1576-44-9

Usage

InChI:InChI=1/C12H10N2O4S/c15-14(16)11-6-8-12(9-7-11)19(17,18)13-10-4-2-1-3-5-10/h1-9,13H

Upstream product

• 62-53-3 aniline 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 73901-01-6 p-nitrobenzenesulfonyl azide 
• 71-43-2 benzene 
• 99072-50-1 2-cyano-2-propyl p-nitrobenzenesulfonate 
• 98-80-6 phenylboronic acid 
• 2937-05-5 4-nitrobenzenesulfonohydrazide 
• 15959-31-6 sodium 4-nitrobenzenesulfinate 
• 98-95-3 nitrobenzene 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 149552-43-2 [N-(nosyl)imino]phenyliodinane 
• 873-55-2 sodium benzenesulfonate 
• 1441409-91-1 (E)-ethyl 2-cyano-2-(4-nitrophenylsulfonyloxyimino)acetate 

Downstream Products

• 542-11-0 aniline hydrobromide 
• 127-77-5 p-aminobenzenesulphonanilide 
• 64999-94-6 N-methyl-N-phenyl-4-nitrobenzene sulphonamide 
• 63826-12-0 N-methyl-N-phenyl-4-aminobenzene sulphonamide 
• 3406-75-5 2-(4-nitrophenylthio)acetic acid 
• 100-61-8 N-methylaniline 
• 59224-71-4 N-Acetyl-4-amino-N-phenyl-benzenesulfonamide 
• 1133046-94-2 N-(2-(4-methoxyphenyl)-2,3-dihydrobenzofuran-5-yl)-4-nitrobenzenesulfonamide 
• 1260172-46-0 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-4-nitro-N-phenylbenzenesulfonamide 
• 1260172-27-7 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)aniline 
• 1286272-06-7 C₂₇H₂₁Br₂N₃O₅S 
• 1337919-54-6 (E)-4-nitro-N-phenyl-N-styrylbenzenesulfonamide 
• 1383579-47-2 N-({4-amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)-4-nitro-N-phenylbenzenesulfonamide 
• 1383579-57-4 2-(methylthio)-5-(phenylaminomethyl)furo[2,3-d]pyrimidin-4-amine 

Relevant academic research and scientific papers

Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides

The application of chitosan, which has received much attention as a natural polymer and effective support, has many advantages such as biodegradability and biocompatibility. In this study, the immobilization of a copper complex on the magnetic chitosan bearing metformin ligand has been developed through immobilizing structurally defined metformin with long tail of (3-chloropropyl)trimethoxysilane (TMOS). The synthesized Fe3O4-chitosan@metformin-Cu(II) complex (Fe3O4-CS@Met-Cu(II)) was used as an effective, reusable and magnetic catalyst in the N-arylation of different derivatives of primary sulfonamides with arylboronic acids in ethanol. The primary sulfonamides were prepared from the reaction of sulfonyl chlorides with sodium cyanate in water under ultrasonic irradiation. Utilizing a wide variety of substrates in EtOH as a green solvent, high yields of the primary and secondary sulfonamides, easy work-up along with the excellent recovery and reusability of the catalyst, make this process a simple, economic and environmentally benign method. The synthesized Fe3O4-CS@Met-Cu(II) was characterized using various techniques such as XRD (X-ray diffraction), EDS (energy-dispersive X-ray spectroscopy), elemental mapping, TEM (transmission electron microscopy), FESEM (field emission scanning electron microscopy), VSM (vibrating sample magnetometer), ICP-MS (inductively coupled plasma mass spectroscopy), TGA (thermogravimetric analysis) and FT-IR (Fourier-transform infrared spectroscopy) analyses. The catalyst can be recycled and reused 5 times with no considerable loss of catalytic activity.

Discovery of N-(3,4-Dimethylphenyl)-4-(4-isobutyrylphenyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2- c]quinoline-8-sulfonamide as a Potent Dual MDM2/XIAP Inhibitor

Murine double minute 2 (MDM2) and X-linked inhibitor of apoptosis protein (XIAP) are important cell survival proteins in tumor cells. As a dual MDM2/XIAP inhibitor reported previously, compound MX69 has low potency with an IC50 value of 7.5 μM against an acute lymphoblastic leukemia cell line EU-1. Herein, we report the structural optimization based on the MX69 scaffold, leading to the discovery of a 25-fold more potent analogue 14 (IC50 = 0.3 μM against EU-1). We demonstrate that 14 maintains its mode of action by dual targeting of MDM2 and XIAP through inducing MDM2 protein degradation and inhibiting XIAP mRNA translation, respectively, which resulted in cancer cell growth inhibition and cell death. The results strongly suggest that the scaffold based on 14 is promising for further optimization to develop a new therapeutic agent for leukemia and possibly other cancers where MDM2 and XIAP are dysregulated.

