- A highly selective dual-channel chemosensor for mercury ions: Utilization of the mechanism of intramolecular charge transfer blocking
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In this study, we developed a novel chemosensor (ATS) that contains the 5-(4-nitrophenyl)-2-furan group and α-naphthylamine for the dual-channel sensing of mercury ions. Under attack from mercury ions, the probe undergoes a blocked process; moreover, it broke the intramolecular charge transfer (ICT) state of the chemosensor, which can be confirmed by 1H NMR, IR and MS studies. We designed this probe to produce a significant change in the color and fluorescence intensity that can achieve naked eye recognition. The experimental results proved that the 5-(4-nitrophenyl)-2-furan group is a very good chromophore. In addition, the ICT state inhibited the fluorescence of naphthylamine. The fluorescent intensity changed significantly when naphthylamine was released. Moreover, high selectivity experiments revealed that the fluorescent sensor is specific to mercury ions even with interference by high concentrations of other metal ions. The test strips based on ATS were fabricated, which could act as a convenient and efficient mercury ion test kit. This journal is
- Zhang, You Ming,Qu, Wen Juan,Gao, Guo Ying,Shi, Bing Bing,Wu, Gui Yuan,Wei, Tai Bao,Lin, Qi,Yao, Hong
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- A rational designed dual-channel chemosensor for mercury ions based on hydrolysis of Schiff base
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A bilateral Schiff base is reported for the colorimetric and fluorometric dual-channel sensing of Hg2+ ions by taking advantage of the hydrolysis of carbon-nitrogen double bond, altering an ICT state mechanism and then Hg2+ ions coordinating with amino moieties of 1,5-DAN and leading to the aggregation of 1,5-DAN. Meanwhile, it formed a stable neutral complex of amino-Hg-amino. In addition, test strips based on L were fabricated, which also exhibited a good selectivity to Hg2+ as in solution. This work provides a novel approach for the selective recognition of mercury ions. Notably, the color changes are very significant and all the recognition processes can be observed by the naked eyes. We believe the test strips can act as a convenient and efficient Hg2+ test kit. Copyright
- Wu, Guiyuan,Shi, Bingbing,Hu, Bing,Zhang, Youming,Lin, Qi,Yao, Hong,Wei, Taibao
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- New calamitic mesogens derived from a furan ring: Synthesis, characterization and study of their mesomorphic behavior
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A new series of mesogens bearing furan moiety, 4-[((5-(4-nitrophenyl)furan-2-yl)methylene)amino]phenyl 4-alkoxybenzoate (Ca-k) was synthesized by different organic methodologies. These mesogens possess an alkoxy chain at one arm and a nitro group at the opposite arm in addition to various linkages (imine and ester). Their chemical structures have been identified by various essential characterization techniques: infrared spectroscopy (FTIR), 1H and 13C nuclear magnetic resonance (NMR), and electron ionization-mass spectrometer (EI-MS). The thermal transition and optical behavior properties of the homologous series have been studied by differential scanning calorimetry (DSC) and a polarizing optical microscope (POM), respectively. The compounds of this series (Ca-Ck) displayed liquid crystalline phases, and all mesogens exhibited an enantiotropic nematic phase (N) in heating and cooling cycles except the compounds (Cd, Ce and Cf), which showed a monotropic nematic phase in the cooling cycle only. Additionally, the last member of this series (Ck) showed a smectic A (SmA) phase in addition to the nematic phase. The obtained results showed that the enantiotropic and monotropic mesogenic properties, in addition to the thermal stability of the mesophase for all mesogens, have been influenced thoroughly by increasing the number of carbon atoms in the terminal alkoxy tail and the nitro group on the other side. In addition to these results, these mesogens could be affected by other factors, such as polarity and polarizability of the linkages and other connected groups in the molecules. The liquid crystalline behaviors of the target compounds have been studied and discussed extensively and compared structurally in related literature.
- Abdulnabi, Nabih M.,Abdul Razzaq Al-Obaidy, Mazin M.,Tomi, Ivan Hameed R.,Jaffer, Hamed Jasim
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Read Online
- Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
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Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.
- Gou, Kun,Luo, Youfu,Luo, Yuan,Sun, Qingxiang,Tan, Yuping,Tao, Lei,Zhao, Yinglan,Zhou, Xia,Zhou, Yue,Zuo, Zeping
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- Design, synthesis, and biological activity of novel semicarbazones as potent Ryanodine receptor1 inhibitors of Alzheimer's disease
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Ryanodine receptors (RyRs) are important ligand-gated Ca2+ channels; their excessive activation leads to Ca2+ leakage in the sarcoplasmic reticulum that may cause neurological diseases. In this study, three series of novel potent RyR1 inhibitors based on dantrolene and bearing semicarbazone and imidazolyl moieties were designed and synthesized, and their biological activity was evaluated. Using a single-cell calcium imaging method, the calcium overload inhibitory activities of 26 target compounds were tested in the R614C cell line, using dantrolene as a positive control. The preliminary investigation showed that compound 12a suppressed Ca2+ release as evidenced by store overload-induced Ca2+release (SOICR) (31.5 ± 0.1%, 77.2 ± 0.1%, 93.7 ± 0.2%) at 0.1 μM, 3 μM and 10 μM, respectively. Docking simulation results showed that compound 12a could bind at the active site of the RyR1 protein. The Morris water-maze test showed that compound 12a significantly improved the cognitive behavior of AD-model mice. Further studies on the structural optimization of this series of derivatives are currently underway in our laboratory.
