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
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.
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.
