cas 2555-30-8, 7-HYDROXY-4-PHENYLCOUMARIN 97

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Implementation of a spraying-assisted fine droplet formation-based simultaneous liquid-phase microextraction method for the determination of copper in clove extract samples
A simultaneous liquid-phase microextraction method was investigated as an alternative to the traditional dispersive liquid–liquid microextraction for the determination of copper. The potential of this approach is based on the simultaneous complexation and
Bakaraki Turan, Nouha,Zaman, Buse T.,Arvas, Bü?ra,Yola?an, ?i?dem,Bakirdere, Sezgin
p. 2929 - 2935
(2021)
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Nano-BFn/cellulose: a bio-based nano-catalyst for synthesis of bio-active 7-hydroxycoumarins
Nano-BFn/cellulose as a modified bio-based nano-catalyst has been synthesized from nanocellulose and boron triflouride via very simple steps. This novel nano-catalyst exhibited many advantages in the synthesis of 7-hydroxycoumarins such as good
Bamoniri, Abdolhamid,Fazeli-Attar, Seyede Azita,Mirjalili, Bi Bi Fatemeh
(2022/01/20)

2-Aminobenzoxazole-appended coumarins as potent and selective inhibitors of tumour-associated carbonic anhydrases
We have carried out the design, synthesis, and evaluation of a small library of 2-aminobenzoxazole-appended coumarins as novel inhibitors of tumour-related CAs IX and XII. Substituents on C-3 and/or C-4 positions of the coumarin scaffold, and on the benzoxazole moiety, together with the length of the linker connecting both units were modified to obtain useful structure-activity relationships. CA inhibition studies revealed a good selectivity towards tumour-associated CAs IX and XII (K i within the mid-nanomolar range in most of the cases) in comparison with CAs I, II, IV, and VII (K i > 10 μM); CA IX was found to be slightly more sensitive towards structural changes. Docking calculations suggested that the coumarin scaffold might act as a prodrug, binding to the CAs in its hydrolysed form, which is in turn obtained due to the esterase activity of CAs. An increase of the tether length and of the substituents steric hindrance was found to be detrimental to in?vitro antiproliferative activities. Incorporation of a chlorine atom on C-3 of the coumarin moiety achieved the strongest antiproliferative agent, with activities within the low micromolar range for the panel of tumour cell lines tested.
Fuentes-Aguilar, Alma,Merino-Montiel, Penélope,Montiel-Smith, Sara,Meza-Reyes, Socorro,Vega-Báez, José Luis,Puerta, Adrián,Fernandes, Miguel X.,Padrón, José M.,Petreni, Andrea,Nocentini, Alessio,Supuran, Claudiu T.,López, óscar,Fernández-Bola?os, José G.
p. 168 - 177
(2021/12/21)

B(C6F5)3-catalyzed synthesis of coumarins via Pechmann condensation under solvent-free conditions
Tris(pentafluorophenyl)borane [B(C6F5)3] catalyzed simple, efficient and environmentally benign protocol has been developed for the Pechmann condensation using variety of phenols and β-ketoesters under solvent-free conditions to afford coumarin derivatives. The present protocol displayed significant advantages such as low catalyst loading, short reaction time, mild reaction conditions, low toxicity, easy work-up, high yields, and compatibility with other functional groups. In addition, it is a convenient, clean, and fast alternative approach for synthesizing variety of coumarin derivatives. Moreover, the applicability of this method towards large-scale synthesis demonstrated its suitability for the industrial application. Graphic abstract: [Figure not available: see fulltext.]
Prajapti, Santosh Kumar,Rao, S. Prakash
p. 469 - 473
(2021/03/26)

Synthesis of C4-substituted coumarins via Pechmann condensation catalyzed by sulfamic acid. Insights into the reaction mechanism by HRMS analysis
A series of functionalized C4-substituted coumarins were synthesized by exploring the reaction of activated and non-activated phenols and β-ketoesters under solvent-free conditions in the presence of sulfamic acid as a Br?nsted acid catalyst. Fifteen exam
Barcellos, Thiago,Lenard?o, Eder J.,Moraes, Maiara C.
p. 151 - 163
(2022/01/28)

