- Coumarin-Fused Coumarin: Antioxidant Story from N, N -Dimethylamino and Hydroxyl Groups
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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.
- Xi, Gao-Lei,Liu, Zai-Qun
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- Synthesis and some transformations of functionally-substituted coumarins and 2-thioxo-2H-chromenes
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A synthesis has been developed for substituted coumarins and 2-thioxo-2H-chromenes and some of the chemical transformations of these compounds were studied. 1997 Plenum Publishing Corporation.
- Avetisyan,Aleksanyan,Alvandzhyan
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- Synthesis of coumarin based Knoevenagel-Ugi adducts by a sequential one pot five-component reaction and their biological evaluation as anti-bacterial agents
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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.
- Kumar, Sitanshu,Mukesh, Kapil,Harjai, Kusum,Singh, Vasundhara
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- Blue fluorescence from pyridinyl coumarincarboxymides structure having high quantum yield in solution
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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.
- Cui, Yanhong,Li, Yujin,Tang, Xue,Xue, Shuai,Yu, Zihua,Zhou, Zichun
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- Monoamine oxidase A and B inhibitory activities of 3,5-diphenyl-1,2,4-triazole substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives
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Monoamine oxidase (EC 1.4.3.4, MAO) is a flavin adenine dinucleotide-containing flavoenzyme located on the outer mitochondrial membrane and catalyzes the oxidative deamination of monoaminergic neurotransmitters and dietary amines. MAO exists in humans as two isoenzymes, hMAO-A and hMAO-B, which are distinguished by their tertiary structures, preferred substrates and inhibitors, and selective inhibition of these isoenzymes are used in the treatment of different diseases such as Alzheimer's, Parkinson's and depression. In the present study, we report the design, synthesis and characterization of 3,5-diphenyl-1,2,4-triazole substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives as novel and selective inhibitors of hMAO-B. Twenty one compounds (38, 39a-h, 41a-d, 42a-h) were screened for their inhibitory activity against hMAO-A and hMAO-B by using in vitro Amplex Red reagent based fluorometric method and all compounds were found to be as selective h-MAO-B inhibitors to a different degree. The compound 42e and 42h displayed the highest inhibitory activity against hMAO-B with IC50 values of 2.51 and 2.81 μM, respectively, and more than 25-fold selectivity towards inhibition of hMAO-B. A further kinetic evaluation of the most potent derivative (42e) was also performed and a mixed mode of inhibition of hMAO-B by the compound 42e was determined (Ki = 0,26 μM). According to our findings the [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole emerged as a promising scaffold for the development of novel and selective hMAO-B inhibitors.
- Bekircan, Olcay,Dan??, ?zkan,?ahin, Mehmet Eren,?etin, Mert
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- 3-carboxylic acid and formyl-derived coumarins as photoinitiators in photo-oxidation or photo-reduction processes for photopolymerization upon visible light: Photocomposite synthesis and 3d printing applications
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In this paper, nine organic compounds based on the coumarin scaffold and different substituents were synthesized and used as high-performance photoinitiators for free radical pho-topolymerization (FRP) of meth(acrylate) functions under visible light irradiation using LED at 405 nm. In fact, these compounds showed a very high initiation capacity and very good polymerization profiles (both high rate of polymerization (Rp) and final conversion (FC)) using two and three-component photoinitiating systems based on coum/iodonium salt (0.1%/1% w/w) and coum/iodonium salt/amine (0.1%/1%/1% w/w/w), respectively. To demonstrate the efficiency of the initiation of photopolymerization, several techniques were used to study the photophysical and photochemical properties of coumarins, such as: UV-visible absorption spectroscopy, steady-state photolysis, real-time FTIR, and cyclic voltammetry. On the other hand, these compounds were also tested in direct laser write experiments (3D printing). The synthesis of photocomposites based on glass fiber or carbon fiber using an LED conveyor at 385 nm (0.7 W/cm2 ) was also examined.
- Dumur, Frédéric,Gigmes, Didier,Graff, Bernadette,Hamieh, Tayssir,Lalevée, Jacques,Noirbent, Guillaume,Rahal, Mahmoud,Toufaily, Joumana
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- 3 - Coumarin formic acid compound and application thereof as antibacterial agent for preparing plant pathogenic bacteria
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The invention relates to a compound with simple structure for inhibiting growth activity of phytopathogens, specifically relates to a 3-coumarin formic acid compound and application of the 3-coumarin formic acid compound as an antibacterial agent for preparing the phytopathogens, and discloses application of the 3-coumarin formic acid compound as the antibacterial agent for preparing the phytopathogens. The two 3-coumarin formic acid compounds has the following characteristics of molecular structure: the formulas are as shown in the specification, wherein R is hydrogen, methyl, methoxyl, hydroxyl, halogen and nitryl. The in vitro inhibitory activity of twenty-eight synthetic target compounds on four common plant pathogenic fungi such as apple decay pathogenic bacteria, apple ring spot pathogenic bacteria, maize curvularia pathogenic bacteria and potato dry rot pathogenic bacteria is measured by adopting a hypha linear growth rate method, so that the condition that all compounds have different inhibiting effects on supplied experimental bacteria is found.
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Paragraph 0039; 0044-0045
(2021/03/24)
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- Mapping Chromone-3-Phenylcarboxamide Pharmacophore: Quid Est Veritas?
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Chromone-3-phenylcarboxamides (Crom-1 and Crom-2) were identified as potent, selective, and reversible inhibitors of human monoamine oxidase B (hMAO-B). Since they exhibit some absorption, distribution, metabolism, and excretion (ADME)-toxicity liabilities, new derivatives were synthesized to map the chemical structural features that compose the pharmacophore, a process vital for lead optimization. Structure-activity relationship data, supported by molecular docking studies, provided a rationale for the contribution of the heterocycle's rigidity, the carbonyl group, and the benzopyran heteroatom for hMAO-B inhibitory activity. From the study, N-(3-chlorophenyl)-4H-thiochromone-3-carboxamide (31) (hMAO-B IC50 = 1.52 ± 0.15 nM) emerged as a reversible tight binding inhibitor with an improved pharmacological profile. In in vitro ADME-toxicity studies, compound 31 showed a safe cytotoxicity profile in Caco-2, SH-SY5Y, HUVEC, HEK-293, and MCF-7 cells, did not present cardiotoxic effects, and did not affect P-gp transport activity. Compound 31 also protected SH-SY5Y cells from iron(III)-induced damage. Collectively, these studies highlighted compound 31 as the first-in-class and a suitable candidate for in vivo preclinical investigation.
