- A selective hydrolytic and restructuring approach through a Schiff base design on a coumarin platform for “turn-on” fluorogenic sensing of Zn2+
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A new Schiff base, CMD, designed based on a coumarin platform was synthesized and fully characterized through single crystal X-ray diffraction studies. CMD underwent selective Zn2+-triggered hydrolysis in ethanolic medium followed by restructur
- Pandey, Abha,Asthana, Sharad Kumar,Prakash, Anand,Roy, Jagat Kumar,Tiwari, Ida,Upadhyay
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- A schiff base fluorescent probe for Mg2+ and Zn2+ based on coumarin
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A novel fluorescent Schiff base (L) based on coumarin was synthesized and characterized. Addition of Mg2+ and Zn2+ to fluorescent Schiff base in acetonitrile resulted in fluorescence enhancement and little influence was observed for other metal ions. It suggested that fluorescent Schiff base could be used as a potential Mg2+ and Zn2+ fluorescent probe in acetonitrile.
- Zhou,Peng
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- A new coumarin based Schiff base fluorescence probe for zinc ion
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Herein, a novel coumarin-based fluorescent probe (FS3) was designed, synthesized, and characterized. It exhibited significant fluorescence quenching in the presence of Zn2+ ions. Just a minor alteration occurred in the fluorescence intensity of
- Arvas, Busra,Ucar, Burcu,Acar, Tayfun,Arvas, Melih Besir,Sahin, Yucel,Aydogan, Feray,Yolacan, Cigdem
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- Synthesis, fluorescence properties and F? detection performance of Eu(III) complexes based on the novel coumarin Schiff base derivatives
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Three novel coumarin Schiff base derivatives and corresponding Eu(III) complexes were designed and synthesized. The aggregation-induced emission (AIE) property of ligands was studied. The fluorescence properties and electrochemical properties of Eu(III) complexes were investigated by comparing different substituent groups. The ion selectivity and ion detection limits of the [EuL2(NO3)3] ?H2O were also studied. The result indicates that all ligands exhibit the AIE property in CH3CN/H2O solution and emit green fluorescence with the maximum emission wavelength of 552 nm. All complexes show characteristic red fluorescence of Eu(III) and the influence of different substituents on the fluorescence intensity of Eu(III) complexes is ordered: -OCH3 > -H > -NO2, and [EuL2(NO3)3] ?H2O exhibits the strongest fluorescence intensity. The density functional theory (DFT) calculations of the ligands indicate that the introduction of electron-donating groups increases the HOMO energy level and the electron cloud density, which enhance the ability to coordinate with Eu(III) and the fluorescence intensity of the corresponding complex. Besides, the electrochemical properties of Eu(III) complexes indicate that the introduction of electron-donating groups increases the energy gaps (Eg) and the conjugation of the complex, which enhances the fluorescence intensity of the complexes. Ion selectivity experiments show that [EuL2(NO3)3] ?H2O has a specific recognition function for F?, and its response limit is between 1.0 × 10?5 mol·L?1 and 2.2 × 10?5 mol·L?1. Based on the above results, all the ligands and Eu(III) complexes have a promising application in optical materials due to the excellent fluorescence properties. In addition, All Eu(III) complexes also have a potential application prospects in the field of fluoride ion detection.
- Du, Hongli,Guo, Dongcai,Hu, Zhongqian,Li, Shiquan,Luan, Fangfei,Xiao, Gangxiang,Zhang, Yuxi
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- A new strategy for synthesis of 9-benzoyl-4-methylpyrano[2,3-f]chromene-2,8-dione using L-proline as a novel and efficient catalyst
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We report the high yield synthesis of novel 9-benzoyl-4-methylpyrano[2,3-f]chromene-2,8-dione derivatives obtained by the reaction of 8-formyl-7-hydroxy-4-methylcoumarin with various active methylene compounds. A mechanism of the tandem Knoevenagel condensation and cyclisation reaction is proposed. Structures of all compounds were elucidated on the basis of 1H and 13C NMR, and mass spectrometry, and elemental analysis.
- Goud,Rao,Hemasri,Thirupathi
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- Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging
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Two new coumarin-based Schiff bases, 8,8′-((1E,1′E)-hydrazine- 1,2-diylidenebis(methanylylidene))bis(7-hydroxy-4-methyl-2H-chromen-2-one), (CHC), and 7-hydroxy-8-((E)-((E)-((2-hydroxynaphthalen-1-yl)methylene)hydrazono) methyl)-4-methyl-2H-chromen-2-one, (CHN), with excited-state intramolecular proton-transfer (ESIPT) properties, were synthesized and characterized. Both of the compounds displayed aggregation-induced emission (AIE) characteristics, of which CHC nanoparticles emitted a reddish orange fluorescence, while the CHN nanoparticles exhibited a saffron yellow fluorescence. The appearance of emission peaks in the long wave regions with large Stokes-shifts demonstrated the occurrence of the ESIPT process. Observations of the nanoparticles' morphologies were undertaken through a transmission electron microscope (TEM) method. Furthermore, due to the good biocompatibilities, high stabilities and the large Stokes-shifts, the two compounds were ideal candidates for cell staining. This journal is the Partner Organisations 2014.
- Xiao, Hongde,Chen, Kun,Cui, Dandan,Jiang, Nannan,Yin, Gui,Wang, Jie,Wang, Ruiyong
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- An enolato-bridged dinuclear Cu(ii) complex with a coumarin-assisted precursor: A spectral, magnetic and biological study
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A new, phenoxo-bridged CuII dinuclear complex Cu2[(L)2(DMF)2] (1) has been obtained by employing the coumarin-assisted tridentate precursor, H2L, [benzoic acid(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl
- Das, Kuheli,Panda, Uttam,Datta, Amitabha,Roy, Suman,Mondal, Sudipa,Massera, Chiara,Askun, Tulin,Celikboyun, Pinar,Garribba, Eugenio,Sinha, Chittaranjan,Anand, Kushi,Akitsu, Takashiro,Kobayashi, Kana
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- Novel coumarin isoxazoline derivatives: Synthesis and study of antibacterial activities
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A highly efficient and mild protocol for the syntheses of ethyl-3-[7-benzyloxy-4-methyl-2-oxo-2H-8-chromenyl]-5-aryl-4,5-dihydro-4-isoxazole carboxylates and ethyl-3-[7-benzyloxy-3-chloro-4-methyl-2-oxo-2H-8-chromenyl]-5-aryl-4,5-dihydro-4-isoxazole carboxylates in good yields via [3 + 2] cycloaddition of in situ–generated nitrile oxides from 7-benzyloxy-4-methyl-coumarin hydroxymoylchlorides and 7-benzyloxy-3-chloro-4-methyl-coumarin hydroxymoylchlorides respectively with ethyl-3-aryl prop-2-enoate has been developed. The new compounds are screened for antibacterial activity.
