6093-72-7Relevant articles and documents
Synthesis, crystal structure, spectroscopic characterization and anti-fungal activity of Ethyl 2-Oxo-2H-chromene-3-carboxylateDerivatives
Gu, Jia,Nie, Xu-Liang,Peng, Da-Yong,Wang, Jie,Xiao, Pan-Lei,Zhong, Liang
, (2022/02/25)
Ethyl 2-oxo-2H-chromene-3-carboxylate derivatives were synthesized and characterized by FT-IR, NMR, MS and X-ray crystal diffraction. Compound 3d crystallizes in the triclinic system with space group P-1. Compound 3e crystallizes in the monoclinic system with space group P21/c. The potential anti-fungal activities have been studied against five kinds of common fungi at concentrations of 200 ppm and 500 ppm. The research showed that the target compounds exhibit certain anti-fungal activity against the tested fungal strains. The inhibition rate of compound 3b was the highest against Fusarium oxysporum, up to 60.29% at 500 ppm. Compound 3b is promising to become the lead compound of pesticide in the future, which is worthy of further study.
3 - Coumarin formic acid compound and application thereof as antibacterial agent for preparing plant pathogenic bacteria
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Paragraph 0036; 0042-0043, (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.
Synthesis, characterization and antioxidant activity studies of new coumarin tethered 1,3,4-oxadiazole analogues
Achutha, Dileep Kumar,Basappa, Vagish Channa,Kariyappa, Ajay Kumar,Penubolu, Sudeep
, (2021/06/01)
The present work describes the synthesis of a series of substituted 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones 7(a–j) using substituted aldehydes with analogues of hydrazine hydrates by grinding technique in the presence of Iodine which helps in the cyclization process. The structures of the synthesized compounds were elucidated by spectroscopic techniques such as IR, 1H NMR, 13C NMR, and LCMS. The comparative antioxidant property (using DPPH and hydroxyl radical scavenging) has been studied with the synthesized compounds 7(a-j) and the standards. Compounds 7d and 7i show the prominent radical scavenging activity. Graphic abstract: [Figure not available: see fulltext.] Synopsis: Series of ten new coumarin-oxadiazole hybrids synthesized in three steps starting from salicylaldehyde and diethylmalonate. All new compounds were spectroscopically characterized. The results of radical scavenging activities show that, two compounds of the series 7d and 7i displayed potent DPPH and hydroxyl radical activity comparable to the standards employed, and therefore acts as antioxidant leads.
Coumarin derivatives act as novel inhibitors of human dipeptidyl peptidase III: Combined in vitro and in silico study
?ubari?, Domagoj,Agi?, Dejan,Be?lo, Drago,Kara?i?, Zrinka,Karna?, Maja,Lisjak, Miroslav,Lon?ari?, Melita,Molnar, Maja,Popovi?, Boris M.,Rastija, Vesna,Tomi?, Sanja
, (2021/06/22)
Dipeptidyl peptidase III (DPP III), a zinc-dependent exopeptidase, is a member of the metalloproteinase family M49 with distribution detected in almost all forms of life. Although the physiological role of human DPP III (hDPP III) is not yet fully elucida
Design, synthesis and biological evaluation of coumarin-based N-hydroxycinnamamide derivatives as novel histone deacetylase inhibitors with anticancer activities
Cheng, Maojun,Ding, Jiaoli,Fang, Yuanying,Guan, Zhiyu,Guo, Jie,Jin, Yi,Liu, Jing,Wan, Yang,Wang, Rikang,Xie, Sai-Sai,Zhang, Zhipeng
, (2020/07/10)
A series of novel coumarin-based N-hydroxycinnamamide derivatives were designed and synthesized as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds showed potent HDAC inhibitory activity and significant antiproliferative activity a
Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity
Bai, Renren,Gu, Jinping,Guo, Jianan,Jiang, Xiaoying,Lv, Yangjing,Mi, Zhisheng,Shi, Yuan,Xie, Yuanyuan,Yao, Chuansheng,Zhang, Changjun,Zhou, Tao
, (2020/05/22)
A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe3+ values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-β1-42 (Aβ1-42) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.
