Furanonyl amino acid derivatives as hemostatic drugs: design, synthesis and hemostasis performance.

Using 3,4-dihalo-2(5H)-furanones and easily available hemostatic drugs, such as tranexamic acid (TA), 4-aminomethylbenzoic acid (ABA), aminocaproic acid (AA) as starting materials, serial multi-functional molecules 2(5H)-furanonyl amino acids are designed by the combination of different pharmacophores, and successfully synthesized by a transition metal-free Michael addition-elimination reaction. The reaction is carried out under mild conditions with ethanol-dichloromethane as solvent and only stirring at room temperature for 24 h, and the yield can be up to 91%. All products are well characterized by infrared spectroscopy (IR), nuclear magnetic resonance (NMR), high-resolution mass spectra (HRMS).

Rational Design and Facile Synthesis of Dual-State Emission Fluorophores: Expanding Functionality for the Sensitive Detection of Nitroaromatic Compounds.

Six novel benzimidazole-based D-π-A compounds 4 a-4 f were concisely synthesized by attaching different donor/acceptor units to the skeleton of 1,3-bis(1H-benzimidazol-2-yl)benzene on its 5-position through an ethynyl link. Due to the twisted conformation and effective conjugation structure, these dual-state emission (DSE) molecules show intense and multifarious photoluminescence, and their fluorescence quantum yields in solution and solid state can be up to 96.16 and 69.

-alkylation briefly constructs tunable multifunctional sensor materials: Multianalyte detection and reversible adsorption.

A series of -alkyl-substituted polybenzimidazoles (), synthesized by simple condensation and -alkylation, act as functional materials with tunable microstructures and sensing performance. For their controllable morphologies, the formation of nano-/microspheres is observed at the (RBr)/(PBI) feed ratio of 5:1. Products with different degrees of alkylation can recognize metal ions and nitroaromatic compounds (NACs).

Preparation of Large Conjugated Polybenzimidazole Fluorescent Materials and Their Application in Metal Ion Detection.

A new type of conjugated polybenzimidazole () was synthesized through a simple polycondensation reaction without metal catalysis, and -alkylation modification was carried out to solve the problems of solubility and fluorescence properties. A series of nano-microsphere polymers with large conjugation, good solubility, and strong fluorescence has been successfully used as "turn-off" fluorescent probes for the first time. The results show that, under suitable -alkylation conditions, the obtained can be used as a highly sensitive and selective fluorescent probe for the detection of Cu and Zn at the same time, and their detection limits are both nM levels.

Controllable preparation and performance of bio-based poly(lactic acid-iminodiacetic acid) as sustained-release Pb chelating agent.

The bio-based lactic acid (LA) and the common metal ion chelating agent iminodiacetic acid (IDA) are used to design and prepare a polymeric sustained-release Pb chelating agent by a brief one-step reaction. After the analysis on theoretical calculation for this reaction, poly(lactic acid-iminodiacetic acid) [P(LA--IDA)] with different monomer molar feed ratios is synthesized via direct melt polycondensation. P(LA--IDA) mainly has star-shaped structure, and some of them have two-core or three-core structure.

Polymer-capped CdSe/ZnS quantum dots for the sensitive detection of Cu and Hg and the quenching mechanism.

In this work, poly(styrene-co-maleic anhydride)-capped CdSe/ZnS quantum dots (QDs) aminolyzed with ethanolamine are proposed as fluorescent probes for the detection of Cu2+ and Hg2+, and two different quenching mechanisms are discussed in detail. The coordination abilities of the surface polymer of CdSe/ZnS QDs and two metal ions are calculated by density functional theory (DFT). The photoinduced electron transfer from excited QDs to Cu2+ unoccupied orbitals is enhanced due to the coordination between Cu2+ and the surface polymer of QDs.

Synthesis of N-2(5H)-furanonyl sulfonyl hydrazone derivatives and their biological evaluation in vitro and in vivo activity against MCF-7 breast cancer cells.

A series of (E)-N-2(5H)-furanonyl sulfonyl hydrazone derivatives have been rationally designed and efficiently synthesized by one-pot reaction with good yields for the first time. This green approach with wide substrate range and good selectivity can be achieved at room temperature in a short time in the presence of metal-free catalyst. The cytotoxic activities against three human cancer cell lines of all newly obtained compounds have been evaluated by MTT assay.

1,1-Diphenylvinylsulfide as a Functional AIEgen Derived from the Aggregation-Caused-Quenching Molecule 1,1-Diphenylethene through Simple Thioetherification.

An efficient and readily scalable thioetherification between 1,1-diphenylethene (DPE) and sodium arylsulfinate was developed for the synthesis of 1,1-diphenylvinylsulfide (DPVS) with the yield up to 99 %. The photophysical properties of DPVS show that the introduction of arylsulfenyl groups onto the parent molecule DPE makes DPVS a novel type of aggregation-induced emission (AIE) luminogen (AIEgen) with large Stoke's shift (up to 188 nm). These DPVS possess AIE properties due to restriction of intramolecular motions (RIM), as demonstrated by crystal structure analysis.

