602-56-2Relevant articles and documents
CONVENIENT SYNTHESIS OF 9-ALKYL AND 9-ARYLACRIDINES FROM METHYL (SEM) PROTECTED ACRIDONE
Zeng, Zijian,Zimmerman, Steven C.
, p. 5123 - 5124 (1988)
The low yielding addition of organolithium reagents to acridone becomes a convenient high yielding route to 9-alkyl and 9-arylacridines when SEM-acridone is used.
Investigation in the field of quinazolines. 8*. New reaction of N-alkylation of 4,4-diphenyl-3,4-dihydroquinazolines
Gromachevskava, Elena V.,Kaigorogova, Elena A.,Bespalov, Alexander V.,Demidov, Oleg P.,Krapivin, Gennady D.
, (2020)
[Figure not available: see fulltext.] The reaction of substituted 4,4-diphenyl-3,4(1,4)-dihydroquinazolines with various alkylating agents in DMSO–KOH leads (depending on the structure of the alkylating agent) to the formation of the corresponding N1
Design, synthesis and evaluation of novel 9-arylalkyl-10-methylacridinium derivatives as highly potent FtsZ-targeting antibacterial agents
Song, Di,Zhang, Nan,Zhang, Panpan,Zhang, Na,Chen, Weijin,Zhang, Long,Guo, Ting,Gu, Xiaotong,Ma, Shutao
, (2021/05/10)
With the increasing incidence of antibiotic resistance, new antibacterial agents having novel mechanisms of action hence are in an urgent need to combat infectious diseases caused by multidrug-resistant (MDR) pathogens. Four novel series of substituted 9-arylalkyl-10-methylacridinium derivatives as FtsZ inhibitors were designed, synthesized and evaluated for their antibacterial activities against various Gram-positive and Gram-negative bacteria. The results demonstrated that they exhibited broad-spectrum activities with substantial efficacy against MRSA and VRE, which were superior or comparable to the berberine, sanguinarine, linezolid, ciprofloxacin and vancomycin. In particular, the most promising compound 15f showed rapid bactericidal properties, which avoid the emergence of drug resistance. However, 15f showed no inhibitory effect on Gram-negative bacteria but biofilm formation study gave possible answers. Further target identification and mechanistic studies revealed that 15f functioned as an effective FtsZ inhibitor to alter the dynamics of FtsZ self-polymerization, which resulted in termination of the cell division and caused cell death. Further cytotoxicity and animal studies demonstrated that 15f not only displayed efficacy in a murine model of bacteremia in vivo, but also no significant hemolysis to mammalian cells. Overall, this compound with novel skeleton could serve as an antibacterial lead of FtsZ inhibitor for further evaluation of drug-likeness.
Compound, pharmaceutical composition, medicine and application of compound, pharmaceutical composition and medicine in preparation of antibacterial products
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, (2021/07/17)
The invention particularly relates to a compound, a pharmaceutical composition, a medicine and application of the compound, the pharmaceutical composition and the medicine in preparation of antibacterial products. The seeking of a novel antibacterial target and the development of a novel chemical entity have important significance for solving the increasingly severe bacterial drug resistance problem at present, and the design of a compound entity acting on the FtsZ target is expected to be developed to obtain an antibacterial drug which has no influence on a host. The invention provides a 9-aralkyl-10-methylacridine quaternary ammonium salt derivative and a preparation method thereof, and the compound has significant bactericidal and/or bacteriostatic activity on gram-positive bacteria, has a good effect of inhibiting bacterial division protein FtsZ, and can be used for preparing antibacterial products.
Tert-Butyl Bromide-Promoted Intramolecular Cyclization of 2-Arylamino Phenyl Ketones and Its Combination with Cu-Catalyzed C-N Coupling: Synthesis of Acridines at Room Temperature
Cao, Zifeng,Zhu, Yuan,Li, Xiaoman,He, Yang,Zhang, Jinli,Xu, Liang,Wei, Yu
, p. 10167 - 10174 (2020/09/03)
Herein, a facile intramolecular cyclization of 2-arylamino phenyl ketones is established to supersede the traditional high-temperature, strongly acidic conditions and achieve 9-substituted acridines, by virtue of the combination of 2,2,2-trifluoroethanol and tert-butyl bromide. This protocol can be merged well with the preceding Cu-catalyzed intermolecular Chan-Evans-Lam cross-coupling reactions, therefore enabling pot-economic modular synthesis of 9-substituted acridines from readily available 2-amino phenyl ketones and aryl boronic acids at room temperature.
