3949-36-8Relevant articles and documents
Two coumarin-based turn-on fluorescent probes based on for hypochlorous acid detection and imaging in living cells
Wang, Qingming,Jin, Lei,Wang, Wenling,Dai, Lihui,Tan, Xiaoxue,Zhao, Cong
, p. 239 - 245 (2019)
This work, two turn-on fluorescent probes (3-acetyl-2H-chromen-2-one (ACO) & (1E)-1-(1-(2-oxo-2H-chromen-3-yl)ethylidene)thiosemicarbazide (CETC)) based on coumarin have been designed and synthesized, which could selectively and sensitively recognize ClO? with fast response time. ACO & CETC were almost non fluorescent possibly due to both the lacton form of coumarin and unbridged C[dbnd]N bonds which can undergo a nonradiative decay process in the excited state. Upon the addition of ClO?, ACO & CETC were oxidized to ring - opened by cleavage the C–O and C[dbnd]N and the fluorescence intensity were increased considerably. Fluorescence titration experiments showed that the detection limit ACO & CETC is as low as 22 nm and 51 nm respectively. In particular, some relevant reactive species, including [rad]OH, 1O2, H2O2, KO2, some anions and cations cannot be interference with the test. In live cell experiments, ACO & CETC were successfully applied to image exogenous ClO? in HepG2 cells. Therefore, ACO & CETC not only could image ClO? in living cells but also proved that C–O and C[dbnd]N can be cleavage by ClO?.
Unexpected transformations of 3-(bromoacetyl)coumarin provides new evidence for the mechanism of thiol mediated dehalogenation of α-halocarbonyls
Magwenzi, Faith N.,Khanye, Setshaba D.,Veale, Clinton G.L.
, p. 968 - 972 (2017)
The mechanism for the thiol mediated dehalogenation of α-halogenated carbonyls has remained an unresolved problem, despite its ongoing application in synthetic organic chemistry. Nakamura and co-workers first proposed that net dehalogenation occurs via sequential nucleophilic substitutions, while Israel and co-workers concluded that the rate at which dehalogenation occurred suggested that dehalogenation proceeds in a single concerted step. In this study, we investigated the debromination and nucleophilic substitution of 3-(bromoacetyl)coumarin with a variety of thiophenols, whose electron donating or withdrawing natures resulted in large variations in the degree of nucleophilic substitution and dehalogenation products, respectively. Results from these experiments, in addition to an unexpected formation of thioether containing dibenzo[b,d]pyran-6-ones from a Robinson annulation, has provided new evidence for this disputed mechanism.
Design, synthesis and computational studies involving Indole-Coumarin hybrids as galectin-1 inhibitors
Sethi, Aaftaab,Sasikala,Jakkula, Pranay,Gadde, Divya,Sanam, Swetha,Qureshi, Insaf A.,Talla, Venu,Alvala, Mallika
, p. 2791 - 2805 (2021)
In continuation of our quest to develop non-carbohydrate galectin-1 inhibitors, we have designed and synthesized 20 indole-coumarin hybrids linked via chalcone. Compounds 6i and 7e were found to decrease galectin-1 levels significantly in galectin-1 enzyme assay at 20?μM concentration. Binding affinity studies carried out by fluorescence spectroscopy revealed that 6i binds to galectin-1 with a binding constant (Ka) value of 5.4 × 105?M?1 while 7e was found to have a slightly higher affinity than 6i with Ka of 6.6 × 105?M?1. Molecular docking was carried out to ascertain the interaction between ligand and protein. To further gain structural insights into the binding of the compounds, 30?ns molecular dynamic simulations were carried out. The studies revealed that compound 7e was stable within the subsite C of galectin carbohydrate recognition domain while 6i fluctuated throughout the simulation. In addition, 7e maintained continuous interaction with Trp68 and His52, the two key amino acid residues are responsible for recognition of ligands within the active site. Furthermore, 7e displayed H-bond interactions with highly conserved amino acids within galectin-1 CRD, i.e., Arg48, Asn61 and Glu71. Free energy of binding evaluated by MM-GBSA calculations was also in accordance with experimental data. 7e was calculated to have binding energy of ??53.40?kcal/mole while 6i was found to have a value of ??45.63?kcal/mole. Graphical abstract: [Figure not available: see fulltext.]
A self-assembled π-conjugated system as an anti-proliferative agent in prostate cancer cells and a probe for intra-cellular imaging
Lalitha, Krishnamoorthy,Jenifer, Preethi,Prasad, Y. Siva,Muthusamy, Kumarasamy,John, George,Nagarajan, Subbiah
, p. 48433 - 48437 (2014)
Multifunctional π-conjugated systems derived from renewable resource that self-assemble into supramolecular structures are reported. The aggregation of compounds in different solvents strongly influences their optical properties. These π-conjugated molecules can be used for live cell imaging applications. They also show low cytotoxicity in fibroblasts and suppress proliferation in PC3 prostate cancer cells.
