- O-prenylated 3-carboxycoumarins as a novel class of 15-LOX-1 inhibitors
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Allyloxy, Isopentenyloxy, geranyloxy and farnesyloxy derivatives of 3-carboxycoumarin, at position 5, 6, 7, and 8, were synthesized and their inhibitory potency against human 15- lipoxygenase-1 (human 15-LOX-1) were determined. Among the synthetic coumarins, Oallyl and O-isopentenyl derivatives demonstrated no considerable lipoxygenase inhibition while O-geranyl and O-farnesyl derivatives demonstrated potent inhibitory activity. 5-farnesyloxy- 3-carboxycoumarin demonstrated the most potent inhibitory activity by IC50 = 0.74 μM while 6-farnesyloxy-3-carboxycoumarin was the weakest inhibitor among farnesyl analogs (IC50 = 10.4 μM). Bonding affinity of the designed molecular structures toward 15- LOX-1 3D structure complexed with RS75091, as potent 15-LOX-1 inhibitor, was studied by utilizing docking analysis. There was a direct relationship between lipoxygenase inhibitory potency and prenyl length chain. The ability of the prenyl portion to fill the lipophilic pocket which is formed by Ile663, Ala404, Arg403, Ile400, Ile173 and Phe167 side chains can explain the observed relationship. Similarity rate between the docked models and complexed form of RS75091, from point of view of configuration and conformation, could explain inhibitory potency variation between each prenyloxy substitution of 3-carboxycoumarins.
- Jabbari, Atena,Mousavian, Mina,Seyedi, Seyed Mohamad,Bakavoli, Mehdi,Sadeghian, Hamid
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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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Read Online
- Solid state synthesis of substituted coumarin-3-carboxylic acids via the knoevenagel condensation under microwave irradiation
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Synthesis of substituted coumarin-3-carboxylic acids using the Knovenagel reaction of malonic acid and O-hydroxyaryl aldehydes supported onto HZSM-5 zeolite under microwave irradiation is described.
- Heravi, Majid M.,Hekmatshoar, Rahim,Emamgholizadeh, Maryam
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Read Online
- 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; 0074; 0079; 0084-0090
(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; 0074
(2021/06/26)
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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 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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- 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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- 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 0145; 0149; 0150
(2020/02/27)
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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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- 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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- 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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- 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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- 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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- Coumarins derivative used as caspase-3 activator and application thereof
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The invention discloses a coumarins derivative used as a caspase-3 activator. A similar structure design and a usage cannot be seen in similar products. This type of compounds has the remarkable caspase-3 activation, and can be used for treating caspase r
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Paragraph 0082; 0091; 0092
(2018/11/22)
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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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- 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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- A Simple One-Pot Synthesis of Fully Substituted 1H-Pyridone[1,2-a]-Fused-1,3-Diazaheterocycles
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An efficient procedure for the synthesis of 7-(aryl)-8-nitro-2,3,6,7-tetrahydroimidazo[1,2-a]pyridinones, 8-(aryl)-9-nitro-3,4,7,8-tetrahydropyridone[1,2-a]pyrimidines and 9-(aryl)-10-nitro-2,3,4,5,8,9-hexahydropyridone[1,2-a]diazepine via one-pot three component reaction of diamine, nitroketene dithioacetal (1,1-bis(methylsulfanyl)-2-nitroethene), and coumarine-3- carboxylic acid derivatives in EtOH under reflux conditions is reported. The advantages of this procedure are simplicity, easy purification, good yields, and catalyst-free conditions. All products were confirmed by 1H- and 13C-NMR, IR, MS, and X-ray crystal structure analyses.
