- 5-(Acridin-9-ylamino)uracil-A hydrolytically labile nucleobase modification in peptide nucleic acid
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5-Aminouracil (5-AU) is a readily available yet underutilized starting material for the synthesis of labelled nucleobase analogues. We have prepared the derivative of 5-AU with the amine-reactive chromophore 9-chloroacridine for the purpose of investigating its potential as a base-discriminating fluorophore. 9-Chloroacridine readily undergoes substitution by reaction with 5-AU to yield a fluorescent nucleobase that after standard manipulations produced a monomer suitable for incorporation into peptide nucleic acid (PNA) by fluorenylmethyloxycarbonyl (Fmoc)-based oligomerization chemistry. Although the monomer was stable in organic solvents, once incorporated into an oligomer the 5-substitution was found to be thermally labile and hydrolyzed to a small degree in neutral aqueous solution during study of its hybridization to cDNA. We have determined that 5-(acridin-9-ylamino)uracil and related derivatives produce the highly fluorescent acridone and 5-AU by hydrolysis in water.
- Matarazzo, Augusto,Moustafa, Mohamed E.,Hudson, Robert H.E.
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- Generation of 9(10H)-acridone from anthranilic acid
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Diazotization of anthranilic acid with butyl nitrite in refluxing THF gave rise to acridone.
- Ho, Tse-Lok,Jou, Der-Guey
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- BASE-INDUCED OXYGENATION AND CHEMILUMINESCENCE OF 10-METHYLACRIDINIUM AND 1-METHYLQUINOLINIUM SALTS IN DIMETHYL SULFOXIDE.
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10-Methylacridinium methyl sulfate and the 1-methylquinolinium salt gave strong light emission, when oxidized with ground state oxygen in the presence of t-BuOK in DMSO, owing to the fluorescence of 10-methyl-9(10H)-acridinone and 1-methyl-1(4H)-quinolinone excited to their S//1 state.
- Suzuki,Kazui,Tsukamoto,Kato,Izawa
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- Targeting tyrosine kinase: Development of acridone – pyrrole – oxindole hybrids against human breast cancer
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Based on the molecular modelling studies, a rational modification of the lead molecule was made to develop highly potent compounds showing anti-cancer activity against human breast cancer cell lines MCF 7, MDA-MB-468 and T-47D. The most potent compounds have Log P and total polar surface area 4.4–5.4 and 59.8 ? respectively and they also exhibited promising ADME profile.
- Kaur, Manpreet,Singh, Palwinder
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- Intramolecular cyclization of N-phenylanthranilic acid catalyzed by MCM-41 with different pore diameters
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Micro-mesoporous sieves MCM-41 with different pore diameters were synthesized under microwave irradiation, characterized by X-ray diffraction, scanning electron microscopy, Fourier transform infrared spectroscopy, N2 adsorption- desorption and temperature-programmed desorption of NH3 (NH3-TPD). Intramolecular cyclization of N-Phenylanthranilic acid to acridone catalyzed by MCM-41 with different pore diameters was investigated. The results indicate that the yields increased significantly with the decrease of pore diameter of MCM-41. Furthermore, the yield of acridone under microwave irradiation was higher than that under conventional heating.
- Xiao, Shangyou,Xu, Guang,Chen, Gang,Mu, Xiaojing,Chen, Zhitao,Zhu, Jun,He, Yi
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- Reduction of Acridine and 9-Chloroacridine with Red Phosphorus in the KOH/DMSO System
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Abstract: Acridine reacts with red phosphorus in the KOH/DMSO(H2O) system on heating (100°C, 3 h) to give 9,10-dihydroacridine regioselectively in quantitative yield. Under similar conditions, 9-chloroacridine reacts with Pred/KOH/DMSO(H2O) system to afford 9,10-dihydroacridine and acridone in 51 and 40% yield, respectively.
- Kuimov,Gusarova,Malysheva,Kon’kova,Trofimov
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- Synthesis, spectroscopic characterization (FT-IR, NMR) and DFT computational studies of new isoxazoline derived from acridone
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In this study, a new isoxazoline derived from acridone, 10‐{[3‐(4‐chlorophenyl)‐4,5‐dihydro‐1,2‐oxazol‐5 yl]methyl} acridone (3) was successfully synthesized and characterized by FT-IR, 1H NMR, 13C NMR and HRMS. The preparation of compound (3) was achieved by 1,3-dipolar cycloaddition reaction between 4?chloro-N-hydroxybenzimidoyl chloride and 10-allylacridone using environment friendly methods. In an effort to complete the chemical structure description of the synthetized compound, Density Functional Theory (DFT) was applied using Gaussian09 and Gaussian view5 programs. The theoretical calculations were used as a compliment to the experimental studies. The computing of geometric parameters, optimization energies, frontier molecular orbital energies, Molecular surface electrostatic potential (MESP) and Mulliken charges were calculated using DFT/B3LYP method with 6–31G(d,p) as basis set. The Infrared vibrational frequencies and 1H and 13C NMR chemical shifts were also calculated and their scaled values are in agreement with the experimental results.
- Aarjane, Mohammed,Slassi, Siham,Ghaleb, Adib,Amine, Amina
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- Novel highly selective and sensitive fluorescent sensor for copper detection based on N-acylhydrazone acridone derivative
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A new N-acylhydrazone based on acridone (S1) was synthesized by Schiff base condensation of 2-(9-oxoacridin-10-yl)acetohydrazide and salicylaldehyde and studied as selective fluorescence turn-off sensing towards Cu2+ ions in aqueous media. S1 demonstrated fluorescence turn-off sensing towards Cu2+ ions. Conversely, the metal ions K+, Mg2+, Zn2+, Fe2+, Al3+, Pb2+, Cr2+, Cd2+, Ag+, Fe3+, Ba2+, Hg2+, Mn2+, Co2+, and Ni2+ produced only minor decrease in the fluorescence of the system. The binding ratio of S1–Cu2+ complex was determined from the Job plot to be 1:2. Moreover, the S1–Cu2+ complex showed good fluorescence turn-off in presence of different counter ions of copper. In addition, the detection limit of S1 towards Cu2+ ions is 0.80 μM, which is enough for sensing the Cu2+ in the biological system and water within the U.S Environmental Protection Agency limit (~20 μM).
