14002-89-2Relevant articles and documents
Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells
Riveiro, Maria E.,Moglioni, Albertina,Vazquez, Ramiro,Gomez, Natalia,Facorro, Graciela,Piehl, Lidia,de Celis, Emilio Rubin,Shayo, Carina,Davio, Carlos
, p. 2665 - 2675 (2008)
In the present study, we sought to establish the effect of diverse structural-related hydroxycoumarins on the proliferation, cytotoxicity, and induction of apoptosis in promonocytic leukemic cells (U-937). The dihydroxylated coumarins, 7,8-dihydroxy-coumarin and esculetin, induced DNA fragmentation as well as characteristic morphological changes of programmed cell death in U-937 cells. With the aim to perform a structure-activity relationship study, the correlation between the physicochemical properties of the molecules and their pro-apoptotic activity was carried out. Results showed that the presence of two adjacent phenolic hydroxyl groups was the most important factor in terms of the SAR. The exposure of leukemic cells to 7,8-dihydroxy-coumarin evoked a phenoxyl radical generation that was detected by electron spin resonance spectroscopy. The present study suggests that reactive oxygen species generation plays a critical role in dihydroxycoumarin-induced apoptosis in U-937 cells. These findings further suggest that these compounds may have a potential therapeutic role in the treatment of hematological malignancies.
An environmentally friendly, chemoselective, and efficient protocol for the preparation of coumarin derivatives by Pechman condensation reaction using new and reusable heterogeneous Lewis acid catalyst polystyrene-supported GaCl 3
Rahmatpour, Ali,Mohammadian, Sara
, p. 271 - 278 (2013)
An environmentally benign Pechman protocol for the one-pot synthesis of 4-substituted coumarins through the condensation reactions of phenol substrates with β-ketoesters using polystyrene-supported GaCl3 (PS-GaCl3) as a highly active and reusable solid Lewis acid catalyst under mild and heterogeneous conditions in good to excellent yields is described. This new protocol is easy, simple, cost-effective, chemoselective, and in addition has the advantages of easy availability, stability, reusability and eco-friendly character of the catalyst, high to excellent yields, simple experimental and work-up procedure.
Preparation of a novel, efficient, and recyclable magnetic catalyst, γ-Fe2O3@HAp-Ag nanoparticles, and a solvent- and halogen-free protocol for the synthesis of coumarin derivatives
Abbasi, Zahra,Rezayati, Sobhan,Bagheri, Maryam,Hajinasiri, Rahimeh
, p. 75 - 82 (2017)
In this protocol, Ag supported on the hydroxyapatite-core–shell magnetic γ-Fe2O3nanoparticles (γ-Fe2O3@HAp-Ag NPs) as a novel, efficient, and magnetically recyclable catalyst is synthesized, and characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), and vibrating sample magnetometry (VSM). The use of the catalyst is described in the synthesis of coumarin derivatives by the Pechmann condensation of various phenols with β-ketoesters under solvent- and halogen-free conditions at 80?°C. This novel and inexpensive method offers advantages, such as recyclability simple experimental protocol, short reaction time, minimal work-up procedure, and excellent yields of products, together with desirable, eco-friendly, green aspects by avoiding toxic elements and solvents, and ease of recovery from the reaction mixture using an external magnet.
Tetrakis(acetonitrile)copper(I) hexafluorophosphate catalyzed coumarin synthesis via pechmann condensation under solvent-free condition
Soleimani, Ebrahim,Khodaei, Mohammad Mehdi,Batooie, Nasim,Samadi, Saadi
, p. 409 - 412 (2012)
Tetrakis(acetonitrile)copper(I) hexafluorophosphate (Cu(CH 3CN)4PF6) is used as an efficient catalyst in the Pechmann condensation reaction of phenols with ethyl acetoacetate leading to the formation of coumarin derivatives in excellent yields under solvent free conditions at ambient temperature. The method is simple, solvent-free and gives excellent yields in a short reaction time. Copyright
A solvent-free synthesis of coumarins using 1,3-disulfonic acid imidazolium hydrogen sulfate as a reusable and effective ionic liquid catalyst
Shirini, Farhad,Yahyazadeh, Asieh,Mohammadi, Kamal
, p. 6207 - 6218 (2015)
Abstract 1,3-Disulfonic acid imidazolium hydrogen sulfate has been used as an effective and reusable ionic liquid catalyst for the synthesis of coumarins from phenol derivatives with β-ketoesters via the Von Pechmann condensation under solvent-free conditions. This method consistently has the advantages of excellent yields, easy and quick isolation of the products, short reaction times, and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be recovered and reused for four times without loss of activity.
Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions
Gulías, Moisés,Marcos-Atanes, Daniel,Mascare?as, José L.,Font, Marc
supporting information, p. 1669 - 1673 (2019/09/04)
Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.
Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition
Samadizadeh, Marjaneh,Nouri, Saeed,Kiani Moghadam, Faeze
, p. 6089 - 6103 (2016/06/01)
This paper reports an efficient heterogeneous catalyst based on sulfonic acid functionalization of magnetic nanoparticles. This new catalyst was prepared using the reaction between magnetic nanoparticles and sodium 2-bromoethane-1-sulfonate. Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA) was found as efficient catalyst for the synthesis of coumarin derivatives using Pechmann condensation under mild condition. This reaction was catalyzed by MNESA under solvent-free condition at 90?°C, to give the corresponding products in excellent yields. The catalyst is easily separated from the reaction condition and can be reused for several times with consistence in the activity.
