorelaxant activity on precontracted rat aortic rings. Such an effect could be attributed to their ionization at physiological pH. By contrast, almost all benzenecarbonylureas and benzenecarbonylthioureas displayed a myorelaxant activity, in particular the benzenecarbonylureas with an oxybenzyl group linked to the ortho position of the phenyl ring. The vasodilatory activity of the most active compounds was reduced when measured in the presence of 80 mM KCl or in the presence of 30 mM KCl and 10 μM glibenclamide. Such results suggested the involvement, at least in part, of KATP channels. Preservation of a vasodilatory activity in rat aortic rings without endothelium indicated that the site of action of such molecules was located on the vascular smooth muscle cells and not on the endothelial cells. Some of the most active compounds also stimulated elastin synthesis by vascular smooth muscle cells. Lastly, most of the active vasorelaxant drugs, except 15k and 15t at high concentrations, did not exhibit marked inhibitory effects on the insulin releasing process and on glycaemia, suggesting a relative tissue selectivity of some of these compounds for the vascular smooth muscle.

Structure-activity relationships of antitubercular salicylanilides consistent with disruption of the proton gradient via proton shuttling

A series of salicylanilides was synthesized based on a high-throughput screening hit against Mycobacterium tuberculosis. A free phenolic hydroxyl on the salicylic acid moeity is required for activity, and the structure-activity relationship of the aniline ring is largely driven by the presence of electron withdrawing groups. We synthesized 94 analogs exploring substitutions of both rings and the linker region in this series and we have identified multiple compounds with low micromolar potency. Unfortunately, cytotoxicity in a murine macrophage cell line trends with antimicrobial activity, suggesting a similar mechanism of action. We propose that salicylanilides function as proton shuttles that kill cells by destroying the cellular proton gradient, limiting their utility as potential therapeutics.

Enantioselective addition of diethylzinc to benzaldehyde catalyzed by chiral titanate complexes with helical ligands

Enantioselective alkylation of benzaldehyde with Et2Zn has been studied. This reaction is catalyzed by helical titanium complexes of tetradentate ligands and has been found to give good to excellent enantioselectivities.

N-Substituted 2-methoxybenzenesulphonamides and medicaments containing them

The invention relates to new N-substituted benzenesulphonamides of general formula STR1 in which N IS 2 OR 3, R1 and R2 are hydrogen atoms, methyl, ethyl groups, or jointly form with the nitrogen a nitrogenized heterocyclic ring having 5 or 6 members, in particular a piperidino, pyrrolidino or morpholino group, R3 is a hydrogen atom, an NO2 group, an NH2 group, or a halogen, R4 is a hydrogen, a halogen, an NH2 group or a sulphonamide group. These compounds are useful as active substances of medicaments, in particular as antiemetic.