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.
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.
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 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.
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.
Anti-Inflammatory Effect of Novel 7-Substituted Coumarin Derivatives through Inhibition of NF-κB Signaling Pathway
Mu, Chaoyu,Wu, Mingfei,Li, Zeng
, (2019)
A series of novel 7-substituted coumarin derivatives were synthesized and evaluated. Biological screening results obtained by the evaluation of the compounds’ inhibition against LPS-induced IL-6 and TNF-α release in RAW 264.7 cells indicated that most compounds exhibited potent anti-inflammatory activity. Among them, N-(3-methoxybenzyl)-2-[(2-oxo-2H-chromen-7-yl)oxy]acetamide (2d) showed the best activity. The potential targets of title compound 2d were reversely screened with the molecular modeling software, Discovery Studio 2017 R2. Screening and molecule docking results showed that 2d could bind to the active site (NLS Polypeptide) of NF-κB p65, and this binding affinity was confirmed by surface plasmon resonance (SPR) analysis. Furthermore, Western blot assay showed that 2d remarkably blocked the NF-κB signaling pathway in vitro. Collectively, all these findings suggested that compound 2d might be a promising lead compound worthy of further pursuit.
Synthesis and Biological Evaluation of Substituted Indole and Its Analogs as Influenza A Virus Inhibitors
Zhang, Xuandi,Zhang, Guo-Ning,Wang, Yujia,Zhu, Mei,Wang, Juxian,Li, Ziqiang,Li, Donghui,Cen, Shan,Wang, Yucheng
, (2019/02/07)
Influenza A virus (IAV), a highly pathogenic virus to human beings, is most susceptible to mutation and thus causes rapid, severe global pandemics resulting in millions of fatalities worldwide. Since resistance to the existing anti-influenza drugs is developing, innovative inhibitors with a different mode of action are urgently needed. The lead compound 6092B-E5 has proven to be an effective antiviral reagent in our previous work. Using the principles of substitution and bioisosterism of the indole ring, six series of novel anti-IAV target products were designed, synthesized and evaluated for their antiviral effect in this work. Compounds D1, D3, D9, G1, G3, G12 and G23 were identified as promising anti-IAV candidates with excellent anti-IAV efficacy (IC50 values of 3.06–5.77 μm) and low cytotoxicity (CC50 values up to and beyond 100 μm). This work represents a successful application of the substitution and bioisosteric replacement strategy for the discovery of novel antiviral molecules that can be used for further structural optimization.
