21626-70-0

Usage

Chemical Properties

White to off-white solid

InChI:InChI=1/C10H14N2O3S/c11-9-1-3-10(4-2-9)16(13,14)12-5-7-15-8-6-12/h1-4H,5-8,11H2

Upstream product

• 110-91-8 morpholine 
• 24939-24-0 4-aminobenzenesulfonyl chloride 
• 21626-69-7 N⁴-acetylsulfanilylmorpholidate 
• 103-84-4 Acetanilid 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 1024-30-2 4-(4-nitrobenzenesulfonyl)morpholine 

Downstream Products

• 71334-09-3 4-(4-benzo[1,3]dioxol-5-ylmethyleneamino-benzenesulfonyl)-morpholine 
• 71334-05-9 p-chlorobenzilidene-p-aminobenzenesulphonylmorpholine 
• 71334-07-1 p-nitrobenzilidene-p-aminobenzenesulphonylmorpholine 
• 71334-03-7 4-(4-benzylideneamino-benzenesulfonyl)-morpholine 
• 71334-06-0 4-[4-(4-methoxy-benzylideneamino)-benzenesulfonyl]-morpholine 
• 71334-04-8 salicilidene-p-aminobenzenesulphonylmorpholine 
• 35959-60-5 4-[4-(2-chloro-acetylamino)-benzenesulfonyl]-morpholine 
• 71334-08-2 4-[4-(4-dimethylamino-benzylideneamino)-benzenesulfonyl]-morpholine 
• 116691-39-5 4-<8-hydroxy-5-quinolylazo>benzenesulphonamyl morpholine 
• 53915-80-3 p-(sulphonylmorpholino)phenylhydrazine 
• 88323-82-4 4-[4-(3,5-Dimethyl-pyrazol-1-yl)-benzenesulfonyl]-morpholine 
• 88328-00-1 C₁₂H₁₅N₃O₆S 
• 88323-68-6 1-[4-(Morpholine-4-sulfonyl)-phenyl]-1H-pyrazole-3,4-dicarboxylic acid dimethyl ester 
• 1056673-41-6 tert-butyl 4-(3-(4-(morpholinosulfonyl)phenyl)ureido)piperidine-1-carboxylate 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel naphthoquinone-4-aminobenzensulfonamide/carboxamide derivatives as proteasome inhibitors

A series of novel 4-aminobenzensulfonamide/carboxamide derivatives bearing naphthoquinone pharmacophore were designed, sythesized and evaluated for their proteasome inhibitory and antiproliferative activities against human breast cancer cell line (MCF-7). The structures of the synthesized compounds were confirmed by spectral and elemental analyses. The proteasome inhibitory activity studies were carried out using cell-based assay. The antiproteasomal activity results revealed that most of the compounds exhibited inhibitory activity with different percentages against the caspase-like (C-L, β1 subunit), trypsin-like (T-L, β2 subunit) and chymotrypsin-like (ChT-L, β5 subunit) activities of proteasome. Among the tested compounds, compound 14 bearing 5-chloro-2-pyridyl ring on the nitrogen atom of sulfonamide group is the most active compound in the series and displayed higher inhibition with IC50 values of 9.90 ± 0.61, 44.83 ± 4.23 and 22.27 ± 0.15 μM against ChT-L, C-L and T-L activities of proteasome compared to the lead compound PI-083 (IC50 = 12.47 ± 0.21, 53.12 ± 2.56 and 26.37 ± 0.5 μM), respectively. The antiproliferative activity was also determined by MTT (3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) assay in vitro. According to the antiproliferative activity results, all of the compounds exhibited cell growth inhibitory activity in a range of IC50 = 1.72 ± 0.14–20.8 ± 0.5 μM and compounds 13 and 28 were found to be the most active compounds with IC50 values of 1.79 ± 0.21 and 1.72 ± 0.14 μM, respectively. Furthermore, molecular modeling studies were carried out for the compounds 13, 14 and 28 to investigate the ligand-enzyme binding interactions.

“TPG-lite”: A new, simplified “designer” surfactant for general use in synthesis under micellar catalysis conditions in recyclable water

Using the oxidized, carboxylic acid-containing form of MPEG-750, esterification with racemic vitamin E affords a new surfactant (TPG-lite) that functions as an enabling, nanoreactor-forming amphiphile for use in many types of important reactions in synthesis. The presence of a single ester bond is suggestive of simplified treatment as a component of (eventual) reaction waste water, after recycling. Many types of reactions, including aminations, Suzuki-Miyaura, SNAr, and several others are compared directly with TPGS-750-M, leading to the conclusion that TPG-lite can function as an equivalent nanomicelle-forming surfactant in water. Prima facie evidence amassed via DLS and cryo-TEM analyses support these experimental observations. In silico evaluations of the aquatic toxicity and carcinogenicity of TPG-lite indicate that it is safe to use.

