- STUDIES ON ENAMIDES. PART-3 : A NOVEL PHOTOCHEMICAL SYNTHESIS OF 9-ARYLACRIDINES
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A unique synthesis of 9-arylacridines has been achieved by the photolysis of N-aroyldiphenylamines alongwith carbazole and photomigrated products.
- Datta, Indira,Das, Tapas Kumar,Ghosh, Somnath
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- Design, synthesis and evaluation of novel 9-arylalkyl-10-methylacridinium derivatives as highly potent FtsZ-targeting antibacterial agents
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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.
- Song, Di,Zhang, Nan,Zhang, Panpan,Zhang, Na,Chen, Weijin,Zhang, Long,Guo, Ting,Gu, Xiaotong,Ma, Shutao
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- Aryl acridine derivative synthesized by palladium catalysis and preparation method thereof (by machine translation)
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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)
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Paragraph 0044-0050
(2020/02/14)
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- Pd-Catalyzed Approach for Assembling 9-Arylacridines via a Cascade Tandem Reaction of 2-(Arylamino)benzonitrile with Arylboronic Acids in Water
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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.
- Ye, Xuanzeng,Xu, Beihang,Sun, Jiani,Dai, Ling,Shao, Yinlin,Zhang, Yetong,Chen, Jiuxi
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p. 13004 - 13014
(2020/11/23)
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- A magnetic nanoparticle-supported N-heterocyclic carbene-palladacycle: An efficient and recyclable solid molecular catalyst for Suzuki-Miyaura cross-coupling of 9-chloroacridine
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A robust magnetic nanoparticle-supported N-heterocyclic carbene-palladacycle has been readily synthesized by directly anchoring the structural defined acenaphthoimidazolylidene palladacycle with a long tail on magnetic nanoparticles (MNPs), and functioned as a solid molecular catalyst and exhibited extremely high catalytic activity towards the challenging Suzuki-Miyaura cross-coupling reactions between less-studied heterocyclic 9-chloroacridine and diverse boronic acids. Remarkably, the catalyst could be used 5 times without obvious loss of activity highlighting the efficiency of our strategy of immobilization of previledged catalysts.
- Deng, Qinyue,Shen, Yajing,Zhu, Haibo,Tu, Tao
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supporting information
p. 13063 - 13066
(2017/12/15)
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- Regioselective C-H bond functionalizations of acridines using organozinc reagents
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Despite the recent advance in C-H bond functionalization chemistry, the C-H bonds in the acridine ring system, which is an important scaffold in medicinal and material science, have met with limited success, due, in part, to the lack of activated C-H bonds adjacent to the ring nitrogen atom. Herein, several protocols that can effect the regioselective arylation and alkylation of acridines at the C-4 and C-9 positions are described.
- Hyodo, Isao,Tobisu, Mamoru,Chatani, Naoto
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supporting information; experimental part
p. 308 - 310
(2012/01/05)
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- STUDIES ON ENAMIDES. PART 4 : PHOTOCHEMICAL INVESTIGATIONS OF N-AROYLDIPHENYLAMINES
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Photolysis of N-aroyldiphenylamines affords 9-arylacridines or phenanthridinone depending on the structure of the substrates.Additionally, carbazole and photomigrated products are also obtained.
- Datta, Indira,Das, Tapas Kumar,Ghosh, Somnath
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p. 6821 - 6830
(2007/10/02)
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