98-68-0Relevant academic research and scientific papers
N-ARYL SULFONAMIDE DERIVATIVES AS VACCINE ADJUVANT
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Page/Page column 101-102, (2021/02/26)
Bis-aryl sulfonamide compounds and methods of using those compounds, e.g., in a method of enhancing or prolonging an immune response, are provided. For example, the compounds may be employed with a vaccine and optionally at least one other adjuvant and/or one or more TLR ligands, at least one MAP kinase inhibitor, or any combination thereof.
3-PHENYLSULPHONYL-QUINOLINE DERIVATIVES AS AGENTS FOR TREATING PATHOGENIC BLOOD VESSELS DISORDERS
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Paragraph 0326, (2021/04/23)
The disclosure provides compounds, and compositions, including pharmaceutical compositions, kits that include the compounds, and methods of using (or administering) and making the compounds. The disclosure further provides compounds or compositions thereof for use in a method of modulating PLXDC1 (TEM7) and/or PLXDC2 or killing pathogenic blood vessles. The disclosure further provides compounds or compositions thereof for use in a method of treating a disease, disorder, or condition that is mediated, at least in part, by PEDF receptors or by angiogenesis.
Sulfonimidesversusketosulfonamides as epoxidized imidazolium counterions: Towards a new generation of ionic liquid monomers
Chardin,Durand,Jarsalé,Rouden,Livi,Baudoux
supporting information, p. 2953 - 2957 (2021/02/26)
The design of novel ionic liquid monomers with attractive properties represents a real challenge in the field of poly(ionic liquid)s (PILs). Here, we describe a comparative study of the synthesis of original PIL precursors from various sulfonimides or ketosulfonamides as unprecedented counteranions of imidazolium ILs. These salts were submitted to the Prilezhaev reaction and a first insight into the intrinsic properties of these new epoxy monomers was unveiled, in particular the thermal stability of these advanced epoxy salts by comparison with traditional counterions.
Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst
Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias
supporting information, p. 20543 - 20550 (2021/08/12)
Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.
Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
, (2021/09/20)
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
Synthesis, biological evaluation, and enzyme assay of some 5-N-substituted-2-N-(arylsulphonyl)-L(+)glutamines as potential anticancer agents
Jha, Tarun,Samanta, Soma,Halder, Amit Kumar,Adhikari, Nilanjan,Abdul Amin,Sanyal, Arpita,Mukherjee, Tanmoy
, p. 1259 - 1264 (2020/12/04)
Thirty 5-N-substituted-2-N-(arylsulphonyl)-L(+)glutamines were synthesized and evaluated biologically for their anticancer activities. The best active compound of this series showed 92.92% inhibition of tumor weight against Ehrlich Ascites Carcinoma cells. The most active compound was proved to be a competitive inhibitor of glutaminase in the enzyme assay. The best active compound may be a starting point to generate 'lead' for further exploration.
Design, synthesis, molecular docking and in vitro evaluation of N-(4-methoxyphenylsulfonyl)pyrrolidine-2-carboxylic acid analogues as antiangiogenic and anticancer agents on multiple myeloma
Sarker,Ghosh,Mishra,Saha,Sen
, p. 3079 - 3086 (2021/01/06)
A series of N-(4-methoxyphenylsulfonyl)pyrrolidine-2-carboxylic acid analogs were designed as bioisosteres of a major metabolite of thalidomide, i.e., N-(o-carboxybenzoyl)-D,L-glutamic acid. Compounds 2b, 2d, 2f, 2i and 2k exhibited anticancer activity on multiple myeloma (RPMI 8226) by MTS assay and were tested for primary antiangiogenic activity on HUVEC cell line by MTT assay. Compound 2f was excluded from further study as it was found to be cytotoxic to normal epithelial cells. 2b, 2d, 2i and 2k were found to have primary antiangiogenic activity along with low cytotoxicity on normal vero cells in MTT assay indicating selective cytotoxicity towards highly angiogenic multiple myeloma. Antiproliferative assay of compounds 2b, 2d, 2i and 2k on HUVECs was carried out using the dye exclusion method with trypan blue. Molecular docking study of compound 2b calculated the binding energy -89.78 kcal/mol and displayed five hydrogen bonds with critical amino acid residues. The compounds are potential candidate drugs for advanced investigations.
Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts
Liu, Yongan,Yu, Donghai,Guo, Yong,Xiao, Ji-Chang,Chen, Qing-Yun,Liu, Chao
supporting information, p. 2281 - 2286 (2020/03/13)
We report herein a general and practical copper-catalyzed fluorosulfonylation reaction of a wide range of abundant arenediazonium salts to smoothly prepare various arenesulfonyl fluorides using the 1,4-diazabicyclo[2.2.2]octane-bis(sulfur dioxide) adduct as a convenient sulfonyl source in combination with KHF2 as an ideal fluorine source and without the need for additional oxidants. Interestingly, the electronic character of the arene ring in the starting arenediazonium salts has a significant impact on the reaction mechanistic pathway.
Proline-Based Allosteric Inhibitors of Zika and Dengue Virus NS2B/NS3 Proteases
Millies, Benedikt,Von Hammerstein, Franziska,Gellert, Andrea,Hammerschmidt, Stefan,Barthels, Fabian,G?ppel, Ulrike,Immerheiser, Melissa,Elgner, Fabian,Jung, Nathalie,Basic, Michael,Kersten, Christian,Kiefer, Werner,Bodem, Jochen,Hildt, Eberhard,Windbergs, Maike,Hellmich, Ute A.,Schirmeister, Tanja
, p. 11359 - 11382 (2019/12/24)
The NS2B/NS3 serine proteases of the Zika and Dengue flaviviruses are attractive targets for the development of antiviral drugs. We report the synthesis and evaluation of a new, proline-based compound class that displays allosteric inhibition of both proteases. The structural features relevant for protease binding and inhibition were determined to establish them as new lead compounds for flaviviral inhibitors. Based on our structure-activity relationship studies, the molecules were further optimized, leading to inhibitors with submicromolar IC50 values and improved lipophilic ligand efficiency. The allosteric binding site in the proteases was probed using mutagenesis and covalent modification of the obtained cysteine mutants with maleimides, followed by computational elucidation of the possible binding modes. In infected cells, antiviral activity against Dengue virus serotype 2 using prodrugs of the inhibitors was observed. In summary, a novel inhibitor scaffold targeting an allosteric site shared between flaviviral NS2B/NS3 proteases is presented whose efficacy is demonstrated in vitro and in cellulo.
Structure-Activity Relationship Studies to Identify Affinity Probes in Bis-aryl Sulfonamides That Prolong Immune Stimuli
Chan, Michael,Lao, Fitzgerald S.,Chu, Paul J.,Shpigelman, Jonathan,Yao, Shiyin,Nan, Jason,Sato-Kaneko, Fumi,Li, Vicky,Hayashi, Tomoko,Corr, Maripat,Carson, Dennis A.,Cottam, Howard B.,Shukla, Nikunj M.
supporting information, p. 9521 - 9540 (2019/11/11)
Agents that safely induce, enhance, or sustain multiple innate immune signaling pathways could be developed as potent vaccine adjuvants or coadjuvants. Using high-throughput screens with cell-based nuclear factor κB (NF-κB) and interferon stimulating response element (ISRE) reporter assays, we identified a bis-aryl sulfonamide bearing compound 1 that demonstrated sustained NF-κB and ISRE activation after a primary stimulus with lipopolysaccharide or interferon-α, respectively. Here, we present systematic structure-activity relationship (SAR) studies on the two phenyl rings and amide nitrogen of the sulfonamide group of compound 1 focused toward identification of affinity probes. The murine vaccination studies showed that compounds 1 and 33 when used as coadjuvants with monophosphoryl lipid A (MPLA) showed significant enhancement in antigen ovalbumin-specific immunoglobulin responses compared to MPLA alone. SAR studies pointed to the sites on the scaffold that can tolerate the introduction of aryl azide, biotin, and fluorescent rhodamine substituents to obtain several affinity and photoaffinity probes which will be utilized in concert for future target identification and mechanism of action studies.