- Mesiti, Francesco,Gaspar, Alexandra,Chavarria, Daniel,Maruca, Annalisa,Rocca, Roberta,Gil Martins, Eva,Barreiro, Sandra,Silva, Renata,Fernandes, Carlos,Gul, Sheraz,Keminer, Oliver,Alcaro, Stefano,Borges, Fernanda
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p. 11169 - 11182
(2021/08/03)
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- Synthesis of xanthene and coumarin derivatives in water by using β-Cyclodextrin
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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.].
- Kamat, Siddharth R.,Mane, Ananda H.,Patil, Audumbar D.,Lohar, Trushant R.,Salunkhe, Rajashri S.
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p. 911 - 924
(2020/11/09)
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- Synthesis and Luminescent Properties of Eu3+ and Tb3+ Complexes with Coumarin-3-carboxylic Acids
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Abstract: New Eu3+ and Tb3+ complex compounds [Ln(H2O)2L2]Cl?H2O were synthesized on the basis of coumarin-3-carboxylic acid and its derivatives. Composition and structure of the ligands an
- Gromak,Kolokolov,Dotsenko,Aksenov,Aksenova
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p. 685 - 692
(2021/06/02)
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- Method for synthesizing coumarin-3-carboxylic acid compounds by one-pot two-step method
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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.
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Paragraph 0053; 0056; 0058; 0061; 0079; 0084-0089
(2021/06/12)
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- Green synthesis method of coumarin-3-carboxylic acid compound
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The invention relates to a green synthesis method of a coumarin-3-carboxylic acid compound. The synthesis process of the coumarin-3-carboxylic acid compound is as follows: R1 is H, Cl, Br, NO2, CH3 and HO. A series of coumarin-3-carboxylic acid compounds are synthesized in one step without a catalyst by taking R1-substituted salicylaldehyde and Meldrum's acid as raw materials and water as a reaction medium, the process steps are simple, the method has universality, reaction liquid can be repeatedly added for reaction, no waste or waste liquid is generated, the yield of a target product is greater than 54.3%, and the method is an environment-friendly green synthesis method.
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Paragraph 0053-0061
(2021/06/26)
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- Synthesis and biological evaluation of some 1,3-benzoxazol-2(3H)-one hybrid molecules as potential antioxidant and urease inhibitors
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A new series of 1,3-benzoxazol-2(3H)-one hybrid compounds, including coumarin, isatin 1,3,4-triazole and 1,3,4-thiadiazole moieties, were synthesized and biologically evaluated for their antioxidant capacities and anti-urease properties. The synthesized benzoxazole-coumarin (6a–e) and benzoxazole-isatin (10a–c) hybrids showed remarkable urease inhibitory activities with IC50 (μM), ranging from 0.0306 ± 0.0030 to 0.0402 ± 0.0030, while IC50 of standard thiourea is 0.5027 ± 0.0293. The synthesized benzoxazole-triazole (8a–c) and benzoxazole-thiadiazole (9a–c) hybrids showed similar urease inhibitory activities with IC50 (μM), ranging from 0.3861 ± 0.0379 to 0.5126 ± 0.0345. The antioxidant activity of the synthesized compounds was evaluated for their antioxidant activities, such as reducing power and ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt) radical scavenging. The results of ABTS radical scavenging activities of some of the synthesized molecules showed higher activities than standard Trolox, SC50 (μM) = 213.04 ± 18.12. One benzoxazole-coumarin (6f), two benzoxazole-isothiocyanate (7b, 7c), and two benzoxazole-triazole (8b, 8c) derivatives showed higher activities (SC50 (μM) values, 82.07 ± 10.34, 120.19 ± 7.30, 104.58 ± 10.55, 153.26 ± 7.14, and 144.82 ± 10.68, respectively) than standard Trolox, (SC50 (μM) = 213.04 ± 18.12).
- Yilmaz, Fatih,Mente?e, Emre,S?kmen, Bahar Bilgin
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p. 260 - 269
(2020/10/21)
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- Synthesis and anticancer activities of some new coumarin derivatives including the triazole ring and their in silico molecular docking studies
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The synthesis, docking study, and investigation of the anticancer activities of some coumarin derivatives containing the triazole ring are reported in this study. The newly synthesized compounds were screened for their in vitro anticancer activity against the cell lines CRL5807 (human bronchioalveolar carcinoma), CRL5826 (human squamous cell carcinoma), MDA-MB231 (human breast cancer cells), HTB177 (human lung cancer), PC-3 (human prostate adenocarcinoma), PANC-1 (human pancreatic cancer cells), used as cancer cells, and CCD34Lu (normal human lung fibroblasts), used as a healthy cell line. Cytotoxicity effects of the samples were determined by the MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) assay. In silico studies were also performed to explore the binding interactions of the molecules.
- Mente?e, Emre,Güner, Adem,Polatl?, Elifsu,Emirik, Mustafa,Bekta?, Hakan,Kahveci, Bahittin
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- Synthesis, antitrypanosomal and antimycobacterial activities of coumarin n-acylhydrazonic derivatives
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Background: Near to 5-7 million people are infected with T. cruzi in the world, and about 10,000 people per year die of problems associated with this disease. Method: Herein, the synthesis, antitrypanosomal and antimycobacterial activities of seventeen coumarinic N-acylhydrazonic derivatives have been reported. Results: These compounds were synthesized using methodology with reactions global yields ranging from 46%-70%. T. cruzi in vitro effects were evaluated against trypomastigote and amastigote, forming M. tuberculosis activity towards H37Rv sensitive strain and resistant strains. Discussion: Against T. cruzi, the more active compounds revealed only moderate activity IC50 /96h~20 μM for both trypomastigotes and amastigotes intracellular forms. (E)-2-oxo-N'-(3,4,5-trimethoxybenzylidene)-2H-chromene-3-carbohydrazide showed meaningful activity in INH resistant/RIP resistant strain. Conclusion: These compound acting as multitarget could be good leads for the development of new trypanocidal and bactericidal agents.
- Capelini, Camila,Camara, Vitória R. F.,Villar, José D. Figueroa,Barbosa, Juliana M. C.,Salom?o, Kelly,de Castro, Solange L.,Sales Junior, Policarpo A.,Murta, Silvane M. F.,Couto, Thais B.,Louren?o, Maria Cristina S.,Wardell, James L.,Low, John N.,da Silva, Edson F.,Carvalho, Samir A.