- Aarjane, Mohammed,Slassi, Siham,Amine, Amina
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- Access to acridones by tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation of anthranils with arylboronic acids
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An efficient and practical approach for the synthesis of medicinally important acridones was developed from anthranils and commercially available arylboronic acids by a tandem copper(i)-catalyzed electrophilic amination/Ag(i)-mediated oxidative annulation strategy. This new and straightforward protocol displayed a broad substrate scope (25 examples) and high functional group tolerance. What's more, a possible mechanistic proposal was also presented.
- Huang, Yan-Xia,Huang, Zhuo-Jun,Jiang, Chun-Yong,Liang, Jing-Yi,Liang, Qiu-Ping,Shu, Bing,Xie, Hui,Zeng, Jun-Yi,Zhang, Shang-Shi,Zhou, Binhua
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p. 8487 - 8491
(2021/10/20)
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- Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen
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The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.
- Wei, Lanfeng,Wei, Yu,Xu, Liang,Zhang, Jinli
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supporting information
p. 4446 - 4450
(2021/06/30)
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- Acid-catalyzed oxidative cross-coupling of acridans with silyl diazoenolates and a Rh-catalyzed rearrangement: two-step synthesis of γ-(9-acridanylidene)-β-keto esters
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A MsOH-catalyzed oxidative cross-coupling of acridans and silyl diazoenolates and a Rh2(OAc)4-catalyzed rearrangement of the resultant diazo products are described. The reactions provide various γ-(9-acridanylidene)-β-keto esters in good yields, which bear an active α-methylene unit for further functionalization.
- Li, Weiyu,Xu, Hao,Zhou, Lei
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p. 5649 - 5657
(2021/07/02)
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- Metal-Free Synthesis of Alkenylazaarenes and 2-Aminoquinolines through Base-Mediated Aerobic Oxidative Dehydrogenation of Benzyl Alcohols
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A metal-free, base-mediated, and atom-efficient oxidative dehydrogenative coupling of substituted phenylmethanols (benzyl alcohols) with methyl azaarenes or phenylacetonitriles to afford substituted alkenylazaarenes or 2-aminoquinolines, respectively is described. CsOH.H2O was discovered to be the base of choice for obtaining optimal yields of the title compounds, although the reaction could proceed with KOH as well. The protocol that works efficiently in the presence of air is amenable over broad range of substrates.
- Batra, Sanjay,Dahatonde, Dipak J.,Ghosh, Aritra
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p. 2746 - 2751
(2021/06/25)
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- Novel series of N-acylhydrazone based on acridone: Synthesis, conformational and theoretical studies
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In this work, novel N-acylhydrazone derivatives from acridone have been synthesized by condensation of 9-oxoacridin-10(9H)-yl)acetohydrazide with various aldehyde and ketone. The structures of these novel compounds were elucidated by 1H NMR, 13C NMR, IR and mass spectroscopy. The NMR data shows two conformations (E, trans and E, cis) due to N–C(O) bond rotation, the conformations of synthesized compounds have been investigated by different NMR methods. The rotational barriers around N–C(O) bond for compound 5a was measured in DMSO using dynamic NMR spectroscopy, this result was confirmed by DFT calculations at B3LYP/6–31 G (d) level in DMSO.
- Aarjane, Mohammed,Amine, Amina,Slassi, Siham
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- Synthesis and biological evaluation of novel isoxazole derivatives from acridone
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The present study was carried out in an?attempt to synthesize a new class of potential antibacterial agents. In this context, novel isoxazoles were synthesized and evaluated for their potential antibacterial behavior against four pathogenic bacterial strains. The synthesized compounds exhibited moderate-to-good antibacterial activity against these strains. The highest antibacterial activity was observed against the Escherichia coli strains, particularly for compounds 4a and 4e with phenyl and para-nitrophenyl groups on the isoxazole–acridone skeleton;?they showed promising minimum inhibitory concentration values of 16.88 and 19.01 μg/ml, respectively, compared with the standard drug chloramphenicol (22.41 μg/ml). The synthesized compounds were subjected to in silico docking studies to understand the mode of their interactions with the DNA topoisomerase complex (PDB ID: 3FV5) of E. coli. The molecular docking results showed that compounds 4a–l occupy the active site of DNA topoisomerase (PDB ID: 3FV5), stabilized via hydrogen bonding and hydrophobic interactions, which may be the reason behind their interesting in vitro antibacterial activity.
- Aarjane, Mohammed,Slassi, Siham,Tazi, Bouchra,Amine, Amina
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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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- Synthesis, antibacterial evaluation and computational studies of new acridone-1,2,3-triazole hybrids
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In continuation of our efforts to develop new drugs with antibacterial properties we have synthesized and evaluated new 1,2,3-triazole derivatives from acridone. The synthetic approach was started by the preparation of acridone skeleton through the Ullman condensation of 2-bromobenzoic acid and aniline derivatives. Subsequently, acridone nucleus was functionalized with propargyl bromide. Then, a click reaction of the latter compound and aromatic azides led to the formation of the title compounds in good yields. The synthesized compounds were screened for their in vitro antibacterial activity against one gram-positive bacteria S. aureus and three gram-negative bacteria P. putida, K. pneumoniae and E. coli. Among the synthesized compounds, 2-methyl-10-((1-(o-tolyl)-1H-1,2,3-triazol-4-yl)methyl)acridone (4e) had the most potent inhibitory activity against S. aureus with MIC = 10.1 μg/mL. Then, in silico docking studies were used in order to understand the binding interactions and mode of action of these compounds.
- Aarjane, Mohammed,Amine, Amina,Slassi, Siham
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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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- Aromatic heterocycle substituted acridine quaternary ammonium salt derivative as well as preparation method and application thereof
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The invention belongs to the technical field of pharmaceutical compounds, relates to an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative and a preparation method and application thereof, and has the structure shown in a formula (I). In-flight R1 A compound selected from the group consisting of aryl and heteroaryl. Substituted aryls. X Is a halogen or benzenesulfonate anion. The invention provides an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative as well as a preparation method and application thereof, and is designed to synthesize an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative through a simplified structure, and is designed to synthesize an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative so as to achieve the unique antibacterial effect by inhibiting the bacteria FtsZ and bacterial biofilm.
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- Preparation method of acridone
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The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of acridone, wherein acidic ionic liquid is used as a catalyst and a solvent. , The volatile organic solvent such as toluene can be replaced by the advantages of small volatility, and VOCs prevention and treatment problems of an increasingly urgent problem can be solved. The method is environment-friendly and meets the requirements of green chemistry.
