126424-85-9Relevant articles and documents
Synthesis, antimicrobial and antioxidant activities of 5-((2-oxo-2H- chromen-7-yloxy)methyl)-1,3,4-thiadiazol-2(3H)-one derived from umbelliferone
Al-Amiery, Ahmed A.,Al-Temimi, Ali A.,Sulaiman, Ghassan M.,Aday, Hamdan A.,Kadhum, Abdul Amir Hassan,Mohamad, Abu Bakar
, p. 950 - 954 (2013)
5-((2-Oxo-2H-chromen-7-yloxy)methyl)-1,3,4-thiadiazol-2(3H)-one was synthesized and characterized by FT-IR and NMR spectra in addition to elemental analysis. The prepared compound shows considerable antibacterial and antifungal activity. The free radical scavenging activity of the synthesized compound was screened for in vitro antioxidant activity.
Coumarins as potential antioxidant agents complemented with suggested mechanisms and approved by molecular modeling studies
Al-Majedy, Yasameen K.,Al-Duhaidahawi, Dunya L.,Al-Azawi, Khalida F.,Al-Amiery, Ahmed A.,Kadhum, Abdul Amir H.,Mohamad, Abu Bakar
, (2016)
Syntheses of coumarins, which are a structurally interesting antioxidant activity, was done in this article. The modification of 7-hydroxycoumarin by different reaction steps was done to yield target compounds. Molecular structures were characterized by different spectroscopical techniques (Fourier transformation infrared and nuclear magnetic resonance). Antioxidant activities were performed by using various in vitro spectrophometric assays against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and hydrogen peroxide (H2O2). All compounds exhibited high efficiency as antioxidants compared to ascorbic acid. The highest efficiency scavenging activity was found for compound 3 (91.0 ± 5.0), followed by compounds 2 and 4 (88.0 ± 2.00; and 87.0 ± 3.00). Ascorbic acid C was used as a standard drug with a percentage inhibition of 91.00 ± 1.5. The mechanism of the synthesized compounds as antioxidants was also studied. Hartree-Fock-based quantum chemical studies have been carried out with the basis set to 3-21G, in order to obtain information about the three-dimensional (3D) geometries, electronic structure, molecular modeling, and electronic levels, namely HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital), to understand the antioxidant activity for the synthesized compounds.
Dual P-glycoprotein and CA XII inhibitors: A new strategy to reverse the P-gp Mediated Multidrug Resistance (MDR) in cancer cells y
Bartolucci, Gianluca,Braconi, Laura,Bua, Silvia,Coronnello, Marcella,Dei, Silvia,Lapucci, Andrea,Manetti, Dina,Romanelli, Maria Novella,Supuran, Claudiu T.,Teodori, Elisabetta
, (2020)
A new series of N,N-bis(alkanol)amine aryl diesters was synthesized and studied as dual P-glycoprotein (P-gp) and carbonic anhydrase XII inhibitors (CA XII). These hybrids should be able to synergistically overcome P-gp mediated multidrug resistance (MDR) in cancer cells. It was reported that the effux activity of P-gp could be modulated by CA XII, as the pH reduction caused by CA XII inhibition produces a significant decrease in P-gp ATPase activity. The new compounds reported here feature both P-gp and CA XII binding moieties. These hybrids contain a N,N-bis(alkanol)amine diester scaffold found in P-glycoprotein ligands and a coumarin or benzene sulfonamide moiety to target CA XII. Many compounds displayed a dual activity against P-gp and CA XII being active in the Rhd 123 uptake test on K562/DOX cells and in the hCA XII inhibition test. On LoVo/DOX cells, that overexpress both P-gp and CA XII, some coumarin derivatives showed a high MDR reversal effect in Rhd 123 uptake and doxorubicin cytotoxicity enhancement tests. In particular, compounds 7 and 8 showed higher activity than verapamil and were more potent on LoVo/DOX than on K562/DOX cells overexpressing only P-gp. They can be considered as valuable candidates for selective P-gp/CA XII inhibition in MDR cancer cells.
Combination of 7-hydroxycoumarin in a platinum(IV) complex derived from cisplatin enhanced cytotoxicity with multiple mechanisms of action
Hua, Wuyang,Zhao, Jian,Hu, Weiwei,Gou, Shaohua
, p. 17 - 23 (2018)
A novel compound, Cou-platin, composed of 7-hydroxycoumarin and a platinum(IV) moiety derived from cisplatin was designed and synthesized. Significantly, Cou-platin exhibited more potent in vitro antitumor activity against all tested cancer cell lines than that of cisplatin, which was mainly attributed to the liberation of cisplatin and 7-hydroxycoumarin upon reduction with a biomolecular agent. Besides, cellular accumulation of Cou-platin was dramatically increased among several cancer cells in contrast to cisplatin. Flow cytometry study revealed that Cou-platin arrested cell cycle at G2 phase and induced cell apoptosis. Western blots results indicated that it not only activated cell apoptosis pathway, but also inhibited extracellular regulated protein kinases/mitogen-activated protein kinase pathway. In vivo tests showed that Cou-platin, at equimolar dose to cisplatin, could inhibit tumor growth in nude mouse HCT116 tumor xenograft models almost as cisplatin and oxaliplatin, but with less toxicity.
A dual-mode molecular switch based on a chiral binaphthol-coumarin compound
Birau, Maria M.,Yuan Wang, Zhi
, p. 4025 - 4028 (2000)
A dual-mode, efficient molecular switching system based on photomodulation of optical rotational power and fluorescence emission of a chiral binaphthol-coumarin compound is presented. (C) 2000 Elsevier Science Ltd.