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p. 630 - 637
(2021/04/02)
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- An efficient one-pot synthesis of coumarin-amino acid derivatives as potential anti-inflammatory and antioxidant agents
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A series of seven coumarinyl-amino acid ester conjugates have been synthesized and characterized by NMR (1H and 13C) and mass spectra. Further, the compounds were investigated for their therapeutic applications such as anti-inflammatory and antioxidant activities. Among the synthesized compounds most of the analogs showed good efficiency compared with the standard.
- Bodke, Yadav D.,Naik, Mamata Devendra,Revanasiddappa, B. C.,Vijay Kumar, M.
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supporting information
(2020/03/19)
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- Synthesis and antioxidant activity of conjugates of hydroxytyrosol and coumarin
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Antioxidants have been the subject of intense research interest due to their numerous health benefits. In this work, a series of new conjugates of hydroxytyrosol and coumarin were synthesized and evaluated for their free radical scavenging, toxicity and antioxidant mechanism in vitro. The all target compounds 14a–t exhibited better radical scavenging activity than BHT, hydroxytyrosol, and coumarin in both DPPH radical and ABTS+ radical cation scavenging assays. The structure-activity relationships study indicated that the number and position of hydroxyl groups on the coumarin ring were vital to a good antioxidant capacity. Furthermore, the most promising compound 14q showed less toxicity in hemolysis assay and weaker antiproliferative effects than BHT against normal WI-38 and GES cells, and enhanced viability of H2O2-induced HepG2 cells. Additionally, 14q decreased the apoptotic percentage of HepG2 cells, reduced the ROS produce and LDH release, and improved GSH and SOD levels in H2O2-treated HepG2 cells. Lastly, 14q exhibited more stability than hydroxytyrosol in methanol solution. These results revealed that conjugations of hydroxytyrosol and coumarin show better antioxidant capacity, and are the efficacious approach to finding novel potential antioxidant.
- Li, Wen-Bo,Qiao, Xue-Peng,Wang, Zi-Xiao,Wang, Shuai,Chen, Shi-Wu
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- Design, synthesis and in vitro evaluation of 2-oxo-n-substituted phenyl-2h-chromene-3-carboxamide derivatives as HIV integrase strand transfer inhibitors
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Background: A series of eighteen 2-Oxo-N-substituted phenyl-2H-chromene-3-carboxamide analogues has been evaluated for HIV-1 integrase (IN) inhibition. Methods: The derivatives were synthesized via a two-step pathway commencing with 2-hydroxybenzaldehyde and diethyl malonate followed by hydrolysis of ester and coupling with various aromatic amines. The HIV-1 IN inhibitory potential of these compounds has been studied relative to dolutegravir, a known HIV-1 IN inhibitor using a standard available kit. Results: Six molecules (compounds 13h, 13i, 13l, 13p to 13r) showed significant inhibition of HIV-1 integrase 3′-strand transfer with IC50 values less than 1.7 μM. The presence of chromene-3-carboxamide motif was shown to be crucial for the enzymatic activity. In addition, molecular modelling studies were also done to justify the IN inhibition and in vitro-in silico correlation was drawn. Conclusion: However, these compounds did not show HIV-1 and HIV-2 inhibition below their cytotoxic concentration indicating that these compounds cannot be taken further for anti-HIV activity as such and require structural modification.
- Jadhav, Hemant R.,Jain, Priti,Wadhwa, Pankaj
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p. 416 - 425
(2020/04/17)
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- Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity
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A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe3+ values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-β1-42 (Aβ1-42) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.
- Bai, Renren,Gu, Jinping,Guo, Jianan,Jiang, Xiaoying,Lv, Yangjing,Mi, Zhisheng,Shi, Yuan,Xie, Yuanyuan,Yao, Chuansheng,Zhang, Changjun,Zhou, Tao
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- Coumarin hybrid pyridinone amide derivative with potential anti-AD activity and preparation method and application of derivative
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The invention discloses a coumarin hybrid pyridinone amide derivative and a preparation method and application thereof. The coumarin hybrid pyridinone amide derivative and pharmacologically acceptablesalt thereof are shown in the formula (I) and the formula (II), and the derivative can be used for preparing drugs for resisting the Alzheimer's disease, the Parkinson's disease or treating other diseases or symptoms by suppressing monoamine oxidase, chelating metallic iron ions, resisting A and resisting oxidation.
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Paragraph 0062; 0066; 0067; 0073; 0077; 0078; 0085; 0091
(2020/02/27)
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- Novel coumarin-thiazolyl ester derivatives as potential DNA gyrase Inhibitors: Design, synthesis, and antibacterial activity
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The design and synthesis of novel coumarin-thiazolyl ester derivatives of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds were examined for their antibacterial activity against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella. Compound 8p exhibited excellent antibacterial activity against four bacteria strains with MIC values of 0.05, 0.05, 8, and 0.05 μg/mL, respectively. In vitro drug-resistant bacterial inhibition experiments indicated that compound 8p exhibited the best bacteriostatic effect in the selected compounds and four positive control drugs with MIC values of 4 μg/mL. In vitro enzyme inhibitory assay showed that compound 8p exhibited potent inhibition against DNA gyrase with IC50 values of 0.13 μM. The molecular docking model indicated that compounds 8p can bind well to the DNA gyrase by interacting with amino acid residues. This study demonstrated that the compound 8p can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the commercial DNA gyrase inhibiting bactericides.
- Cheng, Xiang,Chu, Zhi-Wen,Hu, Rui,Liu, Hao,Lv, Xian-Hai,Xia, Dong-Guo
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- A Primary Amide-Functionalized Heterogeneous Catalyst for the Synthesis of Coumarin-3-carboxylic Acids via a Tandem Reaction
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A crystalline primary amide-based bifunctional heterogeneous catalyst, {[Cd2(2-BPXG)(Fum)2(H2O)2]·2H2O}n (1) (where, 2-BPXG = 2,2′-((1,4-phenylenebis(methylene))bis((pyridin-2-ylmethyl)azanediyl)) diacetamide and Fum = fumarate), has been developed for the one-pot synthesis of a series of potentially biologically active coumarin-3-carboxylic acids at room temperature via a Knoevenagel-intramolecular cyclization tandem reaction. Catalyst 1 is prepared at room temperature from a one-pot self-assembly process in 81% yield and high purity within a few hours and has a ladder-like polymeric architecture based on single-crystal X-ray diffraction. Additional characterization of 1 includes elemental analysis, infrared spectroscopy, thermogravimetric analysis, and powder X-ray diffraction. Based on the optimized conditions, it is determined that 1 is highly efficient (conditions: 2 mol % catalyst, 3 h, and 26-28 °C in methanol) for this reaction. Its recyclability up to five cycles without significant loss of activity and structural integrity is also demonstrated. Using both electron-donating and electron-withdrawing substituents on the salicylaldehyde substrate, seven different derivatives of coumarin-3-carboxylic acid were made. Additionally, the monoamine oxidase (MAO) inhibitor, coumarin-3-phenylcarboxamide, has also been synthesized from coumarin-3-carboxylic acid obtained in the catalysis process. A detailed mechanism of action is also provided.
