25692-59-5Relevant articles and documents
Discovery of a novel inhibitor of nitric oxide production with potential therapeutic effect on acute inflammation
Zhu, Long-Qing,Fan, Xiao-Hong,Li, Jun-Fang,Chen, Jin-Hong,Liang, Yan,Hu, Xiao-Ling,Ma, Shu-Meng,Hao, Xiang-Yong,Shi, Tao,Wang, Zhen
supporting information, (2021/05/26)
Inflammation as a host's excessive immune response to stimulation, is involved in the development of numerous diseases. To discover novel anti-inflammatory agents and based on our previous synthetic work on marine natural product Chrysamide B, it and a series of derivatives were synthesized and evaluated for their anti-inflammatory activity on inhibition of LPS-induced NO production. Then the preliminary structure–activity relationships were conducted. Among them, Chrysamide B is the most potent anti-inflammatory agent with low cytotoxicity and strong inhibition on the production of NO (IC50 = 0.010 μM) and the activity of iNOS (IC50 = 0.082 μM) in LPS-stimulated RAW 264.7 cells. Primary studies suggested that the mechanism of action may be that it interfered the formation of active dimeric iNOS but not affected transcription and translation. Furthermore, its good performance of anti-inflammatory effect on LPS-induced multiple inflammatory cytokines production, carrageenan-induced paw edema, and endotoxin-induced septic mice, was observed. We believe that these findings would provide an idea for the further modification and research of these analogs in the future.
Oxiranyl remote anions from epoxy cinnamates and their application towards the synthesis of α,β-epoxy-γ-butyrolactones
Sermmai, Patpanat,Ruangsupapichat, Nopporn,Thongpanchang, Tienthong
supporting information, (2020/11/19)
A series of α,β-epoxy-γ-butyrolactones were synthesized in moderate yields via oxiranyl remote anions derived from epoxy cinnamate esters. The key synthetic step involved deprotonation of the β-position of α,β-epoxy cinnamate derivatives where the generated β-anion was stabilized by remote chelation from an ester group. The substitution reaction of the anion with a variety of ketones, followed by cyclization, readily furnished the desired substituted α,β-epoxy-γ-butyrolactones.
Synthesis and discovery of 18β-glycyrrhetinic acid derivatives inhibiting cancer stem cell properties in ovarian cancer cells
Li, Xiaojing,Liu, Yihua,Wang, Na,Liu, Yuyu,Wang, Shuai,Wang, Hongmin,Li, Aihua,Ren, Shaoda
, p. 27294 - 27304 (2019/09/12)
Despite advances in ovarian cancer treatment, the five-year overall survival rate is less than 30% with the presence of cancer stem cells (CSCs). To develop CSC-targeting therapy, a series of 18β-glycyrrhetinic acid (GA) derivatives containing cinnamamide moiety have been designed, synthesized, and screened for their antiproliferative activity in SKOV3 and OVCAR3 cells. Most of the compounds exhibited stronger antiproliferative activity than GA, and compound 7c was the most active one. Further biological studies showed that compound 7c could induce apoptosis and suppress migration. In addition, compound 7c could not only observably decrease the colony formation and sphere formation ability, but also significantly reduce the CD44+, CD133+, and ALDH+ subpopulation in SKOV3 and OVCAR3 cells. In conclusion, these results indicate that compound 7c is a promising anti-CSC agent for further anti-ovarian cancer studies.
Recyclable Pd ionic catalyst coated on cordierite monolith for high TOF Heck coupling reaction
Bhat, Shrikanth K,Prasad, Jagadeesh D,Hegde
, (2019/02/19)
Abstract : Pd 2 + ionic catalyst, Ti 0.97Pd 0.03O 1.97 was coated over cordierite monolith by solution combustion method. The catalyst coated on the cordierite is nano-crystalline as seen from XRD studies. Coated catalyst was used for Heck coupling reactions with different substrates of aryl halides and olefins. Thus handling nano-crystalline catalyst powder is avoided by fixing it on a solid catalyst cartridge. Heck coupled products were characterized using 1H NMR, 13C NMR, Mass and FTIR spectroscopy. This catalyst showed high selectivity towards Heck coupling reaction. Turnover frequencies (TOF) for each of the reactions were found to be very high. The catalyst was recycled up to 7 times with total TOF 3017 h - 1, which is found to be a new green technique in the Heck coupling reaction. Graphical abstract: Ti 0.97Pd 0.03O 1.97 catalyst is coated on cordierite monolith honeycomb (HC) by solution combustion method and it is used in the Heck coupling reaction. Reactions are done in a specially designed flask. Catalyst is recycled for 7 times. The total turnover frequency (TOF) after 7 cycles was 3017 h - 1. [Figure not available: see fulltext.].