- Suresh, Garbapu,Venkata Nadh, Ratnakaram,Srinivasu, Navuluri,Kaushal, Kishore
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- A novel coumarin-derived dithioacetal chemosensor for trace detection of Hg2+ in real water samples
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A novel coumarin-derived dithioacetal chemosensor, 8-(1,3-dithian-2-yl)-7-hydroxy-4-methylcoumarin (LS), has been designed and synthesized. The sensor LS showed highly selective fluorescent sensing for Hg2+ with a low detection limit of 0.81 nM in the pH range from 6.15 to 9.96 in ethanol/water (1:1, v/v) solution. The sensing mechanism of LS toward Hg2+ was proposed and verified by 1H nuclear magnetic resonance spectroscopy studies. Under an ultraviolet lamp, the fluorescence color changes could be easily detected by the naked eye. In addition, the sensor LS has been applied in the trace detection of Hg2+ in real water samples.
- Fan, Yilei,Huang, Zhongping,Ke, Xing,Zhou, Jing
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- A new unsymmetrical azine derivative based on coumarin group as dual-modal sensor for CN? and fluorescent “OFF–ON” for Zn2?+
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A simple chemosensor YS based on coumarin group was designed and synthesized. Its structure was determined by single crystal X–ray diffraction analysis. In the presence of cyanide the sensor showed an immediate visible change in color from colorless to pale yellow by naked–eyes and produced a strong blue fluorescence rapidly in DMSO/H2O (3:7, v/v). The detection limit on fluorescence response of the sensor to CN? is down to 1.69?×?10??7?M. In addition YS could show fluorescence turn–on response rapidly for Zn2?+ over other metals ions such as Fe3?+, Hg2?+, Ag+, Ca2?+, Cu2?+, Co2?+, Ni2?+, Cd2?+, Pb2?+, Cr3?+ and Mg2?+ in aqueous solutions. Notably, this sensor served as a molecular switch, which was controlled by Zn2?+ and EDTA cyclically. Test strips based on YS were fabricated, which could act as a convenient and efficient CN? and Zn2?+ test kit. This chemosensor could achieve the detection of two ions, which need not depend on two different sensors.
- Hu, Jing-Han,Sun, You,Qi, Jing,Li, Qiao,Wei, Tai-Bao
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- Synthesis, characterization, anti-diabetic potential and DFT studies of 7-hydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde oxime
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A new compound named 7-hydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde oxime (7-Oxime) was synthesized and characterized by FT-IR, FT-Raman, 1H NMR and 13C NMR techniques. The conformer possibilities were studied to find the most stable conformer and its molecular geometry. Then, the dimer form of the most stable monomer was built and optimized. Density functional theory (DFT) B3LYP method with 6-311++G(d,p) basis set was applied to analyze the molecular electrostatic potential (MEP), HOMO and LUMO orbitals, the vibrational wavenumbers, the infrared intensities, the Raman scattering activities and several thermodynamic properties (at different temperatures). The stability of the molecule derived from hyperconjugative interactions and charge delocalization has been analyzed by using natural bond orbital (NBO) analysis. In order to find the possible inhibitory activity of 7-Oxime, an accurate molecular blind docking simulation was performed. The results indicated that the mentioned compound has a good binding affinity to interact with the active sites of human α-glucosidase and α-amylase. For the first time, our computational finding suggests that this compound has a potential to be used as a supplementary agent in the pre-management of diabetes mellitus.
- Hosseini Ghazvini, Seyed Mohammad Bagher,Safari, Parvin,Mobinikhaledi, Akbar,Moghanian, Hassan,Rasouli, Hassan
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- Ethylenic conjugated coumarin thiazolidinediones as new efficient antimicrobial modulators against clinical methicillin-resistant Staphylococcus aureus
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In an effort for the development of novel antimicrobial agents, ethylenic conjugated coumarin thiazolidinediones as potential multi-targeting new antimicrobial compounds were synthesized through convenient procedures from commercially available resorcinol and were evaluated for their antimicrobial potency. Bioactive evaluation revealed that some of the prepared compounds showed strong antimicrobial activities towards the tested microorganisms including clinically drug-resistant strains. Especially, propargyl derivative 12b exhibited effective anti-MRSA potency with MIC value of 0.006 μmol/mL, which was highly advantageous over clinical antibacterial drug norfloxacin. Compound 12b showed rapid killing effect, low toxicity against hepatocyte LO2 cell line, and no obvious drug resistance development against MRSA. Preliminary exploration of action mechanism manifested that molecule 12b acted upon MRSA through forming stable supramolecular complex with bacterial DNA which might impede DNA replication. Molecular docking showed that compound 12b could bind with DNA-gyrase through hydrogen bonds.
- Hu, Chun-Fang,Zhang, Peng-Li,Sui, Yan-Fei,Lv, Jing-Song,Ansari, Mohammad Fawad,Battini, Narsaiah,Li, Shuo,Zhou, Cheng-He,Geng, Rong-Xia
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- Synthesis, characterization and biological approach of metal chelates of some first row transition metal ions with halogenated bidentate coumarin Schiff bases containing N and O donor atoms
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The impregnation of halogen atoms in a molecule is an emerging trend in pharmaceutical chemistry. The presence of halogens (Cl, Br, I and F) increases the lipophilic nature of molecule and improves the penetration of lipid membrane. The presence of electronegative halogen atoms increases the bio- activity of core moiety. In the present study, Co(II), Ni(II) and Cu(II) complexes are synthesised using Schiff bases (HLI and HLII), derived from 8-formyl-7-hydroxy-4-methylcoumarin/3-chloro-8-formyl-7-hydroxy-4-methylcoumarin with 2,4-difluoroaniline/o-toluidine respectively. The synthesized compounds were characterized by spectral (IR, NMR, UV-visible, Mass, ESI-MS, ESR), thermal, fluorescence and molar conductivity studies. All the synthesized metal complexes are completely soluble in DMF and DMSO. The non-electrolytic nature of the metal complexes was confirmed by molar conductance studies. Elemental analysis study suggest [ML2(H2O)2] stoichiometry, here M = Co(II), Ni(II) and Cu(II), L = deprotonated ligand. The obtained IR data supports the binding of metal ion to Schiff base. Thermal study suggests the presence of coordinated water molecules. Electronic spectral results reveal six coordinated geometry for the synthesized metal complexes. The Schiff bases and their metal complexes were evaluated for antibacterial (Pseudomonas aureginosa and Proteus mirabilis), antifungal (Aspergillus niger and Rhizopus oryzae), anthelmintic (Pheretima posthuma) and DNA cleavage (Calf Thymus DNA) activities.
- Prabhakara, Chetan T.,Patil, Sangamesh A.,Toragalmath, Shivakumar S.,Kinnal, Shivashankar M.,Badami, Prema S.