- Khullar, Sadhika,Mandal, Sanjay K.,Markad, Datta
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- A novel “turn-off” fluorescent sensor for Al3+ detection based on quinolinecarboxamide-coumarin
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Quinolinecarboxamides based on coumarin derivatives were efficiently synthesized and the optical properties were investigated. Compound ZXQ substituted by the diethylamino group on 7-position of coumarin exhibited blue fluorescence (λem ≈ 470 nm) with a high fluorescence quantum yield of 0.92 in Toluene and showed “turn-off” fluorescence property for Al3+. Probe ZXQ formed the 2:1 complex with Al3+ and performed fluorescence quenching in MeCN/H2O (95:5), which exhibited good selectivity and sensitivity. In addition, the mechanism of binding and fluorescence quenching was illustrated by titration experiment, Job’ plot and DFT calculations.
- Cui, Yanhong,Li, Yujin,Lin, Zhangqi,Niu, Wenjie,Tang, Xue,Zhou, Zichun
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- Zirconium(IV) oxychloride: A simple and efficient catalyst for the synthesis of chromen-2-one derivatives
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The present work explores a highly efficient, environmental friendly, green protocol for the synthesis of chromen-2-one derivatives (3a-m) by the condensation of salicylaldehydes with various active methylene compounds using zirconium (IV) oxychloride as catalyst. This is a convenient and rapid method for Knoevenagel condensation and this methodology offers several advantages including shorter reaction time, milder conditions, inexpensive catalyst, simple operational procedure and allowed to achieve the desired products in excellent yields. The structures of all the synthesized compounds were confirmed by spectral data.
- TASQEERUDDIN,ASIRI, YAHYA I.,SHAHEEN
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p. 2611 - 2616
(2020/10/22)
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- Synthesis, antimicrobial and chitinase inhibitory activities of 3-amidocoumarins
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A series of 3-amidocoumarins has been synthesized and tested in vitro for their anitimicrobial and chitinase inhibitory activities. Among these, compounds 5k, 5l, 8b–8d, 8f and 8g exhibited good antibacterial activity with MIC values in the range of 6.25–25 μg/mL against some of the tested strains while compounds 5l, 8b, 8c and 8f showed good activity against at least one or two fungal strains. Some of the assayed compounds 5d, 5k, 5l, 8b and 8c displayed significant chitinase inhibitory activity with IC50 values in the range of 3.74–5.6 μM. Among them, 5l proved to be potent chitinase inhibitor with IC50 value of 3.74 μM. To better understand the enzyme-inhibitor interactions molecular docking study of all the synthesized compounds was carried out on Aspergillus fumigatus chitinase 1W9U. The compound 5l showed high binding affinity with the receptor with binding energy value of ?8.44 Kcal/mol. This study also provides structure activity relationship (SAR) of synthesized compounds.
- Butcher, R. J.,Katiyar, Diksha,Sharma, Rajesh Kumar,Singh, Vineeta,Tiwari, Neha
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- Application of coumarin-3-carboxylic acid as fluorescent probe
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The invention discloses an application of coumarin-3-carboxylic acid as a fluorescent probe, and belongs to the technical field of applications of coumarin derivatives. The coumarin-3-carboxylic acidis used as the fluorescent probe to detect chromium (III) ions. The coumarin-3-carboxylic acid prepared by the invention has good selectivity to the Cr, a stable coordination compound with a certain composition is formed by the coumarin-3-carboxylic acid and the Cr, and the Cr has stronger competitiveness than other metal ions and no interference on the other metal ions; and the novelcoumarin-3-carboxylic acid fluorescent chemical sensor has very good performance and potential application value in detection of the Cr in the fields of organisms and the environment.
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Paragraph 0024; 0028; 0029; 0030; 0033; 0034; 0037
(2019/08/12)
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- Synthesis of coumarin analogs appended with quinoline and thiazole moiety and their apoptogenic role against murine ascitic carcinoma
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The synthesis and antiproliferative effect of a series of quinoline and thiazole containing coumarin analogs 12a-d and 13a-f respectively, on mice leukemic cells was performed. The chemical structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectral analysis. The result indicates that, 7-methoxy-2-oxo-2H-chromene-3-carboxylic acid [4-(4-methoxy-phenyl)-thiazol-2-yl]-amide (13f) showed potent activity against EAC and DLA cells in MTT (15.3 μM), tryphan blue (15.6 μM) and LDH (14.2 μM) leak assay with 5-fluorouracil as a standard. Further, the anti-neoplastic effect of the compound 13f was verified against Ehrlich ascites tumour by BrdU incorporation, TUNEL, FACS and DNA fragmentation assays. Experimental data showed that compound 13f induces the apoptotic cell death by activating apoptotic factors such as caspase-8 &-3, CAD, Cleaved PARP, γ-H2AX and by degrading genomic DNA of cancer cells and thereby decreasing the ascitic tumour development in mice. Besides, compound 13f was also subjected for docking studies to approve the in vitro and in vivo studies. The data revealed that the compound 13f has very good interaction with caspase 3 protein by binding with amino acid Arg 207 through hydrogen bond.
- Prashanth,Avin, B.R. Vijay,Thirusangu, Prabhu,Ranganatha, V. Lakshmi,Prabhakar,Sharath Chandra, J.N. Narendra,Khanum, Shaukath Ara
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- Evaluation of novel N′-(3-hydroxybenzoyl)-2-oxo-2H-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors
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In an attempt to identify potential new agents that are active against HIV-1 IN, a series of novel coumarin-3-carbohydrazide derivatives were designed and synthesised. The toxicity profiles of these compounds showed that they were non-toxic to human cells and they exhibited promising anti-HIV-1 IN activities with IC50 values in nM range. Also, an accompanying molecular modeling study showed that the compounds bind to the active pocket of the enzyme.