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.

Benzoylaniline compound and application of benzoylaniline compound in preparation of sensitizer of P.aeruginosa inhibitor

The invention discloses a benzoylaniline compound. The benzoylaniline compound has a structural general formula shown in the specification. The invention also discloses application of the benzoylaniline compound in preparation of a sensitizer of a P.aeruginosa inhibitor or in preparation of a medicine for preventing or treating bacterial infection diseases caused by P.aeruginosa. The invention also discloses an application of niclosamide in preparation of a sensitizer of a P.aeruginosa inhibitor or in preparation of a medicine for preventing or treating bacterial infection diseases caused by P.aeruginosa. The benzoylaniline compound provided by the invention can be used as a medicine for treating and/or preventing bacterial infection diseases caused by P.aeruginosa.

Synthesis, characterization, and antiplasmodial efficacy of sulfonamide-appended [1,2,3]-triazoles

A series of benzenesulfonamide-appended [1,2,3]-triazole hybrids was synthesized by using [3 + 2] cycloaddition of primary, secondary, and tertiary sulfonamide azides with various phenoxymethylacetylenes under click reaction conditions. After structural c

Coolade. A Low-Foaming Surfactant for Organic Synthesis in Water

Several types of reduction reactions in organic synthesis are performed under aqueous micellar-catalysis conditions (in water at ambient temperature), which produce a significant volume of foam owing to the combination of the surfactant and the presence of gas evolution. The newly engineered surfactant “Coolade” minimizes this important technical issue owing to its low-foaming properties. Coolade is the latest in a series of designer surfactants specifically tailored to enable organic synthesis in water. This study reports the synthesis of this new surfactant along with its applications to gas-involving reactions.

Synthesis and biological evaluation of norcantharidin derivatives as protein phosphatase-1 inhibitors

Cantharidin and norcantharidin display anticancer activity against a broad range of tumor cell lines. In this study, we have synthesized a series of norcantharidin derivatives and evaluated their cytotoxic effects on four human tumor cell lines together with the genetically normal human diploid fibroblast line WI-38. One of our compounds (1S,4R)-3-((4-(4-(4-fluorophenyl)piperazin-1-ylsulfonyl) phenyl)carbamoyl)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid (12) exhibited potent cytotoxic effects on the tumor cell lines A-549, HepG2, HeLa, and HCT-8, whereas it was less toxic to WI-38 cells than its parent compound, norcantharidin. In addition, this compound inhibited protein phosphatase-1 activity and microtubule formation in HeLa cells, and it also interacts with calf thymus DNA.

Ammonium chloride-catalyzed four-component sonochemical synthesis of novel hexahydroquinolines bearing a sulfonamide moiety

Ammonium chloride as a very inexpensive and readily available reagent efficiently catalyzes one-pot four-component condensation of dimedone with aromatic aldehyde, malononitrile or ethyl cyanoacetate, and sulfonamide derivatives in ethanol at 70°C under ultrasonic irradiation to afford the corresponding 2-amino-4-aryl-1,4,5,6,7,8-hexahydroquinolines bearing a sulfonamide moiety in high yields. In comparison to conventional methods, high yields, easy work-up, and short reaction time are advantages of this sonochemical procedure. The effects of the catalyst, solvent, and temperature are assessed.

1,2-Benzisothiazol-3-one derivatives as a novel class of small-molecule caspase-3 inhibitors

A novel series of 1,2-benzisothiazol-3-one derivatives was synthesized and their biological activities were evaluated for inhibiting caspase-3 and -7 activities, in which some of them showed low nanomolar potency against caspase-3 in vitro and significant protection against apoptosis in a camptothecin-induced Jurkat T cells system. Among the tested compounds, compound 5i exhibited the most potent caspase-3 inhibitory activity (IC50 = 1.15 nM). The molecular docking predicted the interactions and binding modes of the synthesized inhibitor in the caspase-3 active site.

CYCLOPROPYL AMIDE DERIVATIVES

The present invention relates to certain cyclopropyl amide compounds, pharmaceutical compositions comprising such compounds, and methods of treating cancer, including leukemias and solid tumors, inflammatory diseases, osteoporosis, atherosclerosis, irritable bowel syndrome, and other diseases and medical conditions, with such compounds and pharmaceutical compositions. The present invention also relates to certain cyclopropyl amide compounds for use in inhibiting nicotinamide phosphoribosyltransferase ("NAMPT").