Design, synthesis and biological evaluation of novel β-pinene-based thiazole derivatives as potential anticancer agents via mitochondrial-mediated apoptosis pathway.

Design, synthesis and anticancer activity of novel nopinone-based thiosemicarbazone derivatives

Three new Schiff-base derivatives with aggregation-induced emission (AIE) characteristics have been designed and successfully synthesized. Their photophysical properties in solution, aqueous suspension and the solid state were investigated systematically. The three compounds showed an obvious 1π–π* transition mixed with intramolecular charge transfer (ICT) properties in the UV-vis spectra, which were evidenced by spectral analysis and theoretical calculations. The compounds exhibited evident AIE characteristics with a relatively high fluorescence quantum yield in the solid state (ΦF = 15–21%). Moreover, the morphologies and sizes of the particles in water/CH3CN solutions were studied using a transmission scanning electron microscope (TEM) and dynamic light scattering (DLS). The crystallographic data for A3 suggest that the existence of intramolecular hydrogen bonding interactions restricted intramolecular rotation. Interestingly, A3 showed fluorescence turn-on sensing towards Cu2+via chelation enhanced fluorescence in a CH3CN–H2O (4 : 1, v/v) solution. It has a fast response time and a linear range of 0–20 μM for Cu2+ ions with a detection limit of 2.3 × 10−7 mol L−1. In addition, A3 also exhibits a piezofluorochromic response.

Highly sensitive and selective fluorescent sensor for copper(II) based on salicylaldehyde Schiff-base derivatives with aggregation induced emission and mechanoluminescence

A series of novel 2-isocamphanyl thiosemicarbazone derivatives were synthesized and characterized by 1 H NMR, 13 C NMR, and HRMS. In in vitro anticancer activity, most derivatives showed considerable cytotoxic activity against four cancer cell lines (RPMI-8226, A549, MDA-MB-231, and HepG2 cancer cells) and showed low toxicity against human gastric mucosal cells (GES-1). Among them, compound 4h exhibited excellent antitumor activity against the tested cancer cells with IC50 values of 0.4, 1.1, 1.6, and 1.7 μM for MDA-MB-231, RPMI-8226, A549, and HepG2, respectively. Further, mechanism studies indicated that compound 4h induced apoptosis in MDA-MB-231 cells through enhancing reactive oxygen species levels, inducing mitochondrial membrane potential decrease, and influencing the expression of Bax, Bcl-2, caspase-3, and caspase-9.

Synthesis and antitumor activity of 2-isocamphanyl thiosemicarbazone derivatives via ROS-enhanced mitochondrial damage.

Five imino salicylidene based bifunctional chelators were developed in order to act as a multipurpose ligand system. The chelators, namely 5-methyl-2-(1,2,4-triazol-3-yliminomethyl)phenol, 2-(9-ethylcarbazol-3-yliminomethyl)-5-methylphenol, 2-[(2-imidazol-4-yl)ethyliminomethyl]-5-methylphenol, 2-[(2-indol-3-yl-ethyl)iminomethyl]-5-methylphenol and 2-[2-(4-hydroxyphenyl)ethyliminomethyl]-5-methylphenol, all of which contain a biological directing functional group on the imine moiety, were investigated via crystallographic and DFT structural studies. Synthesis, in vitro cell testing and photoluminescence are reported indicating specific quantum yields and the respective suitability for radiopharmaceutical development.

Designing model imino bifunctional chelators for radiopharmaceuticals – in vitro antitumor activity, photoluminescence and structural analysis

Salicylaldehyde azine (1), with an aggregation-induced emission (AIE) function, was synthesized from salicylaldehyde and characterized by Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS), and X-ray single crystal diffraction. Compound 1 exhibited high thermal stability and good light-emitting behavior in the solid state. It could be preferably used to dye cellulose and KBr. No obvious changes in fluorescence intensity occurred when compound 1 was dissolved in different pH buffer solutions. The addition of TFA led to slight fluorescence quenching, and the fluorescence intensity gradually increased with increasing potassium tert-butoxide solution concentrations. The fluorescence intensity of compound 1 showed a good linear relationship with the concentration of potassium tert-butoxide (0.5–4.0 × 10−4 M), y = 99.193x + 93.599, R2 = 0.9902; the limit of detection (LOD) was 1.07 × 10−7 M. It could measure the content of potassium tert-butoxide with a relative standard deviation (RSD) value of 1.5%.

Fluorescence staining of salicylaldehyde azine, and applications in the determination of potassium tert-butoxide

/pdf/synthesis-and-biological-activity-of-novel-pinanyl-thiazole-fzfmmf6hu5.pdf

Synthesis and Biological Activity of Novel Pinanyl Thiazole Derivatives

The invention discloses a pinic alkyl thiazole derivative and a synthetic method and application thereof. The synthetic method of the compound comprises the steps that nopinone serves as a raw material, nopinone and thiosemicarbazide are firstly subjected to a condensation reaction, a nopinone thiosemicarbazone intermediate is obtained, then the nopinone thiosemicarbazone intermediate and alpha-haloketone are cyclized under base catalysis, and the novel pinic alkyl thiazole derivative is synthesized. The prepared compound has the remarkable anti-inflammatory function on human umbilical vein endothelial cell inflammation damage caused by lipopolysaccharide, is an anti-inflammatory compound with great potential and has high practicality.

Pinic alkyl thiazole derivative and synthetic method and application thereof

The invention discloses an isolongifolene[1,2,3]thiadiazole compound and a preparation method and an application thereof The synthesis method comprises the steps: carrying out condensation of isolongifolenone with semicarbazide hydrochloride to generate isolongifolenone semicarbazide, then carrying out condensation cyclization with sulfoxide chloride to obtain the isolongifolene[1,2,3]thiadiazole compound, namely 5,5,9,9-tetramethyl-5,6,7,8,8a,9-hexahydro-6,8a-bridged methylene-1,2,3-naphthothiadiazole The isomerized product isolongifolenone of natural renewable resource heavy turpentine is used as a raw material for preparation of the novel isolongifolene[1,2,3]thiadiazole compound 5,5,9,9-tetramethyl-5,6,7,8,8a,9-hexahydro-6,8a-bridged methylene-1,2,3-naphthothiadiazole Researches confirm that the compound can be used as an insecticide and has specific toxic killing effect on diamond back moth

Isolongifolene[1,2,3]thiadiazole compound and preparation method and application thereof

The invention discloses a pyridyl pyrimidine compound and a synthesizing method and application thereof. The synthesizing method includes the steps that nopinone and pyridylaldehyde are subjected to aldol condensation reaction under the basic catalytic function, and pyridine methylene nopinone is obtained; pyridine methylene nopinone and guanidine hydrochloride are subjected to cyclization reaction, and the pyridyl pyrimidine compound is obtained. The synthesized compound has good insecticidal activity and antibacterial activity, and has wide application prospects.

Pyridyl pyrimidine compound and synthesizing method and application thereof

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