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- Fluorescent sensor for selective detection of Al3+ based on quinoline-coumarin conjugate
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A fluorescence probe, 8-formyl-7-hydroxyl-4-methyl coumarin - (2′-methylquinoline-4-formyl) hydrazone (L) has been synthesized. The chemosensor is found preferential binding to Al3+ in presence of other competitive ions with associated changes in its optical and fluorescence spectra behavior. Upon addition of Al3+ to a solution of L, it shows 200-fold enhancement of fluorescence intensity which might be attributed to form a 2:1 stoichiometry of the binding mode of LAl(III) and the chelation enhanced fluorescence (CHEF) process at 479 nm in ethanol. The lowest detection limit for Al3+ is determined as 8.2 × 10-7 M.
- Qin, Jing-Can,Li, Tian-Rong,Wang, Bao-Dui,Yang, Zheng-Yin,Fan, Long
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- Synthesis, antioxidant, antibacterial, and DFT study on a coumarin based salen-type Schiff base and its copper complex
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Synthesis of new efficient compounds is becoming urgent due to the resistance of organisms to drugs. Salen derivatives have interesting therapeutic and industrial applications. A coumarin based derivative of salen, 7-hydroxy-8-((E)-((2-((E)-((7-hydroxy-5-methyl-2-oxo-3,8a-dihydro-2H-chromen-8-yl)methylene)amino)-4-methylphenyl)imino)methyl)-5-methyl-2H-chromen-2-one (L), and its copper complex, CuL, have been synthesized and characterized. Antibacterial and antioxidant activity of these compounds have been evaluated and electronic, optical and molecular properties have been calculated using density functional theory (DFT) with B3LYP. The results were correlated with the biological activity and reactivity of the compounds. Experimental and theoretical calculations indicate that the studied copper complex has the potential to function as a drug.
- Sharma, Vibha,Arora, Ekta Kundra,Cardoza, Savio
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- Highly selective probe of a copper(II) complex based on a coumarin derivative for hydrogen sulfide detection
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A fluorescent probe 1 containing copper(II) had been designed and synthesized based on a coumarin derivative. The molecular structure of probe 1 was characterized by 1H NMR, HRMS, IR, and elemental analysis. The interactions of 1 with biologica
- Chen, Yanmei,Shang, Xuefang,Pan, Weitong,Li, Congshu,Wang, Tianyun
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- Synthesis, characterization, DNA cleavage and in vitro antimicrobial studies of La(III), Th(IV) and VO(IV) complexes with Schiff bases of coumarin derivatives
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A series of La(III), Th(IV) and VO(IV) complexes have been synthesized with Schiff bases derived from 8-formyl-7-hydroxy-4-methylcoumarin and o-phenylenediamine/ethylenediamine. The structure of the complexes has been proposed in the light of analytical, spectral (IR, UV-vis, ESR and FAB-mass), Magnetic and thermal studies. The complexes are soluble in DMF and DMSO. The measured molar conductance values indicate that, the complexes are non-electrolytes in nature. The redox behavior of the complexes was investigated by electrochemical method using cyclic voltammetry. The Schiff bases and their complexes have been screened for their antibacterial (Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella typhi) and antifungal activities (Aspergillus niger, Aspergillus flavus and cladosporium) by Minimum Inhibitory Concentration method. The DNA cleavage activity of La(III) and VO(IV) metal complexes is studied by agarose gel electrophoresis method.
- Kulkarni, Ajaykumar,Patil, Sangamesh A.,Badami, Prema S.
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- A novel OFF-ON-OFF fluorescence probe based on coumarin for Al3+ and F? detection and bioimaging in living cells
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A novel fluorescence probe L2 based on coumarin has been designed and synthesized. The probe L2 can be used for relay recognition of metal ions Al3+ and anion F? in the aqueous HEPES buffer (0.05 M, pH = 7.4), and build a OFF-ON-OFF
- Tang, Xu,Zhu, Zhi,Liu, Renjie,Ni, Liang,Qiu, Yue,Han, Juan,Wang, Yun
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- Photophysical insights and guidelines for blue “turn-on” fluorescent probes for the direct detection of nitric oxide (NO?) in biological systems
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Synthesis and photophysical properties of a family of five blue fluorescent “turn-on” probes for the direct detection of nitric oxide (NO?) is reported. The probes CB1-5 feature a substituted 7-hydroxy coumarin chromophore coupled to 2-methyl-8-aminoquinoline, which act as tridentate ligand for Cu(II) and active site for monitoring NO? using a replacement strategy. The UV/vis absorption and fluorescence emission characteristics of the probes are significantly influenced by the substitution pattern on the coumarin ring, as well as by solvent polarity and pH. Time-dependent density functional theory (TD-DFT) calculations for CB4 and CB5 showed that the absorptions are due to π-π* transitions localised on coumarin, with a small charge transfer contribution from the quinoline system at higher pH where the 7-hydroxy coumarin moiety is deprotonated, which leads to a bathochromic shift of the absorption. Complexation of the probes with Cu(II) quenches the fluorescence, which is turned back on upon reaction with NO?, allowing selective detection of this important signalling molecule in μM concentrations. Preliminary experiments revealed that CB4 and CB5 enable to monitor endogenously produced NO? in living bacterial cells in multi-dye imaging experiments.
- Barzegar Amiri Olia, Mina,Hancock, Amber N.,Schiesser, Carl H.,Goerigk, Lars,Wille, Uta
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- Fluorescent coumarin derivatives with large stokes shift, dual emission and solid state luminescent properties: An experimental and theoretical study
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Coumarin derivatives containing 8-benzothiazole (C-2) and its difluoroboron bound derivative (C-3) were prepared. Both derivatives show dual emission at 322 nm and 513 nm and large Stokes shift (188 nm), compared to the unsubstituted coumarin (C-1), which shows emission at 356 nm with small Stokes shift of 46 nm. C-2 and C-3 show fluorescence in solid state, in contrast the C-1 is non-fluorescent in the solid state. The excited state intramolecular proton transfer (ESIPT) process of C-2 was fully rationalized by DFT/TDDFT calculations with optimization of the ground state (S0) and excited state (S 1) geometries. TDDFT calculations propose that the large Stokes shift of C-2 and C-3 are due to the re-distribution of the frontier molecular orbitals at excited states. Study of the potential energy curve of C-2 indicated that the dual emission of the C-2 is due to the simultaneous S1 and S3 emission, not the rotamer of the enol form.
