4357-57-7Relevant articles and documents
Isolation and low-temperature X-ray analysis of intramolecular triarylmethane-triarylmethylium complex: Preference for a C-H-bridged unsymmetric structure exhibiting a facile 1,5-hydride shift and charge-transfer interaction
Kawai, Hidetoshi,Takeda, Takashi,Fujiwara, Kenshu,Suzuki, Takanori
, p. 12172 - 12173 (2005)
The intramolecular triarylmethane-methylium complex with an averaged C2v-symmetry was successfully generated by N-methylation of the acridine-acridan hybrid. Theoretical calculation and VT-NMR analyses in solution indicate the unsymmetric geometry for the three-center bond, which was finally confirmed crystallographically. Significant degree of CT interaction is induced through the very short C-H...C+ contact. Copyright
A pH-responsive molecular capsule with an acridine shell: Catch and release of large hydrophobic compounds
Kishimoto, Mai,Kondo, Kei,Akita, Munetaka,Yoshizawa, Michito
, p. 1425 - 1428 (2017)
Unlike common polyaromatic hydrocarbons, acridine is a characteristic compound bearing both π-stackable large surfaces and a protonable nitrogen atom. Here we report the first synthesis of a supramolecular capsule with multiple acridine panels. In water, the assembly and disassembly of the capsule reversibly occur under neutral and acidic conditions, respectively (≥10 cycles). Notably, the pH-responsive capsule encapsulates a variety of large hydrophobic compounds (up to 1.6 nm in diameter) such as coumarins, metallophthalocyanines and subphthalocyanine in neutral water and subsequently releases them by simple addition of acid.
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.
Novel acridine compound and organic light-emitting devices thereof
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Paragraph 0083; 0084; 0085, (2017/10/23)
The invention provides a novel acridine compound and organic light-emitting devices thereof, belongs to the technical field of organic photoelectric materials, and aims to solve the technical problems of low light-emitting efficiency, high driving voltage, short service life and low light-emitting performance of the organic photoelectric material in the prior art. Compared with the prior art, the light-emitting performance of the organic light-emitting devices based on organic electroluminescence device compounds and ink compositions can be obviously improved; the novel acridine compound is used as an excellent OLED material.
Dication Ethers, 3. Substitution Reactions on Bis(acridinium) Ethers and 9-Trifloxyacridinium Salts by Halides, Pseudohalides and Sulfur Nucleophiles
Singer, Berndt,Maas, Gerhard
, p. 1399 - 1408 (2007/10/02)
9-Trifloxyacridinium salts 3a, b and 9,9'-oxy-bis(acridinium) salts 4a, b which are easily obtained from the 9-acridones 2a, b react readily with halides, pseudohalides and sulfur nucleophiles to give 9-substituted acridinium ions.This reaction represents an efficient alternative to the commonly used transformation of 9-chloroacridinium into other substituted acridinium salts; the two-step conversion of the carbonyl compound into a (pseudo)halide-substituted carbenium ion or into a thione may be generally applicable to ketones which can be transformed either into trifloxy carbenium ions or into dication ethers. - Keywords: Bis(acridinium) Ethers, 9-Substituted Acridinium Ions