MnSb2O6-chitosan nanocomposite: An efficient catalyst for the synthesis of coumarins via Pechmann reaction
In this work, MnSb2O6-chitosan nanocomposites were synthesized and have been employed in Pechmann condensation for the synthesis of coumarin derivatives. MnSb2O6-chitosan nanocomposites were characterized by Fou
Bahramnezhad, Baharak,Ghazanfari, Dadkhoda,Sheikhhosseini, Enayatollah,Akhgar, Mohammad Reza,Ahmadi, Sayed Ali
supporting information
p. 173 - 181
(2019/11/20)

Promising new inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 4- arylcoumarin and monoterpenoid moieties as components of complex antitumor therapy
Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is an important DNA repair enzyme in humans, and a current and promising inhibition target for the development of new chemosensitizing agents due to its ability to remove DNA damage caused by topoisomerase 1 (Top1) poisons such as topotecan and irinotecan. Herein, we report our work on the synthesis and characterization of new Tdp1 inhibitors that combine the arylcoumarin (neoflavonoid) and monoterpenoid moieties. Our results showed that they are potent Tdp1 inhibitors with IC50 values in the submicromolar range. In vivo experiments with mice revealed that compound 3ba (IC50 0.62 μM) induced a significant increase in the antitumor effect of topotecan on the Krebs-2 ascites tumor model. Our results further strengthen the argument that Tdp1 is a druggable target with the potential to be developed into a clinically-potent adjunct therapy in conjunction with Top1 poisons.
Ayine-tora, Daniel M.,Chand, Raina,Chepanova, Arina A.,Ilina, Ekaterina S.,Kaledin, Vasily I.,Khomenko, Tatyana M.,Korchagina, Dina V.,Lavrik, Olga I.,Leung, Ivanhoe K. H.,Nikolin, Valeriy P.,Patel, Jinal,Popova, Nelly A.,Reynisson, Jóhannes,Salakhutdinov, Nariman F.,Volcho, Konstantin P.,Zakharenko, Alexandra L.,Zakharova, Olga D.
(2020/01/08)

New nanodrug design for cancer therapy: Its synthesis, formulation, in vitro and in silico evaluations
The aim of this study was to develop a novel nanosize drug candidate for cancer therapy. For this purpose, (S)-methyl 2-[(7-hydroxy-2-oxo-4-phenyl-2H-chromen-8-yl)methyleneamino]-3-(1H-indol-3-yl)propanoate (ND3) was synthesized by the condensation reacti
Budama-Kilinc, Yasemin,Kecel-Gunduz, Serda,Ozdemir, Burak,Bicak, Bilge,Akman, Gizem,Arvas, Busra,Aydogan, Feray,Yolacan, Cigdem
(2020/08/07)

Synthesis, computational studies and assessment of in vitro inhibitory activity of umbelliferon-based compounds against tumour-associated carbonic anhydrase isoforms IX and XII
Coumarins are widely diffused secondary metabolites possessing a plethora of biological activities. It has been established that coumarins represent a peculiar class of human carbonic anhydrase (hCA) inhibitors having a distinct mechanism of action involv
Angeli, Andrea,Capasso, Clemente,De Luca, Laura,Del Prete, Sonia,Gitto, Rosaria,Mancuso, Francesca,Supuran, Claudiu T.
p. 1442 - 1449
(2020/07/13)

Dual-core bis-pyrazol acetocoumarin derivative coordination compound laser material preparation method
The invention provides a dual-core bis-pyrazol acetocoumarin derivative coordination compound laser material preparation method which comprises the steps of 4-phenyl-7-hydroxycoumarin preparation, bis-pyrazol acetocoumarin derivative preparation and dual-
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Paragraph 0030-0032; 0034-0035; 0040-0042; 0044-0046; 0048

(2018/06/04)

Preparation method of bispyrazol acetocoumarin derivative laser material
The invention provides a preparation method of a bispyrazol acetocoumarin derivative laser material. The preparation method comprises the steps of preparing 4-phenyl-7-hydroxycoumarin, preparing a bispyrazol acetocoumarin derivative and the like. The prep
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Paragraph 0022-0027; 0032-0034; 0036-0038; 0040-0042

(2018/07/03)

Bispyrazol acetocoumarin derivative laser material and application thereof
The invention provides a bispyrazol acetocoumarin derivative laser material, and the structural formula is shown in the description. The invention further provides a preparation method of the bispyrazol acetocoumarin derivative laser material. The inventi
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Paragraph 0022-0024; 0027; 0034; 0038; 0042