- Xie, Lijuan,Chen, Yinghui,Wu, Wenting,Guo, Huimin,Zhao, Jianzhang,Yu, Xuerong
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- Design of a coumarinyl-picolinoyl hydrazide Schiff base for the fluorescence turn-on-off sequential sensing of Al3+ and nitroaromatics, and electronic device fabrication
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(E)-N′-((7-Hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methylene)picolinohydrazide (H-CPh), a greenish yellow emitter in the solid state, aggregates in DMSO solution upon increasing the percentage of water (>50%) and the maximized emission intensity was reached at 90% water-DMSO medium. Upon excitation at 400 nm in pure aquatic medium (HEPES buffer, pH 7.2) H-CPh shows fluorescence sensitivity to Al3+ (λem, 470 nm) and forms a 1:1 complex, [(CPh)Al(OH)(H2O)]NO3, with a limit of detection (LOD) of 6.99 nM. The complex, [(CPh)Al(OH)(H2O)]NO3 shows sensitivity to nitroaromatics by quenching the strong emission of the fluorogenic complex and the LODs are: 2,4-dinitrophenol (DNP), 1.67 μM and 2,4,6-trinitrophenol (TNP) 0.99 μM. The H-CPh is electronically a semiconductor and the experimental (2.78 eV) and the DFT derived (2.75 eV) band gaps are comparable. The H-CPh forms a Schottky diode and its photoconductivity (19.98 × 10-4 S m-1) is three times higher than the dark phase conductivity (6.42 × 10-4 S m-1).
- Purkait, Rakesh,Dey, Arka,Dey, Sunanda,Ray, Partha Pratim,Sinha, Chittaranjan
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- Synthesis, spectral, thermal, fluorescence, antimicrobial, anthelmintic and DNA cleavage studies of mononuclear metal chelates of bi-dentate 2H-chromene-2-one Schiff base
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The Co(II), Ni(II) and Cu(II) complexes have been synthesized with Schiff base (HL), derived from 8-formyl-7-hydroxy-4-methylcoumarin with benzylamine. The Schiff base and its metal complexes were structurally characterized based on IR, 1H NMR,
- Prabhakara, Chetan T.,Patil, Sangamesh A.,Kulkarni, Ajaykumar D.,Naik, Vinod H.,Manjunatha,Kinnal, Shivshankar M.,Badami, Prema S.
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- L-Proline promoted fluorescent sensor for Mg2+ detection in a multicomponent sensory system
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Mg2+ can lead to the fluorescence enhancement of a dye molecule as high as 47.3-fold while l-proline acts as a promoter in this multicomponent sensory system. The fluorescence color could be easily detected by the naked eye under a UV-lamp.
- Dong, Yu,Mao, Xuerong,Jiang, Xiaoxiang,Hou, Jiali,Cheng, Yixiang,Zhu, Chengjian
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- Synthesis of pyrano isoxazoline/isoxazole annulated coumarins via intramolecular nitrile oxide cycloaddition and their cytotoxicity
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An efficient and straight forward procedure for the syntheses of isoxazoline/isoxazole fused coumarin analogues 7a–7g and 8a–8g from the corresponding 7-O-allyloxy coumarin oximes 5a–5g and 7-O-propargyloxy coumarin oximes 6a–6g is presented. High yields
- Krishna,Bhargavi,Rao,Krupadanam
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- A highly selective and sensitive ESIPT-based coumarin-triazole polymer for the ratiometric detection of Hg2+
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A novel fluorescent polymer for Hg2+ recognition was developed based on the phototautomerism mechanism of 7-hydroxycoumarin in aqueous solution. The developed system showed higher sensitivity and specificity towards Hg2+ in the acetonitrile/water mixture over various other metal ions, with a significant fluorescence quenching of the main emission band. It was shown that the presence of Hg2+ affects the chemical equilibrium of the 7-hydroxycoumarin phototautomers through the excited state intramolecular proton transfer (ESIPT) mechanism, which results in ratiometric fluorescence response upon stepwise addition of Hg2+. The occurrence of ESIPT mechanism was explained based on a comparison of the 1H NMR spectra of the starting alkynylated coumarin (4) in a non-polar aprotic solvent (CDCl3) and in a polar aprotic solvent (DMSO-d6). This was further confirmed by 1H NMR of 4 upon stepwise addition of Hg2+ in a polar aprotic solvent (DMSO-d6). From titration experiments, a higher sensitivity with a detection limit at the nanomolar level (50 nM) was observed and the response was fast and reversible. The real applications of the developed system were investigated in real samples and satisfactory results were obtained for both fresh and lake water samples.
- Ngororabanga, Jean Marie Vianney,Tshentu, Zenixole R.,Mama, Neliswa
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- A label-free turn-on fluorescence probe for rapidly distinguishing cysteine over glutathione in water solution
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A novel label-free fluorescent chemodosimeter (C1) was synthesized, based on coumarin and N-(4-aminobenzoyl)-β-alanine, for the selective detection of cysteine (Cys) over glutathione (GSH), which involved a click reaction of Cys to C=N of a Schiff base. T
- Yan, Liqiang,Kong, Zhineng,Shen, Wei,Du, Wenqi,Zhou, Yan,Qi, Zhengjian
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- Seco-4-methyl-DCK derivatives as potent chemosensitizers
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Twenty-five seco-4-methyl-DCK derivatives were designed, synthesized and evaluated for chemoreversal activity when combined with paclitaxel or vincristine in two drug-resistant cancer cell lines (A2780/T and KB-V) respectively. Most of the new compounds displayed moderate to significant MDR reversal activities in the P-gp overexpressing A2780/T and KB-V cells. Especially, compounds 7o and 7y showed the most potent chemosensitization activities with more than 496 and 735 reversal ratios at a concentration of 10 μM. Unexpectedly the newly synthesized compounds did not show chemosensitization activities observed in a non-P-gp overexpressing cisplatin resistant human ovarian cancer cell line (A2780/CDDP), implying that the MDR reversal effects might be associated with P-gp overexpression. Moreover, these compounds did not exhibit significant antiproliferative activities against nontumorigenic cell lines (HUVEC, HOSEC and T29) compared to the positive control verapamil at the tested concentration, which suggested better safety than verapamil. The pharmacological actions of the compounds will be studied further to explore their merit for development as novel candidates to overcome P-gp mediated MDR cancer.
- Guo, Yalan,Wang, Ke,Chen, Xiaoyu,Li, Haihong,Wan, Qi,Morris-Natschke, Susan,Lee, Kuo-Hsiung,Chen, Ying
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- A highly selective coumarin-based chemosensor for the sequential detection of Fe3+ and pyrophosphate and its application in living cell imaging
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A new chemosensor based on coumarin FB has been designed and synthesized for the detection of Fe3+ and PPi. FB displayed a high affinity to Fe3+ in the presence of other competing cations. The resulting FB-Fe3+ complex displayed highly sensitivity to PPi via Fe3+ displacement approach. The Fe3+ and PPi recognition processes is rapid and reversible, the detection limits of FB to Fe3+ and FB-Fe3+ complex to PPi were estimated to be 8.73 × 10?8 M and 1.25 × 10?8 M, respectively. The good biocompatibility of FB enables the investigation of fluorescent response for Fe3+ and PPi in living cells by confocal microscope. A B3LYP/6-31G(d,p) basis set was employed for optimization of FB and FB-Fe3+ complex.
