5805-39-0Relevant articles and documents
A simple quinoline-derived fluorescent sensor for the selective and sequential detection of copper(II) and sulfide ions and its application in living-cell imaging
Liu, Haiyang,Wu, Fengxu,Zhang, Bibo,Tan, Chunyan,Chen, Yuzong,Hao, Gefei,Tan, Ying,Jiang, Yuyang
, p. 77508 - 77514 (2016)
A simple amide compound (QLBA), prepared from quinoline-2-carboxylic acid and 2-(1H-benzo[d] imidazol-2-yl)aniline, was synthesized and evaluated as an efficient fluorescence chemosensor for the selective recognition of copper ions (Cu2+). This sensor could detect Cu2+ in CH3OH/HEPPES buffer in a wide pH range (4.0-10.0), with obvious fluorescence quenching. The obtained QLBA-Cu2+ complex could be used as a new cascade sensor for detecting sulfide anions (S2-). The corresponding detection limits were found to be 2.2 × 10-7 M for Cu2+ and 4.6 × 10-7 M for S2-. The sensing mechanisms of QLBA toward Cu2+ were systematically investigated in detail by NMR, HR-MS analysis, and density functional theory (DFT) calculations. In addition, this sensor was verified to be of low cytotoxicity and to have good imaging characteristics for the detection of Cu2+ and further for the recognition of S2- in living cells, suggesting that QLBA was a useful tool for tracking Cu2+ and S2- ions in vivo.
Hydrogen-bonded sheets in 2-(2-aminophenyl)-1H-benzimidazol-3-ium dihydrogen phosphate
Shylaja,Mahendra,Varma,Narasimhamurthy,Rathore
, p. o361-o363 (2008)
The title salt, C13H12N3 +·H2PO4 -, contains a nonplanar 2-(2-amino-phenyl)-1H-benzimidazol-3-ium cation and two different dihydrogen phosphate anions, both situated on twofold rotation axes in the space group C2. The anions are linked by O - H...O hydrogen bonds into chains of R 2 2(8) rings. The anion chains are linked by the cations, via hydrogen-bonding complementarities and electrostatic inter-actions, giving rise to a sheet structure with alternating rows of organic cations and inorganic anions. Comparison of this structure with that of the pure amine reveals that the two compounds generate characteristically different sheet structures. The anion-anion chain serves as a template for the assembly of the cations, suggesting a possible application in the design of solid-state materials.
Synthesis, antimicrobial, and mitotic toxicity evaluation of new 6-substituted 2-(benzo[4,5]imidazo[1,2-c]quinazolin-5(6H)-yl)acetic acids
Kravtsov, Dmytro V.,Voskoboinik, Oleksii Yu.,Kovalenko, Serhii I.
, p. 212 - 225 (2020/10/14)
A series of novel 6-substituted 2-(benzo[4,5]imidazo[1,2-c]quinazolin-5(6H)-yl)acetic acids were synthesized and characterized by 1H, 13C, 19F NMR, 1H-1H-COSY, 1H-13C-HSQC, NOESY, LC-MS, IR, and elemental analysis. The mitotic toxicity of the synthesized compounds was determined according to the Allium test procedure. The 2-(6-(pentafluorophenyl)benzo[4,5]imidazo[1,2-c]quinazolin-5(6H)-yl)acetic acid inhibited mitotic spindle formation, which resulted in significant cytotoxic effect for meristematic cells of Allium cepa l. roots. In a preliminary antimicrobial evaluation, only Streptococcus pyogenes and Candida albicans were slightly susceptible to some of the synthesized compounds.
Synthesis and biological evaluation of substituted N-(2-(1H-benzo[d]imidazol-2-yl)phenyl)cinnamides as tubulin polymerization inhibitors
Anchi, Pratibha,Donthiboina, Kavitha,Godugu, Chandraiah,Gurram, Sowmyasree,Kamal, Ahmed,Lakshmi Uppu, Jaya,Sai Mani, Geeta,Shankaraiah, Nagula
, (2020/09/07)
A new series of N-(2-(1H-benzo[d]imidazol-2-yl)phenyl) cinnamides was prepared and evaluated for their in vitro cytotoxic activity using various cancer cell lines viz. A549 (human non-small cell lung cancer), MDA-MB-231 (human triple negative breast cancer), B16-F10 (mouse melanoma), BT-474 (human breast cancer), and 4 T1 (mouse triple negative breast cancer). In the series of tested compounds, 12h showed potent cytotoxic activity against non-small cell lung cancer cell line with IC50 value of 0.29 ± 0.02 μM. The cytoxicity of most potent compound 12h was also tested on NRK-52E (normal rat kidney epithelial cell line) and showed less cytotoxicity compared to cancer cells. Tubulin polymerization assay indicated that the compound 12h was able to impede the cell division by inhibiting tubulin polymerization. Moreover, molecular docking study also suggested the binding of 12h at the colchicine-binding site of the tubulin protein. Cell cycle analysis revealed that the compound 12h arrests G2/M phase. In addition, 12h induced apoptosis in A549 cell lines was evaluated by various staining studies like acridine orange, DAPI, analysis of mitochondrial membrane potential, annexin V-FITC, and DCFDA assays.