2373-31-1Relevant articles and documents
N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazones of 6-alkoxy-2-oxo-2H-chromene-4-carbaldehydes: synthesis, evaluation of their antibacterial, anti-MRSA, antifungal activity, and docking study
Toan, Vu Ngoc,Thanh, Nguyen Dinh,Khuyen, Vu Hong,Tu, Luu Thi Cam,Tri, Nguyen Minh,Huong, Nguyen Thi Thu
, p. 743 - 759 (2021)
Reaction of 6-alkoxy-2-oxo-2H-chromen-4-carbaldehydes with N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazide yielded corresponding thiosemicarbazones having 2H-chromen-2-one ring. In vitro evaluations showed that these 2H-chromen-2-one compounds exhibited remarkable antibacterial and antifungal activities against some typical bacteria and fungi. Representative compounds with MIC values of 0.78 ? 1.56 μg/mL were 6c, 6g (against S. aureus), 6a, 6f (against S. epidermidis) (Gram-positive bacterial strains), 6e, 6g (against E. coli), 6b, 6e (against K. pneumoniae), and 6d–f (against S. typhimurium) (Gram-negative bacterial strains). Almost all thiosemicarbazones 6a–g had no activity against Gram-positive bacterial strain B. subtilis at these MIC values. Some compounds had strong inhibitory activity against several bacteria, such as 6b (for K. pneumoniae and S. typhimurium), 6d, 6e (for E. coli, K. pneumoniae, and S. typhimurium), 6f (for S. aureus, E. coli, and S. typhimurium), and 6g (for B. subtilis, S. aureus, E. coli, and K. pneumoniae). Some compounds had remarkable inhibitory activity against three clinical MRSA isolates with MIC values of 0.78–6.25 μg/mL. Docking study showed that compound 6g is compatible with the active site of S. aureus DNA gyrase 2XCT, which suggested that the tested compounds inhibited the synthesis of this enzyme. [Figure not available: see fulltext.]
A highly selective chemosensor for naked-eye sensing of nanomolar Cu(II) in an aqueous medium
Qian, Yaao,Cao, Li,Jia, Chunman,Boamah, Peter Osei,Yang, Qiuyun,Liu, Chunling,Huang, Yan,Zhang, Qi
, p. 77965 - 77972 (2015)
A novel highly selective and sensitive colorimetric chemosensor L for the detection of Cu2+ ion with a fast response time was designed and synthesized. Receptor L detected Cu2+ ion by changing its color from colorless to magenta in a semi-aqueous solution. The limit of detection for Cu2+ was calculated to be as low as 28 nM. The possible binding mode of compound L with Cu2+ ion was studied using the Job's method, HRMS, FTIR spectroscopy and 1H NMR spectroscopy titration. Importantly, test strips containing L were fabricated as a naked-eye indicator for Cu2+ ion in pure water samples.
Synthesis and antiproliferative activity of 6,7-aryl/hetaryl coumarins
Jayaprakash Rao,Yadaiah Goud,Hemasri,Jain, Nishant,Gabriella, Srujana
, p. 184 - 189 (2016)
Two different series of novel analogs of 6,7-aryl/hetaryl coumarins 4a-4h and 8i-8l have been synthesized by using Suzuki-Miyara cross coupling reaction from 4-methyl-2-oxo-2H-chromen-7-yl trifluoro-methanesulfonate and 4-methyl-2-oxo-2H-chromen-6-yl trifluoromethanesulfonate in high yields (70-90%). All synthesized compounds were elucidated by means of IR, 1H NMR, 13C NMR, and MS spectra. The synthesized compounds were tested for antiproliferative activity against different human cancer cell lines (SiHa, MDAMB-231, and PANC-1) and some of products demonstrated the distinctive effect.
Novel thiazoline-coumarin hybrid compounds containing sugar moieties: synthesis, biological evaluation and molecular docking study as antiproliferative agents
Ngoc Toan, Vu,Dinh Thanh, Nguyen
, p. 10636 - 10653 (2021/06/27)
A new series of 2,3-thiazoline-coumarin hybrid compounds that containedd-glucose andd-galactose moieties (4a-g) were synthesized and their cytotoxic activity was evaluated against breast adenocarcinoma (MCF-7), human liver cancer (HepG2), human cervical cancer (HeLa), human melanoma cancer (SK-Mel-2), and human lung cancer (LU-1) cells. To reveal their selectivity toward cancer cells, the compounds were also tested against the human fibroblast cell line MRC-5. The synthesized compounds exhibited potent cytotoxic activity against the tested cell lines with IC50values of 1.18-11.32, 1.91-9.81, 1.96-13.16, 1.35-16.12, and 2.12-15.92 μM (against MCF-7, HepG2, HeLa, SK-Mel-2, and LU-1 cells, respectively) compared with Sorafenib, doxorubicin, and 5-fluorouracil. Interestingly, compounds4a-gdisplayed selectivity toward cancer cell lines over MRC-5 (IC503.97-25.75 μM). The most active compounds, including4d,4e, and4f, also displayed potent inhibitory activity against EGFR and HER2 kinases (IC500.15-0.31 and 0.15-0.25 μM, respectively) compared with the standard drug Sorafenib (IC50= 0.11 and 0.13 μM, respectively). Molecular docking also showed that the hydrogen binding interactions often occurred between the CO lactone of the coumarin ring and appropriate amino acid residues, which played a key role in enhancing its potency against both enzymes.
