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.
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.
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.
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.