An approach for continuous-flow processing of reactions that involve the in situ formation of organic products
Kelly, Christopher B.,Lee, Christopher,Leadbeater, Nicholas E.
, p. 263 - 265 (2011)
A simple adaptation allows batch protocols developed using microwave heating that involve formation of solid organic products to be scaled up using conventionally-heated flow chemistry with minimal or no re-optimization or modification. The product stream is intercepted with a flow of a suitable organic solvent upon exiting the heated zone, this solubilizing the product and allowing it to pass through the back-pressure regulator without aggregation of particulate material.
Vibrational assignments and electronic structure calculations for 3-acetylcoumarin
Ramoji, Anuradha,Yenagi, Jayashree,Tonannavar,Jadhav,Kulkarni
, p. 504 - 509 (2007)
Laser Raman (3500-50 cm-1) and IR (4000-400 cm-1) spectral measurements have been made on the laboratory prepared solid 3-acetylcoumarin. Molecular electronic energy, equilibrium geometrical structure and harmonic vibrational spectra have been computed at the RHF/6-31G(d,p) and B3LYP/6-31G(d,p) levels of theory. A complete vibrational assignment aided by the theoretical harmonic frequency analysis has been proposed. The B3LYP/6-31G(d,p) geometrical parameters, and frequencies of the C{double bond, long}O in the pyrone and acetyl group are in good agreement with experiment. The difference in the frequencies due to the two carbonyl groups, 50 cm-1, which is attributed to the conjugation effect, is accounted for by the B3LYP to be 56 cm-1.
Isonicotinoylhydrazide modified 3-acetylcoumarin scaffold as an efficient chemical reversible sensor to detect Al3+ selectively and its application in live cells imaging
Wang, Wenling,Jin, Lei,Kuang, Yang,Yuan, Zhongzhong,Wang, Qingming
, p. 2501 - 2511 (2019)
A turn-on photochromic sensor based on coumarin was designed and synthesized for selective and sensitive detection of Aluminium(III) (Al3+) in ethanol (C2H5OH)/water (H2O; 1:1, v/v) with the detection limit of 0.126 μM. The mechanism was proposed to form a kind of 1:1-type complex between probe C1 and Al3+ in which the binding constant was 3.11 × 107 M?1. In addition, the sensor was effectively used for the detection of Al3+ in living HEK293T cells.
Synthesis and characterization of some heteroaromatic derivatives of 3-but-2-enoyl-chromen-2-one and their potential as anti-inflammatory agents
Dixit, Priyanka,Tripathi, Avinash C.,Saraf, Shailendra K.
, p. 1431 - 1436 (2013)
A novel series of chromen-2-ones containing pyrazole, isoxazole, oxazine, and thiazine substitutions have been synthesized by reacting 3-[3-(4-chloro-phenyl)-acryloyl]-chromen-2-one and 3-[3-(3-methoxy-phenyl)- acryloyl]-chromen-2-one with various cyclizing agents such as hydrazine, phenylhydrazine, urea, and thiourea. The structures of all the synthesized compounds were confirmed by the use of IR, 1H-NMR, mass spectroscopy, and elemental analysis data. All the newly synthesized compounds were evaluated for their anti-inflammatory activity at a dose of 100 mg/kg body weight in carrageenan-induced rat paw edema model. The entire series of the compounds exhibited moderate to good anti-inflammatory activity, with the percentage inhibition of edema formation ranging from 39.99 to 63.15 against the reference drug ibuprofen (100 mg/kg) that showed 78.96% inhibition at the third hour. Compounds 3a, 3c, and 3d showed good inhibitory activity, whereas compounds 3b, 3e, 3f, and 3j showed moderate inhibitory activity at the third hour.
One-pot three-component protocol for the synthesis of indolyl-4H-chromene-3-carboxamides as antioxidant and antibacterial agents
Subbareddy, Chitreddy V.,Sumathi, Shanmugam
, p. 9388 - 9396 (2017)
A series of newly synthesized 4-(1H-indol-3-yl)-2-methyl-N-phenyl-4H-chromene-3-carboxamide derivatives were achieved by one-pot reaction between salicylaldehydes, substituted acetoacetanilides, and indoles in methanol catalyzed by 1,4-diazabicyclo [2.2.2]octane (DABCO) (30 mol%) at room temperature. These chromene systems were constructed through Knoevenagel condensation followed by a nucleophilic substitution process. The valuable features of this protocol such as short reaction time, simple operational procedure, broad substrate scope, and high yield of products make it an efficient and promising synthetic strategy. For the first time, various substituted 4H-chromene-3-carboxamide derivatives using DABCO as a catalyst are reported. The synthesized compounds (4a-p) were evaluated in antioxidant and antibacterial studies. The derivatives 4c, 4d, 4k, 4l, and 4p showed good antioxidant activity. Among all the derivatives 4k, 4l, and 4p were found to be active against bacterial strains with MIC values ranging from 9.3 to 18.75 μg mL-1.