Metal-free one-pot synthesis of N-arylsulfonamides from nitroarenes and sodium sulfinates in an aqueous medium

A metal-free one-pot two-step synthesis of sulfonamides from readily available nitroarenes and sodium arylsulfinates in a mixture of methanol and water has been developed. In this procedure, the aryl amines were produced in situ by the reduction of nitroarenes mediated by diboronic acid, and then coupled with sodium arylsulfinates in the presence of iodine. A series of N-arylsulfonamides with various functional groups were obtained in moderate to good yields under the optimal reaction conditions. In addition, this one-pot process is applicable for gram-scale synthesis.

Sulphonamidic Groups as Electron-Withdrawing Units in Ureido-Based Anion Receptors: Enhanced Anion Complexation versus Deprotonation

A sulphonamidic moiety was utilized as an electron-withdrawing group for enhancement of anion complexation features of urea-based receptors. A series of receptors varying in acidity of sulphonamidic and urea NH groups was synthesized and thoroughly tested. The individual complexation properties reflect deprotonation/complexation equilibrium in a given molecule as a function of the substitution. The receptors containing electron-donating groups in conjugation to the sulphonamidic moiety showed higher association constants towards H2PO4? and carboxylate anions, while those containing electron-withdrawing groups inclined to deprotonation of sulphonamidic NH. The deprotonation issue can be avoided by alkylation at the early step of receptor synthesis or it can be utilized for insertion of suitable groups that enable its anchoring on various substrates to form more elaborated receptor structures.

Arylation and alkenylation of activated alkyl halides using sulfonamides

A variety of quaternary aryl amino acid derivatives can be synthesised using tandem SN2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-Caryl bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.

A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce-Smiles rearrangement to build heterocyclic compounds under mild conditions.

Metal-Free β-Amino Alcohol Synthesis: A Two-step Smiles Rearrangement

A novel method for the synthesis of β-amino alcohols has been demonstrated under mild reaction conditions with a broad scope via a two-step Smiles rearrangement. What is more, theoretical calculations have been performed to confirm the rationality of the mechanism. The method has been proved to be notably effective for N-arylated amino alcohols, which are difficult to synthesize by traditional methods.

Nitrene Insertion into Aromatic and Benzylic C?H Bonds Catalyzed by Copper Complexes of Fluorinated Bis- and Tris(pyrazolyl)borates

Fluorinated bis- and tris(pyrazolyl)boratocopper complexes catalyze the nitrene insertion to C?H bonds of aromatic hydrocarbons efficiently producing amination products in good to excellent yields at room temperature. Imidoiodanes, PhI=NTs (Ts=p-toluenesulfonyl) and PhI=NNs (Ns=p-nitrophenylsulfonyl) serve as the nitrene source. The bis(pyrazolyl)borate catalyst [H2B(3,5-(CF3)2Pz)2]Cu(NCMe) with PhI=NNs produced the arene C?H functionalized product of mesitylene in 87 % yield with only trace amounts of benzylic C?H insertion. The use of [H2B(3,5-(CF3)2-4-(NO2)Pz)2]Cu(NCMe) that has an even weakly donating pyrazolate generated the arene C?H insertion product exclusively. The tris(pyrazolyl)borate complex [HB(3,5-(CF3)2Pz)3]Cu(NCMe), in contrast, generated the benzylic amination product from mesitylene and PhI=NNs in 82 % yield with only very minor amounts of arene C?H functionalization. DFT calculations suggest that Cu-nitrene moiety generated from [HB(3,5-(CF3)2Pz)3]Cu(NCMe) and PhI=NNs activates the benzylic C?H bond of mesitylene via a hydrogen atom abstraction (HAA) followed by a radical rebound (RR) pathway, whereas the functionalization of sp2 C?H bonds of mesitylene by [H2B(3,5-(CF3)2Pz)2]Cu(NNs) ensues possibly via a nitrene addition to the arene core.

Regioselective C-H Amidation of (Alkyl)arenes by Iron(II) Catalysis

A nondirected amidation reaction of aromatic C-H bond was developed under iron(II) catalysis, using sulfonyl azides as the nitrogen source. The reaction displayed a broad substrate scope and good regioselectivities in the aspects of aromatic ring vs alkyl

Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex

The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.