- Prediction by 13C NMR of regioselectivity in 1,3-dipolar cycloadditions of acridin-9-yl dipolarophiles
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Strong correlation was found between 13C NMR chemical shifts of dipolarophilic CH=CH carbons and regioselectivity in 1,3-dipolar cycloadditions of new acridin-9-yl dipolarophiles with stable benzonitrile oxides (BNO). Accordingly, two starting
- Vilková, Mária,Ungvarská Ma?u?ká, Lucia,Imrich, Ján
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- DNA binding, anti-tumour activity and reactivity toward cell thiols of acridin-9-ylalkenoic derivatives
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Abstract In this paper, we describe the synthesis, biochemical properties and biological activity of a series of new 9-substituted acridine derivatives with a reactive alkene moiety: 9-[(E)-2-phenylethenyl] acridine (1) and methyl (2E)-3-(acridin-9-yl)-pr
- Salem, O,Vilkova, M,Plsikova, J,Grolmusova, A,Burikova, M,Prokaiova, M,Paulikova, H,Imrich, J,Kozurkova, M
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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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- Compound, pharmaceutical composition, medicine and application of compound, pharmaceutical composition and medicine in preparation of antibacterial products
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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.
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- Hammett type correlations for intramolecular charge transfer (ICT) dipole moments of 4'-substituted 9-styrylacridines in the ground state and in the excited state
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9-Styrylacridine(1a) and a series of 4'-substituted 9-styrylacridines (1b-f) (substituent: Me, OMe, NMe2, Cl, NO2) have been prepared to study their spectroscopic properties in several solvents of different dipolarity. They show stro
- Azami, Mohamed El,Bitit, Najib,Kerbal, Abdelali,Lahlou, Souad,Lyazidi, Saadia Ait,Desvergne, Jean-Pierre,Bouas-Laurent, Henri,Bassani, Dario
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p. 2325 - 2340
(2007/10/03)
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- APPLICATION OF PHASE TRANSFER CATALYSIS IN ACRIDINE SERIES. VI. PREPARATION OF SOME 9-VINYLACRIDINE DERIVATIVES
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The preparation of some 9-vinylacridine derivatives by the Wittig reaction under phase transfer catalysis (PTC) conditions is presented.The analysis of 1H-NMR shows that the compounds exhibit a trans configuration.
- Vlassa, Mircea,Molnariu, Castelia,Silberg, Joan A.
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p. 315 - 317
(2007/10/02)
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- Thermal Isomerization of Photochemically Synthesized (Z)-9-Styrylacridines. An Unusuallly High Enthalpy of Z -> E Conversion for Stilbene-like Compounds
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Eight stable (Z)-9-styrylacridines, have been photochemically synthesized and their enthalpies of thermal isomerization (ΔHZ->E) determined by means of thermal analysis.The enthalpy values were found to be influenced by both electronic and steric effects.The title compounds were used as models in order to gain insight into the energetic implications involved in the Z->E isomerization process and its applicability to photochemical energy conversion by irradiation in the visible wavelength region.
- Bastianelli, Carlo,Caia, Vincenzo,Cum, Giampietro,Gallo, Raffaele,Mancini, Vittorio
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p. 679 - 683
(2007/10/02)
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- A HIGH ENTHALPY VALUE IN THERMAL ISOMERISATION OF PHOTOSYNTHESIZED CIS-9-STYRYLACRIDINES
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Four stable stilbene-like cis-isomers - i.e. 9-styrylacridines - were photosynthesized and their ΔH cis->trans thermal isomerisation determined.
- Caia, V.,Cum, G.,Gallo, R.,Mancini, V.,Pitoni, E.
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p. 3903 - 3904
(2007/10/02)
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