- Wang, Wei,Wu, Jian,Liu, Qinglei,Gao, Yan,Liu, Huimin,Zhao, Bing
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- A fluorogenic probe for recognizing 5-hydroxylysine inspired by serine/threonine ligation
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The 5-lysyl-hydroxylation has been found among protein post-translational modifications. In this report, we have devised a fluorescence turn-on probe which allows for selectively recognizing 5-hydroxylysine-containing peptides. the Partner Organisations 2014.
- Tung, Chun Ling,Lam, Hiu Yung,Xu, Jianchao,Li, Xuechen
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- Synthesis and characterization of heteroleptic Schiff base transition metal complexes: a study of anticancer, antimicrobial, DNA cleavage and anti-TB activity
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In search of effective bioactive compounds, we have synthesized the new Co(II), Ni(II), and Cu(II) complexes of the Schiff base derived from 8-formyl-7-hydroxy-4-methylcoumarin and 2-hydrazino benzothiazole and characterized by analytical, spectroscopic (IR, NMR, UV–vis, Mass), magnetic, powder X-ray diffraction data (PXRD) and TGA studies. Elemental analysis suggests the stoichiometry of the synthesized complexes and the solution electronic spectral study revealed the octahedral geometry of the compounds. Thermal analysis shows the presence of water molecule outside the coordination sphere and powder-XRD patterns have been studied to test the degree of crystallinity of the complexes and unit cell calculations were made. All the synthesized compounds were tested against human ovarian cancer cell line (PA-1). The synthesized metal complexes exhibited enhanced activity against the tested bacterial (Staphylococcus aureus and Escherichia Coli) and fungal strains (Candida albicans and Aspergillus fumigatus) as compared to free ligand (LH). The results of the DNA-cleavage activity suggest that the ligand and its metal complexes can cleave CT-DNA at different degrees. Further, anti-tuberculosis activity was done using microplate almar blue assay. Among all these synthesized compounds, the Cu(II) complex exhibits good cleaving ability compared to other newly synthesized metal complexes.
- Jawoor, Shailaja S.,Patil, Sangamesh A.,Toragalmath, Shivakumar S.
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- A turn-on fluorescent sensor for Zn(II) based on fluorescein-coumarin conjugate
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A novel fluorescent sensor, 7-hydroxy-4-methylcoumarin-8-carbaldehyde- (fluorescein) hydrazone was designed and synthesized for selective recognition of Zn2+ in HEPES buffer medium of PH 7.4. This reagent could be used as a probe for Zn2+ by monitoring changes in the absorption and the fluorescence spectral patterns. More importantly, this sensor displays an extreme selectivity, sensitivity and color change for Zn2+ over other earth- and transition metal ions, which was mainly due to the spirolactam ring-opening power of Zn2+. Upon the addition of Zn2+, an overall emission change of 33-fold was observed and the detection limit was low as 6.54 ppb. Photoinduced electron transfer process, coupled with the intramolecular charge transfer process, are proposed to explain the observed spectral response.
- An, Jun-Mei,Yan, Mi-Hui,Yang, Zheng-Yin,Li, Tian-Rong,Zhou, Qiao-Xia
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- A novel dual-channel chemosensor for CN- based on rhodamine B hydrazide derivatives and its application in bitter almondf
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In this article, we successfully designed and synthesized a novel chemosensor PW bearing rhodamine B hydrazide and 8-formyl-7-hydroxyl-4-methylcoumarin, which displayed both colorimetric and "turn-on" fluorescence responses for CN- in DMSO/H2O (1: 1, v/v, pH = 7.20) solution. The probe could distinguish CN- via a deprotonation process and the mechanism of intramolecular charge transfer (ICT), which was proved by 1H NMR titration, ESI-MS and DFT calculations. The detection limit of the sensor PW towards CN- was 1.592 × 10-7 M. Moreover, the sensor PW was successfully utilized to detect CN-in bitter almond. Test strips containing PW were also prepared, which could act as a colorimetric tool to detect CN- in practical application.
- Pei, Peng-Xiang,Hu, Jing-Han,Ni, Peng-Wei,Long, Chen,Su, Jun-Xia,Sun, You
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- Fluorescence sensing and intracellular imaging of Pd2+ ions by a novel coumarinyl-rhodamine Schiff base
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Coumarinyl-rhodamine, HCR, served as an extremely selective sensor for Pd2+ ions in ethanol/H2O (8:2, v/v, HEPES buffer, pH 7.2) solution and the limit of detection (LOD) was 18.8 nM (3σ method). The free sensor, HCR, was weakly emissive and in the presence of Pd2+, the colour changed from straw to pink with very strong emission at 598 nm in the presence of eighteen other cations. A plausible mechanism involved opening of the spirolactam ring of rhodamine on interaction with Pd2+, which was justified by structure optimization and transition energy calculations using the DFT technique. HCR underwent 1:1 complexation with Pd2+, which was confirmed via the Job's plot, mass spectra and Benesi-Hildebrand plot (association constant Ka, 9.1 × 104 M-1). A separate in vitro experiment showed that HCR could specifically sense Pd2+ in MCF7 (human breast adenocarcinoma) cell lines.
- Adak, Arup Kumar,Purkait, Rakesh,Manna, Saikat Kumar,Ghosh, Bankim Chandra,Pathak, Sudipta,Sinha, Chittaranjan
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- Coumarin-based fluorescent chemosensor for the selective quantification of Zn2+ and AcO? in an aqueous solution and living cells
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In this work, we report a novel fluorescence chemosensor HM based on the coumarin fluorophore for the quantification of Zn2+ and AcO?. HM specifically binds to Zn2+ in the presence of other competing cations, and evident c
- Gao, Yan,Liu, Huimin,Li, Peng,Liu, Qinglei,Wang, Wei,Zhao, Bing
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- Synthesis of novel 2H,8H-pyrano[2,3-f]chromene-2,8-diones from 8-formyl-7-hydroxy-4-methylcoumarin
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We report the synthesis of novel 2H,8H-pyrano[2,3-f]chromene-2,8-dione based scaffolds by the reaction of 8-formyl-7-hydroxy-4-methylcoumarin with various active methylene compounds. A mechanism of a tandem Knoevenagel condensation and cyclisation reaction is proposed. The structure of all compounds was established on the basis of 1H and 13C NMR data, high resolution mass spectrometry and elemental analysis.
