84359-61-5Relevant academic research and scientific papers
New classes of carbazoles as potential multi-functional anti-Alzheimer's agents
Abdolahi, Z.,Ameri, A.,Ayazg?k, B.,Choubdar, Niloufar,Foroumadi, Alireza,Golshani, Mostafa,Jalili-Baleh, L.,Kü?ükkilin?, Tuba Tüylü,Khoobi, M.,Moghadam, Farshad Homayouni,Moradi, Alireza,Nadri, H.,Salehian, Fatemeh
, (2019)
Multi-Target approach is particularly promising way to drug discovery against Alzheimer's disease. In the present study, we synthesized a series of compounds comprising the carbazole backbone linked to the benzyl piperazine, benzyl piperidine, pyridine, quinoline, or isoquinoline moiety through an aliphatic linker and evaluated as cholinesterase inhibitors. The synthesized compounds showed IC50 values of 0.11–36.5 μM and 0.02–98.6 μM against acetyl- and butyrylcholinesterase (AChE and BuChE), respectively. The ligand-protein docking simulations and kinetic studies revealed that compound 3s could bind effectively to the peripheral anionic binding site (PAS) and anionic site of the enzyme with mixed-type inhibition. Compound 3s was the most potent compound against AChE and BuChE and showed acceptable inhibition potency for self- and AChE-induced Aβ1-42 aggregation. Moreover, compound 3s could significantly protect PC12 cells against H2O2-induced toxicity. The results suggested that the compounds 3s could be considered as a promising multi-functional agent for further drug discovery development against Alzheimer's disease.
Synthesis, characterization, crystal structure and evaluation of four carbazole-coumarin hybrids as multifunctional agents for the treatment of Alzheimer's disease
Li, Ming-Cheng,Liu, Wei-Wei,Liu, Yu-Wei,Min, Wei,Shi, Da-Hua,Si, Xin-Xin,Song, Meng-qiu,Zhang, Zhao-yuan
, (2020)
Coupling of two distinct pharmacophores, carbazole and coumarin, endowed with different biological properties, afforded four hybrid compounds. The structures of the carbazole-coumarin hybrids were characterized by FT-IR, NMR, HRMS and single-crystal X-ray diffraction studies. All of these compounds exhibited significant acetylcholinesterase inhibitory activities. Among them, compound 4-((5-(9H-carbazol-9-yl)pentyl)oxy)-2H-chromen-2-one (3d) exhibited the best inhibition activity with IC50 of 3.75 μM for acetylcholinesterase from electric eel and 70.51 μM for human recombinant acetylcholinesterase. Moreover, the compound 7-(3-(9H-carbazol-9-yl propoxy)-4-methyl-2H-chromen-2-one (3a) had the best antioxidant activity. The docking studies demonstrated that compound 3d could interact with both the catalytic active site and the peripheral anionic site of acetylcholinesterase. These attributes imply carbazole-coumarin hybrids as multifunctional agents for the Alzheimer's disease treatment.
A simple but effective fluorescent probe for the detection of bisulfite
Luo, Jing,Song, Guangjie,Xing, Xujiao,Shen, Shili,Ge, Yanqing,Cao, Xiaoqun
, p. 3986 - 3990 (2017)
A new fluorescence probe (PML) for sensing HSO3- was developed based on a Michael addition reaction mechanism. The probe was composed of carbazole and 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile moieties and can be easily synthesized. The carbazole-based probe can selectively detect HSO3- and shows good sensitivity with the limit of detection of 2.08 × 10-6 M in a PBS:DMF = 1:1 buffer solution. Upon addition of HSO3-, the intense fluorescence of the probe was quenched, and the color markedly changed from red to colorless. In addition, the probe can be used to detect HSO3- in dry white wine.
Zn(II)-DPA Coordinative fluorescent probe for enhancing G4 DNA binding
Bai, Yi-Tong,Gao, Juan-Juan,Lang, Xue-Xian,Li, Hong-Yao,Wang, Hai-Jiao,Wang, Ming-Qi,Yu, Quan-Qi
, (2021/08/24)
Novel dipicolylamino functionalized styryl-carbazole derivative (YCJ) was designed and synthesized. This derivative in combination with Zn(II) has exhibited large fluorescence intensity enhancement and prominent red-shift in absorption spectra with G4 DNA. Systematical analysis indicats that YCJ-Zn(II) complex shows much higher binding affinity and spectral response to G4 DNA than our previously reported styryl-carbazole scaffold (E1) due to the incorporationc of a Zn(II)-DPA moiety which could decrease the carbazole core electron density and consequently enhance the ability to display π-π stacking interaction with G4 DNA. Spectroscopic and molecular docking studies have unraveled YCJ-Zn(II) complex can stack both 3′ and 5′-ends and an associated with partial loop/groove interactions. The application of this Zn(II) complex as a fluorescent agent for living cell imaging was also demonstrated. The conjugation of the Zn-DPA moiety results in good cell permeability, endogenous DNA labeling, which is suitable for monitoring of nucleus activities.
