1846-76-0Relevant articles and documents
Novel probes based on coumarin-bisdithiocarbamate system for selective recognition of Ag(I) in aqueous solution
Chen, Guo Feng,Liu, Lin,Wu, Jiu Li,Wu, Suo Juan,Chen, Bao Hua
, p. 1381 - 1395 (2018)
Two novel fluorescent probes (C1, C2), comprising a coumarin moiety as fluorophore and a pair of dithiocarbamates as recognition sites, were designed and synthesized as fluorescent probes for Ag+. The probes exhibited high selectivity for Ag+ with fluorescence enhancement (FE) in CH3CN/4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) (1:9, v/v, pH 7.38); the selectivity was not affected by other metal ions. The binding ratio of C2–Ag+ complex was determined to be 1:1 according to the Job plot and mass spectroscopy (MS) data. The association constant Ka of Ag+ with C2 was 1.6?×?104?M?1. These probes could be applied for monitoring of Ag+ in aqueous solution in the pH range of 5.0–8.0, with calculated detection limit of 0.27?μM.
An efficient one-pot synthesis of coumarin-amino acid derivatives as potential anti-inflammatory and antioxidant agents
Bodke, Yadav D.,Naik, Mamata Devendra,Revanasiddappa, B. C.,Vijay Kumar, M.
, (2020)
A series of seven coumarinyl-amino acid ester conjugates have been synthesized and characterized by NMR (1H and 13C) and mass spectra. Further, the compounds were investigated for their therapeutic applications such as anti-inflammatory and antioxidant activities. Among the synthesized compounds most of the analogs showed good efficiency compared with the standard.
One-pot microwave-assisted synthesis of benzopyrano[2,3-c]pyrazol-3-one derivatives
Chen, Pei,Li, Yan,Chen, Xinbing,An, Zhongwei,Xu, Yiwei,He, Xiaojun
, p. 1210 - 1214 (2014)
A convenient one-pot microwave-assisted synthesis of Benzopyrano[2,3-c] pyrazol-3-one derivatives was developed, where Knoevenagel condensation and hydrazinolysis reactions were continuously performed under microwave irradiation without separation and purification of the intermediates until the last cyclocondensation reaction except the substrates addition. The one-pot procedure exhibited shorter reaction times and higher yields (25-55%) of the objects than the conventional heating method.
A selective colorimetric and fluorescence chemosensing sensor for Cr3+ based on a rhodamine base derivative
Hosseini, Morteza,Khoobi, Mehdi,Tarasi, Roghayeh,Ganjali, Mohammad Reza
, p. 5031 - 5042 (2018)
A rhodamine-conjugated coumarin (L) was used in designing a selective fluorescence chemosensor for the determination of trace amounts of Cr3+ ions in acetonitrile–water (MeCN/H2O (90:10, %v/v) solutions. The intensity of the fluoresce emission of the chemosensor is intensified upon addition of Cr3+ ions in MeCN/H2O (90:10, %v/v) solutions, due to the formation of a selective 1:1 complex between L and Cr3+ ions. The fluorescence enhancement versus Cr3+ concentration has been found to be linear from 1.0 × 10?7 to 1.8 × 10?5 M and a detection limit of 7.5 × 10?8 M. The proposed fluorescent probe proved to be highly selective towards Cr3+ ions as compared to other common metal ions and could be successfully applied to the determination of Cr3+ concentrations in some water and wastewater samples.
P(RNCH2CH2)3N: An efficient promoter for the synthesis of 3-substituted coumarins
Kisanga, Philip,Fei, Xiangshu,Verkade, John
, p. 1135 - 1144 (2002)
The title compounds wherein R = Me or i-Pr function as efficient promoters for the formation of coumarins in good to excellent yields (80-95%) from salicylaldehydes and di-activated methylene compounds of the type R′CH2CO2Et (R′ = CO2Et, COMe, CN). Although the yields are not generally superior to those reported in the literature, our methodology is more convenient in that milder conditions and shorter reaction times are facilitated by the use of the aforementioned commercially available catalysts.