- Al-Kawkabani, Ahmed,Boutemeur-Kheddis, Baya,Makhloufi-Chebli, Malika,Hamdi, Maamar,Talhi, Oualid,Silva, Artur M.S.
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- An efficient photorelease of Zn2+ with turn-on fluorescence monitoring
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Photo-release of Zn2+ with fluorescence monitoring has been described using 8-(2,3-dihydrobenzothiazol-2-yl)-7-hydroxy-4-methyl-2H-chromen-2-one (1) as ligand. It is found that 1 binds to Zn2+ to yield a 1:1 complex (2) with a large binding constant (log K?=?13.35), 2 exhibits photo-active and occurs photo-release in aqueous micelle solution. Upon irradiation with 365?nm light, 2 undergoes efficient (??=?0.56) Zn2+-release in buffer solution (PBS, pH?=?7.2) to give 8-(benzothiazol-2-yl)-7-hydroxy-4-methyl-2H-chromen-2-one (3) as photo-product. 3 exhibits turn-on fluorescence, which is beneficial for monitoring the photo-release.
- Zhang, Xu,Chen, Yi
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- Synthetic studies toward novel pyrrolobenzodiazepine–coumarin hybrids
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[Figure not available: see fulltext.] A comprehensive screening of known methods for the synthesis of coumarins was performed in order to obtain a new type of pyrrolobenzodiazepine–coumarin hybrids. A Pechmann condensation turned out to be the method of c
- Sakaine, Guna,Smits, Gints,Arsenyan, Pavel
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- Na+ triggered fluorescence sensors for Mg2+ detection based on a coumarin salen moiety
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Chemical equations presented. Two coumarin salen-based sensors CS1 and CS2 can exhibit a pronounced fluorescence enhancement response toward Mg 2+ as high as 36-fold (CS1) and 111-fold (CS2) in the presence of Na+ as a synergic trigger. More importantly, the fluorescent color of CS1 was bright green instead of weak yellow after the addition of Mg 2+ and Na+ together, which can be easily detected by the naked eye.
- Dong, Yu,Li, Junfeng,Jiang, Xiaoxiang,Song, Fengyan,Cheng, Yixiang,Zhu, Chengjian
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- A mitochondria-targeted fluorescent probe based on coumarin-pyridine derivatives for hypochlorite imaging in living cells and zebrafish
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Hypochlorite plays a critical role in various physiological processes and is involved in many diseases. Thus, real-time, rapid, and accurate monitoring of hypochlorite has important medical and physiological significance. Herein, a novel coumarin-pyridine derivative (CPD) probe was designed and synthesized, which exhibited fantastic advantages, such as a rapid response (within 10 s), naked eye recognition, large Stokes shift (185 nm), dual-channel detection, and high selectivity and sensitivity toward OCl- (detection limit 0.012 μM, S/N = 3). Furthermore, the current CPD probe was successfully used to image OCl- in the mitochondria of both A549 cells and zebrafish, which further demonstrated its suitability for practical applications in biological systems.
- Zhong, Xiuli,Yang, Qing,Chen, Yingshuang,Jiang, Yuliang,Wang, Bingxiang,Shen, Jian
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- A new turn on coumarin-based fluorescence probe for Ga3 + detection in aqueous solution
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The probe CT was synthesized and investigated as a novel label-free chemosensor for Ga3 + detection in water. Probe CT showed remarkable selectivity and sensitivity for Ga3 + in Tris-HCl aqueous buffer solution (pH 7.0). The chemosensor responded rapidly to Ga3 + with a 1:1 stoichiometry. Meanwhile, the unapparent changes of fluorescence lifetime decays suggest the turn-on process of probe CT by Ga3 + which appears to be a static mechanism.
- Yan, Liqiang,Zhou, Yan,Du, Wenqi,Kong, Zhineng,Qi, Zhengjian
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- A new coumarin-based “turn-on” fluorescence probe with high sensitivity and specificity for detecting hypochlorite ion
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A new type of “turn-on” fluorescence probe coumarin-based DTC was developed for specifically detecting hypochlorite ion (ClO?) with high sensitivity. DTC can display a significant enhancement of fluorescence and emit blue fluorescence at 452 nm after reaction with ClO?. Moreover, probe DTC can detect ClO? without interference from other reactive oxygen species (ROS), and has a low detection limit for ClO? of 96 nM. Meanwhile, DTC can also detect ClO? in the physiological environment, and DTC can be further used as a test paper-strip for portable and rapid detection of ClO?.
- Du, Lei,Qian, Hui,Sun, Xinyu,Wang, Limin,Xie, Yiqiu,Yang, Qingying,Zhou, Wenqi
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- Targeting tubulin polymerization and DNA binding of 4-thiazolidinone-umbelliferone hybrids: synthesis and cytotoxicity evaluation
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The discovery of a series of combretastatin A-4 inspired novel molecular hybrids of 4-thiazolidinone-umbelliferone as prominent cytotoxic agents is reported. Representative compounds exhibited potent anti-proliferative activities against four human cancer cell lines (A549, MDA-MB-231, THP-1 and HL-60). Amongst the compounds tested,7qshowed the highest potency against A549 cells with an IC50value of 0.96 ± 1.09 μM and a selectivity index of 51.7. The flow cytometric analysis of compound7qtreated A549 cells showed apoptosis induction by the annexin-v/PI dual staining assay and the effect of7qon different phases of the cell cycle was also analyzed. Target based studies demonstrated inhibition of tubulin polymerization by7qat an IC50value of 2.65 ± 0.47 μM and its effective binding with CT-DNA. Further, molecular modelling studies revealed that7qhas a prominent binding affinity towards the α/β-tubulin receptor with remarkable protein-ligand interactions and binding energy.
- Ambatwar, Ramesh,Kadagathur, Manasa,Kiranmai, Gaddam,Nagendra Babu, Bathini,Nagesh, Narayana,Nunewar, Saiprasad N.,Shankaraiah, Nagula,Sigalapalli, Dilep Kumar,Tangellamudi, Neelima D.,Tokala, Ramya,Tripura, Chaturvedula
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p. 18908 - 18923
(2021/10/26)
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- Purine parent-based zinc ion detection fluorescent probe as well as preparation method and application thereof
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The invention discloses a purine parent-based zinc ion detection fluorescent probe as well as a preparation method and application thereof. The structural formula of the fluorescent probe is shown asa formula I in the specification. A purine derivative and 8-formyl- 4-methyl umbrella-shaped ketone are used as fluorescent groups, hydrazine hydrate is used as a connecting group, the prepared fluorescent probe shows high sensitivity and high selectivity on Zn in a solution, and the probe can also detect zinc ions in a solid state; the preparation method of the fluorescent probe is simple insteps, raw materials are easy to obtain, and the obtained product is solid powder, easy to store, wide in application prospect and capable of being produced and applied on a large scale.