- Dai, Baozhu,Ma, Xingxing,Tang, Yadong,Xu, Le,Guo, Su,Chen, Xinyan,Lu, Shitong,Wang, Guangjie,Liu, Yajing
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- Carbon–Carbon Bond Formation for the Synthesis of 5-Aryl-2-Substituted Furans Catalyzed by K3[Fe(CN)6]
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An efficient method for the carbon–carbon bond formation at C-5 position of 2-substituted furans to provide a range of π-diverse 5-aryl-2-substituted furan derivatives in 58–80% yield has been reported. The method employs several advantages such as use of catalytic amount of K3[Fe(CN)6] under mild conditions and short reaction time with high yields. Also, a variety of anilines with a variety of functional groups can be employed for the synthesis of 5-aryl-2-substituted furans. Graphic Abstract: [Figure not available: see fulltext.]
- Ambika,Singh, Pradeep Pratap
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- Benzimidazole-based turn-on fluorescence probe developed for highly specific and ultrasensitive detection of hypochlorite ions in living cells
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Hypochlorite (ClO?), as one of the active oxygen species (ROS), plays an essential role in the cellular defence system and organism immunity. In this paper, we successfully synthesized a new ‘turn-on’ fluorescent probe BMF based on benzimidazole and characterized it by spectroscopic methods. The designed probe can quickly respond to ClO? with the obvious colour change from pink to colourless. Notably, the probe BMF exhibited almost no fluorescence, but showed strong fluorescence after adding ClO?, including an excellent fluorescence turn-on effect. The fluorescence turn-on phenomenon of BMF was attributed to the strong oxidation of ClO?, which severed the connecting double bond and disrupted the intramolecular charge transfer (ICT) system, plus light-induced electron transfer effect between the fluorophore and the recognition group was discontinued. In addition, the cytotoxicity assay showed that the probe had lower cytotoxicity. Based on these advantages, we demonstrated that probe BMF might be a good candidate for detecting ClO? in biological systems.
- Yang, Yi,Cheng, Siyao,Dong, Wei
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p. 1377 - 1384
(2021/05/05)
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- Synthesis and Biological Evaluation of Dantrolene-Like Hydrazide and Hydrazone Analogues as Multitarget Agents for Neurodegenerative Diseases
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Dantrolene, a drug used for the management of malignant hyperthermia, had been recently evaluated for prospective repurposing as multitarget agent for neurodegenerative syndromes, including Alzheimer's disease (AD). Herein, twenty-one dantrolene-like hydrazide and hydrazone analogues were synthesized with the aim of exploring structure-activity relationships (SARs) for the inhibition of human monoamine oxidases (MAOs) and acetylcholinesterase (AChE), two well-established target enzymes for anti-AD drugs. With few exceptions, the newly synthesized compounds exhibited selectivity toward MAO B over either MAO A or AChE, with the secondary aldimine 9 and phenylhydrazone 20 attaining IC50 values of 0.68 and 0.81 μM, respectively. While no general SAR trend was observed with lipophilicity descriptors, a molecular simplification strategy allowed the main pharmacophore features to be identified, which are responsible for the inhibitory activity toward MAO B. Finally, further in vitro investigations revealed cell protection from oxidative insult and activation of carnitine/acylcarnitine carrier as concomitant biological activities responsible for neuroprotection by hits 9 and 20 and other promising compounds in the examined series.
- Bolognino, Isabella,Giangregorio, Nicola,Tonazzi, Annamaria,Martínez, Antón L.,Altomare, Cosimo D.,Loza, María I.,Sablone, Sara,Cellamare, Saverio,Catto, Marco
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p. 2807 - 2816
(2021/06/27)
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- Direct (Hetero)arylation of Heteroarenes Catalyzed by Unsymmetrical Pd-PEPPSI-NHC Complexes under Mild Conditions
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With the aim of developing a facile and efficient method to access structurally intriguing and valuable functionalized (hetero)aryls, two unsymmetrical Pd-PEPPSI-type NHC complexes (PEPPSI, pyridine-enhanced precatalyst preparation, stabilization, and initiation; NHC, N-heterocyclic carbene) were designed and synthesized to catalyze the direct arylation of heteroarenes with (hetero)aryl bromides. The results demonstrated that the utilization of this "unsymmetrical"strategy led to much higher efficiency in comparison to the commonly used C2-symmetric Pd-PEPPSI-type NHC complexes. Furthermore, a broad range of heteroaromatics and (hetero)aryl bromide partners with a wide variety of functional groups were all amenable to the developed protocol even at as low as 0.05 mol % catalyst loading and under aerobic conditions. More importantly, along with our study, we also found that the present protocol could provide expedient access to the gram-scale synthesis of the muscle relaxant drug dantrolene and conjugated mesopolymers.
- Song, A-Xiang,Zeng, Xiao-Xiao,Ma, Bei-Bei,Xu, Chang,Liu, Feng-Shou
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p. 3524 - 3534
(2020/10/09)
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- Preparation method of dantrolene
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The invention provides a preparation method of dantrolene. The method comprises the following steps of preparation of 5-p-nitrophenyl furfural: adding cuprous chloride, an acidic reagent, trimethyl orthoformate, sodium nitrite and furfural with 4-nitroaniline serving as a raw material at a reaction temperature of 30-50 DEG C for 16-20 hours by adopting a one-pot method and generating 5-p-nitrophenyl furfural through the steps of extraction, distillation and the like, and preparation of dantrolene: subjecting 5-p-nitrophenyl furfural and 1-aminohydantoin to a condensation reaction in a reactionsolvent so as to obtain the final product dantrolene. According to the method, cheap 4-nitroaniline is used as a raw material, and the high-yield dantrolene is finally obtained through two reaction steps. The whole reaction is simple and suitable for industrial production, good social benefits and economic benefits can be brought, and the economic value potential is large.