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Paragraph 0020-0033
(2021/09/26)
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- Syntheses and Evaluation of New Bisacridine Derivatives for Dual Binding of G-Quadruplex and i-Motif in Regulating Oncogene c-myc Expression
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The c-myc oncogene is an important regulator for cell growth and differentiation, and its aberrant overexpression is closely related to the occurrence and development of various cancers. Thus, the suppression of c-myc transcription and expression has been investigated for cancer treatment. In this study, various new bisacridine derivatives were synthesized and evaluated for their binding with c-myc promoter G-quadruplex and i-motif. We found that a9 could bind to and stabilize both G-quadruplex and i-motif, resulting in the downregulation of c-myc gene transcription. a9 could inhibit cancer cell proliferation and induce SiHa cell apoptosis and cycle arrest. a9 exhibited tumor growth inhibition activity in a SiHa xenograft tumor model, which might be related to its binding with c-myc promoter G-quadruplex and i-motif. Our results suggested that a9 as a dual G-quadruplex/i-motif binder could be effective in both oncogene replication and transcription and become a promising lead compound for further development with improved potency and selectivity.
- Kuang, Guotao,Zhang, Meiling,Kang, Shuangshuang,Hu, Dexuan,Li, Xiaoya,Wei, Zuzhuang,Gong, Xue,An, Lin-Kun,Huang, Zhi-Shu,Shu, Bing,Li, Ding
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p. 9136 - 9153
(2020/10/18)
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- 2-Aminobenzaldehyde, a common precursor to acridines and acridones endowed with bioactivities
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By starting from a common substrate, 2-aminobenzaldehyde, both acridines and acridones were prepared. The former were generated in high yields by copper-catalyzed N-arylation followed by acid-mediated cyclization while the latter were obtained by double copper-catalyzed N-arylation followed by cyclization under the same reaction conditions. Moreover, acridine was subjected to deprotometalation by recourse to a lithium-zinc base and converted to the corresponding 4-iodo derivative, which was involved in copper-catalyzed couplings with pyrrolidinone and pyrazole. Finally, addition of pyrazole, indole and carbazole onto the 9 position of bare acridine was improved. While moderate biological activity was noticed in melanoma cells growth inhibition, the newly prepared compounds feature interesting photophysical properties which were evaluated in a preliminary study.
- Bentabed-Ababsa, Ghenia,Dorcet, Vincent,Erb, William,Mongin, Florence,Mongin, Olivier,Picot, Laurent,Roisnel, Thierry,Thiéry, Valérie,Zeghada, Sarah
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- Visible-Light-Triggered Quantitative Oxidation of 9,10-Dihydroanthracene to Anthraquinone by O2 under Mild Conditions
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The development of mild and efficient processes for the selective oxygenation of organic compounds by molecular oxygen (O2) is key for the synthesis of oxygenates. This paper discloses an atom-efficient synthesis protocol for the photo-oxygenation of 9,10-dihydroanthracene (DHA) by O2 to anthraquinone (AQ), which could achieve quantitative AQ yield (100 %) without any extra catalysts or additives under ambient temperature and pressure. A yield of 86.4 % AQ was obtained even in an air atmosphere. Furthermore, this protocol showed good compatibility for the photo-oxidation of several other compounds with similar structures to DHA. From a series of control experiments, free-radical quenching, and electron paramagnetic resonance spin-trapping results, the photo-oxygenation of DHA was probably initiated by its photoexcited state DHA*, and the latter could activate O2 to a superoxide anion radical (O2.?) through the transfer of its electron. Subsequently, this photo-oxidation was gradually dominated by the oxygenated product AQ as an active photocatalyst obtained from the oxidation of DHA by O2.?, and was accelerated with the rapid accumulation of AQ. The present photo-oxidation protocol is a good example of selective oxygenation based on the photoexcited substrate self-activated O2, which complies well with green chemistry ideals.
- Jiang, Dabo,Hu, Wenwei,Chen, Mengke,Fu, Zaihui,Su, Anqun,Yang, Bo,Mao, Feng,Zhang, Chao,Liu, Yachun,Yin, Dulin
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p. 1785 - 1792
(2020/03/13)
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- Design, synthesis and biological evaluation of acridone analogues as novel STING receptor agonists
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STING (Stimulator of Interferon Genes) has become a focal point in immunology research and a target in drug discovery. The discovery of a potent human-STING agonist is expected to revolutionize current anti-virus or cancer immunotherapy. Inspired by the structure and function of murine STING-specific agonists (DMXAA and CMA), we rationally designed and synthesized four series of novel compounds for the enhancement of human sensitivity. In the cell-based assay, we identified six compounds from all the synthetic small molecules: 2g, 9g, and 12b are STING agonists that are efficacious across species, and all have the skeleton of acridone; 1b, 1c, and 12c just function in the murine STING pathway. Notably, 12b exhibits the best activity among the six agonists, and its inductions of both human and murine STING-dependent signalling are similar to that of 2′3′-cGAMP, which is a well-known STING inducer. While a protein assay indicated that 2 g, 9 g, and 12b could activate the pathway by directly binding human STING, 12b also displayed the strongest binding affinity. Additionally, our studies show that 12b can induce faster, more powerful, and more durable responses of assorted cytokines in a native system than 2′3′-cGAMP. Consequently, our team is the first to successfully modify murine STING agonists to obtain human sensitivity, and these results suggest that 12b is a potent direct-human-STING agonist. Additionally, the acridone analogues demonstrate tremendous potential in the treatment of tumours or viral infections.
- Chang, Jia-jia,Hou, Shi,Lan, Xiu-juan,Li, Song,Li, Wei,Sun, Wei,Xiao, Jun-hai,Yan, Xin-lin,Yang, Xiao-hong
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- Synthesis, antibacterial evaluation and molecular docking studies of novel series of acridone- 1,2,3-triazole derivatives
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Development of new drugs with antibacterial potency is an important solution to overcome drug-resistance problems. In the goal to develop novel structure with antibacterial potency, we designed and synthesized novel acridone derivatives bearing triazole nucleus. The novel synthesized compounds were tested for their in vitro antibacterial activity against four bacterial human pathogenic strains. The compound 4h displayed significant antibacterial activities against Staphylcoccus aureus (MRSA) with MIC = 19.6?μg/mL. The synthesized compounds were subjected for docking study to understand the interaction of our compounds and the dihydropteroate synthase (DHPS) in methicillin-resistant Staphylcoccus aureus (MRSA).
