531-81-7Relevant articles and documents
Coumarin-Fused Coumarin: Antioxidant Story from N, N -Dimethylamino and Hydroxyl Groups
Xi, Gao-Lei,Liu, Zai-Qun
, p. 3516 - 3523 (2015)
Two coumarin skeletons can form chromeno[3,4-c]chromene-6,7-dione by sharing with the C=C in lactone. The aim of the present work was to explore the antioxidant effectiveness of the coumarin-fused coumarin via six synthetic compounds containing hydroxyl and N,N-dimethylamino as the functional groups. The abilities to quench 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+?), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical revealed that the rate constant for scavenging radicals was related to the amount of hydroxyl group in the scaffold of coumarin-fused coumarin. But coumarin-fused coumarin was able to inhibit DNA oxidations caused by ?OH, Cu2+/glutathione (GSH), and 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH) even in the absence of hydroxyl group. In particular, a hydroxyl and an N,N-dimethylamino group locating at different benzene rings increased the inhibitory effect of coumarin-fused coumarin on AAPH-induced oxidation of DNA about 3 times higher than a single hydroxyl group, whereas N,N-dimethylamino-substituted coumarin-fused coumarin possessed high activity toward ?OH-induced oxidation of DNA without the hydroxyl group contained. Therefore, the hydroxyl group together with N,N-dimethylamino group may be a novel combination for the design of coumarin-fused heterocyclic antioxidants.
Synthesis of coumarin based Knoevenagel-Ugi adducts by a sequential one pot five-component reaction and their biological evaluation as anti-bacterial agents
Kumar, Sitanshu,Mukesh, Kapil,Harjai, Kusum,Singh, Vasundhara
, p. 8 - 12 (2019)
An efficient multicomponent synthesis of Ugi compounds comprising coumarin backbone has been achieved by employing one pot five component sequential Knoevenagel-Ugi reaction. This method offers the advantages of easy handling procedure, atom economy, mild reaction conditions and good yields of products. A molecular library was synthesized by changing the substituents on two of the independent starting materials. The synthesized compounds were also tested for anti-microbial activities and were found to be moderate to good anti-bacterial agents.
Blue fluorescence from pyridinyl coumarincarboxymides structure having high quantum yield in solution
Cui, Yanhong,Li, Yujin,Tang, Xue,Xue, Shuai,Yu, Zihua,Zhou, Zichun
, (2021/08/24)
Small molecules having fluorescence quantum yields are required to promote biological and organic material applications. In this work, we introduced a series of pyridinyl coumarincarboxymides derivatives, namely 4-XP. These compounds exhibited intense blue fluorescence with high fluorescence quantum yield. By spectral measurement and analysis, it is identified that these pyridine-coumarin conjugates displayed high fluorescence quantum yields (ΦF = 0.77–0.82) blue fluorescence at about 455 nm in nonpolar solvents. Additionally, the solvent effect and fluorescence properties were verified and explained by DFT and TD-DFT calculations.
Synthesis of xanthene and coumarin derivatives in water by using β-Cyclodextrin
Kamat, Siddharth R.,Mane, Ananda H.,Patil, Audumbar D.,Lohar, Trushant R.,Salunkhe, Rajashri S.
, p. 911 - 924 (2020/11/09)
Simple and green procedure was developed for the synthesis of various xanthene and coumarin derivatives using beta-cyclodextrin (β-CD) as reusable catalyst at 70?°C in water. Condensation of salicylaldehyde (1?mmol) and dimedone (2?mmol) or 1,3 cyclohexadione (2?mmol) gave corresponding xanthene derivatives, while condensation of salicylaldehyde (1?mmol) with Meldrum’s acid (1?mmol) or 4-Hydroxy-6-methyl-2H-pyran-2-one (1?mmol) gave respective coumarin derivatives in impressive yields. Involvement of β-CD as catalyst was ascertained by inclusion complex evaluation of β-CD-salicylaldehyde with 1H NMR analysis at 70?°C. Graphic abstract: [Figure not available: see fulltext.].
Method for synthesizing coumarin-3-carboxylic acid compounds by one-pot two-step method
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Paragraph 0053; 0056; 0058; 0061; 0079; 0084-0089, (2021/06/12)
The invention relates to a method for synthesizing coumarin-3-carboxylic acid compounds by a one-pot two-step method. The structural formula of the coumarin-3-carboxylic acid compounds is shown in the description, wherein R1 is H , Cl , Br, NO2 , CH3 and HO . According to the synthesis process of the coumarin-3-carboxylic acid compounds, malonic acid, acetone and substituted salicylaldehyde serve as raw materials, iodine serves as a catalyst, acetic anhydride serves as a solvent, a series of coumarin-3-carboxylic acid compounds are synthesized through a one-pot cascade reaction, and the efficiency and the yield are greatly improved compared with a fractional step method.