- Jesumoroti, Omobolanle J.,Faridoon,Mnkandhla, Dumisani,Isaacs, Michelle,Hoppe, Heinrich C.,Klein, Rosalyn
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- Antifungal activity, mode of action variability, and subcellular distribution of coumarin-based antifungal azoles
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Azole antifungals inhibit the biosynthesis of ergosterol, the fungal equivalent of cholesterol in mammalian cells. Here we report an investigation of the activity of coumarin-substituted azole antifungals. Screening against a panel of Candida pathogens, including a mutant lacking CYP51, the target of antifungal azoles, revealed that this enzyme is inhibited by triazole-based antifungals, whereas imidazole-based derivatives have more than one mode of action. The imidazole-bearing antifungals more effectively reduced trailing growth associated with persistence and/or recurrence of fungal infections than triazole-based derivatives. The imidazole derivatives were more toxic to mammalian cells and more potently inhibited the activity of CYP3A4, which is one of the main causes of azole toxicity. Using live cell imaging, we showed that regardless of the type of azole ring fluorescent 7-diethylaminocoumarin-based azoles localized to the endoplasmic reticulum, the organelle that harbors CYP51. This study suggests that the coumarin is a promising scaffold for development of novel azole-based antifungals that effectively localize to the fungal cell endoplasmic reticulum.
- Elias, Rebecca,Benhamou, Raphael I.,Jaber, Qais Z.,Dorot, Orly,Zada, Sivan Louzoun,Oved,Pichinuk, Edward,Fridman
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supporting information
p. 779 - 790
(2019/07/10)
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- General Strategy for in Situ Generation of a Coumarin-Cu2+ Complex for Fluorescent Water Sensing
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The detection of moisture in organic solvents is very important before their use in water-sensitive reactions. Herein, we report that coumarins D1 and D2 were able to generate the corresponding water-sensitive copper complexes D1-Cu and D2-Cu in common organic solvents, which can be used as efficient fluorescent turn-on sensors for water. Single-crystal diffraction analysis of the reaction product indicated that the sensing mechanism is based on the formation of a water-bridged 3D supramolecular hydrogen-bonding network. We demonstrated that a hydroxyl or amine group substituted at the 7-position of the coumarin framework played a key role in the water-sensing performance of D1-Cu and D2-Cu, by acting as a hydrogen bond acceptor in the supramolecular network. This provided a general strategy for designing such coumarin-based copper complexes for fluorescent water sensing. The water-sensing behavior of D1-Cu and D2-Cu were determined to be fast, pH tolerant, and sensitive. As low as 0.0525 wt % of water in methanol can be detected using D1-Cu as the sensor. Moreover, D1-Cu was successfully used for moisture sensing in real commercial products.
- Cheng, Wenjing,Xie, Yiting,Yang, Zhiyu,Sun, Yueqing,Zhang, Ming-Zhi,Ding, Yubin,Zhang, Weihua
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p. 5817 - 5823
(2019/05/01)
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- Coumarin-sesamol bio-based photoinitiator and preparation method thereof
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The invention provides a coumarin-sesamol photoinitiator and a preparation method thereof. The initiator provided by the invention has good absorption performance under a light source with the wavelength being 200-450 nm, the absorption band covers an ultraviolet region and extends to a visible region, and the initiator can be used as an ultraviolet/visible light initiator; at the same time, the reaction conditions are mild, and the structural body is a bio-based material. The initiator provided by the invention is short in preparation route, high in purity (more than 95%), good in stability and high in sensitivity, the absorption band covers the ultraviolet region and part of the visible light region, and the initiator can be used in the field of 3D printing, and is a universal type photoinitiator with excellent performance.
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Paragraph 0039; 0040
(2019/09/17)
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- Ugi efficient synthesis, biological evaluation and molecular docking of coumarin-quinoline hybrids as apoptotic agents through mitochondria-related pathways
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Ugi reaction was a reliable procedure for the synthesis of new coumarin-quinoline frameworks. Excellent yields, mild reaction conditions and easily available and inexpensive starting materials are advantages of this protocol. Cytotoxic effects of fourteen products were investigated in A2780 human ovarian cancer cells. Two synthesized compounds (L11 and L12) exhibited more anti-cancer activity than other derivatives with IC50 values of 0.042 mmol/L and 0.102 mmol/L, respectively and were thus selected for further studies. Apoptosis was induced through the intrinsic pathway by activating caspase 9 and ended at the executioner pathway of caspase 3. Measurement of intracellular reactive oxygen species (ROS) and mitochondrial membrane potential (MMP) were also carried out for both of them. Further studies on a mechanism by Real Time-PCR and Western blot analysis were performed for anti-apoptotic proteins Bcl-2 and survivin both in mRNA and protein level relating to the untreated A2780 cells. The treatment of A2780 cells with compound L11 significantly (P-value ≤ 0.05) induced apoptosis by down-regulation of Bcl-2 and survivin both in mRNA and protein level via a single dose (0.042 mmol/L), as well as activation of caspase 9 and 3, loss of MMP, and high ROS. Accordingly, findings supported the first report under which the pro-apoptotic activity of compound L11 as an apoptosis-inducing agent was related to mitochondrial-mediated dysfunction signaling pathways. Molecular docking supports experimental outcomes. Evidently, coumarin-quinoline scaffolds are potentially favorable options for further assessment as influential chemotherapeutic agents for the future.
- Taheri, Salman,Nazifi, Maryam,Mansourian, Mahboubeh,Hosseinzadeh,Shokoohinia
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- Synthesis and Biological Evaluation of Some Succinimide Hybrid Molecules
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In this study, a new series of succinimide hybrid molecules containing isothiocyanate, coumarin, isatin, and furan moieties was synthesized and screened for α-glucosidase and antioxidant activities. Preliminary results revealed that all molecules showed good α-glucosidase inhibition effectiveness. Antioxidant activities of the hybrid molecules were determined using cupric reducing antioxidant capacity (CUPRAC) and ferric reducing antioxidant power (FRAP) assays. Also, the radical scavenging activities of the synthesized compounds were assayed by using ABTS?+?and DPPH??methods. The results showed that all compounds exhibited moderated to high scavenging activity.
