13252-80-7Relevant articles and documents
Synthesis and biological evaluation of novel thiazolyl-coumarin derivatives as potent histone deacetylase inhibitors with antifibrotic activity
Pardo-Jiménez, Viviana,Navarrete-Encina, Patricio,Díaz-Araya, Guillermo
, (2019)
New histone deacetylases (HDAC) inhibitors with low toxicity to non-cancerous cells, are a prevalent issue at present because these enzymes are actively involved in fibrotic diseases. We designed and synthesized a novel series of thiazolyl-coumarins, substituted at position 6 (R = H, Br, OCH3), linked to classic zinc binding groups, such as hydroxamic and carboxylic acid moieties and alternative zinc binding groups such as disulfide and catechol. Their in vitro inhibitory activities against HDACs were evaluated. Disulfide and hydroxamic acid derivatives were the most potent ones. Assays with neonatal rat cardiac fibroblasts demonstrated low cytotoxic effects for all compounds. Regarding the parameters associated to cardiac fibrosis development, the compounds showed antiproliferative effects, and triggered a strong decrease on the expression levels of both α-SMA and procollagen I. In conclusion, the new thiazolyl-coumarin derivatives inhibit HDAC activity and decrease profibrotic effects on cardiac fibroblasts.
Improvement of fluorescence characteristics of coumarins: Syntheses and fluorescence properties of 6-methoxycoumarin and benzocoumarin derivatives as novel fluorophores emitting in the longer wavelength region and their application to analytical reagents
Murata, Chiyomi,Masuda, Toshinobu,Kamochi, Yasuko,Todoroki, Kenichiro,Yoshida, Hideyuki,Nohta, Hitoshi,Yamaguchi, Masatoshi,Takadate, Akira
, p. 750 - 758 (2005)
To improve the fluorescence characteristics, especially emission wavelength, of coumarins, various 3-substituted-6-methoxycoumarin derivatives were synthesized, and then benzocoumarin derivatives were also synthesized in expectation of the shift to the longer wavelength region by the extension of the conjugated system. Their fluorescence properties were investigated spectrophotometrically in acetonitrile and evaluated from the viewpoint of the intramolecular charge transfer (ICT) between push- and pull-substituents in the ground and the excited states. Among them, benzocoumarin derivatives especially fluoresced in the longer wavelength around 540 nm with remarkably large Stokes shifts beyond 10000 cm-1. Using such fluorophores, some novel fluorescence derivatization reagents for carboxylic acids, alcohols, phenols, and amines were preliminarily prepared as an example, and their derivatized products were also found to fluoresce in the longer wavelength region with large Stokes shifts.
Synthesis and in vitro antioxidant activity evaluation of 3-carboxycoumarin derivatives and qsar study of their dpph radical scavenging activity
Martinez-Martinez, Francisco J.,Razo-Hernandez, Rodrigo Said,Peraza-Campos, Ana Lilia,Villanueva-Garcia, Manuel,Sumaya-Martinez, Maria Teresa,Cano, Daniel Jaramillo,Gomez-Sandoval, Zeferino
, p. 14882 - 14898 (2012)
The in vitro antioxidant activities of eight 3-carboxycoumarin derivatives were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazil (DPPH) radical scavenging activity method. 3-Acetyl-6-hydroxy-2H-1-benzopyran-2-one (C1) and ethyl 6-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate (C2) presented the best radical-scavenging activity. A quantitative structure-activity relationship (QSAR) study was performed and correlated with the experimental DPPH scavenging data. We used structural, geometrical, topological and quantum-chemical descriptors selected with Genetic Algorithms in order to determine which of these parameters are responsible of the observed DPPH radical scavenging activity. We constructed a back propagation neural network with the hydrophilic factor (Hy) descriptor to generate an adequate architecture of neurons for the system description. The mathematical model showed a multiple determination coefficient of 0.9196 and a root mean squared error of 0.0851. Our results shows that the presence of hydroxyl groups on the ring structure of 3-carboxy-coumarins are correlated with the observed DPPH radical scavenging activity effects.
Amino-grafted SBA-15 material as dual acid-base catalyst for the synthesis of coumarin derivatives
Aider, Nadia,Smuszkiewicz, Agata,Pérez-Mayoral, Elena,Soriano, Elena,Martín-Aranda, Rosa M.,Halliche, Djamila,Menad, Saliha
, p. 215 - 222 (2014)
We report herein an experimental and theoretical study concerning the preparation of the coumarins (2) from 2-hydroxybenzaldehydes (3) and ethyl acetoacetate (4) promoted by amino-grafted SBA-15 materials. The reaction takes places by Knoevenagel condensation between reagents, in the absence of any solvent and under mild conditions, followed by a non catalytic lactonization step. Amino-grafted SBA-15 loaded with secondary amine groups, MAP/SBA-15, was found to be the most efficient and totally recyclable catalyst as compared with its analog containing tertiary amine groups, DEAP/SBA-15 (where MAP and DEA are methyl aminopropyl and diethyl aminopropyl groups, respectively). Our theoretical analysis confirms that the steric congestion and the absence of NH protons as the catalytic active sites are determining factors for the increasing of the activation barrier and, therefore, for the lower catalytic activity and reactivity to the formation of the coumarin. The computational study herein reported demonstrates that MAP/SBA-15, a traditional basic mesoporous silica having NH protons, shows a dual acid-base catalytic behavior when used in the synthesis of coumarins via Knoevenagel condensation. Otherwise, the substitution in 2-hydroxybenzaldehydes (3) at 5-position clearly influences the acceptor and acidity capacities of the CHO and the OH groups as experimentally and theoretically demonstrated.
Preparation and synthetic use of polymer-supported acetoacetate reagent
Hirai, Takeshi,Togo, Hideo
, p. 2664 - 2668 (2005)
Coumarin synthesis using polymer-supported acetoacetate reagent was carried out to produce various coumarin derivatives in excellent yield and purity with a facile work-up process. It was found that the polymer reagent could be recycled without any diminishment of the yield and purity. Georg Thieme Verlag Stuttgart.
USE OF SYNTHESIZED COMPOUNDS AS AN INHIBITOR OF EF2-KINASE ENZYME
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Page/Page column 5, (2021/08/27)
The invention is related to the use of synthesized compounds, as an inhibitor of the EF2-Kinase enzyme which is active in breast, pancreas, brain, ovarian, lung, skin (melanoma) and blood cancers. The aim of this invention is to make use of synthesized co
FLUORESCENT COMPOUNDS FOR IMAGING OF BLOOD VESSELS AND BLOOD FLOW, AND AN IN VIVO SCREEN FOR PRO- AND ANTI-ANGIOGENIC AGENTS
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Paragraph 0214; 0215, (2018/08/29)
The present invention discloses fluorescent compounds and a method for their use for selective imaging of blood vessels and blood flow. By applying these fluorescent compounds and the imaging process to a zebrafish model, the present invention further pro
