49742-72-5Relevant academic research and scientific papers
Acid-catalyzed oxidative cross-coupling of acridans with silyl diazoenolates and a Rh-catalyzed rearrangement: two-step synthesis of γ-(9-acridanylidene)-β-keto esters
Li, Weiyu,Xu, Hao,Zhou, Lei
supporting information, p. 5649 - 5657 (2021/07/02)
A MsOH-catalyzed oxidative cross-coupling of acridans and silyl diazoenolates and a Rh2(OAc)4-catalyzed rearrangement of the resultant diazo products are described. The reactions provide various γ-(9-acridanylidene)-β-keto esters in good yields, which bear an active α-methylene unit for further functionalization.
Access to acridones by tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation of anthranils with arylboronic acids
Huang, Yan-Xia,Huang, Zhuo-Jun,Jiang, Chun-Yong,Liang, Jing-Yi,Liang, Qiu-Ping,Shu, Bing,Xie, Hui,Zeng, Jun-Yi,Zhang, Shang-Shi,Zhou, Binhua
supporting information, p. 8487 - 8491 (2021/10/20)
An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance. What's more, a possible mechanistic proposal was also presented.
Acridone derivative containing amino sugar structure, and preparation method and application thereof (by machine translation)
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Paragraph 0035; 0041-0045, (2020/01/12)
The invention belongs to, the technical field of pharmaceutical chemistry, and particularly relates, to a preparation method of an acridone derivative containing an. amino sugar structure and a preparation method of the acridone derivative containing an a
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.
Dimethyl sulfoxide-aided copper(0)-catalyzed intramolecular decarbonylative rearrangement of N-aryl isatins leading to acridones
Wu, Hao,Ma, Nana,Song, Mengxiao,Zhang, Guisheng
, p. 1580 - 1583 (2019/12/09)
Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide (DMSO) under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields. This novel transformation is proposed to go through a sequential DMSO-aided Cu insertion into the amide C–N bond, CO extrusion, Cu migration, reductive elimination and DMSO-aided proton migration processes, involving multiple types of bond cleavage and formation in a single chemical step.
Amine compound for inhibiting SSASASASASASASAO/VAP-1 and application thereof in medicine (by machine translation)
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Paragraph 0426; 0432-0433, (2019/08/12)
The invention relates to an amine compound serving as an amino urea-sensitive amine oxidase (SSASAO) and/or a vascular adhesion protein -1 (VAP AP AP-1) inhibitor and application thereof in medicine, and further relates to a pharmaceutical composition containing the compound. The compounds or pharmaceutical compositions described herein may be used to treat inflammation and/or inflammation related diseases, diabetes and/or diabetes-related diseases, psychiatric disorders, ischemic diseases, vascular diseases, fibrosis or tissue transplant rejection. (by machine translation)
Syntheses of Acridones via Copper(II)-Mediated Relay Reactions from o-Aminoacetophenones and Arylboronic Acids
Wu, Hao,Zhang, Zhiguo,Liu, Qingfeng,Liu, Tongxin,Ma, Nana,Zhang, Guisheng
supporting information, p. 2897 - 2901 (2018/05/29)
The reaction of o-aminoacetophenones and arylboronic acids catalyzed by copper(II) salts in the presence of pyridine under an O2 atmosphere provides a general and efficient one-pot preparation of biologically interesting acridones. This relay reaction comprises an intermolecular Suzuki cross-coupling, intramolecular oxidative C(sp3)-H amination, and C(sp2)-H activation with simultaneous rearrangement of the generated isatin intermediates. This strategy tolerates both electron-donating and -withdrawing functionalities to afford various acridones in good to excellent yields.
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
supporting information, 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.
Design, synthesis, pharmacological evaluation, and docking study of new acridone-based 1,2,4-oxadiazoles as potential anticonvulsant agents
Mohammadi-Khanaposhtani, Maryam,Shabani, Mohammad,Faizi, Mehrdad,Aghaei, Iraj,Jahani, Reza,Sharafi, Zainab,Shamsaei Zafarghandi, Narges,Mahdavi, Mohammad,Akbarzadeh, Tahmineh,Emami, Saeed,Shafiee, Abbas,Foroumadi, Alireza
, p. 91 - 98 (2016/10/04)
A number of acridone-based oxadiazoles 11a–n have been synthesized and evaluated for their anticonvulsant activity against pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. Also, their neurotoxicity was evaluated by the rotarod test. Most of the compounds exhibited better anticonvulsant activity and higher safety respect to the standard drug, phenobarbital. Among the tested derivatives, compounds 11l with ED50value of 2.08?mg/kg was the most potent compound in the PTZ test. The anticonvulsant effect of compound 11l was blocked by flumazenil, suggesting the involvement of benzodiazepine (BZD) receptors in the anticonvulsant activity of prototype compound 11l. Also, docking study of compound 11l in the BZD-binding site of GABAAreceptor confirms possible binding of compound 11l with BZD receptors.
Method for synthesizing acridone derivatives by means of palladium-copper co-catalysis
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Paragraph 0026; 0027; 0028; 0029, (2017/02/09)
The invention discloses a method for synthesizing acridone derivatives by means of palladium-copper co-catalysis. The method comprises the steps that on the condition that palladium chloride, copper pivalate and di-tert-butyl peroxide or oxygen co-exist, diphenylamine compounds including symmetric diphenylamine and asymmetric diphenylamine are dissolved in an anhydrous organic solvent, all the materials are mixed to be uniform, a reaction is conducted for 20 h to 30 h under the condition of 80 DEG C to 120 DEG C in a carbon monoxide atmosphere, separation and purification are conducted, and the acridone derivatives can be obtained. According to the method for synthesizing the acridone derivatives by means of palladium-copper co-catalysis, the preparation method is simple, the diphenylamine compounds which are simple and easy to obtain are used as the raw materials, and the acridone derivatives are directly constructed through C-H/C-H oxidative carbonylation; the preparation condition is mild, and the target product can be obtained in a high-selectivity mode at 80 DEG C to 120 DEG C; the acridone derivatives have good substrate applicability, the range of substrates is greatly expanded, and the acridone derivatives have a great application prospect in biological medicine and materials and the like.