Quick construction of a C-N bond from arylsulfonyl hydrazides and C-X compounds promoted by DMAP at room temperature.

An efficient approach for C-N bond construction by the coupling reaction of arylsulfonyl hydrazides and C-X compounds is described for the first time with good yields at room temperature. The reaction promoted by the simple base DMAP displays excellent regioselectivity as well as high functional group tolerance with 41 examples. Even for inactive C-Cl compounds, the metal-free transformation also affords a satisfactory yield after prolonging the reaction time, which is comparable to that of the corresponding C-Br compound.

Synthesis of amino acid derivatives of 5-alkoxy-3,4-dihalo-2(5H)-furanones and their preliminary bioactivity investigation as linkers.

A series of amino acid derivatives are successfully synthesized via a metal-free C-N coupling reaction of 5-alkoxy-3,4-dihalo-2(5H)-furanones and amino acids. Their structures are well characterized with H NMR, C NMR, ESI-MS and elemental analysis. As potential linkers of the 2(5H)-furanone unit with other drug moieties containing a hydroxyl or amino group, the effect of amino acids is investigated by comparison with other 2(5H)-furanone compounds by constructing C-O/C-S bonds.

Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF·OEt: An Approach to Symmetrical/Unsymmetrical Thiosulfonates.

The BF·OEt-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O) bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation.

Novel dual-functional fluorescent sensors based on bis(5,6-dimethylbenzimidazole) derivatives for distinguishing of Ag and Fe in semi-aqueous medium.

Three novel bisbenzimidazole derivatives have been synthesized and developed as dual-functional fluorescent sensors for the rapid and highly selective detection of Ag and Fe ions in semi-aqueous medium with distinct spectral response for the first time. The absorption intensity is drastically decreased after the addition of Ag. Contrarily, it is markedly increased upon the addition of Fe.

Bis-2(5H)-furanone derivatives as new anticancer agents: Design, synthesis, biological evaluation, and mechanism studies.

New bis-2(5H)-furanone derivatives containing a benzidine core were synthesized via a one-step transition-metal-free reaction of benzidine with 5-substituted 3,4-dihalo-2(5H)-furanones. Their antitumor activities against various tumor cells have been evaluated by MTT assay. Among them, compound 4e exhibits significant inhibitory activity against C6 glioma cells with an IC value of 12.

Preparation and Characterization of Poly-1,2,3-triazole with Chiral 2(5)-Furanone Moiety as Potential Optical Brightening Agents.

A series of novel heterocyclic polymers with fluorescent brightening properties are synthesized via Click polymerization. Fast synthesis of poly-1,2,3-triazoles ( ≥ 9.31 kDa) is described herein, with a high yield of up to 95%.

Synthesis and biological evaluation of 4-biphenylamino-5-halo-2(5H)-furanones as potential anticancer agents.

An efficient route without metal catalyst has been developed for synthesis of 4-biphenylamino-5-halo-2(5H)-furanones. The antitumor activities against various tumor cells of all the compounds have been evaluated by MTT assay. Among them, the compound 3j exhibits significant inhibitory activity against MCF-7 human breast cancer cells with an IC value of 11.

Self-assembled structures of N-alkylated bisbenzimidazolyl naphthalene in aqueous media for highly sensitive detection of picric acid.

A 2,6-dibenzimidazole-appended naphthalene derivative flanking with two N-alkyl chains (sensor 4) was designed and applied for highly sensitive detection of picric acid (PA) in aqueous media. Driven by the hydrophobicity of alkyl chain and π-π stacking effect of aryl, sensor 4 can undergo self-assembly to form an orderly rod-like structure in HO/THF (v/v, 90/10) solution, as shown by the dynamic light scattering (DLS) and scanning electron microscopy (SEM) studies. Sensor 4 shows high selectivity and sensitivity toward PA over other nitroaromatic explosives.

Preparation and characterization of amine-functionalized sugarcane bagasse for CO2 capture.

A low-cost solid amine adsorbent for CO2 capture was prepared by using sugarcane bagasse (SB), a dominant agro-industrial residue in the sugar and alcohol industry as raw materials. In this preparation process, acrylamide was grafted on SB, and the grafted fiber was then aminated with different type of amine reagents to introduce primary and secondary amine groups onto the surface of SB fibers. The graft and amination conditions were optimized.

Design, synthesis, and characterization of 1,3,5-tri(1H-benzo[d]imidazol-2-yl)benzene-based fluorescent supramolecular columnar liquid crystals with a broad mesomorphic range.

A new kind of supramolecular columnar liquid crystal T-A with a broad mesomorphic range (up to 164.9 °C), good thermal stability, and strong fluorescence is designed and formed by the H-bonding between 1,3,5-tri(1H-benzo[d]imidazol-2-yl)benzene (T) and serial gallic acid derivatives (A). Two components are easily available because of simple routes, common reactions, high yields, commercial starting materials, and inexpensive catalysts.