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Paragraph 0047-0050
(2021/02/06)
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- AIE type coumarin derivative fluorescent probe and application thereof in cyanide ion detection
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The invention particularly relates to an AIE type coumarin derivative fluorescent probe and application of the AIE type coumarin derivative fluorescent probe in cyanide ion detection, and belongs to the technical field of organic small molecule biological
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Paragraph 0031-0036
(2021/04/14)
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- A novel ratiometric AIE-based fluorescent probe for specific detection of Hcy/Cys and imaging of living cells: In vivo
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Thiol-containing small molecules such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play a key role in a wide range of physiological processes. But it is a challenging work to distinguish these biothiols since they have a similar structure
- Hu, Yi-Meng,Jiang, Zi-Ke,Lv, Hong-Min,Ma, Yan-Yan,Wang, Jing,Wang, Tao,Zhang, Xiao-Nan
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p. 19521 - 19530
(2021/11/09)
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- Ratiometric fluorescent molecular probe for detecting hypochlorite ions and preparation method and application thereof
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The invention relates to a ratiometric fluorescent molecular probe for detecting hypochlorite ions and a preparation method and application thereof, belonging to the technical field of chemical fluorescent materials. According to the invention, a compound, namely 6-bromo-2-(2-morpholinoethyl)-1H-benzo[iso]quinoline-1,3(2H)-dione and coumarin aldehyde are adopted as raw materials, and are synthesized to obtain the probe disclosed by the invention. A novel lysosome-positioned fluorescent probe is constructed on the basis of two fluorophores, namely coumarin and naphthalimide, and is used for detecting the ratio of ClO, so fluorescence imaging of endogenous or exogenous ClO is realized.
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Paragraph 0066-0070; 0087-0089; 0096-0098
(2020/05/30)
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- Coumarin dye ratio type difunctional fluorescence probe as well as synthesis and application thereof (by machine translation)
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A small amount of concentrated hydrochloric acid is added dropwise, and a small amount of concentrated hydrochloric acid is added dropwise to obtain the final target product; and the ion probe can effectively and rapidly identify copper and hypochlorous acid, and has efficient selectivity and 7 - ion -4 - competitiveness, and can be used for identifying related actual water samples. (by machine translation)
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Paragraph 0010; 0056-0058; 0061-0063; 0066-0069
(2020/11/23)
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- Oxidovanadium (V and IV) complexes incorporating coumarin based O^N^O ligand: Synthesis, structure and catalytic activities
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The tridentate ligand H2L1, [(E)-7-Hydroxy-8-[(2-hydroxy-phenylimino)-methyl]-4-methyl-chromen-2-one] has been used in the present work towards the synthesis of mononuclear oxidovanadium complexes. Three mononuclear complexes [VOL1(OMe)(MeOH)], 1; [VO(L1)(8-Hq)], 2 and [VO(L1)(1,10-phen)], 3 have been successfully synthesized with high yields by reacting [VO(acac)2] with H2L1 in 1:1 ratio in methanol under refluxing conditions where 8-hydroxyquinoline and 1,10-phenanthroline were used as co-ligands in the synthesis of complex 2 and 3. X-ray crystallographic studies reveal that in all the complexes synthesized in the present study, the ligand H2L1 binds as O^N^O coordinating ligand. The synthesized complexes were well characterized by using UV–Vis, IR, NMR and Mass spectral techniques. The physiochemical properties have been well interpreted by density functional theory (DFT) and time dependent density functional theory (TDDFT) calculations. The synthesized complexes were established to show some distinctive properties e.g. oxidative bromination of aromatic aldehyde with high conversion rate and enhanced selectivity as well as high TON and TOF. The above properties were all well matched and demonstrated by using UV–visible and fluorescence as well as quenching studies. Complex 1 reacts with 3,5-DTBC catalytically in presence of molecular oxygen to generate corresponding ortho-benzoquinone.
- Majumder, Mitali,Krishna Rajak, Kajal
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- Coumarin derivative containing 7-substituent and 8-substituent, preparation method and uses thereof
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The invention belongs to the field of chemical pharmacy, and relates to a coumarin derivative containing a 7-substituent and a 8-substituent, a preparation method and uses thereof, particularly a derivative containing 7-alkoxy and 8-aromatic acid or aromatic hydrocarbon acid methanol ester substituted coumarin mother nucleus. According to the present invention, the experiment results show that thederivatives have almost no toxicity to normal cells and drug-resistant tumor cells; by combining the derivatives, paclitaxel and vincristine, the drug resistance activity of A2780/T and KB-V over-expressing P-gp can be significantly reversed, and the drug sensitivity of non-P-gp-dependent drug-resistant tumor cells is not increased; and the compound can deep develop sensitizers capable of restoring the drug sensitivity of P-gp over-expression induced MDR tumors, and can establish the foundation for the overcoming of P-gp over-expression induced MDR tumors.
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Paragraph 0036; 0037; 0038
(2019/01/16)
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- Coumarin thiadione compound and preparation method and application thereof
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The invention relates to a coumarin thiadione compound and a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The coumarin thiadione compound and medicinal salt thereof are shown in formulas I to VIII; and the compound has a certain inhibiting activity for growth of gram positive bacteria, gram negative bacteria and fungi, and can be used for preparing an antibacterial and/or antifungal medicament, so that the coumarin thiadione compound gets a chance of providing diversified safer and more efficient candidate medicaments for clinical antimicrobial treatment and is helpful for solving clinical treatment problems of increasingly serious drug resistance, stubborn pathogenic microorganisms, emerging harmful microorganisms and the like. Thecoumarin thiadione compound is simple in preparation raw material, cheap, easy to obtain and short in synthetic route, and has the important significance for application in the aspect of infection resistance. (The formulas are shown in the description.).
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Paragraph 0047; 0048; 0049; 0050
(2018/12/14)
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- Fluorescence detection of serum albumin with a turnover-based sensor utilizing Kemp elimination reaction
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The Kemp elimination reaction is a well-known chemical reaction that is facilitated on a protein surface microenvironment, and in particular is highly accelerated in a unique binding pocket of serum albumin. We have designed and synthesized a fluorescently activatable coumarin derivative with a benzisoxazole scaffold to enable monitoring of the Kemp elimination reaction in terms of fluorescence change for the first time. We show that this fluorescent sensor can sensitively and selectively quantitate serum albumin in blood samples. It also works in a dry-chemistry format.
