14002-90-5Relevant articles and documents
Carbostyril derivatives: Synthesis of novel carbostyril-3′-carbonitrilselenophene hybrid compounds and investigation of their antiproliferative properties on prostate and breast cancer
Er?at?r, Mehmet,Y?ld?r?m, Metin,Giray, Elife Sultan
, p. 290 - 301 (2020/10/12)
To synthesize a new series of carbostyril-3′-carbonitrilselenophene hybrid compounds, Pechmann coumarin compounds were reacted with 2-amino-3′-carbonitrilselenophene derivatives and their anticancer activities on MCF7 and DU145 cell lines and antioxidant activities were investigated. Anticancer and antioxidant activities of the starting compounds and their corresponding new hybrid compounds were compared. It was determined that IC50 values of hybrid compounds (3e, 3f, 3g, and 3h) on the MCF7 breast cancer cell line showed the highest cytotoxic activity with 7.99, 3.64, 7.72, and 2.74 μM values, respectively. In the case of anticancer activity on the DU145 prostate cancer cell line, compounds 3f and 3h were found to have the highest cytotoxic activity with IC50 values of 4.21 and 3.90 μM, respectively. The compound 3g is also the most radical scavenging compound with an inhibition value of 88.78%.
Design, synthesis, and antifungal evaluation of novel coumarin-pyrrole hybrids
Zhang, Shuguang,Tan, Xin,Liang, Chaogen,Zhang, Weihua
, p. 450 - 458 (2020/11/30)
A series of coumarin derivatives bearing a pyrrole scaffold were designed, prepared, and assessed for their in vitro antifungal activities against six phytopathogenic fungi. The antifungal activity screening results suggest that some synthesized hybrids exhibited potential fungicidal activities against the tested fungi. In particular, compounds 6j, 6k, 6o, 6p, and 6r displayed significant antifungal effects against Rhizoctorzia solani, and possessed EC50 values of 3.94, 7.75, 6.38, 6.25, and 7.67 μg/ mL, respectively. The above activities are more potent than the commercialized fungicide Boscalid (11.52 μg/mL) and Osthole (9.79 μg/mL). These results provide a significant reference for further rational design of coumarin-based fungicides.
B(C6F5)3-catalyzed synthesis of coumarins via Pechmann condensation under solvent-free conditions
Prajapti, Santosh Kumar,Rao, S. Prakash
, p. 469 - 473 (2021/03/26)
Tris(pentafluorophenyl)borane [B(C6F5)3] catalyzed simple, efficient and environmentally benign protocol has been developed for the Pechmann condensation using variety of phenols and β-ketoesters under solvent-free conditions to afford coumarin derivatives. The present protocol displayed significant advantages such as low catalyst loading, short reaction time, mild reaction conditions, low toxicity, easy work-up, high yields, and compatibility with other functional groups. In addition, it is a convenient, clean, and fast alternative approach for synthesizing variety of coumarin derivatives. Moreover, the applicability of this method towards large-scale synthesis demonstrated its suitability for the industrial application. Graphic abstract: [Figure not available: see fulltext.]
Immobilized ionic liquid on the zeolite: its characterization and catalytic activity in the synthesis of coumarins via Pechmann reaction
Zendehdel, Mojgan,Khaghaninejad, Soheila,Tavakoli, Fatemeh,Ganji, Shiva
, p. 2555 - 2565 (2020/05/22)
In this work, in the first step, the 1-methyl-3-(3-trimethoxysilylpropyl) imidazolium chloride ([MTMSPIm]Cl) is immobilized on HY and NaY zeolites as an acidic catalyst. The synthesized catalysts were well characterized by different methods such as FTIR, TGA, XRD, BET, SEM, EDX and ICP. The characterizations of catalysts indeed show the ionic liquid supported on amine-functionalized zeolites. Also, the result shows the micro-/mesoporous structure for catalysts which have been emerged as an important class of catalytic materials. The micro-/mesocatalyst ([MTMSPIm]Cl@zeolite) was used as an acidic catalyst to synthesize coumarins via Pechmann reaction in solvent-free condition. The effect of different factors such as catalyst amount, solvent and time was investigated. Finally, catalyst can be easily separated and reused for the next reactions at least for five runs without any significant changes in yield and structure of the catalyst. Comparison of modified zeolite with [MTMSPIm]Cl shows higher yield and selectivity and mild condition related to other works.
Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun
supporting information, p. 1585 - 1591 (2019/08/07)
A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.
Recyclable cellulose nanocrystal supported Palladium nanoparticles as an efficient heterogeneous catalyst for the solvent-free synthesis of coumarin derivatives via von Pechmann condensation
Mirosanloo, Atieh,Zareyee, Daryoush,Khalilzadeh, Mohammad A.
, (2018/10/15)
2-Amino pyrimidine nanocellulose-supported Palladium nanoparticles (CNC-AMPD-Pd) as a novel bio supported nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA and EDX techniques. The nanocatalyst demonstrated outstanding performance in Pechmann condensation between different substituted phenols and ethyl acetoacetate to obtain coumarin derivatives in good to excellent yields. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst and solvent-free reaction conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup.
Anionic SO3H-functionalized ionic liquid: An efficient and recyclable catalyst for the Pechmann reaction of phenols with ethyl acetoacetate
Song, Dayong,Chen, Jing,Liang, Yong-Min
supporting information, p. 692 - 698 (2018/02/16)
This paper has reported an anionic SO3H-functionalized ionic liquid N-methylimidazolium sulfomethylsulfonate ([Hmim][HO3SCH2SO3]) for the synthesis of coumarins by Pechmann reaction. The [Hmim][HO3SCH2SO3] is easier to prepare by one-step neutralization reaction of N-methylimidazole with methanedisulfonic acid and show high catalytic performance for Pechmann reaction. Besides, the catalyst can simply be separated from the reaction mixture and recycled ten times without noticeable loss of activity.
Thymol, and preparation method and pharmaceutical composition thereof
-
Paragraph 0056; 0057; 0065; 0072; 0073; 0081; 0089, (2019/01/07)
The invention discloses thymol, and a preparation method and pharmaceutical composition thereof. The preparation method comprises the steps of: conducting a condensation reaction on m-cresol and ethylacetoacetate to obtain 4,7-dimethylcoumarin, performing hydrolysis decarboxylation on the 4,7-dimethylcoumarin under conditions of a strong alkali and high temperature to obtain an organic phase C containing 5-methyl-2-(prop-1-en-2-yl)phenol, and reducing the organic phase C to obtain thymol. The preparation method of thymol disclosed by the invention is mild in conditions, does not need specialreaction equipment, and facilitates industrial production. With the preparation method, position selectivity is high, almost no position isomer is generated, the separated product is high in purity, the total yield is high and the product quality accords with current drug declaration requirements.
A green and convenient approach for the one-pot solvent-free synthesis of coumarins and β-amino carbonyl compounds using Lewis acid grafted sulfonated carbon@titania composite
Kour, Manmeet,Paul, Satya
, p. 327 - 337 (2017/02/10)
Abstract: This paper reports an efficient protocol for the synthesis of coumarins via Pechmann reaction, and β-amino carbonyl compounds via aza-Michael reaction using catalytic amount of solid Lewis acid catalyst, C@TiO2–SO3–SbCl2. Six different catalysts were prepared by covalent immobilization of homogeneous Lewis acids onto sulfonated carbon@titania composite derived from amorphous carbon and nano-titania. Among various catalysts tested, C@TiO2–SO3–SbCl2 showed superior catalytic activity. The catalyst could be recycled without significant loss of its catalytic activity and demonstrated versatile catalysis for a wide range of substrates. Graphical abstract: [Figure not available: see fulltext.]
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 (2017/01/13)
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.