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Paragraph 0033; 0034
(2020/07/24)
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- Carbazole based Electron Donor Acceptor (EDA) catalysis for the synthesis of biaryl and aryl-heteroaryl compounds
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A highly regioselective, carbazole based Electron Donor Acceptor (EDA) catalyzed synthesis of biaryl and aryl-heteroaryl compounds is described. Various indole and carbazole derivatives were screened for the Homolytic Aromatic Substitution (HAS) reaction. Tetrahydrocarbazole (THC) was very efficient for the HAS transformation and proceeded via a complex formation between diazonium salt and electron rich tetrahydrocarbazole. The UV-Vis spectroscopy technique has been used to confirm the complex formation. The in situ generated EDA complex even in a catalytic amount is found to be efficient for the Single Electron Transfer (SET) process without any photoactivation. Biaryl compounds, 2-phenylfuran, 2-phenylthiophene, and 2-phenylpyrrole and bioactive compounds such as dantrolene and canagliflozin have been synthesized in moderate to excellent yields.
- Annes, Sesuraj Babiola,Ramesh, Subburethinam,Saravanan, Subramanian,Saritha, Rajendhiran
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supporting information
p. 2510 - 2515
(2020/04/15)
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- Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties
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A virtual screening campaign aimed at finding structurally new compounds active at 5-HT6R provided a set of candidates. Among those, one structure, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (1, 5-HT6R Ki = 91 nM), was selected as a hit for further optimization. As expected, the chemical scaffold of selected compound was significantly different from all the serotonin receptor ligands published to date. Synthetic efforts, supported by molecular modelling, provided 43 compounds representing different substitution patterns. The derivative 42, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (5-HT6R Ki = 25, 5-HT2AR Ki = 32 nM), was selected as a lead and showed a good brain/plasma concentration profile, and it reversed phencyclidine-induced memory impairment. Considering the unique activity profile, the obtained series might be a good starting point for the development of a novel antipsychotic or antidepressant with pro-cognitive properties.
- Staroń, Jakub,Kurczab, Rafa?,Warszycki, Dawid,Sata?a, Grzegorz,Krawczyk, Martyna,Bugno, Ryszard,Lenda, Tomasz,Popik, Piotr,Hogendorf, Adam S.,Hogendorf, Agata,Dubiel, Krzysztof,Mat?oka, Miko?aj,Moszczyński-P?tkowski, Rafa?,Pieczykolan, Jerzy,Wieczorek, Maciej,Zajdel, Pawe?,Bojarski, Andrzej J.
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supporting information
(2019/11/28)
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- Structure-based discovery of new selective small-molecule sirtuin 5 inhibitors
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Human sirtuin 5 (SIRT5) is a protein deacylase regulating metabolic pathways and stress responses and is implicated in metabolism-related diseases. Small-molecule inhibitors for SIRT5 are sought as chemical tools and potential therapeutics. Herein, we proposed a customized virtual screening approach targeting catalytically important and unique residues Tyr102 and Arg105 of SIRT5. Of the 20 tested virtual screening hits, six compounds displayed marked inhibitory activities against SIRT5. For the hit compound 19, a series of newly synthesized (E)-2-cyano-N-phenyl-3-(5-phenylfuran-2-yl)acrylamide derivatives/analogues were carried out structure–activity relationship analyses, resulting in new more potent inhibitors, among which 37 displayed the most potent inhibition to SIRT5 with an IC50 value of 5.59?±?0.75?μM. The biochemical studies revealed that 37 likely acts via competitive inhibition with the succinyl-lysine substrate, rather than the NAD+ cofactor, and it manifested substantial selectivity for SIRT5 over SIRT2 and SIRT6. This study will aid further efforts to develop new selective SIRT5 inhibitors as tools and therapeutics.
- Liu, Sha,Ji, Sen,Yu, Zhu-Jun,Wang, Hua-Li,Cheng, Xu,Li, Wei-Jian,Jing, Li,Yu, Yamei,Chen, Qiang,Yang, Ling-Ling,Li, Guo-Bo,Wu, Yong
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p. 257 - 268
(2017/12/29)
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- Continuous Visible-Light Photoflow Approach for a Manganese-Catalyzed (Het)Arene C?H Arylation
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Manganese photocatalysts enabled versatile room-temperature C?H arylation reactions by means of continuous visible-light photoflow, thus allowing for efficient C?H arylations in 30 minutes with ample scope. The robustness of the manganese-catalyzed photoflow strategy was shown by visible light-induced gram-scale synthesis, clearly outperforming the batch performance.
- Liang, Yu-Feng,Steinbock, Ralf,Yang, Long,Ackermann, Lutz
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supporting information
p. 10625 - 10629
(2018/08/01)
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- 5-Aryl-2-furaldehydes in the synthesis of tetrahydropyrimidinones by Biginelli reaction
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5-Aryl-2-furaldehydes, obtained by furfural arylation with arenediazonium salts, react with ethyl acetoacetate or acetylacetone and (thio)- urea in the presence of FeCl3·6H2O as a catalyst. A series of ethyl 4-(5-aryl-2-furyl)-6-methyl-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine- 5-carboxylates was obtained.
