2725-81-7Relevant academic research and scientific papers
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.
Polyphosphoric acid-promoted synthesis of coumarins lacking substituents at positions 3 and 4
Yang, Li-Shou,Wang, Yu,Wang, En-Hua,Yang, Jan,Pan, Xiong,Liao, Xiu,Yang, Xiao-Sheng
supporting information, p. 1 - 6 (2020/07/25)
Coumarins have recently emerged as a hot topic of research due to their diverse pharmacological properties. This work described a method for the synthesis of 3,4-diunsubstituted coumarins promoted by polyphosphoric acid (PPA) from salicylaldehydes and acetic anhydride. Various coumarins were produced in good to excellent yields.
Synthesis method of coumarin derivatives
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Paragraph 0039-0041, (2020/09/23)
The invention provides a synthesis method of coumarin derivatives. The synthesis method comprises the following steps: adding polyphosphoric acid PPA and a solvent N,N-dimethylformamide DMF, sequentially adding substituted salicylaldehyde and acetic anhydride, and carrying out a heating stirring reaction for 3-6 h under nitrogen protection; and after the reaction is finished, separating and purifying to obtain the coumarin derivative pure products. The synthesis method disclosed by the invention is disclosed for the first time, is short in reaction time, simple to operate, low in catalyst usage amount, cheap, easy to obtain and relatively good in derivative yield, not only provides a new method for synthesizing coumarin derivatives, but also provides more possibilities for large-scale production of products and improvement of production efficiency.
Design, synthesis and agricultural evaluation of derivatives of N-Acyl-N-(m-fluoro-benzyl)-6-amino-coumarin
Ding, Yin-hao,Dong, Jing-jing,Feng, Bai-cheng,Hao, Shuang-hong,Jin, Yan,Wei, Yan
supporting information, (2020/08/19)
ABTRACT: This study aims to design and synthesize a series of N-Acyl-N-(m-fluoro- benzyl)-6- amino-coumarins through the principle of active substructure stitching, which are based on the core structure of N-(m-fluoro-benzyl)-6-amino-coumarin. The structures of target compounds e1–e25 have been characterized by 1H NMR, 13C NMR, ESI-MS and elemental analysis. Meanwhile, their agricultural activity have been evaluated in two weeds (Amaranth and Crabgrass) and four widespread noxious pathogens (V.mali, B.cinerea, F.axysporium and C.bacteria). The herbicidal activity results showed that almost all synthetic molecules have a greater impact on the stem system than on the root. Excellent inhibition rates were discovered from compounds e2–e5 and e20–e23 against Amaranth on stems, which were above 58percent(20 mg/L), 68percent(100 mg/L) respectively. Compounds e2 and e21 also exhibited striking inhibition on stems growth of both weeds. Anti-pathogenic activity showed that all the compounds exerted a better inhibitory activity on B.cinerea at 20 ppm compared to control carbendazim. All the heterocyclic substituted compounds (e17–e24, >57percent) made a better influence than the control (54.1percent) at the100 ppm. This research provides promising herbicidal and anti-pathogenic agents that have the better effects and can be potential for further development.
New copper(I) complex with a coumarin as ligand with antibacterial activity against flavobacterium psychrophilum
Aldabaldetrecu, Maialen,Parra, Mick,Soto, Sarita,Arce, Pablo,Tello, Mario,Guerrero, Juan,Modak, Brenda
, (2020/09/04)
A new copper (I) complex, [Cu(NN1)2](ClO4), was synthesized, where NN1 was a imine ligand 6-((quinolin-2-ylmethylene)amino)-2H-chromen-2-one obtained by a derivatization of natural compound coumarin. The structural characterization in solution was done by NMR techniques, UV-Vis and cyclic voltammetry. The potential antibacterial effect of [Cu(NN1)2](ClO4), was assessed for F. psychrophilum isolated 10094. F. psychrophilum is a Gram-negative bacterium which causes diseases such as bacterial cold-water disease and rainbow trout fry syndrome, causing large economic losses in the freshwater salmonid aquaculture industry. This complex show to have antibacterial activity against F. psychrophilum 10094 at non-cytotoxic concentration in cell line derived from trout (F. psychrophilum 10094 IC50 16.0 ± 0.9; RT-GUT IC50 53.0 ± 3.1 μg/mL).