- Bayat, Mohammad,Rezaee, Monireh,Zhu, Long-Guan
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p. 2748 - 2754
(2017/09/26)
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- Design, synthesis and biological evaluation of novel coumarin-based benzamides as potent histone deacetylase inhibitors and anticancer agents
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Histone deacetylases (HDACs) are attractive therapeutic targets for the treatment of cancer and other diseases. It has four classes (I-IV), among them especially class I isozyme are involved in promoting tumor cells proliferation, angiogenesis, differentiation, invasion and metastasis and also viable targets for cancer therapeutics. A novel series of coumarin-based benzamides was designed and synthesized as HDAC inhibitors. The cytotoxic activity of the synthesized compounds (8a-u) was evaluated against six human cancer cell lines including HCT116, A2780, MCF7, PC3, HL60 and A549 and a single normal cell line (Huvec). We evaluated their inhibitory activities against pan HDAC and HDAC1 isoform. Four compounds (8f, 8q, 8r and 8u) showed significant cytotoxicity with IC50 in the range of 0.53–57.59?μM on cancer cells and potent pan-HDAC inhibitory activity (consists of HDAC isoenzymes) (IC50?=?0.80–14.81?μM) and HDAC1 inhibitory activity (IC50?=?0.47–0.87?μM and also, had no effect on Huvec (human normal cell line) viability (IC50?>?100?μM). Among them, 8u displayed a higher potency for HDAC1 inhibition with IC50 value of 0.47?±?0.02?μM near equal to the reference drug Entinostat (IC50?=?0.41?±?0.06?μM). Molecular docking studies and Molecular dynamics simulation of compound 8a displayed possible mode of interaction between this compound and HDAC1enzyme.
- Abdizadeh, Tooba,Kalani, Mohammad Reza,Abnous, Khalil,Tayarani-Najaran, Zahra,Khashyarmanesh, Bibi Zahra,Abdizadeh, Rahman,Ghodsi, Razieh,Hadizadeh, Farzin
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- Design, synthesis and biological evaluation of coumarin derivatives as novel acetylcholinesterase inhibitors that attenuate H2O2-induced apoptosis in SH-SY5Y cells
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A novel series of coumarin derivatives were designed, synthesized and investigated for inhibition of cholinesterase, including acetyl cholinesterase (AChE) and butyrylcholinesterase (BuChE). This biological study showed that these compounds containing piperazine ring had significant inhibition activities on AChE rather than BuChE. Further study suggested that 9x, as one of this kind of structure derivative, showed the strongest inhibition activity on AChE with an IC50 value of 34?nM. Moreover, molecular docking, flow cytometry (FCM), and western blot assay suggested that 9x could induce cytoprotective autophagy to attenuate H2O2-induced cell death in human neuroblastoma SH-SY5Y cells. These findings highlight a new approach for the development of a novel potential neuroprotective compound targeting AChE with autophagy-inducing activity in future Alzheimer's disease (AD) therapy.
- Yao, Dahong,Wang, Jing,Wang, Guan,Jiang, Yingnan,Shang, Lei,Zhao, Yuqian,Huang, Jian,Yang, Shilin,Wang, Jinhui,Yu, Yamei
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p. 112 - 123
(2016/08/01)
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- Synthesis and anticholinesterase activity of coumarin-3-carboxamides bearing tryptamine moiety
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A number of N-(2-(1H-indol-3-yl)ethyl)-2-oxo-2H-chromene-3-carboxamides were synthesized and tested against AChE and BuChE. The in?vitro assessment of the synthesized compounds 4a-o revealed that most of them had significant activity toward AChE. The SAR study demonstrated that the introduction of benzyloxy moiety on the 7-position of coumarin scaffold can improve the anti-AChE activity. The best result was obtained with 7-(4-fluorobenzyl)oxy moiety in the case of compound 4o, displaying IC50value of 0.16?μM. Based on the docking study of AChE, the prototype compound 4o was laid across the active site and occupied both peripheral anionic site (PAS) and catalytic anionic site (CAS).
- Ghanei-Nasab, Samaneh,Khoobi, Mehdi,Hadizadeh, Farzin,Marjani, Azam,Moradi, Alireza,Nadri, Hamid,Emami, Saeed,Foroumadi, Alireza,Shafiee, Abbas
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- A cost-effective and green aqueous synthesis of 3-substituted coumarins catalyzed by potassium phthalimide
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An efficient procedure for the synthesis of various 2-imino-2H-chromene-3-carbonitriles, 2-oxo- 2H-chromene-3-carbonitriles as well as 2-oxo-2H-chromene-3-carboxylic acids is reported. It has been found that potassium phthalimide (PPI) catalyse the Knoevenagel condensation reaction of salicylaldehydes and activated β- dicarbonyl compounds efficiently under aqueous conditions at room temperature. This approach provides many merits such as high yields of products, clean, simple work-up, waste free, mild reaction conditions, commercially available organocatalyst, and the use of water as environmentally benign solvent.