- Vakhula, Andriy R.,Horak, Yuriy I.,Lytvyn, Roman Z.,Lesyuk, Alexandra I.,Kinzhybalo, Vasyl,Zubkov, Fedor I.,Obushak, Mykola D.
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p. 545 - 549
(2018/07/05)
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- Discovery of selective protein arginine methyltransferase 5 inhibitors and biological evaluations
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Protein arginine methyltransferase 5 (PRMT5) is an important protein arginine methyltransferase that catalyzes the symmetric dimethylation of arginine resides on histones or non-histone substrate proteins. It has been thought as a promising target for many diseases, particularly cancer. Despite the potential applications of PRMT5 inhibitors in cancer treatment, very few of PRMT5i have been publicly reported. In this investigation, virtual screening and structure–activity relationship studies were carried out to discover novel PRMT5i, which finally led to the identification of a number of new PRMT5i. The most active compound, P5i-6, exhibited a considerable inhibitory potency against PRMT5 with an IC50 value of 0.57?μm, and a high selectivity for PRMT5 against other tested PRMTs. It displayed a very good antiviability activity against two colorectal cancer cell lines, HT-29 and DLD-1, and one hepatic cancer cell line, HepG2, in a sensitivity assay against 36 different cancer cell lines. Western blot assays indicated that P5i-6 selectively inhibited the symmetric dimethylations of H4R3 and H3R8 in DLD-1 cells. Overall, P5i-6 could be used as a chemical probe to investigate new functions of PRMT5 in biology and also served as a good lead compound for the development of new PRMT5-targeting therapeutic agents.
- Ji, Sen,Ma, Shuang,Wang, Wen-Jing,Huang, Shen-Zhen,Wang, Tian-Qi,Xiang, Rong,Hu, Yi-Guo,Chen, Qiang,Li, Lin-Li,Yang, Sheng-Yong
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p. 585 - 598
(2017/04/06)
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- Direct C–H Arylation of Heteroarenes with Aryl Chlorides by Using an Abnormal N-Heterocyclic-Carbene–Palladium Catalyst
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Herein, we report a versatile catalytic system for the direct C–H arylation of heteroarenes with activated aryl chloride substrates. The catalyst works successfully for a variety of heteroarenes and aryl chloride coupling partners under very low catalyst-loading conditions. We have successfully performed the direct C–H arylations of 1-methylpyrrole, 1-methylindole, furan, thiophene, furfural, and N-benzyl-1,2,3-triazole with aryl chloride partners in good yields without the use of any additives. Furthermore, we used this catalytic process to develop a one-pot synthetic protocol for the muscle relaxant dantrolene on a gram scale. Additionally, the present catalytic system can be used to perform consecutive arylations in one pot.
- Ahmed, Jasimuddin,Sau, Samaresh Chandra,Sreejyothi,Hota, Pradip Kumar,Vardhanapu, Pavan K.,Vijaykumar, Gonela,Mandal, Swadhin K.
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supporting information
p. 1004 - 1011
(2017/02/15)
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- Multicomponent one pot synthesis and characterization of novel 4-furyl-1,4-dihydropyridines
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A series of dihydropyridines were prepared from the multi-component reaction of 5-arylfuran-2-carbaldehydes, ethylacetoacetate and ammonium acetate. These compounds were characterized through elemental analysis and various spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass).
- Zafar, Ansa Madeeha,Aslam, Samina,Khakwani, Samia,Khan, Muhammad Naeem,Munawar, Munawar Ali,Khan, Misbahul Ain
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p. 735 - 741
(2017/02/10)
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- Blue light mediated C-H arylation of heteroarenes using TiO2 as an immobilized photocatalyst in a continuous-flow microreactor
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Titanium dioxide was applied as an immobilized photocatalyst in a microstructured falling film reactor for the continuous-flow C-H arylation of heteroarenes with aryldiazonium salts as the starting material. Detailed investigations of the catalyst and a successful long-term run proved its excellent usability for this process. Very good yields up to 99% were achieved with broad substrate scope and were compared with batch synthesis. The transfer to the continuous-flow mode revealed an impressive boost in reactor performance solely resulting from the improved irradiation and contact of the catalyst, substrate and light.
- Fabry, David C.,Ho, Yee Ann,Zapf, Ralf,Tremel, Wolfgang,Panth?fer, Martin,Rueping, Magnus,Rehm, Thomas H.
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supporting information
p. 1911 - 1918
(2017/06/09)
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- Unexpected dual role of titanium dioxide in the visible light heterogeneous catalyzed C-H arylation of heteroarenes
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The direct arylation of heteroaromatics with an easily accessible and recyclable, heterogeneous TiO2 catalyst and visible light was developed. Electron-rich as well as electron-poor heteroarenes could be applied in this transformation, and the corresponding products were isolated in very good yields. Azoethers were detected as reactive intermediates, and the unexpected role of TiO2 in their formation as well as reaction was established.
