4115-76-8Relevant academic research and scientific papers
Design, synthesis and aggregation induced emission properties of two bichromophores with a triphenylamine-coumarin dyad structure
Yan, Han,Meng, Xinlei,Li, Baoyan,Ge, Shusheng,Lu, Yun
, p. 479 - 490 (2017)
On the basis of molecular design about the donor-acceptor (D-A) triphenylamine-coumarin (TPA-coumarin) dyad, two new bichromophores 7-butoxy-6-(4-(diphenylamino)phenyl)-4,8-dimethyl-2H-chromen-2-one (TC) and 7-butoxy-6-(4-(diphenylamino)phenyl)-8-methyl-4-(trifluoromethyl)-2H-chromen-2-one (TF), were synthesized and characterized by using IR, 1H NMR, 13C NMR and HRMS. Both TC and TF exhibited the expected solid-state fluorescence emission due to the aggregation induced emission effect and different degrees of positive solvatochromism due to their different molecular conformations in various solvents. Owing to the different push-pull electronic effects of substituents on the coumarin moiety, TC and TF, acting as the D-A compounds, showed different HOMO-LUMO gaps and a variable red-shifted emission in their solid-state, substantiating the possibility to effectively tune the photophysical properties of these bichromophores by rational molecular design.
Biotransformation of 4-methylcoumarins by cambial meristematic cells of Camptotheca acuminata
Zhang, Yuhua,Jiang, Jiayi,Qin, Ningbo,Zhang, Qian,Yan, Chunyan
, p. 9449 - 9456 (2019)
Cambial meristematic cell (CMC) suspension cultures were investigated as a new biotransformation system for the first time. Four 4-methylcoumarins substrates were transformed by CMCs of Camptotheca acuminata into four corresponding products, including 4,8-dimethylcoumarin-7-O-β-d-glucopyranoside (I-1), 4,7-dimethylcoumarin-6-O-β-d-glucopyranoside (II-1), 6-hydroxy-7-methoxyl-4- methylcoumarin (III-1), and 4,7-dimethylcoumarin-5-O-β-d-glucopyranoside (IV-1), of which I-1, II-1, and IV-1 were new compounds. In addition, the biotransformation time and the amount of substrate were investigated to compare the biotransformation rate and optimize the biotransformation conditions of the four substrates in C. acuminata CMCs suspension cultures. The results suggested C. acuminata CMCs were able to select glycosylate phenolic hydroxyl groups of 4-methylcoumarins I, II, and IV, with high regio- and stereoselectivity, but no corresponding glycoside of any phenolic hydroxyl group of compound III was detected. Simultaneously, the result also showed that the C. acuminata CMCs were able to transform the 7-hydroxy groups of substrate III to its corresponding methylated products. Furthermore, the monoamine oxidase (MAO) inhibition activities of biotransformed products were evaluated, and the data showed that all the products possessed good MAO inhibition activities in vitro. In conclusion, C. acuminata CMCs could be applied to glycosylation biotransformation as a novel plant-based system due to the successful application of bioconversion of exogenous coumarins.
Discovery of triaromatic flexible agents bearing 1,2,3-Triazole with selective and potent anti-breast cancer activity and CDK9 inhibition supported by molecular dynamics
Ahmed, Hany E. A.,Alawi, Ali,Aldhafiri, Ahmed J.,Aljuhani, Ateyatallah,Alsehli, Mosa,Aouad, Mohamed R.,Ihmaid, Saleh K.,Rezki, Nadjet,Salama, Samir A.
, (2021/10/05)
This study reports an efficient and convenient click synthesis of novel series of chromene scaffold linked to 1,2,3 triazole ring and terminal lipophilic fragments. Structures of all newly synthesized compounds were well characterized by IR, 1H NMR, 13C NMR and elemental analyses. In vitro MTT cytotoxic screening was performed using staurosporine as a reference drug against three different types: aggressive and invasive human breast cancer cell line (MDA-MB 231), Michigan cancer foundation-7 (MCF-7) and human colorectal carcinoma cell line (HCT116). These screening data showed considerable anticancer activity for these newly synthesized compounds compared to reference staurosporine drug with high degree of cell line selectivity and excellent activity with micromolar (μM) half maximal inhibitory concentration (IC50) values against tumor cells. In addition, Cyclin-Dependent Kinase1 and 9 (CDK1 and 9) assays were performed for the most active compounds to get more details about their mechanism of action. In order to assess and explain their binding affinities, molecular docking simulation was studied against CDK9 site. The results obtained from molecular docking study and those obtained from cytotoxic screening and enzyme inhibition were correlated. One of the most prominent analogs is 34 that showed high selective cytotoxicity profile against single breast cancer cell line MCF-7 and MDA-MB 231 with IC50 3.4 μM and 1.4 uM respectively. Molecular dynamics (MD) simulation of the CDK9 complex by Desmond revealed stability during 100 ns with RMSD of CDK9 complex converged at 2.1 ? after 20 ns. During MD, the interaction fractions confirmed multiple interactions of 34 with Cys106, a crucial residue for inhibition of CDK9 activity. A novel 34 triazole compound was introduced for drug design works as potent and selective hit for treatment of breast cancers after processing of optimization steps.