- Kiyani, Hamzeh,Daroonkala, Masoumeh Darzi
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p. 449 - 456
(2015/10/19)
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- Spectral switching of naphthalimide-coumarin induced by F-
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A highly selective color sensor based on naphthalimide and coumarin was reported. Upon addition of F-, the solution color changed from pale yellow to deep blue. The sensor shows excellent selectivity against other common anions. The underlying mechanism for the color change is based on the deprotonation/protonation of the dye. Frontier molecular orbitals analysis gives further insight about the signaling mechanism.
- Li, Xiaochuan,Son, Young-A.
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p. 5370 - 5373
(2015/01/30)
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- Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors
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Abstract Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study.
- Asadipour, Ali,Alipour, Masoumeh,Jafari, Mona,Khoobi, Mehdi,Emami, Saeed,Nadri, Hamid,Sakhteman, Amirhossein,Moradi, Alireza,Sheibani, Vahid,Homayouni Moghadam, Farshad,Shafiee, Abbas,Foroumadi, Alireza
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supporting information
p. 623 - 630
(2013/12/04)
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- Potassium phosphate catalyzed efficient synthesis of 3-carboxycoumarins
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An efficient and rapid synthesis of 3-carboxycoumarins has been expediently accomplished by a reaction of salicylaldehyde with Meldrum's acid using potassium phosphate as an inexpensive catalyst at ambient temperature.
- Undale, Kedar A.,Gaikwad, Dipak S.,Shaikh, Tarannum S.,Desai, Uday V.,Pore, Dattaprasad M.
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experimental part
p. 1039 - 1042
(2012/10/08)
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- Rapid synthesis of novel and known coumarin-3-carboxylic acids using stannous chloride dihydrate under solvent-free conditions
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Various coumarin-3-carboxylic acid (=2-oxo-2H-1-benzopyran-3-carboxylic acid; CcaH) derivatives have been synthesized in good yields using catalytic amounts of SnCl2·2 H2O under solvent-free conditions. This inexpensive, nontoxic, and readily available catalytic system (10 mol-%) efficiently catalyzes the Knoevenagel condensation and intramolecular cyclization of various 2-hydroxybenzaldehydes or acetophenones with Meldrum's acid. High product yields, use of inexpensive and safe catalyst, and solvent-free conditions display both economic and environmental advantages. Copyright
- Karami, Bahador,Farahi, Mahnaz,Khodabakhshi, Saeed
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experimental part
p. 455 - 460
(2012/05/04)
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- A green method for the synthesis of 3-substituted coumarins catalyzed by L-lysine in water via knoevenagel condensation
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L-lysine was applied to the synthesis of 3-substituted coumarins through the condensation of various salicylaldehyde with reactive methylene compounds in water. In this work, waste minimization, catalyst recovery, simple operation and easier product work-up were achieved.
- You, Xinwen,Yu, Hua,Wang, Mangang,Wu, Jun,Shang, Zhicai
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experimental part
p. 19 - 23
(2012/07/03)
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- Synthesis and Biological Evaluation of Coumarin Derivatives as Inhibitors of Mycobacterium bovis (BCG)
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The coumarin compounds are an important class of biologically active molecules, which have attractive caught the attention of many organic and medicinal chemists, due to potential pharmaceutical implications and industrial applications. We herein report t
- Rezayan, Ali Hossein,Azerang, Parisa,Sardari, Soroush,Sarvary, Afshin
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p. 929 - 936,8
(2020/08/24)
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- Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors
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All of the mono isopentenyloxy, -geranyloxy and -farnesyloxy derivatives of coumarin were synthesized and their inhibitory potency against soybean 15-lipoxygenase (SLO) and human 15-lipoxygenase-1 (HLO-1) were determined. Amongst the synthetic analogs, 5-farnesyloxycoumarin showed the most potent inhibitory activity against SLO (IC50 = 0.8 μM) while 6-farnesyloxycoumarin was the strongest HLO-1 inhibitor (IC50 = 1.3 μM). The IC50 variations of the farnesyl derivatives for HLO-1 (1.3 to ~75 μM) were much higher than that observed for SLO (0.8-5.8 μM). SAR studies showed that hydrogen bonding, CH/π, anion-π and S-OC interactions with FeIII-OH, Leu408, Glu357 and Met419 were the distinct intermolecular interactions which can lead to important role of the coumarin substitution site in HLO-1 inhibitory potency, respectively.
