40333-47-9Relevant academic research and scientific papers
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.
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.
SYNTHESIS OF PHOSPHINE LIGANDS BEARING TUNABLE LINKAGE: METHODS OF THEIR USE IN CATALYSIS
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Page/Page column 16; 17, (2017/12/02)
A series of novel linked indolyl phosphine ligands for transition metals, the synthesis thereof and their use in catalytic coupling reactions are provided. The ligands provide improvements of trasition-metal-catalyzed reactions, including the range of substrates scope, reaction conditions and efficieny.
A magnetic nanoparticle-supported N-heterocyclic carbene-palladacycle: An efficient and recyclable solid molecular catalyst for Suzuki-Miyaura cross-coupling of 9-chloroacridine
Deng, Qinyue,Shen, Yajing,Zhu, Haibo,Tu, Tao
supporting information, p. 13063 - 13066 (2017/12/15)
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.
Regioselective C-H bond functionalizations of acridines using organozinc reagents
Hyodo, Isao,Tobisu, Mamoru,Chatani, Naoto
supporting information; experimental part, p. 308 - 310 (2012/01/05)
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.
Highly efficient carbazolyl-derived phosphine ligands: Application to sterically hindered biaryl couplings
Chun To, Sheung,Yee Kwong, Fuk
supporting information; experimental part, p. 5079 - 5081 (2011/06/10)
A new family of phosphine ligands bearing a bulky carbazolyl scaffold is described. With the combination of ligand 2a and Pd(OAc)2, difficult tri-ortho-substituted biaryl couplings are accomplished smoothly. In particular, the catalyst loading as low as 0.02 mol% of Pd for non-activated 2,6-disubstituted aryl chloride coupling can be achieved.
Cation complexation with functionalized 9-arylacridinium ions: possible applications in the development of cation-selective optical probes
Jonker, S. A.,Ariese, F.,Verhoeven, J. W.
, p. 109 - 116 (2007/10/02)
Absorptive and emissive properties of 9-arylacridinium ions 2-6 have been studied and shown to be dependent on the electron-donating properties of the aryl group.While for 2 and 3 the first excited state remains largely localized on the acridinium chromophore, interaction of this chromophore with the electron-donor-substituted aryl group 4-6 produces a low-lying intramolecular charge-transfer state, resulting in a state inversion.This state inversion leads to the appearance of a new long-wavelength absorption in the visible region and to complete quenching of the acridinium fluorescence.Protonation of the amino function in 4-6 cancels this state inversion, thereby causing a dramatic chromofluoroionophoric effect, i.e. cation-induced change of both colour and fluorescence properties.Replacing the amino function by an aza crown ether resulted in system 7, which displays similar effects, not only upon protonation but also upon metal ion complexation.
