80-09-1Relevant articles and documents
Sulfonylbis(acylhydrazones) as anticholinesterase inhibitors: Synthesis, in vitro biological evaluation and computational studies
Ahmad, Manzoor,Ahmad, Sajjad,Akbar, Nazia,Al-Harrasi, Ahmed,Ali, Akbar,Ali, Mumtaz,Ibrahim, Muhamad,Khan, Ajmal,Latif, Abdul,Saadiq, Mohammad,Siddique, Abu Bakar,farooq, Umar
, (2022/01/03)
This current research work is focused on the synthesis of sulfonyl-mediated hydrazones, its exploration as anticholinesterase inhibitors, in vitro biological evaluation, and computational studies. A series of 21 novel bis(acylhydrazones) (4a-u) have been synthesized in good to excellent yields using 4,4?-sulfonyldiphenol as the precursor. Characterization of the synthesized compounds was achieved via spectroscopic techniques i.e. UV, FT-IR, NMR (1H and 13C), and HRMS. In vitro anticholinesterase activity of these compounds was performed using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) as cholinesterase enzymes. Among all the compounds tested, compounds 4 g and 4 h were found to be the most significant AChE inhibitions with IC50 values of 101.4 and 102.7 μM as compared to the standard cholinesterase inhibitor i.e., galantamine (IC50 = 104.5 μM). Additionally, compound 4 g was also found to be an excellent inhibitor of BChE with an IC50 value of 136.0 μM as compared to the standard galantamine (IC50 = 156.8 μM). Molecular docking of the most active compounds 4 g and 4 h also supported their potential to interact with cholinesterase enzymes. Further affirmation on the intermolecular stability of the docked complexes was achieved by molecular dynamics simulation for 100 ns with mean deviations ～2 ?. Residue level fluctuations analysis also interpreted the good stability of compounds interacting pocket residues. Lastly, binding free energy analysis was performed that decipher the intermolecular interactions that are dominated by both van der Waals and electrostatic energies. In short, both theoretical and experimental studies unveiled the compounds as potent blockers of cholinesterase enzymes.
One-step hydroxylation of aryl and heteroaryl fluorides using mechanochemistry
Braje, Wilfried,Geneste, Hervé,Rodrigo, Eduardo,Walter, Magnus W.,Wiechert, Rainer
supporting information, p. 1469 - 1473 (2022/03/07)
Simple use of KOH allows the direct F to OH exchange of aromatic and heteroaromatic substrates under mechanochemical conditions. The reaction is performed in the absence of solvent with potassium hydroxide as OH source. As a result, this approach is both more atom economical and environmentally friendly than previously described methods for this transformation.
Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide
Cao, Zhong-Yan,Li, Xiaolong,Lu, Hao,Wang, Panpan,Wang, Shengqiang,Xu, Xiaobo,Yan, Leyu,Yang, A-Xiu
supporting information, p. 8691 - 8695 (2021/10/22)
A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.
Macrocyclic sulfone derivatives: Synthesis, characterization, in vitro biological evaluation and molecular docking
Ibrahim, Muhammad,Latif, Abdul,Ammara,Ali, Akbar,Ribeiro, Alany Ingrid,Farooq, Umar,Ullah, Farhat,Khan, Ajmal,Al-Harrasi, Ahmed,Ahmad, Manzoor,Ali, Mumtaz
, p. 562 - 574 (2020/12/25)
An artificial series of macrocycles based on 4,4′-sulfonyldiphenol intermediate was synthesized using a multistep procedure involving oxidation of bisphenol sulfide, etherification of phenolic hydroxyl groups, and final ring closure with different diamines. Different chemical species having aromatic, heteroaromatic, and aliphatic characters were incorporated into macrocyclic frameworks in the final step of ring closure. This simple and easily executable synthetic strategy was applied to synthesize 15 macrocycles (5a-o) in excellent yields. Characterization of the synthesized products was achieved through well-known modern spectroscopic techniques such as IR, NMR, and Mass. Macrocycles 5m and 5n were found to show significant AChE inhibition with IC50 values of 76.9 ± 0.24 and 71.2 ± 0.77 μM, respectively. Macrocycle 5n was also found to be an active inhibitor of butyrylcholinesterase (BChE) with IC50 score of 55.3 ± 0.54 μM. Among others, macrocycle 5l cyclized with o-phenylenediamine demonstrated moderate inhibition with IC50 value of 81.1 ± 0.54 μM. Increasing interest in studying interactions of macrocycles with different enzymatic targets compelled us to design and synthesize sulfone-based macrocycles that might prove as highly potent class of biologically active compounds.