- Iranshahi, Mehrdad,Jabbari, Atena,Orafaie, Ala,Mehri, Robabeh,Zeraatkar, Soudabeh,Ahmadi, Taraneh,Alimardani, Maliheh,Sadeghian, Hamid
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p. 134 - 142
(2013/01/15)
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- Nickel nanoparticles catalyzed chemoselective Knoevenagel condensation of Meldrum's acid and tandem enol lactonizations via cascade cyclization sequence
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A novel protocol has been reported wherein, polyethylene glycol (PEG) stabilized nickel nanoparticles have been used as catalyst for chemoselective Knoevenagel condensation of aromatic aldehydes and Meldrum's acid to give 5-arylidene Meldrum's acid which underwent tandem enol lactonization by Michael addition/cyclization sequence with active methylene compounds in the presence of Ni nanoparticles to give corresponding enol lactone derivatives.
- Khurana, Jitender M.,Vij, Kanika
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experimental part
p. 3666 - 3669
(2011/07/29)
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- COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING A POLYMER BEARING JUNCTION GROUPS, AND COSMETIC TREATMENT PROCESS
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The present patent application relates to a cosmetic or dermatological composition comprising, in a cosmetically or dermatologically acceptable medium, a polymer comprising: (a) a polymer backbone that may be obtained by reaction: of a polyol comprising 3 to 6 hydroxyl groups;of a monocarboxylic acid containing 6 to 32 carbon atoms;of a polycarboxylic acid comprising at least two carboxylic groups COOH, and/or of a cyclic anhydride such as a polycarboxylic acid and/or of a lactone comprising at least one carboxylic group COOH; and(b) at least one junction group linked to the said polymer backbone and capable of establishing H bonds with one or more partner junction groups, each pairing of a junction group involving at least three H (hydrogen) bonds. The patent application also concerns a cosmetic treatment process using the said composition.
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- Synthesis of 7-(furan-2-yl)-7,8,10,10a-tetrahydro-6H-benzo[c]-chromen-6, 9(6aH)-diones
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Methods of synthesis were developed for 7-(furan-2-yl)-substituted 7,8,10,10a-tetrahydrobenzo[c] chromen-6,9-diones by regioselective [4+2]-cycloaddition of coumarin-3-carboxylic acids to 2-(3-trimethylsiloxybuta- 1,3-dien-1-yl)furans. The [4+2]-cycloaddi
- Shults,Bondarenko,Shakirov,Bagryanskaya,Tolstikov
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experimental part
p. 1709 - 1718
(2011/03/18)
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- Synthesis of 2-(alkylamino)-5-{alkyl[(2-oxo-2H-chromen-3-yl)carbonyl]amino} -3,4-furandicarboxylates using a multi-component reaction in water
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A simple synthesis of 2-(alkylamino)-5-{alkyl[(2-oxo-2H-chromen-3-yl) carbonyl]amino}-3,4-furandicarboxylates via a one-pot multi-component reaction is described. The reactive 1:1 zwitterionic intermediate generated from the addition of isocyanides to dialkyl acetylenedicarboxylates was trapped at room temperature by coumarin-3-carboxylic acids prepared in situ from a 2-hydroxy aromatic aldehyde and Meldrum's acid to afford the title compounds in good to excellent yields.
- Adib, Mehdi,Sheikhi, Ehsan,Kavoosi, Azadeh,Bijanzadeh, Hamid Reza
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experimental part
p. 9263 - 9269
(2011/01/12)
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- Silica sulfuric acid: A versatile and reusable catalyst for synthesis of coumarin-3-carboxylic acids in a solventless system
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Synthesis of substituted coumarin-3-carboxylic acid via Knoevenagel condensation of meldrum's acid with ortho-hydroxyaryl aldehydes in solventless system is described.