- Aarjane, Mohammed,Slassi, Siham,Tazi, Bouchra,Maouloua, Mohamed,Amine, Amina
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p. 1523 - 1531
(2020/03/19)
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- Dimethyl sulfoxide-aided copper(0)-catalyzed intramolecular decarbonylative rearrangement of N-aryl isatins leading to acridones
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Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide (DMSO) under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields. This novel transformation is proposed to go through a sequential DMSO-aided Cu insertion into the amide C–N bond, CO extrusion, Cu migration, reductive elimination and DMSO-aided proton migration processes, involving multiple types of bond cleavage and formation in a single chemical step.
- Wu, Hao,Ma, Nana,Song, Mengxiao,Zhang, Guisheng
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supporting information
p. 1580 - 1583
(2019/12/09)
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- Method for continuously synthesizing acridone (by machine translation)
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The invention provides a method for continuously synthesizing acridone, the adopted reactor is a microchannel reactor, and the method comprises the following steps: feeding. N - phenyl O-aminobenzoic acid is adopted as a raw material, concentrated sulfuric acid or p-toluenesulfonic acid is used as a dehydrating agent, and the temperature 80 - 130 °C is kept 30 - 60s in a continuous flow reactor to obtain an acridone with a yield 88percent - 93.1percent and a purity of 94 - 99.7percent. The method shortens the reaction time of N - phenyl O-aminobenzoic acid ring, reduces the solvent consumption, reduces the amount of the dehydrating agent, improves the yield and realizes continuous production. (by machine translation)
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Paragraph 0034-0051
(2020/06/16)
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- Single-Atom Fluorescence Switch: A General Approach toward Visible-Light-Activated Dyes for Biological Imaging
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Photoactivatable fluorophores afford powerful molecular tools to improve the spatial and temporal resolution of subcellular structures and dynamics. By performing a single sulfur-for-oxygen atom replacement within common fluorophores, we have developed a facile and general strategy to obtain photoactivatable fluorogenic dyes across a broad spectral range. Thiocarbonyl substitution within fluorophores results in significant loss of fluorescence via a photoinduced electron transfer-quenching mechanism as suggested by theoretical calculations. Significantly, upon exposure to air and visible light residing in their absorption regime (365-630 nm), thio-caged fluorophores can be efficiently desulfurized to their oxo derivatives, thus restoring strong emission of the fluorophores. The effective photoactivation makes thio-caged fluorophores promising candidates for super-resolution imaging, which was realized by photoactivated localization microscopy (PALM) with low-power activation light under physiological conditions in the absence of cytotoxic additives (e.g., thiols, oxygen scavengers), a feature superior to traditional PALM probes. The versatility of this thio-caging strategy was further demonstrated by multicolor super-resolution imaging of lipid droplets and proteins of interest.
- Tang, Juan,Robichaux, Michael A.,Wu, Kuan-Lin,Pei, Jingqi,Nguyen, Nhung T.,Zhou, Yubin,Wensel, Theodore G.,Xiao, Han
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supporting information
p. 14699 - 14706
(2019/10/11)
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- Palladium-Catalyzed Late-Stage ortho-C-H Bond Aroylation of Anilines Using 4-Methoxy-2-pyridinyl as a Removable Directing Group
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A synthetic methodology for the late-stage ortho-C-H bond aroylation of anilines with aryl aldehydes led to a variety of ortho-aroylated anilines by the use of palladium(II) acetate, tert-butyl hydroperoxide, and 1,4-dioxane as the catalyst, oxidant, and solvent, respectively, is presented. An N-phenylpyridin-2-amine palladacycle was isolated and characterized by X-ray crystallography. Controlled experiments, radical trapping experiments, and the experiments of the kinetic isotope effect were undertaken to support the proposed reaction mechanism. Syntheses of 2-aminobenzophenone and 9(10H)-acridanone based on the developed methodology were successfully demonstrated.
- Chu, Jean-Ho,Chiang, Meng-Fan,Li, Chin-Wei,Su, Zhe-Hong,Lo, Shao-Chi,Wu, Ming-Jung
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p. 2105 - 2119
(2019/05/08)
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- Degradation of diclofenac, trimethoprim, carbamazepine, and sulfamethoxazole by laccase from Trametes versicolor: Transformation products and toxicity of treated effluent
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The degradation of diclofenac (DCF), trimethoprim (TMP), carbamazepine (CBZ), and sulfamethoxazole (SMX) by laccase from Trametes versicolor was investigated. Experiments were conducted using the pharmaceuticals individually, or as a mixture at different initial concentrations (1.25 and 5 mg/L each). The initial enzymatic activity of all the treated samples was around 430–460 U(DMP)/L. The removal of the four selected pharmaceuticals tested individually was more effective than when tested in mixtures under the same conditions. For example, 5 mg DCF/L was completely removed to below its detection limit (1 μg/L) within 8 h in the individual experiment vs. after 24 h when dosed as a mixture with the other pharmaceuticals. A similar trend was visible with other three pharmaceuticals, with 95 vs. 39%, 82 vs. 34% and 56 vs. 49% removal after 48 h with 5 mg/L of TMP, CBZ, and SMX tested individually or as mixtures, respectively. In addition, at the lower initial concentration (1.25 mg/L each), the removal efficiency of TMP, CBZ, and SMX in mixtures was lower than that obtained at the higher initial concentrations (5 mg/L each) during both the individual and combined treatments. Four enzymatic transformation products (TPs) were identified during the individual treatments of DCF and CBZ by T. versicolor. For TMP and SMX, no major TPs were observed under the experimental conditions used. The toxicity of the solution before and after enzymatic treatment of each pharmaceutical was also assessed and all treated effluent samples were verified to be non-toxic.
- Alharbi, Sultan K.,Nghiem, Long D.,van de Merwe, Jason P.,Leusch, Frederic D. L.,Asif, Muhammad B.,Hai, Faisal I.,Price, William E.