- Sakamoto, Shingo,Komatsu, Toru,Ueno, Tasuku,Hanaoka, Kenjiro,Urano, Yasuteru
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supporting information
p. 3464 - 3467
(2017/07/07)
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- Umbelliferone-oxindole hybrids as novel apoptosis inducing agents
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In furtherance of our endeavour towards the synthesis of novel bioactive agents, a panel of (E)-3-((7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methylene)indolin-2-one derivatives were synthesized using diverse 5-substituted oxindoles and 7-hydroxy-4-methyl-
- Nagarsenkar, Atulya,Guntuku, Lalita,Prajapti, Santosh Kumar,Guggilapu, Sravanthi Devi,Sonar, Rajkiran,Vegi, Ganga Modi Naidu,Babu, Bathini Nagendra
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p. 12604 - 12610
(2017/11/06)
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- Synthesis, pharmacological assessment, molecular modeling and in silico studies of fused tricyclic coumarin derivatives as a new family of multifunctional anti-Alzheimer agents
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A series of fused tricyclic coumarin derivatives bearing iminopyran ring connected to various amido moieties were developed as potential multifunctional anti-Alzheimer agents for their cholinesterase inhibitory and radical scavenging activities. In vitro studies revealed that most of these compounds exhibited high inhibitory activity on acetylcholinesterase (AChE), with IC50 values ranging from 0.003 to 0.357 μM which is 2-220 folds more potent than the positive control, galantamine. Their inhibition selectivity against AChE over butyrylcholinesterase (BuChE) has increased about 194 fold compared with galantamine. The developed compounds also showed potent ABTS radical scavenging activity (IC50 7.98-15.99 μM). Specifically, the most potent AChE inhibitor 6n (IC50 0.003 ± 0.0007 μM) has an excellent antioxidant profile as determined by the ABTS method (IC50 7.98 ± 0.77 μM). Moreover, cell viability studies in SK N SH cells showed that the compounds 6m-q have significant neuroprotective effects against H2O2-induced cell death, and are not neurotoxic at all concentrations except 6n and 6q. The kinetic analysis of compound 6n proved that it is a mixed-type inhibitor for EeAChE (Ki1 0.0103 μM and Ki2 0.0193 μM). Accordingly, the molecular modeling study demonstrated that 6m-q with substituted benzyl amido moiety possessed an optimal docking pose with interactions at catalytic active site (CAS) and peripheral anionic site (PAS) of AChE simultaneously and thereby they might prevent aggregation of Aβ induced by AChE. Furthermore, in silico ADMET prediction studies indicated that these compounds satisfied all the characteristics of CNS acting drugs. Most active inhibitor 6n is permeable to BBB as determined in the in vivo brain AChE activity. To sum up, the multipotent therapuetic profile of these novel tricyclic coumarins makes them promising leads for developing anti-Alzheimer agents.
- Shaik, Jeelan Basha,Palaka, Bhagath Kumar,Penumala, Mohan,Kotapati, Kasi Viswanath,Devineni, Subba Rao,Eadlapalli, Siddhartha,Darla, M. Manidhar,Ampasala, Dinakara Rao,Vadde, Ramakrishna,Amooru, G. Damu
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p. 219 - 232
(2015/11/24)
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- Coumarin light-emitting compound preparation and application (by machine translation)
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The invention discloses a coumarin preparation and application of the light-emitting compound, which belongs to the technical field of synthesis of inorganic material. The light-emitting compound from 5- chlorine salicylic aldehyde, acetyl glycine and anhydrous sodium acetate in acetic anhydride heating reaction in the reaction solvent and further processing to obtain the 3-amino-6-chloro-coumarin precursor, then the inter-phenol, acetyl acetic acid ethyl ester as the raw material to prepare another kind of coumarin compound 4-methyl -7 hydroxy-8-aldehyde group coumarin, then two in the 1:1 in ethanol in the molar ratio of amine aldehyde condensation and through. Method for synthesizing the light-emitting compound has comparatively simple operation, low material price, mild condition, less side reaction, the ethanol solvent green pollution-free, product separation and purification of the product is convenient, stable structure. The light-emitting compounds can be used as a molecular probe for identifying MANGANESETION, high sensitivity, good anti-interference, quantitative detection can even be realized. (by machine translation)
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- Beta-1,4-galactosyltransferase I substrate fluorescent molecular probe, and intermediate and preparation method thereof
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The invention relates to a chemically synthesized beta-1,4-galactosyltransferase I (beta-1,4-GalT I) substrate fluorescent molecular probe targeting to tumor cells, and an intermediate and a preparation method thereof. The chemical structure of the beta-1,4-GalT I substrate fluorescent molecular probe is shown in the description, and Ac in the formula represents an acetyl group. Tumor cell strains are screened to obtain high-expression beta-1,4-GalT I adopted as a target, a 8-difluoromethyl-7-hydroxycoumarin-beta-acetylglucoside specific substrate is designed and synthesized based on an ASPs strategy, the galactosyl group of a donor UDP-Gal is transferred to the substrate through using the transglycosylation of beta-1,4-GalT I in order to generate a lactosyl group, aglucones are released in the glycosidase hydrolysis process and undergo an elimination reaction to form a quinonylmethyl compound with high reaction activity, and the quinonylmethyl compound is covalently combined with the nucleophilic substrate nearby the enzyme to finally complete targeting fluorescent labeling process of the tumor cells, so early diagnosis of the tumors is realized.
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Paragraph 0024; 0025; 0026
(2016/10/10)
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- Cupric ion fluorescence enhancement type molecular probe and preparation method as well as application thereof
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The invention discloses a cupric ion fluorescence enhancement type molecular probe and a preparation method as well as application thereof. The molecular formula of the probe is shown in the description; 4-methyl-7-hydroxy coumarin is taken as a fluorescence matrix, and reacts with hexamethylene second-amine; a formyl group is introduced at an ortho-position of hydroxy, and an obtained intermediate reacts with o-ethoxyphenol benzylamine; then nitrogen atoms and oxygen atoms are introduced; meanwhile the fluorescent light of a compound is enabled to close, and a specific reaction with cupric ions can be performed. By introducing the nitrogen atoms and the oxygen atoms for performing specific coordination with the cupric ions in the reaction matrix, a cupric ion sensor can quickly cooperate with the cupric ions in a detection process, so that fluorescent light is increased rapidly, thus realizing detection on the cupric ions and being capable of effectively avoiding the disturbance of other metal ions. The fluorescence probe prepared by the method is a high-selectivity fluorescence enhancement type cupric ion chemosensor simple in structure, cheap and easily available in material, easy to prepare and high in yield.
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Paragraph 0041-0047
(2018/02/04)
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- IRE-1α INHIBITORS
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PROBLEM TO BE SOLVED: To provide compounds which directly inhibit inositol requiring enzyme 1 (IRE-1α activity) in vitro, prodrugs, and pharmaceutically acceptable salts thereof. SOLUTION: The present invention provides a compound represented by formula (A) [R3 and R4 are H or the like; Q5-Q8, together with the benzene ring to which they are attached, form a benzofused ring, where at least one of Q5-Q8 is a heteroatom selected from N, O, and S. COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0831; 0834; 0835
(2016/10/07)
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