A Dual Emissive Coumarin–urea Derivative with an Electron-withdrawing Substituent in the Presence of Acetate Anion
Shinoda, Tomoyuki,Nishimura, Yoshinobu,Arai, Tatsuo
, p. 21 - 27 (2019/11/11)
We investigated the fluorescent properties, including the excited-state intermolecular proton transfer, of urea derivatives comprising a coumarin ring, which is a widely used fluorophore. We prepared two different coumarin–urea derivatives, 6CU and 7CU, which bear a urea-based substituent at the 6 and 7 positions of a coumarin ring, respectively. In the presence of the acetate ion, 7CU showed additional tautomer fluorescence emission with respect to 6CU, indicating that tautomer formation depends on the positions of the urea-based substituent on the coumarin ring. Thus, the resonance structures of urea derivatives might play an important role in the behavior of dual fluorescence, which is an important phenomenon applicable to photochemical anion sensing. Moreover, in order to further improve the fluorescence properties of the mentioned derivatives, a CF3 group was introduced in a phenyl ring opposite to a coumarin ring. The fluorescence quantum yield of 7CUCF3 thus synthesized was 65 times as large as that of 7CU, an observation that renders 7CUCF3 a suitable anion sensor candidate. The results of this study will contribute to the development of new molecular designs for highly fluorescent sensing.
Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran-2-one Aromaticity-Mediated Regioselective Control and Biogenetic Implications
álvarez, José María,Jorge, Zacarías D.,Massanet, Guillermo M.
supporting information, (2020/03/05)
The synthetic feasibility of the oxidative cleavage: epoxidation of 7-O-geranylscopoletin followed by electrocyclic ring-opening, proposed in the biogenesis of transtaganolides/basiliolides is studied. Unlike the proposed pericyclic reactions, this pathway has not yet been addressed. Three synthetic strategies have been tested consisting of: i) Baeyer–Villiger oxidation of p-quinoids, ii) hydrolysis of quinone monoketals, or iii) direct fragmentation by using oxygen donors. Oxidation of the benzene ring of hydroxylated coumarins has been achieved using peroxyacids, but cleavage took place between undesired positions. The aromaticity conservation of the pyran-2-one cycle during oxidation is the controlling factor of these observed regioselectivities. The use of a 4,5-dihydroxy-2-methoxycinnamate model, in which the pyran-2-one ring does not exert influence on oxidation, has allowed the design of a synthetic sequence toward an analogue of the natural pyran-2-one isolated from Thapsia transtagana, key in the biogenesis. Mechanistic proposals for the obtained results as well as their biogenetic implications are raised.
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.
Coumarin compound and drug combination and preparation and application methods thereof
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Paragraph 0053; 0054; 0055, (2019/06/30)
The invention discloses a coumarin compound with BRD (bromodomain-containing protein 4) inhibiting effects. The coumarin compound comprises a compound with a structure shown as the formula (I) and medically acceptable salts thereof. The coumarin compound in a brand-new structure containing coumarin nucleuses can inhibit BRD4 to various degrees and accordingly can be applied to preparing BRD4 inhibitors or to preventing and treating BRD4 activity-related diseases, and due to a huge variety of the related diseases, can be extremely wide in application range. The invention also discloses a preparation method of the coumarin compound. The preparation method of the coumarin compound is rich in material resources, simple in operation, mild in condition, low in cost and highly applicable large-scale industrial production.
Discovery of novel coumarin derivatives as potent and orally bioavailable BRD4 inhibitors based on scaffold hopping
Zhang, Zhimin,Gu, Lili,Wang, Beibei,Huang, Wenhai,Zhang, Yanmin,Ma, Zhen,Zeng, Shenxin,Shen, Zhengrong
, p. 808 - 817 (2019/03/23)
The bromodomain and extra-terminal (BET) bromodomains, particularly BRD4, have been identified as promising therapeutic targets in the treatment of many human disorders such as cancer, inflammation, obesity, and cardiovascular disease. Recently, the discovery of novel BRD4 inhibitors has garnered substantial interest. Starting from scaffold hopping of the reported compound dihydroquinazolinone (PFI-1), a series of coumarin derivatives were designed and synthesised as a new chemotype of BRD4 inhibitors. Interestingly, the representative compounds 13 exhibited potent BRD4 binding affinity and cell proliferation inhibitory activity, and especially displayed a favourable PK profile with high oral bioavailability (F = 49.38%) and metabolic stability (T1/2 = 4.2 h), meaningfully making it as a promising lead compound for further drug development.