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p. 399 - 408
(2019/04/26)
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- Cu(I)-Based Metal-Organic Frameworks as Efficient and Recyclable Heterogeneous Catalysts for Aqueous-Medium C-H Oxidation
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The enantioselective transformation of ubiquitous C-H bonds into valuable C-O bonds offers an efficient synthetic approach to construct carbonyl functionalized molecules. However, the grand obstacles in the reaction are the selectivity issues and side reactions under the harsh reaction conditions. In order to overcome the limits, two Cu(I)-based MOFs {(NEt4)0.5[Cu3(TTPB)0.75(CN)0.5(H2O)]·H2O}n (1) and {[Cu2(TTPB)0.5]·DMF·2H2O}n (2) were synthesized (H4TTPB = 5,5′-(4′,5′-bis(4-(1H-tetrazol-5-yl)phenyl)-[1,1′:2′,1′′-terphenyl]-4,4′′-diyl) bis(1H-tetrazole)) under hydrothermal conditions with (triethylamine (TEA) and ethyldiisopropylamine (DIPEA) as structure-directing agents, respectively. Of these, 1 shows an anionic three-dimensional (3D) framework composed of two kinds of cagelike micropores with 7 × 17 ? and 10 × 17 ?, respectively. In comparison, 2 exhibits a 3D framework with open channels (14 × 8 ?). The stability studies showed that the crystallinity of 1 and 2 could remain in a series of organic solvents (ethanol, N,N-dimethylformamide, chloroform, dioxane, toluene) and acid and alkali aqueous solutions (pH = 1-13) at room temperature for 48 h. 1 and 2 with coordinatively unsaturated Cu(I) sites were applied as heterogeneous catalysts for the oxidation of arylacycloalkanes in aqueous medium and exhibited excellent catalytic activities, selectivities, and recyclabilities. Moreover, free-radical reaction mechanism and reversible valence-tautomeric conversions of central copper were confirmed during the process by control experiment.
- Gao, Kuan,Huang, Chao,Yang, Yisen,Li, Hong,Wu, Jie,Hou, Hongwei
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p. 976 - 982
(2019/02/15)
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- Co(ii)-cluster-based metal-organic frameworks as efficient heterogeneous catalysts for selective oxidation of arylalkanes
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To explore metal-organic frameworks (MOFs) based on Co-clusters as heterogeneous catalysts to selectively catalyze the reaction of C-H bond oxidation of aromatic alkanes to their corresponding ketones, three MOFs {[Co5(pmbcd)2(μ3-OH)2(H2O)4(DMF)2]·4DMF}n (MOF 1), {[Co2(pmbcd)(bpea)2]·2H2O·2DMF}n (MOF 2), and {[Co2(pmbcd)(dpp)2]·3H2O·2DMF}n (MOF 3) (H4pmbcd = 9,9′-(1,4-phenylenebis(methylene))bis(9H-carbazole-3,6-dicarboxylic acid), bpea = 1,2-bis(4-pyridyl)ethane, dpp = 1,3-di(4-pyridyl)propane) were successfully synthesized and structurally characterized. MOF 1 was constructed from a pentanuclear Co(ii) cluster and exhibited a porous framework with channels of 8 × 10 ?2 along the b axis. MOF 2 was constructed from [Co2(CO2)4] units and presented a porous three-dimensional (3D) framework with channels of 11 × 13 ?2 along the b axis and of 10 × 12 ?2 along the c axis. MOF 3 was a flat two-dimensional (2D) layer based on binuclear Co(ii) units when dpp as an auxiliary ligand was introduced. The Co5-cluster-based MOF 1 exhibited excellent catalytic activity for the direct C-H bond activation of arylalkanes to ketones in H2O under room temperature because of its high density of Lewis acidic sites within the frameworks and suitable channel size to access the catalytic sites. It also presented the spatial confinement effect and catalyzed the reaction with high regioselectivity, forming mono-ketones as the sole products. Easy product separation, simple reaction procedures, and recyclability of these catalysts make the catalytic system attractive. Our work highlights the superiority of the MOF-based materials as heterogeneous catalysts.
- Fan, Yanru,Li, Xiao,Gao, Kuan,Liu, Yu,Meng, Xiangru,Wu, Jie,Hou, Hongwei
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p. 1666 - 1673
(2019/03/07)
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- Visible-Light-Induced Aerobic Oxidation of Benzylic C(sp 3)-H of Alkylarenes Promoted by DDQ, tert -Butyl Nitrite, and Acetic Acid
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A visible-light photocatalytic aerobic oxidation of benzylic C(sp 3)-H bonds proceeded in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tert -butyl nitrite, and acetic acid. Advantages of this aerobic oxidation method include its relatively mild conditions, the use of visible-light irradiation instead of conventional thermal methods, the use of a low catalyst loading, and the ability to oxidize a range of alkylarenes, including xanthenes, thioxanthenes, and 9,10-dihydroacridines, to the corresponding ketones in excellent yields.
- Pan, Decheng,Wang, Yiqing,Li, Meichao,Hu, Xinquan,Sun, Nan,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu
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p. 218 - 224
(2019/01/14)
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- Method for driving molecular oxygen to selectively oxidize 9,10-dihydroanthracene and quantitatively convert 9,10-dihydroanthracene into anthraquinone by visible light
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The invention relates to the technical field of photooxidation synthesis, and discloses a simple, convenient and practical visible light synthesis method for quantitatively converting 9, 10-dihydroanthracene into anthraquinone based on molecular oxygen selective oxidation. Under a condition of normal temperature, normal pressure, pure oxygen atmosphere and no catalysts and additives, the synthesismethod can realize 100% raw material conversion and provide a anthraquinone yield of 99.3%, and 86.4% of anthraquinone yield can be obtained even in an air atmosphere. Moreover, the synthesis methodalso shows a good effect on photooxidation of other compounds with structures similar to the structure of 9, 10-dihydroanthracene, and the synthesis method is indicated to have relatively wide applicability. The visible light synthesis method provided by the invention provides a very good example for participation of active O2 of a substrate in selective oxidation, and accords with the concept ofgreen chemistry.
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Paragraph 0017-0026
(2020/01/03)
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- Boron trifluoride etherate promoted microwave-assisted synthesis of antimalarial acridones
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A microwave-assisted, rapid and efficient method using boron trifluoride etherate (BF3.Et2O) for the synthesis of acridones, via an intramolecular acylation of N-phenylanthranilic acid derivatives, has been developed. The reaction proceeds under solvent-free conditions, tolerates a wide range of functional groups, and provides rapid access to a range of acridones in good to excellent yields. Several of the synthesized acridones exhibited potent antimalarial activities against CQ sensitive and multi-drug resistant (MDR) parasites.
- Kancharla, Papireddy,Dodean, Rozalia A.,Li, Yuexin,Kelly, Jane X.