- Zoller, Jochen,Fabry, David C.,Rueping, Magnus
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p. 3900 - 3904
(2015/06/16)
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- Polyaniline-Induced C-H Arylation of Arenes with Arenediazonium Salts
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A reduced form of polyaniline has been shown to induce direct arylation of an arenediazonium salt with an arene (Gomberg-Bachmann reaction) to give the cross-coupling product in moderate to good yields under mild conditions. Various arenediazonium salts and arenes, including heteroarenes such as furans, thiophenes, and pyrroles, are employed for the reaction. The most favorable combination of substrates is an electron-poor arenediazonium salt with an electron-rich heteroarene. Investigation of the mechanism by reactions with radical scavengers and experiments on kinetic isotope effects indicated the occurrence of a radical chain reaction initiated by one-electron reduction of an arenediazonium salt by the polyaniline. Only 1 mol % (based on aniline tetramer) of the polyaniline is required for the cross-coupling reaction to occur. This reaction proceeds under metal-free conditions and with no need for photonic activation.
- Amaya, Toru,Hata, Dai,Moriuchi, Toshiyuki,Hirao, Toshikazu
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p. 16427 - 16433
(2015/11/10)
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- Synthesis and biological evaluation of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-ones as IKK2 inhibitors
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In a search for novel molecules to treat inflammatory disorders, we identified several compounds with inhibitory action against the IKK2 enzyme using in silico methods. Based on the virtual hit of compounds 1 and 2, a novel series of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-one derivatives was designed, synthesized, and evaluated for IKK2 inhibitory activity. Among the synthesized derivatives, compounds 17f and 19f showed good IKK2 inhibitory potency, which have 4-carboxaminophenyl on the 2-furan ring and a methoxy group on the phenylimino moiety at the 2-position of the core structure. The most potent compound was 2-(2,4-dimethoxyphenyl)imino-5((5(4-carboxaminophenyl)furan-2-yl)methylene)thiazolidin-4-one (19f, IC50 = 0.94 μM), which represents a synergic effect of the two virtual hit compounds against IKK2. We also identified compounds showing inhibitory activities against interleukin (IL)-17, CCK-8, and tumor necrosis factor-alpha (TNF-α), which are NF-κB-dependent pro-inflammatory cytokine mediators.
- Kim, Hee Sook,Shin, Min Jae,Lee, Byungho,Oh, Kwang-Seok,Choo, Hyunah,Pae, Ae Nim,Roh, Eun Joo,Nam, Ghilsoo
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p. 2621 - 2626
(2015/11/16)
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- Colorimetric probes designed to provide high sensitivity and single selectivity for CN- in aqueous solution
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The specific colorimetric detection of CN- in the context of interference from coexisting anions, such as F-, AcO-, and H2PO4-, in aqueous solutions is still a challenge. Therefore, easily-made CN- colorimetric probes L1-L4 bearing hydrazone moieties as the binding sites and nitrophenylfuran moieties as the signal groups were designed and synthesized. Probe L1 showed excellent colorimetric single selectivity and sensitivity for CN- in DMSO/H2O solution. When CN- was added to the solution of L1, a dramatic color change from yellow to violet was observed, while the anions F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4- and ClO4- did not interfere with the recognition process for CN-. The detection limits of CN- were 8 × 10-5 and 5 × 10-6 mol L-1 according to the visual color changes and UV-vis changes, respectively.
- Zhu, Xin,Lin, Qi,Lou, Jin-Chao,Lu, Tao-Tao,Zhang, You-Ming,Wei, Tai-Bao
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p. 7206 - 7210
(2015/09/02)
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- Light-Induced C-H Arylation of (Hetero)arenes by in Situ Generated Diazo Anhydrides
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Diazo anhydrides (Ar-N=N-O-N=N-Ar) have been known since 1896 but have rarely been used in synthesis. This communication describes the development of a photochemical catalyst-free C-H arylation methodology for the preparation of bi(hetero)aryls by the one-pot reaction of anilines with tert-butyl nitrite and (hetero)arenes under neutral conditions. The key step in this procedure is the in situ formation and subsequent photochemical (>300 nm) homolytic cleavage of a transient diazo anhydride intermediate. The generated aryl radical then efficiently reacts with a (hetero)arene to form the desired bi(hetero)aryls producing only nitrogen, water, and tert-butanol as byproducts. The scope of the reaction for several substituted anilines and (hetero)arenes was investigated. A continuous-flow protocol increasing selectivity and safety has been developed enabling the experimentally straightforward preparation of a variety of substituted bi(hetero)aryls within 45 min of reaction time.
- Cantillo, David,Mateos, Carlos,Rincon, Juan A.,De Frutos, Oscar,Kappe, C. Oliver
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supporting information
p. 12894 - 12898
(2015/09/07)
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- Synthesis of 12-hetaryl-9,9-dimethyl-7,8,9,10-tetrahydrobenzo[a]acridin- 11(12H)-ones
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Three-component condensation of naphthalen-2-amine with 5-arylfuran(thiophene, N-methylpyrrole)-2-carbaldehyde and 5,5- dimethylcyclohexane-1,3-dione, as well as condensation of N-[(5- arylfuran(thiophen)-2-ylmethylidene]naphthalen-2-amine with 5,5- dimethylcyclohexane-1,3-dione gave the corresponding 12-[5-arylfuran(thiophen, N-methylpyrrol)-2-yl]-7,8,9,10-tetradrobenzo[a]acridin-11(12H)-ones.