FRET-based Fluorescent and Colorimetric Probe for Selective Detection of Hg(II) and Cu(II) with Dual-mode
Luo, Xue,He, Xu-Dong,Zhao, Yuan-Chao,Chen, Chong,Chen, Biao,Wu, Zhi-Bing,Wang, Pei-Yi
, p. 2650 - 2655 (2017)
A dual-function fluorescence resonance energy transfer (FRET)-based fluorescent and colorimetric probe was rationally fabricated from an energy donor coumarin moiety and an energy acceptor rhodamine moiety linked by a thiohydrazide arm for selective detection of Hg2+ and Cu2+. Two distinct mechanisms were used for the selective detection. Results revealed that probe 1 showed high fluorescent selectivity towards Hg2+ and evident colorimetric selectivity for Cu2+, which was suitable for ‘naked-eye’ detection.
Green synthesis and characterization of 3-carboxycoumarin and ethylcoumarin-3-carboxylate via Knoevenagel condensation
Shafqat, Syed Salman,Khan, Amir Azam,Khan, Misbahul Ain,Salleh, Shanti Faridah,Jamaludin, Mohd Syahmi,Cem, Pang Suh
, p. 261 - 266 (2017)
Environmentally benign, simple, efficient and clean syntheses of 3-carboxycoumarins and ethyl coumarin-3-carboxylate have been synthesized via Knoevenagel condensation using green catalysts such as aqueous extract of Acacia concinna pods and amino acids. These syntheses were carried out in solvents as well as solvent-less media. The yields obtained (between 86 % to 96 %) for the reactions were equal or better than those previously reported. The products were isolated, purified and characterized through melting points, TLC, IR, GC Mass and 1H NMR spectroscopy. The characterized molecules showed structural and compositional conformity with the predicted reactions. The green route used for these reactions has shown to be efficient in reducing the time of reaction and in avoiding the toxic nature of the catalysts employed in classical reaction.
Synthesis, characterization, in vitro antimicrobial and DNA cleavage studies of Co(II), Ni(II) and Cu(II) complexes with ONOO donor coumarin Schiff bases
Patil, Sangamesh A.,Unki, Shrishila N.,Kulkarni, Ajaykumar D.,Naik, Vinod H.,Badami, Prema S.
, p. 330 - 338 (2011)
A series of Co(II), Ni(II) and Cu(II) complexes have been synthesized with Schiff bases derived from 2-hydroxy-1-naphthaldehyde and 2-oxo-2H-chromene-3- carbohydrazide/6-bromo-2-oxo-2H-chromene-3-carbohydrazide. The chelation of the complexes has been proposed in the light of analytical, spectral (IR, UV-Vis, 1H NMR, ESR, FAB-mass and fluorescence), magnetic and thermal studies. The measured molar conductance values indicate that, the complexes are non-electrolytic in nature. The redox behavior of the complexes was investigated with electrochemical method by using cyclic voltammetry. The Schiff bases and their metal complexes have been screened for their in vitro antibacterial (Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Salmonella typhi) and antifungal activities (Candida albicans, Cladosporium and Aspergillus niger) by MIC method. The DNA cleavage is studied by agarose gel electrophoresis method.
Biological evaluation of coumarin derivatives as mushroom tyrosinase inhibitors
Liu, Jinbing,Wu, Fengyan,Chen, Lingjuan,Zhao, Liangzhong,Zhao, Zibing,Wang, Min,Lei, Sulan
, p. 2872 - 2878 (2012)
A series of coumarin derivatives were synthesised and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesised compounds exhibited significant inhibitory activities. Especially, 2-(1-(coumarin-3-yl)ethylidene) hydrazinecarbothioamide bearing thiose-micarbazide group exhibited the most potent tyrosinase inhibitory activity with IC50 value of 3.44 μM. The inhibition mechanism analysis of 2-(1-(coumarin-3-yl)-ethylidene) hydrazinecarbothioamide and 2-(1-(6-chlorocoumarin-3-yl)ethylidene)- hydrazinecarbothioamide demonstrated that the inhibitory effects of the compounds on the tyrosinase were irreversible. Preliminary structure activity relationships' (SARs) analysis suggested that further development of such compounds might be of interest.