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p. 42284 - 42293
(2020/01/08)
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- Stabilized Carbenium Ions as Latent, Z-type Ligands
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Controlling the reactivity of transition metals using secondary, σ-accepting ligands is an active area of investigation that is impacting molecular catalysis. Herein we describe the phosphine gold complexes [(o-Ph2P(C6H4)Acr)AuCl]+ ([3]+; Acr=9-N-methylacridinium) and [(o-Ph2P(C6H4)Xan)AuCl]+ ([4]+; Xan=9-xanthylium) where the electrophilic carbenium moiety is juxtaposed with the metal atom. While only weak interactions occur between the gold atom and the carbenium moiety of these complexes, the more Lewis acidic complex [4]+ readily reacts with chloride to afford a trivalent phosphine gold dichloride derivative (7) in which the metal atom is covalently bound to the former carbocationic center. This anion-induced AuI/AuIII oxidation is accompanied by a conversion of the Lewis acidic carbocationic center in [4]+ into an X-type ligand in 7. We conclude that the carbenium moiety of this complex acts as a latent Z-type ligand poised to increase the Lewis acidity of the gold center, a notion supported by the carbophilic reactivity of these complexes.
- Wilkins, Lewis C.,Kim, Youngmin,Litle, Elishua D.,Gabba?, Fran?ois P.
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supporting information
p. 18266 - 18270
(2019/11/14)
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- Synthesis of dibenzocycloketones by acyl radical cyclization from aromatic carboxylic acids using methylene blue as a photocatalyst
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An efficient intramolecular radical cyclization reaction via photoredox catalysis was developed for the synthesis of dibenzocycloketone derivatives using methylene blue as a photosensitizer. This strategy could be widely used to synthesize large heterocycles due to the unique reactivity of phosphoranyl radicals formed by a polar/SET crossover between an aromatic carboxylic acid and a phosphine radical cation. Attractive features of this process include generation of an acyl radical by an inexpensive and metal-free photocatalyst, which effectively undergoes a cyclization process.
- Jiang, Hongshuo,Mao, Guijie,Wu, Hongfeng,An, Qi,Zuo, Minghui,Guo, Weihao,Xu, Chunzhao,Sun, Zhizhong,Chu, Wenyi
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supporting information
p. 5368 - 5373
(2019/10/11)
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- Facile synthesis of novel bis-derivatives of 2,5-diamino-thiadiazole/N,N′-thiocarbohydrazide and their biological perspective
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A series of new bis derivatives of 2,5-thiadiazole and N,N′-thiocarbohydrazide along with their transition metal complexes were synthesized by green methods (sonochemical and microwave), i.e., energy and time efficient and operationally more simple than existing conventional methods. All the synthesized compounds were fully characterized by routine analytical techniques and subjected to a preliminary biological screening. These novel characterized compounds were screened for antimicrobial activities and showed promising results. A few potent compounds were also tested for antitumor activities against MDA-MB231 (human breast carcinoma cell line) and compound 5 has emerged as a potential antitumor compound followed by compound 2, 10 and 9, with IC50 values of 29.48, 32.25, 32.34 and 34.34?μg/ml, respectively. To understand the binding interactions of these compounds, in silico studies were performed using the AUTODOCK 4.2 suite and found to be supportive of the experimental results.
- Bhatt, Priyanka,Sreekanth,Jha, Anjali
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p. 7241 - 7258
(2018/09/06)
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- Synthesis method of acridone derivative
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The application relates to a synthesis method of an acridone derivative. The synthesis method comprises the following steps: mixing a compound shown in a formula (I), a photocatalyst and a solvent, reacting under the conditions of oxygen and lighting and obtaining the acridone derivative. The synthesis method of the acridone derivative has the beneficial effects that the photocatalyst can catalyzethe compound shown in the formula (I) to carry out intramolecular hydrocarbon ammoniation reaction under the conditions of oxygen and lighting so as to synthesize the acridone derivative, and the pretreatment for the compound shown in the formula (I) is not needed; the operation is simple and convenient, and the condition is mild, the yield is high; the synthesis method conforms to the economic and environment-friendly characteristics of atoms and has high practical value for industrial preparation of the acridone derivative.
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Paragraph 0054; 0055; 0056; 0116; 0117; 0118; 0123; 0124
(2019/01/05)
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- Transition-Metal-Free Synthesis of Acridones via Base-Mediated Intramolecular Oxidative C?H Amination
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Intramolecular oxidative C?H amination of 2-aminobenzophenones was achieved in the presence of potassium tert-butoxide and dimethyl sulfoxide. A series of functionalized acridones were prepared in moderate to excellent yields in a mild, efficient, and transition-metal-free manner. (Figure presented.).
- Wei, Wen-Tao,Sheng, Jian-Fei,Miao, Hui,Luo, Xiang,Song, Xian-Heng,Yan, Ming,Zou, Yong
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supporting information
p. 2101 - 2106
(2018/06/14)
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- Syntheses of Acridones via Copper(II)-Mediated Relay Reactions from o-Aminoacetophenones and Arylboronic Acids
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The reaction of o-aminoacetophenones and arylboronic acids catalyzed by copper(II) salts in the presence of pyridine under an O2 atmosphere provides a general and efficient one-pot preparation of biologically interesting acridones. This relay reaction comprises an intermolecular Suzuki cross-coupling, intramolecular oxidative C(sp3)-H amination, and C(sp2)-H activation with simultaneous rearrangement of the generated isatin intermediates. This strategy tolerates both electron-donating and -withdrawing functionalities to afford various acridones in good to excellent yields.
- Wu, Hao,Zhang, Zhiguo,Liu, Qingfeng,Liu, Tongxin,Ma, Nana,Zhang, Guisheng
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supporting information
p. 2897 - 2901
(2018/05/29)
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- Synthesis of Acridines from o-Aminoaryl Ketones and Arylboronic Acids by Copper Trifluoroacetate-Mediated Relay Reactions
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An efficient and practical method for the synthesis of medicinally important acridines from readily available o-aminoaryl ketones and arylboronic acids was developed using copper(II)-mediated relay reactions that involve intermolecular Chan-Lam cross-coupling and subsequent intramolecular Friedel-Crafts-type reactions. A sole promoter, i.e., Cu(OTf)2, was used; therefore, strongly acidic and basic conditions, nonreadily available or expensive substrates, additives, and noble-metal catalysts were not needed.
- Wu, Hao,Zhang, Zhiguo,Ma, Nana,Liu, Qingfeng,Liu, Tongxin,Zhang, Guisheng
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p. 12880 - 12886
(2018/10/09)
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- Pd-NHC catalysed Carbonylative Suzuki coupling reaction and its application towards the synthesis of biologically active 3-aroylquinolin-4 (1H)-one and acridone scaffolds
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We have unfolded a convenient and mild protocol for the synthesis of diaryl ketones via Pd- NHC catalysed carbonylative Suzuki coupling reaction. Notably, this method offers advantages like no use of toxic CO gas, shorter reaction time, high yield, and broad substrate scope. Several sensitive functional groups (like-COMe, -COOMe, -F, -Cl, -Br, -NH2, -CN) are well tolerated in this reaction. In addition, we have also demonstrated a new efficient route for the synthesis of biologically active and pharmaceutically important 2-substituted 3-Aroylquinolin-4(1H)-ones and acridone scaffolds.