- Hekmatshoar, Rahim,Rezaei, Akram,Beheshtiha, S. Y. Shirazi
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experimental part
p. 2491 - 2496
(2010/04/03)
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- Naphthyl and coumarinyl biarylpiperazine derivatives as highly potent human β-secretase inhibitors. Design, synthesis, and enzymatic BACE-1 and cell assays
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Twenty novel β-secretase inhibitors containing biarylpiperazine moieties belonging to naphthyl and coumarinyl series were designed for their potential use in Alzheimer's disease therapy. Enzymatic and cell-based assays have been carried out. The biological results clearly demonstrate that specific substituents located at the N4-position of the piperazine ring result in excellent in vitro inhibitory potency (IC50 values ranging between 40 and 70 nM), Variable temperature NMR and modeling studies are consistent with the obtained biological data, since these studies confirmed that introduction at the N4-position of the piperazine ring allows productive interactions within the BACE-1 active site, which appear to be determinative for high BACE-1 inhibitory activity. These results are of particular interest since some of the new analogues belonging to the naphthyl series are almost one log more active than the best inhibitor of the similar family recently reported.
- Garino, Cédrik,Tomita, Taisuke,Pietrancosta, Nicolas,Laras, Younes,Rosas, Roselyne,Herbette, Ga?tan,Maigret, Bernard,Quéléver, Gilles,Iwatsubo, Takeshi,Kraus, Jean-Louis
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p. 4275 - 4285
(2007/10/03)
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- BACE-1 inhibitory activities of new substituted phenyl-piperazine coupled to various heterocycles: Chromene, coumarin and quinoline
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The protease β-secretase plays a central role in the synthesis of pathogenic amyloid-β in Alzheimer's disease. Here, we report a new series of analogues based on the phenyl-piperazine scaffold coupled to various heterocyclic moieties, which demonstrate improved inhibitory activities on BACE-1 (FRET assay) compared to already known naphthyl counterparts. The obtained results suggest further structural modifications to access to more potent BACE-1 inhibitors.
- Garino, Cedrik,Pietrancosta, Nicolas,Laras, Younes,Moret, Vincent,Rolland, Amandine,Quelever, Gilles,Kraus, Jean-Louis
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p. 1995 - 1999
(2007/10/03)
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- A practical and environmentally friendly preparation of 3-carboxycoumarins
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The condensation of salicylaldehydes with Meldrum's acid in water at 75°C to produce 3-carboxycoumarin derivatives is described.
- Deshmukh,Burud, Rahila,Baldino, Carmen,Chan, Philip C. M.,Liu, Jifeng
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p. 3299 - 3303
(2007/10/03)
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- Solid phase synthesis of substituted coumarin-3-carboxylic acids via the Knoevenagel condensation
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A solid phase synthesis of substituted coumarin-3-carboxylates using the Knoevenagel condensation reaction between ethyl malonate bound to the Wang resin and ortho-hydroxyarylaldehydes is described. The reaction has been shown to proceed cleanly to give the desired products.
- Watson, Brett T.,Christiansen, Gerda E.
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p. 6087 - 6090
(2007/10/03)
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- A One-Pot Synthesis of Coumarins from Dipotassium O-Methoxybenzylidenemalonates
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o-Methoxybenzylidenemalonates 1, which are available from o-methoxybenzaldehydes and diethylmalonate, were hydrolysed to the dipotassium malonates 2.Treatment of the salts 2 with trifluoroacetic acid-trifluoroacetic anhydride gave the title coumarins by a demethylative ring-closure reaction in 60-80percent yield.
- Hormi, Osmo E.O.,Peltonen, Carita,Bergstroem, Riitta
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p. 219 - 222
(2007/10/02)
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- NOVEL REACTIONS OF CARBON SUBOXIDE. IV. SYNTHESIS OF SOME N-HYDROXY-2-OXO-2H-1-BENZOPYRAN-3-CARBOXAMIDES
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Some N-hydroxy-2-oxo-2H-1-benzopyran-3-carboxamides have been prepared by reaction of carbon suboxide with 2-hydroxyaryloximes.
- Bonsignore, Leonardo,Loy, Guiseppe,Secci, Mario
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p. 5013 - 5016
(2007/10/02)
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