(2018/07/03)

Inhibitory effects and structural insights for a novel series of coumarin-based compounds that selectively target human CA IX and CA XII carbonic anhydrases
Coumarin derivatives are a peculiar class of inhibitors of the family of metalloenzymes carbonic anhydrases (CA, EC 4.2.1.1). Several coumarins display higher affinity and selectivity toward most relevant and druggable CA isoforms. By decorating the natur
De Luca, Laura,Mancuso, Francesca,Ferro, Stefania,Buemi, Maria Rosa,Angeli, Andrea,Del Prete, Sonia,Capasso, Clemente,Supuran, Claudiu T.,Gitto, Rosaria
p. 276 - 282
(2017/12/07)

Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation
A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 μM for hAChE; 0.101 μM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.
He, Qi,Liu, Jing,Lan, Jin-Shuai,Ding, Jiaoli,Sun, Yongbing,Fang, Yuanying,Jiang, Neng,Yang, Zunhua,Sun, Liyuan,Jin, Yi,Xie, Sai-Sai
supporting information
p. 512 - 528
(2018/09/29)

Synthesis of Novel Anti-inflammatory Psoralen Derivatives?-?Structures?with?Distinct?Anti-Inflammatory?Activities
As a continuum to our work with coumarins, 12 psoralens were synthesized and evaluated for their anti-inflammatory activity. Psoralens were prepared in three steps; at first, 7-hydroxycoumarins were synthesized by von Pechmann condensation and then converted to 7-(2-oxopropoxy)coumarins. In the final step, a fused furan ring was introduced in an intramolecular ring-formation reaction. Based on a SciFinder search, two out of the 12 synthesized psoralen derivatives (compounds 9 and 12) were found to be novel. The derivatives displayed anti-inflammatory activity by suppressing iNOS and IL-6 expression, but their mechanism of action seemed to be dependent on the substitution. Compound 6 with propyl side chain inhibited NF-κB mediated transcription, while compound 10 with a phenyl substituent down-regulated iNOS expression in a posttranscriptional manner. The results introduce psoralen derivatives as promising anti-inflammatory compounds with potential for treatment of conditions involving iNOS and/or IL-6-mediated adverse responses.
Timonen, Juri M.,Vuolteenaho, Katriina,Lepp?nen, Tiina,Nieminen, Riina M.,Aulaskari, Paula,J?nis, Janne,Vainiotalo, Pirjo,Moilanen, Eeva
p. 2590 - 2597
(2018/09/25)

Preparation of a novel, efficient, and recyclable magnetic catalyst, γ-Fe2O3@HAp-Ag nanoparticles, and a solvent- and halogen-free protocol for the synthesis of coumarin derivatives
In this protocol, Ag supported on the hydroxyapatite-core–shell magnetic γ-Fe2O3nanoparticles (γ-Fe2O3@HAp-Ag NPs) as a novel, efficient, and magnetically recyclable catalyst is synthesized, and characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), and vibrating sample magnetometry (VSM). The use of the catalyst is described in the synthesis of coumarin derivatives by the Pechmann condensation of various phenols with β-ketoesters under solvent- and halogen-free conditions at 80?°C. This novel and inexpensive method offers advantages, such as recyclability simple experimental protocol, short reaction time, minimal work-up procedure, and excellent yields of products, together with desirable, eco-friendly, green aspects by avoiding toxic elements and solvents, and ease of recovery from the reaction mixture using an external magnet.
Abbasi, Zahra,Rezayati, Sobhan,Bagheri, Maryam,Hajinasiri, Rahimeh
p. 75 - 82
(2017/01/13)

Synthesis and biological evaluation of novel 7-hydroxy-4-phenylchromen-2-one–linked to triazole moieties as potent cytotoxic agents
A new series of novel 7-hydroxy-4-phenylchromen-2-one (1a)–linked 1,2,4-triazoles were synthesised using a click chemistry approach. All derivatives were subjected to 3-(4,5-dimethylthiazol-yl)-diphenyl tetrazolium bromide (MTT) cytotoxicity screening aga
Liu, Chuan-Feng,Shen, Qing-Kun,Li, Jia-Jun,Tian, Yu-Shun,Quan, Zheshan
p. 1111 - 1119
(2017/08/15)