- Ghosh, Prasanjit,Ganguly, Bhaskar,Das, Sajal
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- Synthesis and Properties of Acridine and Acridinium Dye Functionalized Bis(terpyridine) Ruthenium(II) Complexes
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We present first principle studies on the rational design of an acridine/N-methylacridinium dye (Acr/MeAcr+) substituted terpyridine ligand to investigate if these chromophores can act as triplet-energy storage units in bis(terpyridine) ruthenium(II) complexes. We studied the influence of the dye form (Acr/MeAcr+) as well as the interconnecting linker unit (none, 4-phenyl, or 5-thien-2-yl) and investigated these aspects by steady-state/time-resolved spectroscopy, cyclic voltammetry, X-ray structure analysis, and DFT calculations.
- Eberhard, Jens,Peuntinger, Katrin,Fr?hlich, Roland,Guldi, Dirk M.,Mattay, Jochen
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supporting information
p. 2682 - 2700
(2018/06/04)
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- Method for synthesizing oxo-10-acridineacetic acid by adopting phase-transfer catalysis method
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The invention discloses a method for synthesizing oxo-10-acridineacetic acid by adopting a phase-transfer catalysis method. The method comprises the following steps of 1, preparing acridone, wherein diphenylamine and an acid catalyst are dissolved into an organic solvent, the mixture reacts with CO2 under the pressure of 0.6-0.7 MPa, pressure relief is performed, water is added, stirring is performed, filtering is performed, standing and layering are performed, an organic phase is sampled for washing, the solvent is evaporated out, and drying is performed to obtain the acridone; 2, preparing oxo-10-acridineacetic acid, wherein the acridone, chloroacetic acid and the phase transfer catalyst are added into a mixed solvent containing DMF and NaOH for a reaction under the temperature of 80-100DEG C, TLC is adopted for monitoring the complete reaction, the reaction is stopped, cooling is performed till room temperature is reached, ice water is added to obtain solid precipitates, the precipitates are filtered and washed to obtain a wet product midbody, the wet product midbody is added into a NaOH water solution, stirring is performed under the room temperature for dissolution, filteringis performed, the NaOH water solution is use for cleaning the filtered solid, washing solutions are mixed, the pH value is adjusted to be 4-5, solid precipitates are obtained, and filtering, washingand drying are performed to obtain the oxo-10-acridineacetic acid.
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Paragraph 0028; 0035; 0038; 0040-0042; 0049; 0056; 0063
(2018/09/14)
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- Palladium/copper Co-catalyzed oxidative C-H/C-H carbonylation of diphenylamines: A way to access acridones
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An efficient palladium/copper co-catalyzed oxidative double C(sp2)-H functionalization/carbonylation of diphenylamines for synthesis of acridones has been developed. This method utilizes readily available starting materials and mild reaction conditions. The protocol provides a simple, efficient, and atomeconomic way to access acridones. Notably, the present protocol has excellent functional group tolerance and application value.
- Wen, Jiangwei,Tang, Shan,Zhang, Fan,Shi, Renyi,Lei, Aiwen
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supporting information
p. 94 - 97
(2017/11/27)
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- Method for construction of C-N bond for synthesis of acridone derivative by intramolecular decarboxylation coupling
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The present invention provides a method for construction of a C-N bond for synthesis of an acridone derivative by intramolecular decarboxylation coupling, the synthesis process is as follows: a formula (I) compound, anhydrous 1, 10-phenanthroline, copper acetate, palladium acetate and silver carbonate are added to solvent anhydrous DMF, and heated in O2 atmosphere to 120 to 160 DEG C for reaction for 12-16h, and after postprocessing of a reaction liquid, the acridone derivative shown as a formula (II) can be obtained; the C-N bond can be constructed in one step for synthesis of an acridone product, the method has the advantages of high efficiency, low cost and good yield, conventional reagents are used in the reaction, and the conventional reagents are low-toxicity, environmental-friendly and economic.
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Paragraph 0017; 0018; 0019
(2017/10/07)
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- Design and synthesis of some acridine-piperazine hybrids for the improvement of cognitive dysfunction
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A novel series of hybrid molecules (5a–5m) was designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against cognitive dysfunction. Heterocyclic moieties acridine and piperazine were conjugated with suitable linkers in a single scaffold, and the structures of the target compounds were confirmed by IR, 1H NMR, 13C NMR, and LC-MS analysis. The pharmacological activity of synthesized compounds was evaluated using behavioral models of amnesia viz. step-down passive avoidance and elevated plus maze at a dose 0.5?mg/kg as compared to standard rivastigmine. In vitro acetylcholinesterase (AChE) inhibition studies using brain homogenate of mice as the enzyme source revealed that most of the compounds exhibited a significant ability to inhibit the enzyme cholinesterase with compound 5c being the most potent (IC50 0.33?μm). Biochemical estimation of oxidative stress markers viz. plasma nitrite, thiobarbituric acid reactive substances, catalase, superoxide dismutase, and glutathione has been carried out using the respective assays to see the effect of the synthesized compounds on the scopolamine-induced oxidative damage. The molecular docking studies indicated the binding mode of the compounds to the catalytic site, peripheral site, and mid-gorge of AChE simultaneously. The calculated absorption, distribution, metabolism and excretion properties ensured the drug-likeness of the target compounds. The synthesized compounds were found to be potential cognitive enhancers, which were able to interfere with the scopolamine-induced oxidative stress also.
- Sharma, Anuradha,Piplani, Poonam
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p. 926 - 935
(2017/10/06)
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- Method for synthesizing acridone derivatives by means of palladium-copper co-catalysis
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The invention discloses a method for synthesizing acridone derivatives by means of palladium-copper co-catalysis. The method comprises the steps that on the condition that palladium chloride, copper pivalate and di-tert-butyl peroxide or oxygen co-exist, diphenylamine compounds including symmetric diphenylamine and asymmetric diphenylamine are dissolved in an anhydrous organic solvent, all the materials are mixed to be uniform, a reaction is conducted for 20 h to 30 h under the condition of 80 DEG C to 120 DEG C in a carbon monoxide atmosphere, separation and purification are conducted, and the acridone derivatives can be obtained. According to the method for synthesizing the acridone derivatives by means of palladium-copper co-catalysis, the preparation method is simple, the diphenylamine compounds which are simple and easy to obtain are used as the raw materials, and the acridone derivatives are directly constructed through C-H/C-H oxidative carbonylation; the preparation condition is mild, and the target product can be obtained in a high-selectivity mode at 80 DEG C to 120 DEG C; the acridone derivatives have good substrate applicability, the range of substrates is greatly expanded, and the acridone derivatives have a great application prospect in biological medicine and materials and the like.