- Kozlov,Zhikharko,Lytvyn,Gorak,Skakovskii,Baranovskii,Basalaeva,Obushak
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p. 833 - 839
(2014/08/18)
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- Ascorbic acid as an initiator for the direct C-H arylation of (hetero)arenes with anilines nitrosated in situ
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Ascorbic acid (vitaminC) has been used as a radical initiator in a metal-free direct C-H arylation of (hetero)arenes. Starting from an aniline, the corresponding arenediazonium ion is generated in situ and immediately reduced by vitaminC to an aryl radical that undergoes a homolytic aromatic substitution with a (hetero)arene. Notably, neither heating nor irradiation is required. This procedure is mild, operationally simple, and constitutes a greener approach to arylation. Copyright
- Crisostomo, Fernando Pinacho,Martin, Tomas,Carrillo, Romen
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supporting information
p. 2181 - 2185
(2014/03/21)
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- Synthesis and antioxidant activity study of pyrazoline carrying an arylfuran/arylthiophene moiety
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A novel series of N-acetyl-3-aryl-5-(5-(p/o-nitrophenyl)-2-furyl/ /thienyl)-substituted pyrazolines (3a-o) were synthesized by the reaction of 1-aryl-3-(5-(p/o-nitrophenyl)-2-furyl/thienyl)-2-propene-1-ones with hydrazine hydrate in acetic acid medium. The structures of the newly synthesized compounds were established by IR, 1 H-NMR, mass spectra and a single-crystal X-ray study. The antioxidant activities of the synthesized compounds were determined using the DPPH scavenging assay. The compounds 3a, 3f, 3h and 3o showed moderate activity.
- Jois, Vidyashree H. S.,Kalluraya, Balakrishna,Girisha, Kotathattu S.
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p. 1469 - 1475
(2015/03/03)
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- Synthesis and biological evaluation of nitromethylene neonicotinoids based on the enhanced conjugation
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The neonicotinoids with a nitroconjugated system had excellent bioactivity, which could rival imidacloprid, and has been previously reported. However, the photodegradation and hydrolysis of this series of neonicotinoids was very quick according to our further investigation, which cannot be developed as a pesticide further. The approach to further enhance the conjugation was tried not only to increase the bioactivities but also to improve the stability in water and in the sun. A substituted phenyl group was introduced into the furan ring of compound 3. A total of 13 novel neonicotinoid analogues with a higher conjugation system were designed and synthesized. The target molecular structures have been confirmed on the basis of satisfactory analytical and spectral data. All compounds presented significant insecticidal activities on cowpea aphid (Aphis craccivora), cotton aphid (Aphis gossypii), and brown planthopper (Nilaparvata lugens). The stability test exhibited that the stability of novel analogues in water and under the mercury lamp has been improved significantly in comparison to compound 3.
- Lu, Siyuan,Zhuang, Yingying,Wu, Ningbo,Feng, Yue,Cheng, Jiagao,Li, Zhong,Chen, Jie,Yuan, Jing,Xu, Xiaoyong
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p. 10858 - 10863
(2014/01/06)
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- A reversible fluorescent chemosensor for mercury ions based on 1H-imidazo[4,5-b]phenazine derivatives
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A series of non-sulfur, fluorescent sensors (S6, S6-1 or S6-2) for mercury ions bearing 1H-imidazo[4,5-b]phenazine derivatives have been designed and synthesized. Among these sensors, a furan group into the sensor S6 molecule was as the functional group, compound S6-1 containing the 5-(4-Nitrophenyl)-2-furan group was synthesized, and in order to establish the furan group's contribution to the sensor's fluorescent sensing abilities, compound S6-2, which without containing the furan group was also synthesized. S6 showed excellent fluorescent specific selectivity and high sensitivity for Hg2+ in aqueous solution. The detection limit of the sensor towards Hg2+ is 1.6×10-7 M, and other ions, including Fe3+, Ca 2+, Cu2+, Co2+, Ni2+, Cd 2+, Pb2+, Zn2+, Cr3+, and Mg 2+ had nearly no influence on the probing behavior. Notably, this sensor serves as a recyclable component in sensing materials. The test strips based on S6 were fabricated, which could act as a convenient and efficient Hg2+ test kits.
- Shi, Bingbing,Zhang, Peng,Wei, Taibao,Yao, Hong,Lin, Qi,Liu, Jun,Zhang, Youming
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p. 7981 - 7987
(2013/08/23)
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- A selective fluorogenic chemodosimeter for Hg2+ based on the dimerization of desulfurized product
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A simple Hg2+-selective chemodosimetric system based on thiosemicarbazone was investigated. The transformation of thiosemicarbazone into semicarbazone selectively exerted by Hg2+ ions and the dimerization of semicarbazone resulted in a pronounced OFF-ON-type fluorescent signaling behavior. The coexistent metal ions, such as Fe3+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb 2+, Zn2+, Cr3+, Mg2+, Na +, K+, and Fe2+, had no obvious interference with the detection of Hg2+. In addition, S12-Hg 2+ plays a high sensitivity for basic anions to form an 'OFF-ON-OFF' type signaling behavior, with the Hg2+-induced emission spectra can be quenched. Moreover, test strips based on S12 exhibited a good selectivity to Hg2+. We believe the test strips could act as a convenient and efficient Hg2+ test kit.
- Zhang, Peng,Shi, Bingbing,Zhang, Youming,Lin, Qi,Yao, Hong,You, Xingmei,Wei, Taibao
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p. 10292 - 10298
(2013/11/19)
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- Synthesis of novel arylfurfurylchalcones
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Various aryl furans-2-carbaldehyde chalcones with different acetophenones were prepared and characterized through their elemental analyses and spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass spectra).
