21240-56-2Relevant articles and documents
Vilsmeier reaction on carbazole: Theoretical and experimental aspects
Das, Gourab Kanti,Choudhury, Bijali,Das, Kalpita,Das, Basudeb Prasad
, p. 244 - 245 (1999)
The pathway of the Vilsmeier reaction on carbazole has been studied by AM1 semiempirical MO calculations, which includes the characterization of the various transition structures; an experimental study of the actual reaction shows the formation of diformyl derivative along with a monoformyl derivative.
Carbazole-based 1D and 2D hemicyanines: Synthesis, two-photon absorption properties and application for two-photon photopolymerization 3D lithography
Gu, Jie,Yulan, Wang,Chen, Wei-Qiang,Dong, Xian-Zi,Duan, Xuan-Ming,Kawata, Satoshi
, p. 63 - 68 (2007)
One and two dimensional (1D and 2D) carbazole based hemicyanines, where methyl pyridinium, methyl indolium and methyl benzothiazolium were used as acceptor group, were synthesized by Knoevenagel condensation. One-photon absorption, fluorescence and two-photon fluorescence spectra were investigated. The experimental results indicated that the different ionic acceptors affect their one-photon and two-photon properties. Among them, 2D methyl pyridinium carbazole derivatives exhibited low quantum yields and large two-photon absorption cross sections more than 1600 GM. The synthesized compounds were used as photoinitiator of two-photon photopolymerization (TPP), and three-dimensional (3D) microstructure was successfully fabricated by TPP 3D lithography. They could be utilized as effective two-photon polymerization photoinitiators. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
One-pot synthesis and UV-Visible absorption studies of novel tricyclic heterocycle tethered Xanthene-1,8-diones
Yempala, Thirumal,Sridhar, Balasubramanian,Kantevari, Srinivas
, p. 803 - 810 (2015)
Abstract A series of new tricyclic heterocyclic xanthene-1,8-diones tethered with chromophoric dibenzo [b, d]furan, dibenzo[b, d]thiophene and 9-methyl-9H-carbazoles were synthesized through one-pot condensation of dibenzo[b, d]furan-2-carbaldehyde, dibenzo[b, d] thiophene-2-carbaldehyde and 9-methyl-9H-carbazole-3-carbaldehyde with cyclic 1,3-dicarbonyls in the presence of recyclable PPA-SiO2 catalyst under solvent-free conditions. Further, UV-Visible absorption properties of all the synthesized compounds were investigated in CHCl3, THF and acetonitrile. [Figure not available: see fulltext.]
Novel yellow- to red-emitting fluorophores: Facile synthesis, aggregation-induced emission, two-photon absorption properties, and application in living cell imaging
Dong, Qi-Ji,Cai, Zhi-Bin,Ding, Ling,Luo, Pei-Hua,He, Qiao-Jun,Li, Sheng-Li,Chen, Li-Jun,Ye, Qing,Tian, Yu-Peng
, (2020/10/29)
Four novel yellow-to red-emitting fluorophores with a 1-(2-hydroxyethyl) pyridinium core and different electron-donating terminal moieties (N-methylcarbazole, N,N-dibutylbenzenamine, N-methylpyrrole, and 2-methylfuran) were designed and facilely synthesized via the one-step Knoevenagel condensation. All these compounds (HPs) were characterized by 1H NMR, 13C NMR, and HRMS. Their photophysical properties including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated in various solvents. And the density functional theory calculations were conducted to analyze the electronic structures of HPs. The two-photon absorption cross-sections (δ) values of HPs measured by the Z-scan technique were determined to be as large as 1354 (1HP-CZ), 4462 (2HP-BA), 836 (3HP-PR), and 2944 GM (4HP-FU) in DMSO. The two-photon action cross-sections (Φ × δ) values of 1HP-CZ and 2HP-BA in H2O measured by the two-photon induced fluorescence method were about 50 GM. 1HP-CZ, 3HP-PR, and 4HP-FU also exhibited good water solubility. Meanwhile, it was found that 2HP-BA exhibited notable aggregation-induced emission characteristic in DMSO/H2O mixture. The aggregate particle size distribution of 2HP-BA was measured by the dynamic light scattering method, and the aggregation characteristic of 2HP-BA was observed by the transmission electron microscopy. Besides, 2HP-BA also exhibited red emission. Then, HPs with relatively low cytotoxicity were used for one- and two-photon excited fluorescence imaging in living HepG2 cells. The results indicate that HPs are potential candidates in the bioimaging field due to their photophysical properties and biocompatibility.
Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents
Xue, Yi-Jie,Li, Ming-Yue,Jin, Xue-Jun,Zheng, Chang-Ji,Piao, Hu-Ri
, p. 295 - 306 (2021/01/13)
Five series of novel carbazole derivatives containing an aminoguanidine, dihydrotriazine, thiosemicarbazide, semicarbazide or isonicotinic moiety were designed, synthesised and evaluated for their antimicrobial activities. Most of the compounds exhibited potent inhibitory activities towards different bacterial strains (including one multidrug-resistant clinical isolate) and one fungal strain with minimum inhibitory concentrations (MICs) between 0.5 and 16 μg/ml. Compounds 8f and 9d showed the most potent inhibitory activities (MICs of 0.5–2 μg/ml). Furthermore, compounds 8b, 8d, 8f, 8k, 9b and 9e with antimicrobial activities were not cytotoxic to human gastric cancer cell lines (SGC-7901 and AGS) or a normal human liver cell line (L-02). Structure–activity relationship analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency and reducing the toxicity of the carbazole compounds. In vitro enzyme activity assays suggested that compound 8f binding to dihydrofolate reductase might account for the antimicrobial effect.
Synthesis and Biological Evaluation of Novel Carbazole Hybrids as Promising Antimicrobial Agents
Shaikh, Mahamadhanif S.,Chandrasekaran, Balakumar,Palkar, Mahesh B.,Kanhed, Ashish M.,Kajee, Afsana,Mlisana, Koleka P.,Singh, Parvesh,Ghai, Meenu,Cleopus Mahlalela, Mavela,Karpoormath, Rajshekhar
, (2020/04/23)
Two series of carbazole analogs of 8-methoxy-N-substituted-9H-carbazole-3-carboxamides (series 1) and carbazolyl substituted rhodanines (series 2) were synthesized through facile synthetic routes. All the final compounds from these two series were evaluated for their preliminary in vitro antifungal and antibacterial activity against four fungal (Candida albicans, Cryptococcus neoformans, Cryptococcus tropicalis and Aspergillus niger) and four bacterial (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa) strains, respectively. Among the tested compounds, three compounds of series 1 displayed promising antifungal and antibacterial activity, especially against C. neoformans and S. aureus. In addition, one compound of series 1 displayed notable antimicrobial activity (MIC: 6.25 μg/mL) against clinical isolates of C. albicans and C. neoformans (MIC: 12.5 μg/mL). From the second series, four compounds exhibited significant antifungal and antibacterial activity, especially against C. neoformans and S. aureus. The most active compound of series 2 displayed a prominent antimicrobial activity against C. neoformans (MIC: 3.125 μg/mL) and S. aureus (MIC: 1.56 μg/mL), respectively.
Design, synthesis, and evaluations of the antiproliferative activity and aqueous solubility of novel carbazole sulfonamide derivatives as antitumor agents
Sun, Lianqi,Wang, Chenxi,Hu, Xinyue,Wu, Yanbin,Jiang, Zhi,Li, Zhuorong,Chen, Xiaofang,Hu, Laixing
, (2020/04/08)
Optimization of IG-105 (1) on the carbazole ring provided five series of new carbazole sulfonamides derivatives, 7a–e, 8a–g, 9a–g, 10a–e, and 11a–g. All of the compounds were evaluated against HepG2, MCF-7, MIA PaCa-2, and Bel-7402 cells for antiproliferative activity. Each series of compounds was 2–5 times more active against HepG2 cells (IC50: 1.00–10.0 μM) than the other three tumor cell lines. Several representative compounds, selected from each series, showed aqueous solubility (13.4–176.5 μg/mL at pH 7.4 and 2.0) better than 1, with the aqueous solubility of corresponding salts > 30 mg/mL. From the results of evaluating the effects of the compounds 7b, 8c, 9c, 10c and 11c on tubulin in vitro, we speculated that their targets were different from those of 1 and CA-4P. We tested the antitumor activity of the representative compound 7b·HCl (10 mg/kg) in an in vivo study and found that its tumor growth inhibition rate was 41.1%. The tumor growth inhibition rate of 7b·HCl (20 mg/kg) was 54.6%, whereas the tumor growth inhibition rate of CA-4P (50 mg/kg) was 48.3%. And in another batch of in vivo antitumor activity testing, 9c·HCl and 11c·HCl at doses of 10 mg/kg resulted in 61.1% and 50.0% inhibition, respectively. These promising results warrant further development of the derivatives, which may use a novel mechanism and show potential potency as antitumor drug candidates.