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Paragraph 0018; 0019; 0020; 0021
(2017/02/09)
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- Design, synthesis, pharmacological evaluation, and docking study of new acridone-based 1,2,4-oxadiazoles as potential anticonvulsant agents
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A number of acridone-based oxadiazoles 11a–n have been synthesized and evaluated for their anticonvulsant activity against pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. Also, their neurotoxicity was evaluated by the rotarod test. Most of the compounds exhibited better anticonvulsant activity and higher safety respect to the standard drug, phenobarbital. Among the tested derivatives, compounds 11l with ED50value of 2.08?mg/kg was the most potent compound in the PTZ test. The anticonvulsant effect of compound 11l was blocked by flumazenil, suggesting the involvement of benzodiazepine (BZD) receptors in the anticonvulsant activity of prototype compound 11l. Also, docking study of compound 11l in the BZD-binding site of GABAAreceptor confirms possible binding of compound 11l with BZD receptors.
- Mohammadi-Khanaposhtani, Maryam,Shabani, Mohammad,Faizi, Mehrdad,Aghaei, Iraj,Jahani, Reza,Sharafi, Zainab,Shamsaei Zafarghandi, Narges,Mahdavi, Mohammad,Akbarzadeh, Tahmineh,Emami, Saeed,Shafiee, Abbas,Foroumadi, Alireza
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- Antitumor compound and preparation method thereof
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The present invention is an antitumor compound belonging to the field of medicines, and particularly relates to an antitumor-active compound with a specific chemical structure and a preparation method and use of the antitumor-active compound. The antitumor-active compound is as shown in a general formula, wherein n is an integer from 0 to 3, R1 is methyl, fluorine, chlorine, bromine, carboxyl and a methyl ester, an ethyl ester, a propyl ester, an isopropyl ester, a n-butyl ester, an iso-butyl ester and a tert-butyl ester, R2 is acetyl, propionyl, benzoyl, and an alkyl group having 1-5 carbon atoms, X is CH2 or CO (carbonyl); positions of substituents on the aromatic ring may be 2-site-substituted, 3-site-substituted and 4-site-substituted, and the substitution may be mono-substituted and poly-substituted. The present invention provides the preparation method of the antitumor-active compound. Experiments show that the antitumor-active compound as a new-structure-type topoisomerase inhibitor plays a good role in inhibition of tumor activity.
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- 9-amino acridine derivative and its synthetic method
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The invention discloses a novel aminoacridine derivative, and particularly relates to a 9-aminoacridine derivative and a synthetic method thereof, belonging to the technical field of organic chemical synthesis. The structure of the 9-aminoacridine derivative is shown in the specification, wherein R1 and R2 are independently selected from H, methoxyl, C1-C10 alkyl and C1-C10 halo-alkyl. The compound has better fluorescence property and can be applied to an organic light-emitting material.
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- Tandem arylation/friedel-crafts reactions of o-acylanilines with diaryliodonium salts: A modular synthesis of acridine derivatives
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A modular method to synthesize acridine derivatives was developed with o-acylanilines and diaryliodonium salts. The reactions proceeded smoothly under Cu-catalyzed or metal-free reaction conditions at elevated temperature through tandem arylation/Friedel-Crafts reactions.
- Pang, Xinlong,Lou, Zhenbang,Li, Ming,Wen, Lirong,Chen, Chao
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supporting information
p. 3361 - 3369
(2015/05/20)
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- Potent acetylcholinesterase inhibitors: Design, synthesis, biological evaluation, and docking study of acridone linked to 1,2,3-triazole derivatives
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A novel series of acridone linked to 1,2,3-triazole derivatives have been synthesized and evaluated in vitro for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. The synthetic approach was started from the reaction of 2-bromobenzoic acid with aniline derivatives and subsequent cyclization reaction to give acridone derivatives. Then, reaction of the later compounds with propargyl bromide followed by azide-alkyne cycloaddition reaction (click reaction) led to the formation of the title compounds in good yields. Among the synthesized compounds, 10-((1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-2-methoxyacridin-9(10H)-one 9g, depicted the most potent anti-AChE activity (IC50 Combining double low line 7.31 μ1/4M). Also, docking study confirmed the results obtained through in vitro experiments and predicted possible binding conformation.
- Mohammadi-Khanaposhtani, Maryam,Saeedi, Mina,Zafarghandi, Narges Shamsaei,Mahdavi, Mohammad,Sabourian, Reyhaneh,Razkenari, Elahe Karimpour,Alinezhad, Heshmatollah,Khanavi, Mahnaz,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
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p. 799 - 806
(2015/03/05)
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- Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9(10H-acridinone-1,2,3-triazoles
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A new series of 9(10H-acridinone-1,2,3-triazole derivatives were designed, synthesized and evaluated for their cytotoxic activity against human breast cancer cell lines. The acridone skeleton was prepared through the Ullman condensation of 2-bromobenzoic acid and anilines. Subsequently, it was functionalized with propargyl bromide. Then, a click reaction of the latter compound and in situ prepared 1-(azidomethyl)-4-methoxybenzene derivatives led to the formation of the desired triazole products. Finally, all products were investigated for their capability to cause cytotoxicity against MCF-7, T-47D, and MDA-MB-231 cell lines. Among them, 2-methoxy-10-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)acridin-9(10H-one 8c exhibited the most potency (hbox {IC}_{50},{=},11.0,{pm }, 4.8, upmu hbox {M})(IC50=11.0±4.8μM) against MCF-7 cells, being more potent than etoposide (hbox {IC}_{50},{=}, 12.4,{pm }, 4.7 upmu hbox {M})(IC50=12.4±4.7μM). Also, apoptosis induced by compound 8c was confirmed via acridine orange/ethidium bromide and Annexin V-FITC/propidium iodide (PI) double staining.
- Mohammadi-Khanaposhtani, Maryam,Safavi, Maliheh,Sabourian, Reyhaneh,Mahdavi, Mohammad,Pordeli, Mahboobeh,Saeedi, Mina,Ardestani, Sussan Kabudanian,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
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p. 787 - 795
(2015/10/12)
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