Preparation of a novel, efficient, and recyclable magnetic catalyst, Cu(II)-OHPC-Fe3O4 nanoparticles, and a solvent-free protocol for the synthesis of coumarin derivatives
Yuan, Jingjing,Mohammadnia, Majid
, p. 2327 - 2343 (2021/07/26)
Cu(II) supported on 5-oxo-4,5-dihydro-pyrrole-3-carboxylic acid functionalized Fe3O4 nanoparticles (Cu(II)-OHPC-Fe3O4) as a new magnetic nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA, XRD, VSM and EDX techniques. Prepared nanocatalyst (Cu(II)-OHPC-Fe3O4) is employed for Pechmann reactions between different substituted phenols and ethyl acetoacetate to obtain new products of coumarin derivatives in good to excellent yields. This green catalyst was easily removed, reused several times with no significant loss of its activity and provided clean synthesis with excellent yield and reduced time.
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.
N-Doped Carbon Wrapped Polyoxometalate Derived from POM-IL Hybrid: A Heterogeneous Catalyst for the Synthesis of Coumarin Derivatives under Solvent-Free Conditions
Ramalingam, Meenakshi,Mani, Chandhru,Manickam, Sundar,Srinivasalu, Kutti Rani
, p. 1904 - 1910 (2019/04/01)
Vanadium substituted Keggin type polyoxometalate loaded N-doped carbon was prepared from polyoxometalate ionic liquid hybrid by carbonization process. The decomposition of organic part generates various functional groups leaving polyoxometalate part intact. The catalyst was characterized by elemental analysis, FTIR, MAS 13C NMR, XPS and electron microscopy studies. The presence of carboxylic acids, aromatic and hetero-aromatic groups in the catalyst was confirmed by 13C NMR. The high resolution C1s and O1s XPS analysis further confirmed the presence of these groups. Various oxidation states of nitrogen were confirmed by deconvoluted N1s XPS spectra. Pyridine adsorption study confirms the presence of Bronsted and Lewis acid sites in the catalyst. Layered structure of the catalyst was confirmed by HR TEM analysis. The hybrid material displayed excellent catalytic activity towards the synthesis of coumarin derivatives under solvent-free conditions.
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.
Synthesis method of coumarin compounds
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Paragraph 0050; 0051; 0053, (2018/06/23)
The invention relates to a synthesis method of coumarin compounds. The method particularly comprises the following steps: performing reaction for 40 to 120 minutes by taking substituted phenol and beta-keto ester as substrates and DES as a catalyst under the condition of no solvents and at the temperature of 50 to 100 DEG C to prepare the coumarin compounds. In the preparation process of the coumarin compounds, other organic solvents do not need to be added and the DES serves as a reaction catalyst and solvent. The DES can be reused and is environment-friendly, and the catalytic effect basically maintains unchanged after the DES is recovered for four times. The preparation method provided by the invention is simple in process, high in catalytic activity and high in yield; and after reaction, treatment is simple, convenient and environment-friendly.
SnCl4 grafted on silica gel: an efficient catalyst for solvent-free synthesis of coumarins via the Pechmann condensation
Sun, Rui,Gao, Yanjuan,Ma, Ying,Yang, Guangde,Li, Yiping
, p. 737 - 742 (2017/01/17)
A facile synthesis of substituted coumarins via Pechmann condensation catalyzed by SnCl4 grafted on silica gel is described, which was conducted under solvent-free condition in high yields. The catalyst is noncorrosive and can be easily prepared and separated from the reaction mixture. This methodology offers some advantages with regard to yield of products, simplicity in operation and green aspects.