Preparation process of low-cost and environment-friendly bisphenol S
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Paragraph 0034-0038; 0046-0050; 0058-0062, (2021/11/26)
The invention discloses a preparation process of bisphenol S with low cost and environmental protection. When the corrosion-resistant paint is sprayed into the interior of the reaction kettle, N atoms and O atoms of the reinforcing filler can interact with the metal ions to form a chelate. The acid resistance of the reaction kettle is higher, and the preparation cost is further reduced.
Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
, p. 2447 - 2458 (2020/04/15)
A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
A biradical oxo-molybdenum complex containing semiquinone and: o -aminophenol benzoxazole-based ligands
Galindo, Agustín,Jagli?i?, Zvonko,Masoumpour, Marzieh Sadat,Nasibipour, Mina,Safaei, Elham,Wojtczak, Andrzej
, p. 40853 - 40866 (2020/11/23)
We report a new mononuclear molybdenum(iv) complex, MoOLBISLSQ, in which LSQ (2,4-di-tert-butyl o-semibenzoquinone ligand) has been prepared from the reaction of the o-iminosemibenzoquinone form of a tridentate non-innocent benzoxazole ligand, LBIS, and MoO2(acac)2. The complex was characterized by X-ray crystallography, elemental analysis, IR and UV-vis spectroscopy and magnetic susceptibility measurements. The crystal structure of MoOLBISLSQ revealed a distorted octahedral geometry around the metal centre, surrounded by one O and two N atoms of LBIS and two O atoms of LSQ. The effective magnetic moment (μeff) of MoOLBISLSQ decreased from 2.36 to 0.2 μB in the temperature range of 290 to 2 K, indicating a singlet ground state caused by antiferromagnetic coupling between the metal and ligand centred unpaired electrons. Also, the latter led to the EPR silence of the complex. Cyclic voltammetry (CV) studies indicate both ligand and metal-centered redox processes. MoOLBISLSQ was applied as a catalyst for the oxidative cleavage of cyclohexene to adipic acid and selective oxidation of sulfides to sulfones with aqueous hydrogen peroxide. This journal is
Sulfoxidation inside a hypercrosslinked microporous network nanotube catalyst
Shi, Zhaocheng,Ying, Zhong,Yang, Liusai,Meng, Xiaoyan,Wu, Lidan,Yu, Leshu,Huang, Sen,Xiong, Linfeng
supporting information, p. 1542 - 1547 (2020/02/06)
In the present work, a kind of efficient heterogeneous catalyst was synthesized from amine-functionalized hypercrosslinked bottlebrush copolymers of microporous network nanotubes (amine-MNNs) and Na2WO4. The synthesized tungstate-supported microporous network nanotubes (TMNNs) catalyst was shown to be highly active in the selective H2O2 oxidation of sulfides to sulfoxides or sulfones under mild conditions due to the high specific surface area (800 m2 g-1) and firm structure of the nanotubes. The catalyst was found to be very stable and could be recycled at least 8 times without any significant loss of activity. These results present a new opportunity for the development of efficient green organic catalytic materials with high activity.
Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
, p. 3048 - 3055 (2019/03/21)
A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.
Palladium-catalyzed one-step synthesis of symmetrical diaryl sulfones from aryl halides and a sulfur dioxide surrogate
Tanaka, Hiromichi,Konishi, Hideyuki,Manabe, Kei
supporting information, p. 760 - 763 (2019/08/02)
A convenient method for the one-step synthesis of symmetrical diaryl sulfones from aryl halides has been developed. A keystone of the method is the use of K2S2O5, which can be easily and safely handled, as a sulfur dioxide surrogate. The palladium catalyst bearing P(t-Bu)3 as a ligand enables formation of the desired sulfones without significant formation of byproducts.