- Fatih Y?lmaz,Mente?e, Emre,Balta?, Nimet
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p. 575 - 584
(2020/01/21)
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- Synthesis, CYP 450 evaluation, and docking simulation of novel 4-aminopyridine and coumarin derivatives
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Four series of novel compounds based on 4-aminopyridine, glatiramer acetate, pyrone, and coumarin backbones were sufficiently synthesized and identified by spectroscopic methods. CYP enzyme inhibition assays of five predominate human P450 isozymes indicate that all compounds, except for 4-hydrazide pyridine 1c, seem to be less toxic than 4-aminopyridine. Further investigation of the compounds using molecular docking experiments revealed different, the same, or stronger binding modes for most of the synthesized compounds, with both polar and hydrophobic interactions with the 1WDA and 1J95 receptors compared to benzoyl l-arginine amide and 4-aminopyridine, respectively. These results introduce the synthesized compounds as K+ channel blockers that could be considered for in vivo CNS disease studies.
- Ghalehshahi, Hajar G.,Balalaie, Saeed,Sohbati, Hamid R.,Azizian, Homa,Alavijeh, Mohammad S.
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- Design, Synthesis, and Cholinesterase Inhibition Assay of Coumarin-3-carboxamide-N-morpholine Hybrids as New Anti-Alzheimer Agents
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A new series of coumarin-3-carboxamide-N-morpholine hybrids 5a–5l was designed and synthesized as cholinesterases inhibitors. The synthetic approach for title compounds was started from the reaction between 2-hydroxybenzaldehyde derivatives and Meldrum's acid to afford corresponding coumarin-3-carboxylic acids. Then, amidation of the latter compounds with 2-morpholinoethylamine or N-(3-aminopropyl)morpholine led to the formation of the compounds 5a–5l. The in vitro inhibition screen against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) revealed that most of the synthesized compounds had potent AChE inhibitory while their BuChE inhibitions are moderate to weak. Among them, propylmorpholine derivative 5g (N-[3-(morpholin-4-yl)propyl]-2-oxo-2H-chromene-3-carboxamide) bearing an unsubstituted coumarin moiety and ethylmorpholine derivative 5d (6-bromo-N-[2-(morpholin-4-yl)ethyl]-2-oxo-2H-chromene-3-carboxamide) bearing a 6-bromocoumarin moiety showed the most activity against AChE and BuChE, respectively. The inhibitory activity of compound 5g against AChE was 1.78 times more than that of rivastigmine and anti-BuChE activity of compound 5d is approximately same as rivastigmine. Kinetic and docking studies confirmed the dual binding site ability of compound 5g to inhibit AChE.
- Tehrani, Maliheh Barazandeh,Rezaei, Zahra,Asadi, Mehdi,Behnammanesh, Hossein,Nadri, Hamid,Afsharirad, Fatemeh,Moradi, Alireza,Larijani, Bagher,Mohammadi-Khanaposhtani, Maryam,Mahdavi, Mohammad
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- Coumarin derivative as - well as preparation method and application thereof (by machine translation)
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The coumarin-thiazole ester derivative has a broad-spectrum antibacterial activity, and the coumarin,thiazole ester derivative has, a broad-spectrum antibacterial activity, so that 4 the coumarin 7-thiazole, ester derivative has a DCC, DMAP, broad 0 °C-spectrum 10 - 15 antibacterial activity, and the application is a novel antibacterial, agent developed with coumarin-thiazole ester, derivatives as active ingredients 24. (by machine translation)
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Paragraph 0037-0039
(2020/01/03)
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- Naphthimide-coumarin DNA targeting bisintercalating agent and synthesis and application thereof
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The invention discloses a naphthimide-coumarin DNA targeting bisintercalating agent and synthesis and an application thereof, and belongs to the field of biological organic synthesis. A naphthimide intercalating agent parent is connected together with a coumarin intercalating agent parent through certain bridged chains, and the DNA bisintercalating agent having better DNA intercalating ability andbetter anticancer effect than corresponding monomers is synthesized. The naphthalimide-coumarin bisintercalating agent adopts different cyclamine or fatty amine groups for substituting Br at the tailend of naphthalene anhydride, and is used for study of a structure-function relationship of drug molecules; and moreover, with alcohol amine and diamine as bridged chains, the naphthalimide parent and coumarin acyl chloride are connected together through an esterification reaction or an amidation reaction, and the novel naphthimide-coumarin bisintercalating agent having the anticancer activity issynthesized.
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Paragraph 0024; 0025; 0026; 0027
(2018/03/26)
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- Novel probes based on coumarin-bisdithiocarbamate system for selective recognition of Ag(I) in aqueous solution
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Two novel fluorescent probes (C1, C2), comprising a coumarin moiety as fluorophore and a pair of dithiocarbamates as recognition sites, were designed and synthesized as fluorescent probes for Ag+. The probes exhibited high selectivity for Ag+ with fluorescence enhancement (FE) in CH3CN/4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES) (1:9, v/v, pH 7.38); the selectivity was not affected by other metal ions. The binding ratio of C2–Ag+ complex was determined to be 1:1 according to the Job plot and mass spectroscopy (MS) data. The association constant Ka of Ag+ with C2 was 1.6?×?104?M?1. These probes could be applied for monitoring of Ag+ in aqueous solution in the pH range of 5.0–8.0, with calculated detection limit of 0.27?μM.
- Chen, Guo Feng,Liu, Lin,Wu, Jiu Li,Wu, Suo Juan,Chen, Bao Hua
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p. 1381 - 1395
(2017/11/16)
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- Design, synthesis and biological evaluation of novel furoxan-based coumarin derivatives as antitumor agents
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In order to find new anticancer drugs, a series of novel furoxan-based coumarin derivatives (10a–k) were synthesized and evaluated for their antiproliferative activities in vitro. All compounds displayed more potent inhibition on human cervical cancer HeLa cell proliferation than coumarin-3-carboxylic acid, and compounds 10b, 10c, 10f, 10h, and 10i with IC50 values ranging from 0.88 to 5.95 μM were even stronger than doxorubicin (IC50 = 10.21 μM). The further study showed that compound 10i exerted the highest antiproliferative activity (IC50 = 0.60 μM) against human breast cancer MCF-7 cells, and compound 10f had broader spectrum antiproliferative activity against five cancer cells with IC50 values in the low micromolar range of 1.86–9.85 μM. More interestingly, compound 10f had little effect on normal intestinal epithelial CCD841 cells. Our findings suggest that these novel furoxan-based coumarin derivatives may provide a new framework for the discovery of novel antitumor agents for the intervention of human carcinoma cells.