A organic long afterglow compound and its preparation method and application (by machine translation)
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Paragraph 0100; 0102-0105, (2019/10/23)
The invention relates to a kind of organic long afterglow compound and its preparation method and application, the organic long afterglow compounds have the formula (I) indicated by the structure, the present invention provides compounds of formula (I) have shown long afterglow compound long service life, and different structure sub compound of different service life, various colors, when the stop of the excitation light source is illuminated, its emitted light by the fluorescence can be realized to the phosphorescent color change, after gradually reducing the brightness, the nature of the time-resolved technology can be combined with the four-dimensional coding, a large amount of information storage and information encryption. (by machine translation)
Synthesis of N-Alkyl-Carbazole Derivatives as 5-HT7R Antagonists
Kim, Youngjae,Yeom, Miyoung,Lee, Soyeon,Tae, Jinsung,Kim, Hak Joong,Rhim, Hyewhon,Seong, Jihye,Choi, Kyung Il,Min, Sun-Joon,Choo, Hyunah
, p. 1083 - 1089 (2018/09/19)
We designed and synthesized a series of N-alkyl-carbazoles with different alkyl chains and amine moieties, and biological evaluation was performed to discover novel 5-HT7R antagonists. Among 27 synthesized compounds, 20, 21, 23, and 24 showed excellent binding affinities to 5-HT7R (Ki = 65, 64, 55, and 31 nM, respectively), and good selectivity profiles over other serotonin receptors. In functional assays, those compounds showed weak antagonistic activities against 5-HT7R. In particular, the compound 24, 2-(4-(5-(9H-carbazol-9-yl)pentyl)piperazin-1-yl)phenol, could be considered as a potent and selective 5-HT7R ligand with weak antagonistic effect. From the molecular docking study, the aromatic hydroxyl group in 24 was shown to play an important role in binding to 5-HT7R through a hydrogen bonding interaction with Asp142 in the ligand binding pocket of 5-HT7R.
Fluorescent probe for simply and effectively detecting sulfite
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Paragraph 0017, (2018/10/27)
The invention discloses a novel fluorescent probe for simply and effectively detecting sulfite based on a carbazole matrix. A chemical structure formula of the probe is shown as a formula (I). The fluorescent probe disclosed by the invention has unique fluorescence selectivity to the sulfite in a buffer solution system with PBS to DMF=1:1, higher sensitivity and stronger interference resistance toother ions, thereby having huge application prospects.
Inhibition of Human Topoisomerase II by N,N,N-Trimethylethanammonium Iodide Alkylcarbazole Derivatives
Saturnino, Carmela,Caruso, Anna,Iacopetta, Domenico,Rosano, Camillo,Ceramella, Jessica,Muià, Noemi,Mariconda, Annaluisa,Bonomo, Maria Grazia,Ponassi, Marco,Rosace, Giuseppe,Sinicropi, Maria Stefania,Longo, Pasquale
, p. 2635 - 2643 (2018/12/11)
Chemotherapy is used for the treatment of all stages of breast cancer, including the metastatic stage of the disease. Treatment regimens are generally tailored for each patient′s particular situation. However, chemotherapeutic agents are the leading cause of serious drug-related adverse effects; moreover, drug resistance often occurs. In this study, we designed and synthesized a new series of N-alkylcarbazoles derived from ellipticine, an alkaloid with a carbazole skeleton initially used in the treatment of metastatic breast cancer and later dismissed because of poor aqueous solubility and severe side effects. After evaluating the binding modes of our class of newly synthesized compounds with human topoisomerase II (hTopo II), we performed hTopo II decatenation assays, identifying compound 4 f (2-(4-((3-chloro-9H-carbazol-9-yl)pentyl)piperazin-1-yl)-N,N,N-trimethylethanammonium iodide) as a good inhibitor. Moreover, 4 f and 4 g (2-(4-((3-chloro-9H-carbazol-9-yl)hexyl)piperazin-1-yl)-N,N,N-trimethylethanammonium iodide) showed a good anti-proliferative activity toward breast cancer cells, causing apoptosis by activation of the caspase pathway. Interestingly, the activity of these two compounds on triple-negative MDA-MB-231 cells, which tend to be highly metastatic and aggressive, is strictly connected to the observed inhibition of hTopo II.
Preparation method of light trigger of carbazole oxime ester
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Paragraph 0016, (2018/01/09)
The invention discloses a preparation method of a light trigger of carbazole oxime ester, and particularly relates to a method for preparing the carbazole oxime ester by using carbazole, nitric acid, 1-bromo-3-chloropropane, diethyl phosphite, o-Methoxybenzoyl chloride, hydroxylamine hydrochloride and acetic anhydride as raw materials through six steps of reactions including N-alkylation reaction, substitution reaction, nitratlon reaction, Friedel-Crafts reaction, and oxime and acetylation reaction. The preparation method of the carbazole oxime ester provided by the invention belongs to a preparation method with the advantages that the yield is high; the cost is low; the environment is protected; the operation is easy; the preparation method is suitable for industrialization.
A steam-color-changing nature of the carbazole skeleton bridge chain gold isocyanate compound, preparation and application (by machine translation)
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Paragraph 0031, (2017/08/25)
The present invention provides a steam-color-changing nature of the carbazole skeleton bridge chain gold isocyanate compound, preparation and application. The formula IV - 1 - 6 of the structure. This kind of compound film of benzene, pyridine, acetone, methylene chloride, toluene, chloroform, tetrahydrofuran, acetonitrile, diethyl ether, ethyl acetate and the like organic solvent vapor of the atmosphere, fluorescent rapidly from a green khaki, showed a sensitive thin film steam color-changing nature. Therefore, such compounds are expected to be present in the environment for future identification or we in the workplace in the harmful volatile chemical solvent. (by machine translation)