New green, recyclable magnetic nanoparticles supported amino acids as simple heterogeneous catalysts for knoevenagel condensation
Girija,Naik, H.S. Bhojya,Kumar, B. Vinay,Sudhamani,Harish
, p. 468 - 477 (2013)
Coumarin derivatives were synthesized using magnetically recoverable iron oxide nanoparticles supported amino acids as heterogeneous catalysts via one-pot multi component reaction using MW irradiation. Easy recovery of the catalyst using an external magne
Organic–inorganic hybrid material, dichloro N,N'-(1,2-phenylene)bis(2-aminobenzamide) cobalt(II)@Al-SBA-15: an environment friendly catalyst for the synthesis of 3-benzoxazol-2-yl-chromen-2-ones
Safaei Ghomi, Javad,Akbarzadeh, Zeinab,Bakhtiari, Atefeh
, p. 826 - 840 (2019)
A new organic-inorganic hybrid material, CoCl2N,N'-(1,2-phenylene)bis(2-aminobenzamide)@Al-SBA-15, was synthesized by modification of Al-SBA-15 with (3-chloropropyl) trimethoxysilane (CPTMS), then the ligand was covalently attached to CPTMS@Al-SBA-15 and finally addition of CoCl2 to form the complex. The mesoporous CoCl2NN'PhBIA@Al-SBA-15 was an efficient catalyst in the preparation of 3-benzoxazol-2-yl-chromen-2-one derivatives through reaction of different coumarin-3-carboxylates and 2-aminophenol derivatives. The nanocatalyst increased rate and facility of the aforementioned reaction and had influence in the green synthesis of different 3-benzoxazol-2-yl-2H-chromen-2-one derivatives. The nanocatalyst was characterized by N2 adsorption–desorption, Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), powder X-ray diffraction (XRD), and energy dispersive spectroscopy (EDS). Some advantages of this procedure are mild reaction condition, high yields of 3-benzoxazol-2-yl-2H-chromen-2-one, short reaction times, environmentally benign, recoverability of the catalyst and reusability without significant loss of its catalytic performance.
Synthesis and biological evaluation of novel coumarin derivatives as antiplatelet agents
Huang, Peng,Gao, Lei-Lei,Zhang, Zhuo,Liu, Jing-Ru,He, Li-Qin
, p. 511 - 520 (2016)
In order to develop anti-thrombotic agents with higher potency, a series of novel coumarin derivatives (5a-m) were designed, synthesized and biologically evaluated. Compound 5e displayed the strongest activity in inhibiting the adenosine diphosphate (ADP)-induced platelet aggregation in vitro, with 2.3-fold more effectiveness than clinically used antiplatelet drug aspirin (ASP). Thus, Compound 5e could deserve further investigations as antiplatelet agents.
A “turn-on” fluorescent probe based on V-shaped bis-coumarin for detection of hydrazine
Jiang, Xingzong,Shangguan, Mingqin,Lu, Zhen,Yi, Sili,Zeng, Xiaoyang,Zhang, Yongle,Hou, Linxi
, (2020)
Hydrazine (N2H4) has been classified as an environmental contaminant and human carcinogen owing to its high toxicity. Exposed to high concentration of hydrazine can cause irreversible damage to human bodies. Hence, it is significant to explore an effective analytical method to selectively recognize and detect it. In this work, an intramolecular charge transfer (ICT) based probe 1 was designed and synthesized by condensation of V-shaped bis-coumarin and 4-bromobutyric acid. The V-shaped bis-coumarin with π-expanded system endowed the probe 1 larger stokes shift and superior tolerance to photobleaching. This “turn-on” probe exhibited a high selectivity towards hydrazine over other common ions and amine-containing species with a distinct fluorescent enhancement at 555 nm. It could rapidly detect hydrazine over a wide pH range and the detection limit was as low as 4.2 ppb. The large shift of absorption spectrum enabled it to detect hydrazine in real water samples and gas-state hydrazine by “naked-eyes".