- Zhang, Zhuo,Bai, Zhi-Wei,Ling, Yong,He, Li-Qin,Huang, Peng,Gu, Hong-Xia,Hu, Rong-Feng
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p. 1198 - 1205
(2018/03/26)
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- A selective colorimetric and fluorescence chemosensing sensor for Cr3+ based on a rhodamine base derivative
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A rhodamine-conjugated coumarin (L) was used in designing a selective fluorescence chemosensor for the determination of trace amounts of Cr3+ ions in acetonitrile–water (MeCN/H2O (90:10, %v/v) solutions. The intensity of the fluoresce emission of the chemosensor is intensified upon addition of Cr3+ ions in MeCN/H2O (90:10, %v/v) solutions, due to the formation of a selective 1:1 complex between L and Cr3+ ions. The fluorescence enhancement versus Cr3+ concentration has been found to be linear from 1.0 × 10?7 to 1.8 × 10?5 M and a detection limit of 7.5 × 10?8 M. The proposed fluorescent probe proved to be highly selective towards Cr3+ ions as compared to other common metal ions and could be successfully applied to the determination of Cr3+ concentrations in some water and wastewater samples.
- Hosseini, Morteza,Khoobi, Mehdi,Tarasi, Roghayeh,Ganjali, Mohammad Reza
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p. 5031 - 5042
(2018/04/02)
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- Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity
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The identification of novel Topoisomerase II (Topo II) inhibitors is one of the most attractive directions in the field of bactericide research and development. In our ongoing efforts to pursue the class of inhibitors, six series of 70 novel coumarin-pyrazole carboxamide derivatives were designed and synthesized. As a result of the evaluation against four destructive bacteria, including Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella. Compound 8III-k (MIC = 0.25 mg/L) showed considerable inhibitory activity than ciprofloxacin (MIC = 0.5 mg/L) against Escherichia coli and 8V-c (MIC = 0.05 mg/L) exhibited excellent antibacterial activity than ciprofloxacin (MIC = 0.25 mg/L) against Salmonella. The selected compounds (8III-k, 8V-c and 8V-k) exhibit potent inhibition against Topo II and Topo IV with IC50 values (9.4–25 mg/L). Molecular docking model showed that the compounds 8V-c and 8V-k can bind well to the target by interacting with amino acid residues. It will provide some valuable information for the commercial Topo II inhibiting bactericides.
- Liu, Hao,Ren, Zi-Li,Wang, Wei,Gong, Jie-Xiu,Chu, Ming-Jie,Ma, Quan-Wei,Wang, Jie-Chun,Lv, Xian-Hai
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- Ordered mesoporous Γ-Al2O3 as highly efficient and recyclable catalyst for the Knoevenagel reaction at room temperature
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Coumarins are important class of organic compounds and intensively used in agricultural and pharmaceutical industries. We have developed a strategy for the synthesis of coumarin derivatives quantitatively via Knoevenagel condensation reaction of an ortho-hydroxyaryl aldehyde and an activated methylene compounds in the presence of ordered mesoporous γ-Al2O3 as a heterogeneous catalyst. The catalyst has been thoroughly characterized through powder X-ray diffraction, N2 sorption analysis, FTIR spectroscopy, TG/DTA, NH3-TPD and CO2-TPD (temperature programmed desorption) analysis. The material possesses periodicity in mesopores and both surface acidic and basic sites having strengths of 1.47 and 1.11 mmol g?1, respectively, which is highly favorable for carrying out the Knoevenagel condensation reaction for the synthesis of a wide range of condensation product (yields ～98%) under very mild conditions. This amphoteric catalyst exhibits good surface Lewis acidity/basicity and high recyclability up to sixth reaction cycles without any significant loss in the product yield.
- Bhanja, Piyali,Kayal, Utpal,Bhaumik, Asim
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p. 220 - 227
(2018/04/05)
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- Synthesis and evaluation of coumarin/piperazine hybrids as acetylcholinesterase inhibitors
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A series of new coumarin/piperazine hybrids were synthesized and evaluated for anticholinesterase activity. Among them, compounds 4d and 4t exhibited potent human acetylcholinesterase (hAChE) inhibitory activity with IC50 values of 2.42 and 9.89 μM, respectively, and 4t displayed highest selectivity toward hAChE over human butyrylcholinesterase (hBChE) by 9.8-fold. In addition, both compounds did not show observed cytotoxicity against SH-SY5Y neuroblastoma cell line at 100 μM. Kinetic analysis in tandem with molecular docking study revealed that these hybrids targeted both catalytic active site (CAS) and peripheral anionic site (PAS) of hAChE. The preliminary results highlighted 4t as an anti-Alzheimer’s disease lead compound worthy of further investigation.
- Zhang, Juan,Jiang, Cheng-Shi
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p. 1717 - 1727
(2018/05/14)
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- Peptides N-connected to hydroxycoumarin and cinnamic acid derivatives: Synthesis and fluorescence spectroscopic, antioxidant and antimicrobial properties
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The tripeptide Tyr-Gly-Ser and a series of conjugations to coumarin, cinnamic and gallic acid were synthesized in salt form and their antioxidant and antimicrobial activities were investigated. The N-connecting hydroxycoumarin, cinnamic and gallic acid derivatives to peptides and the use of BBr3 as a demethylating agent for peptides was reported. Their activities were investigated based on the conjugated moiety structures. Studies of their activities showed that conjugated tripeptides 7,8-dihydroxycoumarin-peptide (17), caffeic acid-peptide (22) and gallic acid-peptide (28) were found to be superior to ascorbic acid with respect to their antioxidant activity, and 12, 14, 24, and 25 exhibited the most antimicrobial activity in the series compared to amoxicillin. Additionally, the incredible florescence intensity and brightness of 17 in water and DMSO, compared to other synthesized compounds, qualified this peptide as a suitable probe in the human body.