Ros inhibitory activity and cytotoxicity evaluation of benzoyl, acetyl, alkyl ester, and sulfonate ester substituted coumarin derivatives
Salar, Uzma,Mohammed Khan, Khalid,Jabeen, Almas,Faheem, Aisha,Naqvi, Farwa,Ahmed, Shakil,Iqbal, Erum,Ali, Farman,Kanwal,Perveen, Shahnaz
, p. 1099 - 1111 (2020/11/09)
Background: A number of non-steroidal anti-inflammatory drugs (NSAIDs) including aspirin, indomethacin, ibuprofen, flufenamic acid, and phenylbutazone are being clinically used to treat inflammatory disorders. These NSAIDs are associated with serious side
Synthesis of coumarin analogs appended with quinoline and thiazole moiety and their apoptogenic role against murine ascitic carcinoma
Prashanth,Avin, B.R. Vijay,Thirusangu, Prabhu,Ranganatha, V. Lakshmi,Prabhakar,Sharath Chandra, J.N. Narendra,Khanum, Shaukath Ara
, (2019/02/28)
The synthesis and antiproliferative effect of a series of quinoline and thiazole containing coumarin analogs 12a-d and 13a-f respectively, on mice leukemic cells was performed. The chemical structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectral analysis. The result indicates that, 7-methoxy-2-oxo-2H-chromene-3-carboxylic acid [4-(4-methoxy-phenyl)-thiazol-2-yl]-amide (13f) showed potent activity against EAC and DLA cells in MTT (15.3 μM), tryphan blue (15.6 μM) and LDH (14.2 μM) leak assay with 5-fluorouracil as a standard. Further, the anti-neoplastic effect of the compound 13f was verified against Ehrlich ascites tumour by BrdU incorporation, TUNEL, FACS and DNA fragmentation assays. Experimental data showed that compound 13f induces the apoptotic cell death by activating apoptotic factors such as caspase-8 &-3, CAD, Cleaved PARP, γ-H2AX and by degrading genomic DNA of cancer cells and thereby decreasing the ascitic tumour development in mice. Besides, compound 13f was also subjected for docking studies to approve the in vitro and in vivo studies. The data revealed that the compound 13f has very good interaction with caspase 3 protein by binding with amino acid Arg 207 through hydrogen bond.
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 (2019/05/17)
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.
Antifungal activity, mode of action variability, and subcellular distribution of coumarin-based antifungal azoles
Elias, Rebecca,Benhamou, Raphael I.,Jaber, Qais Z.,Dorot, Orly,Zada, Sivan Louzoun,Oved,Pichinuk, Edward,Fridman
supporting information, p. 779 - 790 (2019/07/10)
Azole antifungals inhibit the biosynthesis of ergosterol, the fungal equivalent of cholesterol in mammalian cells. Here we report an investigation of the activity of coumarin-substituted azole antifungals. Screening against a panel of Candida pathogens, including a mutant lacking CYP51, the target of antifungal azoles, revealed that this enzyme is inhibited by triazole-based antifungals, whereas imidazole-based derivatives have more than one mode of action. The imidazole-bearing antifungals more effectively reduced trailing growth associated with persistence and/or recurrence of fungal infections than triazole-based derivatives. The imidazole derivatives were more toxic to mammalian cells and more potently inhibited the activity of CYP3A4, which is one of the main causes of azole toxicity. Using live cell imaging, we showed that regardless of the type of azole ring fluorescent 7-diethylaminocoumarin-based azoles localized to the endoplasmic reticulum, the organelle that harbors CYP51. This study suggests that the coumarin is a promising scaffold for development of novel azole-based antifungals that effectively localize to the fungal cell endoplasmic reticulum.
