7147-77-5Relevant articles and documents
A highly selective dual-channel chemosensor for mercury ions: Utilization of the mechanism of intramolecular charge transfer blocking
Zhang, You Ming,Qu, Wen Juan,Gao, Guo Ying,Shi, Bing Bing,Wu, Gui Yuan,Wei, Tai Bao,Lin, Qi,Yao, Hong
, p. 5075 - 5080 (2014)
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
A rational designed dual-channel chemosensor for mercury ions based on hydrolysis of Schiff base
Wu, Guiyuan,Shi, Bingbing,Hu, Bing,Zhang, Youming,Lin, Qi,Yao, Hong,Wei, Taibao
, p. 637 - 644 (2014)
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
New calamitic mesogens derived from a furan ring: Synthesis, characterization and study of their mesomorphic behavior
Abdulnabi, Nabih M.,Abdul Razzaq Al-Obaidy, Mazin M.,Tomi, Ivan Hameed R.,Jaffer, Hamed Jasim
, (2021)
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.
Design, synthesis, and biological activity of novel semicarbazones as potent Ryanodine receptor1 inhibitors of Alzheimer's disease
Dai, Baozhu,Ma, Xingxing,Tang, Yadong,Xu, Le,Guo, Su,Chen, Xinyan,Lu, Shitong,Wang, Guangjie,Liu, Yajing
, (2020/12/09)
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.
Carbon–Carbon Bond Formation for the Synthesis of 5-Aryl-2-Substituted Furans Catalyzed by K3[Fe(CN)6]
Ambika,Singh, Pradeep Pratap
, (2021/10/05)
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.]
Benzimidazole-based turn-on fluorescence probe developed for highly specific and ultrasensitive detection of hypochlorite ions in living cells
Yang, Yi,Cheng, Siyao,Dong, Wei
, p. 1377 - 1384 (2021/05/05)
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.
Synthesis and Biological Evaluation of Dantrolene-Like Hydrazide and Hydrazone Analogues as Multitarget Agents for Neurodegenerative Diseases
Bolognino, Isabella,Giangregorio, Nicola,Tonazzi, Annamaria,Martínez, Antón L.,Altomare, Cosimo D.,Loza, María I.,Sablone, Sara,Cellamare, Saverio,Catto, Marco
, p. 2807 - 2816 (2021/06/27)
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.
Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
Gou, Kun,Luo, Youfu,Luo, Yuan,Sun, Qingxiang,Tan, Yuping,Tao, Lei,Zhao, Yinglan,Zhou, Xia,Zhou, Yue,Zuo, Zeping
, (2021/07/26)
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.
Preparation method of dantrolene
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Paragraph 0033; 0034, (2020/07/24)
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.
Carbazole based Electron Donor Acceptor (EDA) catalysis for the synthesis of biaryl and aryl-heteroaryl compounds
Annes, Sesuraj Babiola,Ramesh, Subburethinam,Saravanan, Subramanian,Saritha, Rajendhiran
supporting information, p. 2510 - 2515 (2020/04/15)
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.