Pd-Catalyzed Approach for Assembling 9-Arylacridines via a Cascade Tandem Reaction of 2-(Arylamino)benzonitrile with Arylboronic Acids in Water
Ye, Xuanzeng,Xu, Beihang,Sun, Jiani,Dai, Ling,Shao, Yinlin,Zhang, Yetong,Chen, Jiuxi
, p. 13004 - 13014 (2020/11/23)
A novel palladium-catalyzed protocol for the synthesis of 9-arylacridines via tandem reaction of 2-(arylamino)benzonitrile with arylboronic acids in water has been developed with good functional group tolerance. The present synthetic route could be readily scaled up to gram quantity without difficulty. This methodology was further extended to the synthesis of a 4′-OH derivative, which showed estrogenic biological activity. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular Friedel-Crafts acylation and dehydration to acridines.
A Direct S0→Tn Transition in the Photoreaction of Heavy-Atom-Containing Molecules
Kuribara, Takahito,Matsumoto, Koki,Muranaka, Atsuya,Nagasawa, Sho,Nakajima, Masaya,Nemoto, Tetsuhiro,Uchiyama, Masanobu
, p. 6847 - 6852 (2020/03/23)
According to the Grotthuss–Draper law, light must be absorbed by a substrate to initiate a photoreaction. There have been several reports, however, on the promotion of photoreactions using hypervalent iodine during irradiation with light from a non-absorbing region. This contradiction gave rise to a mystery regarding photoreactions involving hypervalent iodine. We demonstrated that the photoactivation of hypervalent iodine with light from the apparently non-absorbing region proceeds via a direct S0→Tn transition, which has been considered a forbidden process. Spectroscopic, computational, and synthetic experimental results support this conclusion. Moreover, the photoactivation mode could be extended to monovalent iodine and bromine, as well as bismuth(III)-containing molecules, providing new possibilities for studying photoreactions that involve heavy-atom-containing molecules.
Aryl acridine derivative synthesized by palladium catalysis and preparation method thereof (by machine translation)
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Paragraph 0030-0035, (2020/02/14)
When the reaction is carried out, the reaction temperature of the catalyst is very moderate, the reaction 2 - (temperature) of the catalyst is very moderate, the reaction; time of the, catalyst is, very moderate, and the reaction, is carried out at a reaction . temperature ranging from the reaction, time of the; reaction to the, solvent, 90 - 110 °C, 20 - 25, 94%. (by machine translation)
Preparation method of 9-phenyl acridine compound (by machine translation)
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Paragraph 0030; 0031, (2019/11/21)
The preparation method comprises the following 9 - steps: under the action 1 of a palladium catalyst, reacting the halogenated acridine compound of the formula I with 2 the phenylboronic acid or derivative thereof in a solvent under the action of a palladium catalyst 20 - 80 °C 3 9 . The halogen atom in the first X alkyl R group is 1 - 18 at least one halogen atom, and the alkyl group second is an alkyl group, an alkenyl group, an alkynyl group or a halogen atom. By adopting the method disclosed by the invention, the reaction 97% conversion rate is equal to or higher, the finished 99% product content after being subjected to post-treatment is higher than or equal to, and the process can meet the requirements of industrial production. (by machine translation)
Method for preparing acridine derivative
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Paragraph 0014-0017; 0019, (2019/07/16)
The invention relates to a method for preparing an acridine derivative, and specifically relates to a method for preparing the acridine derivative from an organic azide compound and a benzene compoundunder the action of an acid. According to the method disclosed by the invention, no transition metal catalyst is used, and the acridine derivative with an anthracene structure is obtained from a simple and easily-available raw material through simple operation steps.