Discovery of novel N-methyl carbazole tethered rhodanine derivatives as direct inhibitors of Mycobacterium tuberculosis InhA
Shaikh, Mahamadhanif S.,Kanhed, Ashish M.,Chandrasekaran, Balakumar,Palkar, Mahesh B.,Agrawal, Nikhil,Lherbet, Christian,Hampannavar, Girish A.,Karpoormath, Rajshekhar
supporting information, p. 2338 - 2344 (2019/06/20)
InhA (Enoyl-ACP reductase) plays a crucial role in the biosynthetic pathway of cell wall synthesis in Mycobacterium tuberculosis (Mtb). Isoniazid (INH) is an important first-line drug, which inhibits InhA. The rapid increase in resistance to INH and currently marketed drugs as well as emergence of MDR-TB and XDR-TB has complicated the diagnosis and treatment of Mtb with ever increasing threat to human kind. Herein, we report novel N-methyl carbazole derivatives as potential anti-TB compounds acting directly via InhA inhibition. All the synthesized final compounds were screened against Mtb virulent cell line H37Rv and investigated the InhA enzyme inhibition. Interestingly, compound 9e displayed promising inhibition (91%) at 50 μM concentration and IC50 of 2.82 μM against InhA. To understand the ligand receptor interaction between compound 9e and InhA, molecular docking and molecular dynamics experiments were performed. The computational results were in agreement with the observed experimental data. Further, the cytotoxicity studies on mammalian cells revealed that all the compounds were safe.
Design, synthesis of organic sensitizers containing carbazole and triphenylamine π-bridged moiety for dye-sensitized solar cells
Velu, Sadhasivam,Muniyasamy, Harikrishnan,Ayyanar, Siva,Maniarasu, Suresh,Veerappan, Ganapathy,Sepperumal, Murugesan
, p. 1923 - 1937 (2019/07/04)
Abstract: A series of novel push–pull-based D–π–A-containing organic dyes have been synthesized using triphenylamine and carbazole act as π-conjugated donor and cyanoacrylic acid acceptor as well as anchoring group for application of dye-sensitized solar cells. These organic dyes D1, D2 and D3 exhibited excellent photophysical, electrochemical properties, superior stoke shift, high thermal stabilities and sufficient HOMO–LUMO energy levels, which is facilitated to dye regeneration and effective injection of electron from the excited state of the dyes into the conduction band (TiO2). Our results suggested that carbazole π-bridge has an important role in the photovoltaic performance. The D1 and D2 dyes are planar linear structure, longer π-conjugated bridging units, when compared to the starburst structure of D3 organic dye. Moreover, the carbazole π-bridged conjugated D1 dye showed promising photovoltaic conversion efficiency (η) of 1.4%, Voc = 735?mV, Jsc = 2.7?mA/cm2, ff = 0.73 (fill factor), when compared with the conventional N719 and D5 organic dyes.
Quinoline carbazole fluorescence dye and preparation method and application thereof
-
Paragraph 0053; 0055; 0057, (2018/07/30)
The invention relates to a quinoline carbazole fluorescence dye and a preparation method and an application thereof. The fluorescence dye has a structural general formula I, wherein Y is selected from halogen negative ions, which are I, Cl and Br, and preferably selects I. The quinoline carbazole fluorescence dye is a two-photon fluorescence dye, has high efficiency and specific identification capability on a PBS buffer solution and mtDNA in living cells, and has high light stability and low biotoxicity. In addition, the compound preparation route is simple, and the industry application is easy.