- Aslam, Samina,Asif, Nadia,Khan, Muhammad Naeem,Khan, Misbahul Ain,Munawar, Munawar Ali,Nasrullah, Muhammad
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p. 7738 - 7742
(2013/09/23)
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- Synthesis of novel diarylpyrrole-2-carbaldehydes by ring transformations
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Various diarylpyrrole-2-carbaldehydes were prepared by ring transformation of arylfuran-2-carbaldehydes with anilines in the presence of an acid. The synthesized compounds were characterized through elemental analysis and spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass spectra).
- Aslam, Samina,Nazeer, Areesha,Khan, Muhammad Naeem,Parveen, Najma,Khan, Misbahul Ain,Munawar, Munawar Ali
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p. 9595 - 9600
(2014/01/06)
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- Development of a novel class of B-RafV600E-selective inhibitors through virtual screening and hierarchical hit optimization
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Oncogenic mutations in critical nodes of cellular signaling pathways have been associated with tumorigenesis and progression. The B-Raf protein kinase, a key hub in the canonical MAPK signaling cascade, is mutated in a broad range of human cancers and especially in malignant melanoma. The most prevalent B-RafV600E mutant exhibits elevated kinase activity and results in constitutive activation of the MAPK pathway, thus making it a promising drug target for cancer therapy. Herein, we describe the development of novel B-RafV600E selective inhibitors via multi-step virtual screening and hierarchical hit optimization. Nine hit compounds with low micromolar IC 50 values were identified as B-RafV600E inhibitors through virtual screening. Subsequent scaffold-based analogue searching and medicinal chemistry efforts significantly improved both the inhibitor potency and oncogene selectivity. In particular, compounds 22f and 22q possess nanomolar IC 50 values with selectivity for B-RafV600Ein vitro and exclusive cytotoxicity against B-RafV600E harboring cancer cells.
- Kong, Xiangqian,Qin, Jie,Li, Zeng,Vultur, Adina,Tong, Linjiang,Feng, Enguang,Rajan, Geena,Liu, Shien,Lu, Junyan,Liang, Zhongjie,Zheng, Mingyue,Zhu, Weiliang,Jiang, Hualiang,Herlyn, Meenhard,Liu, Hong,Marmorstein, Ronen,Luo, Cheng
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experimental part
p. 7402 - 7417
(2012/10/08)
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- Methods and Compositions for Modulating P300/CBP Activity
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The present invention relates to a method for identifying compounds that modulate the activity of p300/CBP. Compounds of the invention are identified by designing or screening for a compound which binds to at least one amino acid residue of the newly identified lysine-CoA inhibitor binding site, L1 loop, electronegative pocket, or electronegative groove of the HAT domain of p300/CBP and testing the compound for its ability to modulate the activity of p300/CBP. Compositions and methods for preventing or treating diseases or disorders associated with p300/CBP are also provided as is a method for producing a semi-synthetic HAT domain.
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Page/Page column 20
(2010/09/05)
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- Mechanism of Meerwein arylation of furan derivatives
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Catalytic arylation of furan-2-carbaldehyde with arenediazonium salts was studied. The yields of 5-arylfuran-2-carbaldehydes were found to depend on the solvent, catalyst, and anion in the arenediazonium salt. Redox catalysis and generation of aryl radicals are not sufficient conditions for the reaction to occur. The reaction is successful only under conditions ensuring formation of complex intermediates. A mechanism involving two Cu2+ ? Cu + catalytic series and generation of furan-2-carbaldehyde was proposed.
- Obushak,Lesyuk,Gorak, Yu. I.,Matiichuk
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experimental part
p. 1375 - 1381
(2010/01/11)
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- Inhibitors of HCV NS5B polymerase. Part 1: Evaluation of the southern region of (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid
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A novel series of nonnucleoside HCV NS5B polymerase inhibitors were prepared from (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid, a high throughput screening lead. SAR studies combined with structure based drug design focusing on the southern heterobiaryl region of the template led to the synthesis of several potent and orally bioavailable lead compounds. X-ray crystallography studies were also performed to understand the interaction of these inhibitors with HCV NS5B polymerase.
- Pfefferkorn, Jeffrey A.,Greene, Meredith L.,Nugent, Richard A.,Gross, Rebecca J.,Mitchell, Mark A.,Finzel, Barry C.,Harris, Melissa S.,Wells, Peter A.,Shelly, John A.,Anstadt, Robert A.,Kilkuskie, Robert E.,Kopta, Laurice A.,Schwende, Francis J.
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p. 2481 - 2486
(2007/10/03)
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- Dantrolene analogues revisited: General synthesis and specific functions capable of discriminating two kinds of Ca2+ release from sarcoplasmic reticulum of mouse skeletal muscle
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The general synthesis of dantrolene analogues with various substituents on its phenyl ring has been developed via palladium-catalyzed cross-coupling reactions, the Stille or Suzuki reaction, as the key step. The effects of synthesized analogues have been evaluated by two kinds of Ca2+ release modes from sarcoplasmic reticulum (SR) of mouse skeletal muscle fibers based on: (1) the measurement of twitch contraction caused by the physiological Ca2+ release (PCR) of intact skeletal muscle and (2) the rate of Ca2+-induced Ca2+ release (CICR) in saponin-treated skinned muscle fibers. Although dantrolene, a lead compound, inhibits both twitch contraction and CICR, some structurally modified analogues exhibit one or the other of these effects. The methoxy congener, GIF-0185, potently inhibits the twitch contraction without affecting the CICR, while GIF-0166 and GIF-0248, the ortho-nitro regioisomer and ortho, ortho-dinitro substituted analogues, respectively, doubly potentiate the CICR exclusively.
