38609-97-1Relevant articles and documents
Development of a HPLC-FL method to determine benzaldehyde after derivatization with: N -acetylhydrazine acridone and its application for determination of semicarbazide-sensitive amine oxidase activity in human serum
Dong, Xiuli,Tang, Jiayuan,Ren, Yan,Chen, Xiangming
, p. 6717 - 6723 (2019)
A novel fluorescence labeling reagent N-acetylhydrazine acridone (AHAD) was designed and synthesized. A highly sensitive high performance liquid chromatography (HPLC) method coupled with fluorescence detection to determine benzaldehyde after derivatization with AHAD was developed. Optimum derivatization was obtained at 40 °C for 30 min with trichloroacetic acid as catalyst. Benzaldehyde derivative was separated on a reversed-phase SB-C18 column in conjunction with a gradient elution and detected by fluorescence detection at excitation and emission wavelengths of 371 nm and 421 nm. The established method exhibited excellent linearity over the injected amount of benzaldehyde of 0.003 to 5 nmol mL-1. The method was successfully applied to the determination of serum semicarbazide-sensitive amine oxidase (SSAO) activity in humans. SSAO is a significant biomarker because serum SSAO activity is elevated in patients with Alzheimer's disease, vascular disorders, heart disease and diabetes mellitus. It was demonstrated that the SSAO activity of the hyperglycemic group (60 ± 4 nmol mL-1 h-1) was significantly higher than that of normal blood sugar group (44 ± 4 nmol mL-1 h-1) with P 0.05.
Design, synthesis and biological evaluation of acridone analogues as novel STING receptor agonists
Chang, Jia-jia,Hou, Shi,Lan, Xiu-juan,Li, Song,Li, Wei,Sun, Wei,Xiao, Jun-hai,Yan, Xin-lin,Yang, Xiao-hong
, (2020/01/09)
STING (Stimulator of Interferon Genes) has become a focal point in immunology research and a target in drug discovery. The discovery of a potent human-STING agonist is expected to revolutionize current anti-virus or cancer immunotherapy. Inspired by the structure and function of murine STING-specific agonists (DMXAA and CMA), we rationally designed and synthesized four series of novel compounds for the enhancement of human sensitivity. In the cell-based assay, we identified six compounds from all the synthetic small molecules: 2g, 9g, and 12b are STING agonists that are efficacious across species, and all have the skeleton of acridone; 1b, 1c, and 12c just function in the murine STING pathway. Notably, 12b exhibits the best activity among the six agonists, and its inductions of both human and murine STING-dependent signalling are similar to that of 2′3′-cGAMP, which is a well-known STING inducer. While a protein assay indicated that 2 g, 9 g, and 12b could activate the pathway by directly binding human STING, 12b also displayed the strongest binding affinity. Additionally, our studies show that 12b can induce faster, more powerful, and more durable responses of assorted cytokines in a native system than 2′3′-cGAMP. Consequently, our team is the first to successfully modify murine STING agonists to obtain human sensitivity, and these results suggest that 12b is a potent direct-human-STING agonist. Additionally, the acridone analogues demonstrate tremendous potential in the treatment of tumours or viral infections.
Method for synthesizing oxo-10-acridineacetic acid by adopting phase-transfer catalysis method
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Paragraph 0030; 0044; 0045; 0047; 0050; 0051; 0072, (2018/09/14)
The invention discloses a method for synthesizing oxo-10-acridineacetic acid by adopting a phase-transfer catalysis method. The method comprises the following steps of 1, preparing acridone, wherein diphenylamine and an acid catalyst are dissolved into an organic solvent, the mixture reacts with CO2 under the pressure of 0.6-0.7 MPa, pressure relief is performed, water is added, stirring is performed, filtering is performed, standing and layering are performed, an organic phase is sampled for washing, the solvent is evaporated out, and drying is performed to obtain the acridone; 2, preparing oxo-10-acridineacetic acid, wherein the acridone, chloroacetic acid and the phase transfer catalyst are added into a mixed solvent containing DMF and NaOH for a reaction under the temperature of 80-100DEG C, TLC is adopted for monitoring the complete reaction, the reaction is stopped, cooling is performed till room temperature is reached, ice water is added to obtain solid precipitates, the precipitates are filtered and washed to obtain a wet product midbody, the wet product midbody is added into a NaOH water solution, stirring is performed under the room temperature for dissolution, filteringis performed, the NaOH water solution is use for cleaning the filtered solid, washing solutions are mixed, the pH value is adjusted to be 4-5, solid precipitates are obtained, and filtering, washingand drying are performed to obtain the oxo-10-acridineacetic acid.
Palladium/copper Co-catalyzed oxidative C-H/C-H carbonylation of diphenylamines: A way to access acridones
Wen, Jiangwei,Tang, Shan,Zhang, Fan,Shi, Renyi,Lei, Aiwen
, p. 94 - 97 (2017/11/27)
An efficient palladium/copper co-catalyzed oxidative double C(sp2)-H functionalization/carbonylation of diphenylamines for synthesis of acridones has been developed. This method utilizes readily available starting materials and mild reaction conditions. The protocol provides a simple, efficient, and atomeconomic way to access acridones. Notably, the present protocol has excellent functional group tolerance and application value.
A quinacridone N - alkylated derivatives of preparation method
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Paragraph 0016; 0017; 0018, (2017/08/02)
The invention discloses a preparation method of acridone N-alkylation derivative, which comprises the following steps: adding an alkaline ion liquid and acridone into a three-neck flask provided with a condensation reflux unit at room temperature, stirring uniformly, adding halide, stirring to react at 20-50 DEG C for 6-12 hours, standing at room temperature, filtering, washing the filter cake with methanol, and drying to obtain the acridone N-alkylation derivative product. The method has the advantages of mild reaction conditions, high yield and recyclable ion liquid, is safe and convenient to operate, and has favorable industrialized application value.
Design, synthesis and biological evaluation of new oligopyrrole carboxamides linked with tricyclic DNA-intercalators as potential DNA ligands or topoisomerase inhibitors
David-Cordonnier, Marie-Helene,Hildebrand, Marie-Paule,Baldeyrou, Brigitte,Lansiaux, Amelie,Keuser, Christoph,Benzschawel, Kerstin,Lemster, Thomas,Pindur, Ulf
, p. 752 - 771 (2008/02/13)
In the context of the design and synthesis of minor groove binding and intercalating DNA ligands some new oligopyrrole carboxamides were synthesized. These hybrid molecules (combilexins) possess a variable and conformatively flexible spacer at the N-terminal end. As intercalating tricyclic systems acridone, acridine, anthraquinones and in a special case iminostilbene terminate the N-terminal end of the pyrrole chain. The cytotoxicity was examined by the NCI antitumor screening, furthermore, biophysical as well as biochemical studies were performed in order to get some information about the DNA binding properties and topoisomerase inhibition effect of this new series of molecules.