- Ghalehshahi, Hajar G.,Balalaie, Saeed,Aliahmadi, Atousa
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p. 8831 - 8842
(2018/06/11)
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- 3-substituted coumarin derivative and application and GPR35 receptor agonist
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The invention discloses a 3-substituted coumarin derivative and a pharmaceutically acceptable salt, a solvate, a hydrate or a crystal form. The compound of the invention generally exhibits high agonistic activity against human G protein-coupled receptor 35 (GPR35) and is specific agonists of the human GPR35 receptor. The compound provided by the invention is an active ligand of the novel GPR35 receptor, and the compound and the pharmaceutically acceptable salt, the solvate, the hydrate or the crystal form thereof generally exhibit higher activity and good selectivity to the human GPR35. The 3-substituted coumarin derivative is the specific agonist of the GPR35 receptor and can be used in the preparation of a medicament for treating, preventing and inhibiting a disease mediated by the GPR35receptor.
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Paragraph 0048; 0067-0069
(2018/06/04)
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- Synthesis and characterisation of some new hybrid molecules containing thiophene, triazole and coumarin rings under microwave conditions
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In this work, a new series of N′-([4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetyl)-2-oxo-2H-1-benzopyran-3-carbohydrazides (thiophene–triazole–coumarin hybrid molecules) was synthesised from the reaction of 2-[4-amino-5-oxo-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide and 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-ones by using microwave irradiation and conventional heating procedures and their results were compared. The reaction was performed using a very small amount of organic solvent and without using a catalyst.
- Yilmaz, Fatih
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p. 361 - 365
(2018/08/21)
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- Peroxy mediated Csp2-Csp3 dehydrogenative coupling: Regioselective functionalization of coumarins and coumarin-3-carboxylic acids
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A regioselective direct alkylation of coumarins at C-3 via cross-dehydrogenative coupling of unactivated Csp2-Csp3 bonds is developed. This protocol employs tert-butyl hydroperoxide as the sole reagent of the reaction to combine coumarins and ethers in reasonable yields under metal- and solvent-free reaction conditions. This protocol also worked well with coumarin-3-carboxylic acids to unveil a rare instance of a catalyst-free tandem alkylation/decarboxylation reaction with conservation of the double bond.
- Jafarpour, Farnaz,Darvishmolla, Masoumeh
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supporting information
p. 3396 - 3401
(2018/05/23)
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- Design, synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives
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A series of coumarin-3-carboxamides/hydrazides have been designed and synthesized, all the target compounds were evaluated in vitro for their antifungal activity against Botrytis cinerea, Alternaria solani, Gibberella zeae, Rhizoctorzia solani, Cucumber anthrax and Alternaria leaf spot, some of the designed compounds 4a-4g exhibited potential activity in the primary assays, this highlighted by the compounds 4a, 4d, 4e and 4f, EC50 values of which against Rhizoctorzia solani were as low as 1.80 μg/mL, 2.50 μg/mL, 2.25 μg/mL and 2.10 μg/mL, respectively, exhibiting more effective control with that of the positive control than Boscalid. Furthermore, compounds 4a and 4e represented equivalent antifungal activity with Boscalid against Botrytis cinerea.
- Yu, Xiang,Teng, Peng,Zhang, Ya-Ling,Xu, Zhao-Jun,Zhang, Ming-Zhi,Zhang, Wei-Hua
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p. 387 - 395
(2018/04/19)
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- Development of coumarin–benzofuran hybrids as versatile multitargeted compounds for the treatment of Alzheimer’s Disease
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Alzheimer’s disease (AD), the most common cause of dementia, is a neurodegenerative disorder characterized by progressive deterioration of memory and cognition. The evidenced multifactorial nature of AD has been considered the main reason for the absence of cure so far. Therefore, the development of novel hybrids to treat the disease is very much essential. Focusing on this, a novel series of coumarin–benzofuran hybrids have been designed and screened as anti-Alzheimer’s disease agents. The strategy is to obtain an effective mimetic of donepezil, which is acetylcholinesterase inhibitor. Herein, the two main scaffolds namely coumarin and benzofuran are known pharmacophore moieties and we have performed their molecular design, pharmacokinetic descriptor studies for drug-likeliness. Further, in vitro studies such as antioxidant capacity, acetylcholinesterase (AChE) inhibition and amyloid-β (Aβ) self-aggregation inhibition have also been performed. Most importantly, these studies revealed that the newly synthesized hybrids can be versatile and promising drug-like moieties as efficient anti-AD agents.
- Hiremathad, Asha,Chand, Karam,Keri, Rangappa S.
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p. 1497 - 1503
(2018/07/31)
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- Tosylmethylisocyanide (TosMIC) [3+2] cycloaddition reactions: A facile Van Leusen protocol for the synthesis of the new class of spirooxazolines, spiropyrrolines and Chromeno[3,4-c]pyrrols
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The reactivity and chemo-, regio- and diastreo-selectivity of tosylmethyl isocyanides (TosMIC) are investigated in Van Leusen type [3 + 2] cycloaddition reactions with the various activate cyclic ketones and double C–C bonds in the synthesis of spirooxazolines, spiropyrrolines and chromeno[3,4-c]pyrrols in good to excellent yields under catalyst-free conditions without any activation at ambient temperature.
- Shaabani, Ahmad,Sepahvand, Heshmatollah,Bazgir, Ayoob,Khavasi, Hamid Reza
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p. 7058 - 7067
(2018/11/02)
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- Nitric oxide donor type coumarin derivatives, preparation methods therefor and medicinal use of nitric oxide donor type coumarin derivatives
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The invention relates to the fields of pharmacochemistry and pharmacotherapeutics and particularly relates to nitric oxide donor type coumarin derivatives, preparation methods therefor and an application of the nitric oxide donor type coumarin derivatives. The compounds play a role in resisting tumors and can be applied to the preparation of antitumor drugs.
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Paragraph 0487; 0506; 0507; 0509
(2017/09/01)
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- FRET-based Fluorescent and Colorimetric Probe for Selective Detection of Hg(II) and Cu(II) with Dual-mode
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A dual-function fluorescence resonance energy transfer (FRET)-based fluorescent and colorimetric probe was rationally fabricated from an energy donor coumarin moiety and an energy acceptor rhodamine moiety linked by a thiohydrazide arm for selective detection of Hg2+ and Cu2+. Two distinct mechanisms were used for the selective detection. Results revealed that probe 1 showed high fluorescent selectivity towards Hg2+ and evident colorimetric selectivity for Cu2+, which was suitable for ‘naked-eye’ detection.
- Luo, Xue,He, Xu-Dong,Zhao, Yuan-Chao,Chen, Chong,Chen, Biao,Wu, Zhi-Bing,Wang, Pei-Yi
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p. 2650 - 2655
(2017/09/26)
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