7454-54-8Relevant academic research and scientific papers
The anilinium chloride adduct of 4-bromo-N-phenylbenzene-sulfonamide
Gelbrich, Thomas,Threlfall, Terence L.,Hursthouse, Michael B.
, p. o470-o472 (2006)
The title compound anilinium chloride-4-bromo-N-phenylbenzenesulfonamide (1/1), C6H8N+·Cl -·C12H10BrNO2S, displays a hydrogen-bonded ladder motif with four independent N-H...Cl bonds in which both the NH group of the sulfonamide molecule and the NH3 group of the anilinium ion [N...Cl = 3.135 (3)-3.196 (2) A and N-H...Cl = 151-167°] are involved. This hydrogen-bonded chain contains two independent R42(8) rings and each chloride ion acts as an acceptor of four hydrogen bonds.
Nickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor-Acceptor Complex Photoactivation
Polites, Viktor C.,Badir, Shorouk O.,Keess, Sebastian,Jolit, Anais,Molander, Gary A.
supporting information, p. 4828 - 4833 (2021/06/30)
The use of bicyclo[1.1.1]pentanes (BCPs) as para-disubstituted aryl bioisosteres has gained considerable momentum in drug development programs. Carbon-carbon bond formation via transition-metal-mediated cross-coupling represents an attractive strategy to generate BCP-aryl compounds for late-stage functionalization, but these typically require reactive organometallics to prepare BCP nucleophiles on demand from [1.1.1]propellane. In this study, the synthesis and Ni-catalyzed functionalization of BCP redox-active esters with (hetero)aryl bromides via the action of a photoactive electron donor-acceptor complex are reported.
Rational Design, Optimization, and Biological Evaluation of Novel MEK4 Inhibitors against Pancreatic Adenocarcinoma
Kwong, Ada J.,Munshi, Hidayatullah G.,Oelschlager, Hannah E.,Pham, Thao N. D.,Scheidt, Karl A.
supporting information, p. 1559 - 1567 (2021/10/04)
Growth, division, and development of healthy cells relies on efficient response to environmental survival cues. The conserved mitogen-activated protein kinase (MAPK) family of pathways interface extracellular stimuli to intracellular processes for this purpose. Within these pathways, the MEK family has been identified as a target of interest due to its clinical relevance. Particularly, MEK4 has drawn recent attention for its indications in pancreatic and prostate cancers. Here, we report two potent MEK4 inhibitors demonstrating significant reduction of phospho-JNK and antiproliferative properties against pancreatic cancer cell lines. Furthermore, molecular inhibition of MEK4 pathway activates the MEK1/2 pathway, with the combination of MEK1/2 and MEK4 inhibitors demonstrating synergistic effects against pancreatic cancer cells. Our inhibitors provided insight into the crosstalk between MAPK pathways and new tools for elucidating the roles of MEK4 in disease states, findings which will pave the way for better understanding of the MAPK pathways and development of additional probes.
Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides
Ahmadpoor, Fatemeh,Nasrollahzadeh, Mahmoud,Nezafat, Zahra,Pakzad, Khatereh
, (2021/06/25)
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.
P-cyclopropyl substituted benzenesulfonylaniline and preparation method thereof
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Paragraph 0005; 0010-0013; 0018-0021, (2020/05/01)
The invention discloses p-cyclopropyl substituted benzenesulfonylaniline and a preparation method thereof. The preparation method comprises the following steps: dissolving p-bromobenzenesulfonic acidand aniline in pyridine, then adding a condensing agent EDC-HCl, and carrying out a reaction for 2 to 3 h at a temperature of 50 to 80 DEG C so as to obtain p-bromobenzenesulfonylaniline; dissolving p-bromobenzenesulfonylaniline into a dioxane solution; adding cyclopropylboronic acid, sodium carbonate, an aqueous solution and Pd(dppf)Cl2, carrying out a reaction on the mixed system at a temperature of 110 DEG C for 8-10 h in a nitrogen atmosphere, and carrying out aftertreatment to obtain p-cyclopropylbenzenesulfonylaniline. The preparation method has the advantages of relatively mild conditions, easiness in product treatment and purification and suitability for batch preparation.
Copper-catalyzed synthesis of sulfonamides from nitroarenes: Via the insertion of sulfur dioxide
Wang, Xuefeng,Yang, Min,Kuang, Yunyan,Liu, Jin-Biao,Fan, Xiaona,Wu, Jie
supporting information, p. 3437 - 3440 (2020/03/30)
Nitroarenes are used as the coupling partners in the preparation of sulfonamides via the insertion of sulfur dioxide. A three-component reaction of arylboronic acids, nitroarenes, and potassium metabisulfite under copper catalysis proceeds smoothly, giving rise to a range of sulfonamides in good to excellent yields with broad substrate scope. Various functional groups including hydroxyl, cyano, amino, and carbonyl are all tolerated. A plausible mechanism is proposed, showing that arylsulfinate is the intermediate and the copper-assisted interaction of the nitroarene and arylsulfinate is the key step. This approach is also extended to the late-stage modification of a currently marketed drug (flutamide).
Sequential C-S and S-N Coupling Approach to Sulfonamides
Chen, Kai,Chen, Wei,Han, Bing,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
supporting information, p. 1841 - 1845 (2020/03/04)
A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.
Lewis Base Promoted, Direct 1,4-Conjugate Addition to Quinone Imine Ketals: Efficient Access to Unsymmetrical Diaryl Sulfones
Liu, Teng,Liu, Jianjun,Shen, Xianfu,Xu, Jianbin,Nian, Beifang,He, Ni,Zeng, Shunqun,Cheng, Feixiang
, p. 1365 - 1376 (2019/03/08)
An alternative approach with eco-friendliness and high efficiency for the preparation of unsymmetrical diaryl sulfones has been developed. The strategy takes advantage of the reaction of sulfonyl hydrazides with quinone imine ketals catalyzed by DABCO (triethylenediamine) in ethanol. This transformation proceeds via a Lewis base promoted, direct 1,4-conjugate addition/sulfonylation/alcohol elimination reaction sequence. The protocol provides an efficient approach to access an array of diverse unsymmetrical diaryl and heterodiaryl sulfones, aryl alkyl sulfones and aryl vinyl sulfones in good to excellent yields.
Multicomponent synthesis of sulfonamides from triarylbismuthines, nitro compounds and sodium metabisulfite in deep eutectic solvents
Marset, Xavier,Torregrosa-Crespo, Javier,Martínez-Espinosa, Rosa M.,Guillena, Gabriela,Ramón, Diego J.
supporting information, p. 4127 - 4132 (2019/08/07)
A sustainable synthesis of sulfonamides using a copper-catalysed process starting from triarylbismuthines, Na2S2O5 and nitro compounds in a Deep Eutectic Solvent (DES) as a reaction medium is described. Thus, triarylbismuthines are used as reagents for the incorporation of SO2 into organic motifs. The bismuth salts formed as by-products can be easily removed from the crude reaction mixture by precipitation with water, while the use of volatile organic compounds (VOCs) as solvents can be avoided in the entire process. The eutectic mixture employed as the solvent is fully characterised, with the preliminary results proving its low toxicity. The designed DES also allows for a novel multicomponent reaction which saves time and reduces purification steps, energy and cost.
Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines
Dong, Wanrong,Liu, Chaoyang,Ma, Xinchi,Zhang, Yingjun,Peng, Zhihong,Xie, Dexun,An, Delie
, p. 3886 - 3893 (2019/06/18)
A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by arylhydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance (up to 36 examples). The protocol was proposed to take place through the free radical pathway based on the results of control reactions and EPR analysis.