- Hosoya, Takamitsu,Aoyama, Hiroshi,Ikemoto, Takaaki,Kihara, Yasutaka,Hiramatsu, Toshiyuki,Endo, Makoto,Suzuki, Masaaki
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p. 663 - 673
(2007/10/03)
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- Preparation of novel phenylfuran-based cyanohydrin esters: Lipase-catalysed kinetic and dynamic resolution
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A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantioselective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yl cyanomethyl butanoates in toluene with E ?100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions.
- Paizs, Csaba,Taehtinen, Petri,Lundell, Katri,Poppe, Laszlo,Irimie, Florin-Dan,Kanerva, Liisa T.
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p. 1895 - 1904
(2007/10/03)
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- Facile synthesis of 5-aryl-furan-2-aldehyde and 5-aryl-furan-2-carboxylic acid using ceric ammonium nitrate
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A new method for the synthesis of furan-2-carboxaldehyde and 5-(substituted-phenyl)-furan-2-carboxylic acids using ceric ammonium nitrate (CAN) is reported.
- Subrahmanya Bhat,Shivarama Holla
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p. 625 - 628
(2007/10/03)
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- Synthesis of 5-Pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates
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(Equation Presented) 5-Pyridyl-and 5-aryl-2-furaldehydes are prepared from furaldehyde diethyl acetal in a four-step, one-pot procedure: (i) deprotonation; (2) Li to Zn transmetalation; (3) Pd-mediated cross-coupling; (4) aldehyde deprotection. Triorganozincate 7 was found to transfer all three groups in the Pd-catalyzed cross-coupling reaction with haloaromatics.
- Gauthier Jr., Donald R.,Szumigala Jr., Ronald H.,Dormer, Peter G.,Armstrong III, Joseph D.,Volante,Reider, Paul J.
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p. 375 - 378
(2007/10/03)
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- Structure-activity relationships of novel anti-malarial agents. Part 4: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides
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In a previous report, we have described novel anti-malarial compounds based on a 2,5-diaminobenzophenone scaffold. Here, we have invesigated acryloyl derivatives carrying a biaryl structure consisting of a terminal aryl residue and a central 2-furyl ring. Several compounds were obtained in the series of para-substituted phenylfurylacryloyl derivatives that displayed improved anti-malarial activity in comparison to earlier described derivatives. From the structure-activity relationships it can be deduced that there has to be a lipophilic moiety in the para-position of the terminal phenyl residue. Furthermore, there are indications that, alternatively, activity may benefit from the presence of a polar moiety with hydrogen bond acceptor properties.
- Wiesner, Jochen,Mitsch, Andreas,Wissner, Pia,Kraemer, Oliver,Jomaa, Hassan,Schlitzer, Martin
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p. 2681 - 2683
(2007/10/03)
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- A practical one-pot synthesis of 5-aryl-2-furaldehydes
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A useful one-pot synthesis of 5-aryl-2-furaldehydes via palladium-mediated Suzuki coupling of aryl halides with in situ generated 5-(diethoxymethyl)-2-furylboronic acid is described. The procedure has general applicability, delivers high yields, and is amenable to scale-up.
- McClure,Roschangar,Hodson,Millar,Osterhout
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p. 1681 - 1685
(2007/10/03)
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- Regioselective palladium-catalyzed arylation of 2-furaldehyde.
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An efficient regioselective method for the direct arylation of 2-furaldehyde to provide a range of pi-diverse 5-aryl-2-formylfuran derivatives is described. The method employs functionalized aryl halides and a catalytic amount of palladium(II) chloride under relatively mild conditions.
- McClure,Glover,McSorley,Millar,Osterhout,Roschangar
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p. 1677 - 1680
(2007/10/03)
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- Synteza niektorych pochodnych 4-nitrofenylfuranu analogow dantrolenu
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Six new phenylacylidene derivatives of 5-(4-nitrophenyl)furan were obtained by reacting 5-(nitrophenyl)furfural with 4-substituted acetophenones.
- Skwarski, Dionizy,Sobiak, Stanislaw
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- 5-Phenyl-2-furamidines: A new chemical class of potential antidepressants
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A series of 5-phenyl-2-furamidines has been synthesized and evaluated for antidepressant activities. Substitution in the phenyl ring with a nitro (4) or an amino (12) group in the ortho-position resulted in an increase in antidepressant activity. Both 4 and 12 antagonized tetrabenazine-induced ptosis in rodents and inhibited norepinephrine (noradrenaline) uptake into crude synaptosomes of whole mouse brain at doses or concentrations comparable to those of the tricyclic antidepressants. However, these compounds did not possess the anticholinergic and antihistaminic activities common to tricyclic antidepressants. In addition, they lacked monoamine oxidase inhibitory activity. The 5-phenyl-2-furamidines represent a new chemical class of antidepressants and may be useful for depressive patients who cannot tolerate the compromising side effects of the tricyclic antidepressants and monoamine oxidase inhibitors.
- Pong,Pelosi Jr.,Wessels,Yu,Burns,White,Anthony Jr.,Ellis,Wright,White Jr.
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p. 1411 - 1416
(2007/10/02)
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