Synthesis and structural characterization for novel mixed-donor ligand palladium (II) based on graphene and oxime: its application as a highly stable and efficient recyclable catalyst
Ashiri, Samira,Mehdipour, Ebrahim
, p. 2383 - 2393 (2018/08/28)
In this article, the palladium (II) mixed-ligand complex synthesized with reduced graphene oxides containing tetraethoxysilane and menthone oxime was used as an efficient solid catalyst for the Heck coupling reaction. To maintain stability and catalytic activity in the C–C bond reaction, graphene was considered due to the available surface as the solid support. Then, the structure of new heterogeneous catalyst was investigated by FT-IR, UV–Vis DRS, FE-SEM, EDX, AFM, XRD, ICP-OES, Raman, and TGA. The newly synthesized nanocatalyst have beneficial properties, including product’s easy separation, the shorter time to react, purity products (yield 79–99%), and easier work-up procedure. Furthermore, the catalyst was reused six times without significant degradation in catalytic activity and performance.
Preparation of a novel palladium catalytic hydrogel based on graphene oxide/chitosan NPs and cellulose nanowhiskers
Ashiri, Samira,Mehdipour, Ebrahim
supporting information, p. 32877 - 32885 (2018/10/15)
The present paper focuses on the synthesis of a novel hydrogel support by combining polysaccharides (chitosan NPs and dialdehyde cellulose nanowhiskers) and graphene oxide nanosheets to obtain a biocompatible material for catalytic applications. The hydrogel was synthesized via green chemistry processes and used as a support to prepare Pd nanoparticles. Finally, the hydrogel@Pd NPs was employed as the catalyst in the Mizoroki-Heck reaction to generate new C-C bonds. SEM analysis indicated that the hydrogel has macroporous morphology, which is in good correlation with its high crosslinking degree. The as-synthesized nanocomposite hydrogel exhibits beneficial properties such as ease of separation and excellent recyclability for at least six cycles without considerable loss in its activity. The yields of the products range from 81% to 98%. Additionally, this study provides the possibility to perform the Mizoroki-Heck reaction with aryl chloride in the presence of the as-prepared catalyst.
An ionic liquid catalyzed probase method for one-pot synthesis of α,β-unsaturated esters from esters and aldehydes under mild conditions
Wang, Gang,Xu, Yiming,Zhang, Suojiang,Li, Zengxi,Li, Chunshan
, p. 4838 - 4848 (2017/10/23)
A one-pot synthesis of α,β-unsaturated esters from unactivated esters and aldehydes using strong bases, such as sodium alkoxide and potassium tert-butoxide, was reported. However, the ionic liquid (IL) catalyzed probase method for producing α,β-unsaturated esters was not reported until now. In this work, a series of ILs with fluoride anions were firstly prepared and used as catalysts in combination with the probase N,O-bis(trimethylsilyl) acetamide (BSA) for the α,β-unsaturated esters synthesis. This process could also be promoted through the introduction of another IL with Lewis acid sites. The yield and selectivity of the product could reach up to 84.2% and 95.0%, respectively, when [Bmim]F was used in combination with [Bmim]Cl/AlCl3 (the molar fraction of AlCl3 is 0.67). The mechanism investigation through GC-MS indicates that BSA would convert into onium amide, which acted as a strong base for α-H abstraction, with the catalysis of [Bmim]F. Meanwhile, [Bmim]Cl/AlCl3 played an important role in the condensation step between enolates and aldehydes. On the basis of mechanism insights, kinetic and thermodynamic studies were also carried out for a better understanding of this new route.