Novel 6- and 7-substituted coumarins with inhibitory action against lipoxygenase and tumor-associated carbonic anhydrase IX
Peperidou, Aikaterini,Bua, Silvia,Bozdag, Murat,Hadjipavlou-Litina, Dimitra,Supuran, Claudiu T.
, (2018)
A series of carboxamide derivatives of 6- and 7-substituted coumarins have been prepared by an original procedure starting from the corresponding 6- or 7-hydroxycoumarins which were alkylated with ethyl iodoacetate, and the obtained ester was converted to the corresponding carboxylic acids which were thereafter reacted with a series of aromatic/aliphatic/heterocyclic amines leading to the desired amides. The new derivatives were investigated as inhibitors of two enzymes, human carbonic anhydrases (hCAs) and soy bean lipoxygenase (LOX). Compounds 4a and 4b were potent LOX inhibitors, whereas many effective hCA IX inhibitors (KIs in the range of 30.2–30.5 nM) were detected in this study. Two compounds, 4b and 5b, showed the phenomenon of dual inhibition. Furthermore, these coumarins did not significantly inhibit the widespread cytosolic isoforms hCA I and II, whereas they were weak hCA IV inhibitors, making them hCA IX-selective inhibitors. As hCA IX and LOX are validated antitumor targets, these results are promising for the investigation of novel drug targets involved in tumorigenesis.
Novel silver(I) complexes of coumarin oxyacetate ligands and their phenanthroline adducts: Biological activity, structural and spectroscopic characterisation
Mujahid, Muhammad,Trendafilova, Natasha,Arfa-Kia, Agnieszka Foltyn,Rosair, Georgina,Kavanagh, Kevin,Devereux, Michael,Walsh, Maureen,McClean, Siobhán,Creaven, Bernadette S.,Georgieva, Ivelina
, p. 53 - 67 (2016)
Novel silver(I) complexes of coumarin oxyacetate ligands and their phenanthroline adducts have been prepared and characterised by microanalytical data and spectroscopic techniques (IR, 1H, 13C NMR, UV–Vis). The crystal structure of one Ag(I) complex was determined by X-ray diffraction analysis. The experimental spectroscopic data have been interpreted on the basis of molecular structure modeling and subsequent spectra simulation with density functional theory method. The binding modes of the coumarins and phenanthroline ligands (monodentate, bidentate, bridging) to Ag(I) have been theoretically modelled and discussed as to the most probable ligand binding in the series of complexes studied. The antimicrobial and antifungal activities have been determined and the complexes were found to have mostly moderate antibacterial activity but some of the phenanthroline adducts were found to have antifungal activity against the clinically important fungus C. albicans, comparable to that of the commercial agents, Amphotericin B and Ketoconazole. Preliminary investigations into the possible mechanism of action of the silver complexes indicated that they did not interact with DNA via nuclease activity or intercalation but the ability to act as a superoxide dismutase mimetic may be related to their antimicrobial activity.
Anticancer drug delivery of PEG based micelles with small lipophilic moieties
Lei, Ying,Lai, Yusi,Li, Yuanlin,Li, Sai,Cheng, Gang,Li, Dong,Li, Haiping,He, Bin,Gu, Zhongwei
, p. 579 - 586 (2013)
Herein, we reported a new type of self-assembly micelles based on amphiphilic polymers of cinnamate and coumarin derivatives modified PEG for drug delivery applications. Lipophilic cinnamic acid (CIN) and 7-carboxyl methoxycoumarin (COU) were immobilized on the terminal groups of poly(ethylene glycol) (PEG) to prepare amphiphiles. The amphiphiles self-assembled into micelles. The amphiphiles and micelles were characterized by 1H NMR, FT-IR, DLS and TEM. Doxorubicin (DOX) was used as a model drug to investigate the lipophilic moieties effects on the drug release behaviors. The DOX loaded micelles were incubated with HepG2 liver cancer cells to study the in vitro anticancer activities. The results showed that DOX could be encapsulated in the micelles efficiently. The mean diameter of the drug loaded micelles was around 100 nm. Drug release profile revealed that the release rate of DOX loaded COU-PEG-COU micelles was significantly slower than that of CIN-PEG-CIN micelles. The DOX loaded micelles could be internalized in HepG2 cells. Both CLSM and flow cytometry results showed that the DOX loaded CIN-PEG-CIN micelles exhibited better anticancer efficacy. Crown Copyright
A new convenient route to 2-oxoethoxycoumarins: Key intermediates in the synthesis of natural products
Chimichi, Stefano,Boccalini, Marco,Cosimelli, Barbara
, p. 4851 - 4858 (2002)
A new synthetic route to coumarinyloxyaldehydes starting from hydroxycoumarins is presented; these compounds, useful intermediates in the preparation of natural products such as geiparvarin and psoralens, are now available in excellent yields with a simple workup procedure. Moreover the reported route has been applied to dihydroxycoumarins.
Construction of Dual Stimuli-Responsive Platinum(IV) Hybrids with NQO1 Targeting Ability and Overcoming Cisplatin Resistance
Fang, Lei,Qin, Xiaodong,Zhao, Jian,Gou, Shaohua
, p. 2191 - 2200 (2019)
Quinone oxidoreductase isozyme I (NQO1) is a cytoprotective two-electron-specific reductase that highly expresses in various cancer cells. Taking NQO1 as the target, we herein report three hybrid compounds from Pt(IV) complexes and a quinone propionic aci