Coumarin-naphthohydrazone ligand with a rare coordination mode to form Mn(II) and Co(II) 1-D coordination polymers: synthesis, characterization, and crystal structure
Bikas, Rahman,Farzaneh-Bonab, Hossein,Noshiranzadeh, Nader,Aygün, Muhittin,Emami, Marzieh,Lis, Tadeusz
, p. 1127 - 1146 (2018)
The hydrazone (E)-3-hydroxy-N’-(1-(2-oxo-2H-chromen-3-yl)ethylidene)-2-naphthohydrazide (H2L) was synthesized from the reaction of 3-acetylcoumarin and 3-hydroxy-2-naphthoic hydrazide in methanol. Compounds [Mn(H2L)(NO3)2(CH3OH)]?CH3OH (1a), [Mn(HL)(NO3)(CH3OH)]n (1b), [Co(HL)(NO3)(CH3OH)]n (2), and [Cu(HL)(NO3)] (3) were obtained by reaction of an equimolar amount of H2L with nitrate salts of Mn(II), Co(II), or Cu(II) in methanol. The reaction of ligand and Mn(NO3)2·4H2O was also carried out in the presence of sodium azide which led to the 1-D coordination polymer, [Mn(HL)(N3)(CH3OH)]n (4). All of the synthesized compounds were characterized by elemental analyses and spectroscopic methods. Single-crystal X-ray analysis of 1–4 indicated that H2L is neutral (in 1a) or mononegative ligand (in 1b, 2, 3 and 4). In 1b, 2 and 4 the 1-D polymeric chain is found by a rare coordination mode of this kind of hydrazone ligand since the naphtholic oxygen is coordinated to the neighboring metal ions while the NH moiety of hydrazone remains intact, also confirmed by FT-IR spectroscopic studies. The thermal stability of 2 and 4 were also studied from 30–1000?°C.
Efficient one-pot three-component method for the synthesis of highly fluorescent coumarin-containing 3,5-disubstituted-2,6-dicyanoaniline derivatives under microwave irradiation
Ayd?ner, Burcu,Yal??n, Ergin,Korkmaz, Vildan,Sefero?lu, Zeynel
, p. 2174 - 2188 (2017)
A simple and concise approach to the synthesis of coumarin-containing highly fluorescent asymmetric/symmetric 3,5-diaryl/heteroaryl-2,6-dicyanoaniline derivatives are reported. The compounds were synthesized through base catalyzed three-component one-pot synthesis reaction of 2-(1-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)ethylidene)malononitrile, aliphatic, aromatic/heteroaromatic aldehydes, and malononitrile in solvent-free reaction medium, catalyzed by piperidine under microwave irradiation method. The reaction gave the novel, highly fluorescent coumarin-containing 3,5-disubstituted-2,6-dicyanoaniline derivatives in good yields at 300 W, 80 °C in 2 min. This method provides several advantages; such as shorter reaction time, environmental friendliness, simple workup procedure, lower energy consumption and, generally, good yields with high purity. In addition, the synthesized compounds are fluorescently active dyes even in day light, except for compounds including nitro substituent, and show maximum absorption wavelengths (λabs.max) in the visible region in DMSO at room temperature. Thermal properties of all the synthesized compounds were also evaluated with thermal gravimetric analysis for usability as optic dye. Optical and thermal screening studies of the compounds showed that the dyes have excellent photophysical and thermal stability properties.
One-pot synthesis of novel (E)-3-(3,8a-dihydro-2H-oxazolo[3,2-a]pyridin-2-ylidene)chroman-2-one derivatives
Olyaei, Abolfazl,Feizy, Elaheh,Aghajanzadeh, Atiye
, p. 757 - 765 (2021/01/12)
An efficient synthetic procedure for the preparation of novel (E)-3-(3,8a-dihydro-2H-oxazolo[3,2-a]pyridin-2-ylidene)chroman-2-one derivatives was developed. A sequential one-pot, two-step tandem reaction starting from 3-(2-bromoacetyl)-2H-chromen-2-one derivatives synthesized, pyridine, and naphthols in the presence of triethylamine proceeded smoothly in acetonitrile under reflux conditions. In this process, 2-oxo-2H-chromen-3-yl)ethyl)pyridinium bromide derivatives as intermediate produced in situ, followed by Michael addition of naphthoxide anion and intramolecular cylization, resulted the corresponding products in good to high yields. All of the compounds were obtained in high purity without any use of more purification.
