1584-58-3Relevant academic research and scientific papers
Synthesis and evaluation of 3-(4-(phenoxymethyl)phenyl)propanoic acid and N-phenylbenzenesulfonamide derivatives as FFA4 agonists
Xu, Fangfang,Zhao, Yaopeng,Zhou, Han,Li, Chunzhi,Zhang, Xiuli,Hou, Tao,Qu, Lala,Wei, Lai,Wang, Jixia,Liu, Yanfang,Liang, Xinmiao
, (2020)
Free fatty acid receptor 4 (FFA4) has been recognized as an attractive target in metabolic diseases. To find potent and selective FFA4 agonist, 28 compounds of 3-(4-(phenoxymethyl)phenyl)propanoic acid and N-phenylbenzenesulfonamide derivatives were designed and synthesized, featuring O[sbnd]C and SO2-N linkage. For the O[sbnd]C linkage compounds, 1g showed the most potent FFA4 agonistic activity with a pEC50 of 5.81 ± 0.04 and exhibited at least 64-fold selectivity against FFA1. For SO2-N linkage agonists, 2m had a pEC50 of 5.66 ± 0.04 and displayed>46-fold selectivity against FFA1. Among these two series of compounds, 1g was the most potent agonist at FFA4 and the best selectivity against FFA1, demonstrated by docking simulation. Moreover, 1g showed receptor selectivity on other seven GPCRs. In anti-diabetic evaluation, 1g dose-dependently reduced blood glucose, which was better than a clinical phase III drug TAK875. This study provides guidance for FFA4 ligand design and drug optimization.
Fe-based metal-organic frameworks for the synthesis of N-arylsulfonamides via the reactions of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes in water
Li, Xinxin,Chen, Fei,Lu, Guo-Ping
supporting information, p. 4226 - 4230 (2018/10/26)
A newly developed chemoselective reaction of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes has been disclosed. The chemistry, in which non-toxic water and recyclable iron-based metal-organic frameworks are employed as the solvent and catalyst, respectively, provides an efficient approach for the generation of N-arylsulfonamides, which are widely present in biologically active compounds and drugs, rendering this methodology attractive to both synthetic and medicinal chemistry.
NaI-Catalyzed Oxidative Amination of Aromatic Sodium Sulfinates: Synergetic Effect of Ethylene Dibromide and Air as Oxidants
Fu, Ying,Li, Quan-Zhou,Xu, Qin-Shan,Hügel, Helmut,Li, Ming-Peng,Du, Zhengyin
supporting information, p. 6966 - 6970 (2018/11/23)
A novel NaI-catalyzed oxidative amination of sodium sulfinates, employing both ethylene dibromide (EDB) and air as the oxidants, is described. EDB was first demonstrated to be a promising mild organic oxidant that in air, converted NaI into molecular iodine to promote the cross-coupling reactions of aromatic sodium sulfinates with amines to produce arylsulfonamides. Mechanistic studies indicated that a radical pathway might be involved in the reaction process.
Palladium nanoparticles as reusable catalyst for the synthesis of N-aryl sulfonamides under mild reaction conditions
Khalaj, Mehdi,Ghazanfarpour-Darjani, Majid,Talei Bavil Olyai, Mohamad Reza,Shamami, Sakineh Faraji
, p. 211 - 221 (2016/03/30)
An efficient palladium nanoparticles-catalyzed N-arylation of sulfonamides and sulfonyl azides is described. This procedure serves as an active protocol for intermolecular C-N bond formation using Pd(OAc)2 in PEG-400 under air. Aryl bromides and triflates react at 35°C, while aryl chlorides require heating to 50°C and give the desired products only in low yields. This reaction proceeds smoothly in acceptable yields using low catalyst loading.
Palladium-catalyzed N-arylsulfonamide formation from arylsulfonyl hydrazides and nitroarenes
Zhao, Feng,Li, Bin,Huang, Huawen,Deng, Guo-Jun
, p. 13010 - 13013 (2016/02/12)
A palladium-catalyzed construction for N-arylsulfonamide from nitroarenes and arylsulfonyl hydrazides is developed. In this protocol, abundant and stable nitroarenes serve as the nitrogen sources by in situ reduction reaction of hydrogen released from arylsulfonyl hydrazides. No external oxidants or reductants are needed for this kind of transformation.
Identification of N -phenyl-2-(N -phenylphenylsulfonamido)acetamides as new RORγ inverse agonists: Virtual screening, structure-based optimization, and biological evaluation
Song, Yu,Xue, Xiaoqian,Wu, Xishan,Wang, Rui,Xing, Yanli,Yan, Weiqun,Zhou, Yulai,Qian, Chao-Nan,Zhang, Yan,Xu, Yong
, p. 13 - 26 (2016/04/19)
Retinoic acid receptor-related orphan receptors (RORs) are ligand-dependent transcriptional factors and members of the nuclear receptor superfamily. RORs regulate inflammation, metabolic disorders and circadian rhythm. RORγ is a promising therapeutic drug
Iron-catalyzed N -arylsulfonamide formation through directly using nitroarenes as nitrogen sources
Zhang, Weixi,Xie, Junyao,Rao, Bin,Luo, Meiming
, p. 3504 - 3511 (2015/04/14)
One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.
Acylative Suzuki coupling of amides: Acyl-nitrogen activation via synergy of independently modifiable activating groups
Li, Xijing,Zou, Gang
supporting information, p. 5089 - 5092 (2015/03/30)
A highly efficient palladium-catalyzed acylative cross-coupling of carboxylic amides with arylboronic acids has been achieved via synergistic activation of the Cacyl-N bond by independently modifiable activating groups. Coupling of amides features not only good functional group tolerance but also modifiable reactivities to overcome steric hindrance. This journal is
Fabrication, characterization and application of nanopolymer supported copper (II) complex as an effective and reusable catalyst for the CN bond cross-coupling reaction of sulfonamides with arylboronic acids in water under aerobic conditions
Nasrollahzadeh, Mahmoud,Rostami-Vartooni, Akbar,Ehsani, Ali,Moghadam, Majid
, p. 123 - 129 (2014/04/03)
This paper reports on the synthesis and use of nanopolymer supported copper (II) complex, as separable catalysts for N-arylation of sulfonamides with arylboronic acids in water. This method has the advantages of high yields, elimination of homogeneous cat
Natural Indian Natrolite zeolite-supported Cu nanoparticles: A new and reusable heterogeneous catalyst for N-arylation of sulfonamides with boronic acids in water under ligand-free conditions
Azarifar, Davood,Soleimanei, Fatemeh
, p. 12119 - 12126 (2014/03/21)
We report here on the preparation of primary sulfonamides and efficient, easily recoverable and reusable copper nanoparticles supported on natural Indian Natrolite zeolite as a catalyst for arylation of sulfonamides with arylboronic acids in water. The catalyst was characterized using the powder XRD, SEM, EDS and FT-IR spectroscopy. The significant advantages of this methodology are high yields, elimination of organic solvents, and simple work-up procedure. The catalyst was easily isolated from the reaction mixture and reused with no significant loss in its activity.