Tetrakis [N-(2-pyridyl) sulfonamide] di palladium: synthesize, X-ray diffraction, antibacterial properties and as a novel binuclear Pd-complex for coupling reactions
Mehdipour, Ebrahim,Shafieyoon, Parvaneh,Salahvarzi, Maryam,Amani, Vahid
, p. 1575 - 1582 (2017/06/06)
The N-(2-pyridyl) 4-toluene sulfonamide as a free ligand (PTS) was prepared from the reaction of 2-amino pyridine and 4-toluenesulfonyl chloride in the presence of potassium hydroxide solution 1?M as a base and THF was used as a solvent. The complex tetrakis [N-(2-pyridyl) sulfonamide] di palladium (1) (Pd2L4) was also prepared from the reaction of PdCl2(CH3CN)2 using (PTS) in the presence of NaOH 0.5?M and its application in Heck and Suzuki reactions. This complex consists of a binuclear unit consisting of four ligands linked to two palladium atoms via the nitrogen of pyridines ring and the nitrogen of sulfonamides. These compounds were confirmed by FT-IR and 1H NMR spectroscopy. Moreover, the structure of the complex was studied by single-crystal X-ray diffraction method. The green crystal of Pd2L4 [L?=?N-(2-pyridyl) sulfonamide](1) was found to crystallize in the monoclinic space group C2/c with a?=?18.2013(19), b?=?19.7544(16), c?=?17.2898(19) ?, β?=?120.179(8) °; V?=?5374.0(9) ?3; Z =?4; the final R1?=?0.0894, wR2?=?0.1754 (or 5867 observed reflections and 318 variables). The Pd–Pd distance is 2.567(2) ?. In addition, PTS and Pd2L4 presented different antibacterial behaviors. The free ligand was active against Staphylococcus aureus and Escherichia coli, but the complex was inactive against them.
A New Mode of Operation of Pd-NHC Systems Studied in a Catalytic Mizoroki-Heck Reaction
Astakhov, Alexander V.,Khazipov, Oleg V.,Chernenko, Andrey Yu.,Pasyukov, Dmitry V.,Kashin, Alexey S.,Gordeev, Evgeniy G.,Khrustalev, Victor N.,Chernyshev, Victor M.,Ananikov, Valentine P.
supporting information, p. 1981 - 1992 (2017/06/14)
Metal complexes bearing N-heterocyclic carbene (NHC) ligands are typically considered the system of choice for homogeneous catalysis with well-defined molecular active species due to their stable metal-ligand framework. A detailed study involving 19 different Pd-NHC complexes with imidazolium, benzimidazolium, and triazolium ligands has been carried out in the present work and revealed a new mode of operation of metal-NHC systems. The catalytic activity of the studied Pd-NHC systems is predominantly determined by the cleavage of the metal-NHC bond, while the catalyst performance is strongly affected by the stabilization of in situ formed metal clusters. In the present study, the formation of Pd nanoparticles was observed from a broad range of metal complexes with NHC ligands under standard Mizoroki-Heck reaction conditions. A mechanistic analysis revealed two different pathways to connect Pd-NHC complexes to "cocktail"-type catalysis: (i) reductive elimination from a Pd(II) intermediate and the release of NHC-containing byproducts and (ii) dissociation of NHC ligands from Pd intermediates. Metal-NHC systems are ubiquitously applied in modern organic synthesis and catalysis, while the new mode of operation revealed in the present study guides catalyst design and opens a variety of novel opportunities. As shown by experimental studies and theoretical calculations, metal clusters and nanoparticles can be readily formed from M-NHC complexes after formation of new M-C or M-H bonds followed by C-NHC or H-NHC coupling. Thus, a combination of a classical molecular mode of operation and a novel cocktail-type mode of operation, described in the present study, may be anticipated as an intrinsic feature of M-NHC catalytic systems.
Suzuki and Heck cross-coupling reactions using ferromagnetic nanoparticle-supported palladium complex as an efficient and recyclable heterogeneous nanocatalyst in sodium dodecylsulfate micelles
Bahrami, Kiumars,Khodaei, Mohammad M.,Meibodi, Farhat Sadat
, (2017/05/22)
A novel heterogeneous Pd catalyst was synthesized by anchoring Pd(II) onto 4′-(4-hydroxyphenyl)-2,2′:6′,2″-terpyridine-coated Fe3O4 (FMNPs@TPy-Pd). This catalyst has been demonstrated for the first time as a recoverable and reusable heterogeneous nanocatalyst in Suzuki and Heck cross-coupling reactions. The catalyst is very easy to handle and is environmentally safe and economical. FMNPs@TPy-Pd was characterized using transmission and scanning electron microscopies, X-ray diffraction, and Fourier transform infrared and energy-dispersive X-ray spectroscopies.
