2373-31-1Relevant academic research and scientific papers
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.]
N-Doped Carbon Wrapped Polyoxometalate Derived from POM-IL Hybrid: A Heterogeneous Catalyst for the Synthesis of Coumarin Derivatives under Solvent-Free Conditions
Ramalingam, Meenakshi,Mani, Chandhru,Manickam, Sundar,Srinivasalu, Kutti Rani
, p. 1904 - 1910 (2019)
Vanadium substituted Keggin type polyoxometalate loaded N-doped carbon was prepared from polyoxometalate ionic liquid hybrid by carbonization process. The decomposition of organic part generates various functional groups leaving polyoxometalate part intact. The catalyst was characterized by elemental analysis, FTIR, MAS 13C NMR, XPS and electron microscopy studies. The presence of carboxylic acids, aromatic and hetero-aromatic groups in the catalyst was confirmed by 13C NMR. The high resolution C1s and O1s XPS analysis further confirmed the presence of these groups. Various oxidation states of nitrogen were confirmed by deconvoluted N1s XPS spectra. Pyridine adsorption study confirms the presence of Bronsted and Lewis acid sites in the catalyst. Layered structure of the catalyst was confirmed by HR TEM analysis. The hybrid material displayed excellent catalytic activity towards the synthesis of coumarin derivatives under solvent-free conditions.
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 of 6- and 7-alkoxy-4-methylcoumarins from corresponding hydroxy coumarins and their conversion into 6- and 7-alkoxy-4-formylcoumarin derivatives
Ngoc Toan, Vu,Dinh Thanh, Nguyen
, p. 3603 - 3615 (2020)
Hydroxy derivatives of 4-methyl-2H-chromen-2-one were prepared from hydroquinone and resorcinol through their reaction with ethyl acetoacetate. These hydroxy coumarins were then converted into corresponding alkoxy derivatives by reaction with alkyl halides. The yields of 6- and 7-alkoxy-4-methylcoumarins 3a–i and 4a–i were 55?95%. Oxidation of these compounds by selenium dioxide under conventional and microwave-assisted heating conditions produced corresponding 4-formyl compounds 5b–h and 6b–h with yields of 40?67% and 90?93%, respectively. Several 6- and 7-alkoxy-4-methylcoumarins 3a–i, 4a–i and nearly all 6- and 7-alkoxy-4-formylcoumarins 5b–h, 6b–h are novel compounds.
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.
A Reusable Column Method Using Glycopolymer-Functionalized Resins for Capture–Detection of Proteins and Escherichia coli
Ajish, Juby K.,Abraham, Hephziba Maria,Subramanian, Mahesh,Kumar, K. S. Ajish
, (2020/12/21)
The use of glycopolymer-functionalized resins (Resin–Glc), as a solid support, in?column mode for bacterial/protein capture and quantification is explored. The Resin–Glc is synthesized?from commercially available chloromethylated polystyrene?resin and glycopolymer, and is characterized by fourier transform infrared spectroscopy, thermogravimetry, and elemental analysis. The percentage of glycopolymer functionalized on Resin–Glc is accounted to be 5 wt%. The ability of Resin–Glc to selectively capture lectin, Concanavalin A, over Peanut Agglutinin, reversibly, is demonstrated for six cycles of experiments. The bacterial sequestration study using SYBR (Synergy Brands, Inc.) Green I tagged?Escherichia coli/Staphylococcus aureus?reveals the ability of Resin–Glc to selectively capture?E. coli?over?S. aureus. The quantification of captured cells in the column is carried out by enzymatic colorimetric assay using methylumbelliferyl glucuronide?as the substrate. The?E. coli?capture studies reveal a consistent capture efficiency of 105?CFU (Colony Forming Units) g?1 over six cycles. Studies with spiked tap water samples show satisfactory results for?E. coli?cell densities ranging from 102 to 107?CFU mL?1. The method portrayed can serve as a basis for the development of a reusable solid support in capture and detection of proteins and bacteria.
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.
Recyclable cellulose nanocrystal supported Palladium nanoparticles as an efficient heterogeneous catalyst for the solvent-free synthesis of coumarin derivatives via von Pechmann condensation
Mirosanloo, Atieh,Zareyee, Daryoush,Khalilzadeh, Mohammad A.
, (2018/10/15)
2-Amino pyrimidine nanocellulose-supported Palladium nanoparticles (CNC-AMPD-Pd) as a novel bio supported nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA and EDX techniques. The nanocatalyst demonstrated outstanding performance in Pechmann condensation between different substituted phenols and ethyl acetoacetate to obtain coumarin derivatives in good to excellent yields. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst and solvent-free reaction conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup.
Cu (I) Catalyzed One Pot SN-Click Reactions of Halogenated Coumarins and 1-aza-coumarins
Revankar, Hrishikesh M.,Kulkarni, Manohar V.
, p. 537 - 544 (2018/01/10)
A one pot three component, copper catalyzed azide-alkyne cycloaddition reaction has been employed for the synthesis of bis-coumarinyl triazoles (A–D) using 4-chloro, 4-bromomethyl, 3-bromoacetyl and 4-bromomethyl-1-aza-coumarins (I–IV), sodium azide, and coumarin propargyl ethers (V–IX) in moderate yields.
Acetamide Derivatives of Chromen-2-ones as Potent Cholinesterase Inhibitors
Prasad, Suchita,Kumar, Bipul,Kumar, Shiv,Chand, Karam,Kamble, Shashank S.,Gautam, Hemant K.,Sharma, Sunil K.
, (2017/08/07)
Alzheimer's disease (AD), a neurodegenerative disorder, is a serious medical issue worldwide with drastic social consequences. Inhibition of cholinesterase is one of the rational and effective approaches to retard the symptoms of AD and, hence, consistent efforts are being made to develop efficient anti-cholinesterase agents. In pursuit of this, a series of 19 acetamide derivatives of chromen-2-ones were synthesized and evaluated for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory potential. All the synthesized compounds exhibited significant anti-AChE and anti-BChE activity, with IC50 values in the range of 0.24–10.19 μM and 0.64–30.08 μM, respectively, using donepezil hydrochloride as the standard. Out of 19 compounds screened, 3 compounds, viz. 22, 40, and 43, caused 50% inhibition of AChE at 0.24, 0.25, and 0.25 μM, respectively. A kinetic study revealed them to be mixed-type inhibitors, binding with both the CAS and PAS sites of AChE. The above-selected compounds were found to be effective inhibitors of AChE-induced and self-mediated Aβ1–42 aggregation. ADMET predictions demonstrated that these compounds may possess suitable blood–brain barrier (BBB) permeability. Hemolytic assay results revealed that these compounds did not lyse human RBCs up to a thousand times of their IC50 value. MTT assays performed for the shortlisted compounds showed them to be negligibly toxic after 24 h of treatment with the SH-SY5Y neuroblastoma cells. These results provide insights for further optimization of the scaffolds for designing the next generation of compounds as lead cholinesterase inhibitors.