Facile construction of pH- and redox-responsive micelles from a biodegradable poly(β-hydroxyl amine) for drug delivery
Li, Dawei,Bu, Yazhong,Zhang, Lining,Wang, Xing,Yang, Yanyu,Zhuang, Yaping,Yang, Fei,Shen, Hong,Wu, Decheng
, p. 291 - 300 (2016)
Here we demonstrate a type of pH and reduction dual-sensitive biodegradable micelles, which were self-assembled by a cationic polymer in an aqueous solution. Due to tumor cells or tissues showing low pH and high reduction concentration, these micelles possessed specific tumor targetability and maximal drug-release controllability inside tumor cells upon changes in physical and chemical environments, but presented good stability at physiological conditions. CCK-8 assay showed that the DOX-loaded micelles had a similar cytotoxicity for MCF-7 tumor cells as free DOX, and blank micelles had a very low cytotoxicity to the cells. Fluorescent microscopy observation revealed that the drug-loaded micelles could be quickly internalized by endosomes to inhibit cancer cell growth. These results indicated these biodegradable micelles, as a novel and effective pH- and redox-responsive nanocarrier, have a potential to improve drug delivery and enhance the antitumor efficacy.
ZnO nanoparticle as catalyst for efficient green one-pot synthesis of coumarins through Knoevenagel condensation
Kumar, B Vinay,Naik, Halehatty S. Bhojya,Girija,Kumar, B Vijaya
, p. 615 - 621 (2011)
Green chemistry protocols with the reusability of the nano particle as catalyst in the synthesis of coumarins is described. The zinc oxide (ZnO) nanoparticles functions as highly effective catalyst for the reactions of various o-hydroxy benzaldehydes with 1,3-dicarbonyl compounds under microwave and thermal conditions to afford the corresponding coumarins in moderate to good yields. The catalyst is inexpensive, stable, can be easily recycled and reused for several cycles with consistent activity. Indian Academy of Sciences.
KPF6-Mediated Esterification and Amidation of Carboxylic Acids
Sonam, None,Shinde, Vikki N.,Kumar, Anil
, p. 2651 - 2661 (2022/02/07)
A novel KPF6-promoted green method has been developed for the synthesis of esters and amides. A wide range of carboxylic acids and alcohols or amines worked well under the developed reaction conditions, thus providing good to excellent (61-98%) yields of
3 - Coumarin formic acid compound and application thereof as antibacterial agent for preparing plant pathogenic bacteria
-
Paragraph 0036; 0041-0042, (2021/03/24)
The invention relates to a compound with simple structure for inhibiting growth activity of phytopathogens, specifically relates to a 3-coumarin formic acid compound and application of the 3-coumarin formic acid compound as an antibacterial agent for preparing the phytopathogens, and discloses application of the 3-coumarin formic acid compound as the antibacterial agent for preparing the phytopathogens. The two 3-coumarin formic acid compounds has the following characteristics of molecular structure: the formulas are as shown in the specification, wherein R is hydrogen, methyl, methoxyl, hydroxyl, halogen and nitryl. The in vitro inhibitory activity of twenty-eight synthetic target compounds on four common plant pathogenic fungi such as apple decay pathogenic bacteria, apple ring spot pathogenic bacteria, maize curvularia pathogenic bacteria and potato dry rot pathogenic bacteria is measured by adopting a hypha linear growth rate method, so that the condition that all compounds have different inhibiting effects on supplied experimental bacteria is found.