SnCl4 grafted on silica gel: an efficient catalyst for solvent-free synthesis of coumarins via the Pechmann condensation
A facile synthesis of substituted coumarins via Pechmann condensation catalyzed by SnCl4 grafted on silica gel is described, which was conducted under solvent-free condition in high yields. The catalyst is noncorrosive and can be easily prepared and separated from the reaction mixture. This methodology offers some advantages with regard to yield of products, simplicity in operation and green aspects.
Sun, Rui,Gao, Yanjuan,Ma, Ying,Yang, Guangde,Li, Yiping
p. 737 - 742
(2017/01/17)

Synthesis and in vitro evaluation of leishmanicidal activity of 7-hydroxy-4-phenylcoumarin derivatives
Eight coumarin derivatives (2–8) were synthesized from 7-hydroxy-4-phenylcoumarin 1 and were evaluated for their in vitro leishmanicidal activity against promastigote and amastigote forms of Leishmania amazonensis, as well their toxicity in murine macroph
Rosa, Isael A.,de Almeida, Letícia,Alves, Karina F.,Marques, Marcos J.,Fregnan, Ant?nio M.,Silva, Claudinei A.,Giacoppo, Juliana O. S.,Ramalho, Teodorico C.,Carvalho, Diogo T.,dos Santos, Marcelo H.
p. 131 - 139
(2017/01/12)

Nanosilica molybdic acid: synthesis, characterization and application as a green and reusable catalyst for the Pechmann condensation
Abstract: Nanosilica molybdic acid (SMA NPs) was founded as an efficient and recyclable nanocatalyst for the synthesis of coumarin derivatives in excellent yields with good purity. Nano-SMA as a new solid acid was characterized by X-ray fluorescence, X-ray diffraction, energy-dispersive X-ray analyzer, transmission electron microscopy and Fourier transform infrared spectroscopy. Coumarin derivatives were obtained via the Pechmann condensation reaction of phenols and β-ketoesters at 80?°C under solvent-free conditions. The main advantages of the present procedure are high yields, shorter reaction time and green chemistry procedure, simple work-up and inexpensive and reusability of the catalyst. Graphical Abstract: [Figure not available: see fulltext.]
Kiani, Mahtab,Karami, Bahador
p. 655 - 663
(2017/01/17)

Neoflavonoids as inhibitors of HIV-1 replication by targeting the Tat and NF-κB pathways
Twenty-eight neoflavonoids have been prepared and evaluated in vitro against HIV-1. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase reporter gene. Inhibition of HIV transcription and Tat function were teste
Olmedo, Dionisio A.,López-Pérez, José Luis,Del Olmo, Esther,Bedoya, Luis M.,Sancho, Rocío,Alcamí, José,Mu?oz, Eduardo,San Feliciano, Arturo,Gupta, Mahabir P.
(2017/03/08)

Meglumine sulfate catalyzed solvent-free one-pot synthesis of coumarins under microwave and thermal conditions
A convenient method has been developed for the Pechmann reaction of phenols and β-keto esters catalyzed by meglumine sulfate. Solvent-free conditions, inexpensive catalyst, short reaction times, high yield, and ease of purification of the products are the advantages of this protocol. This novel catalytic system is expected to contribute to the development of more benign Pechmann condensation reactions of phenols with β-keto esters.
Moradi, Leila,Rabiei, Khadijeh,Belali, Fateme
supporting information
p. 1283 - 1291
(2016/08/16)

Microwave-assisted Synthesis and antifungal activity of coumarin[8,7-e][1,3]oxazine derivatives
The synthesis of novel coumarin[8,7-e][1,3]oxazine derivatives through a microwave-assisted three-component one-pot Mannich reaction is described in this study. All the target compounds were evaluated in vitro for their antifungal activity against Botryti
Zhang, Ming-Zhi,Zhang, Rong-Rong,Yin, Wen-Zheng,Yu, Xiang,Zhang, Ya-Ling,Liu, Pin,Gu, Yu-Cheng,Zhang, Wei-Hua
p. 611 - 618
(2016/07/12)

Rational Design, Synthesis and Evaluation of Coumarin Derivatives as Protein-protein Interaction Inhibitors
Herein we describe the design and synthesis of a new series of coumarin derivatives searching for novel HIV-1 integrase (IN) allosteric inhibitors. All new obtained compounds were tested in order to evaluate their ability to inhibit the interaction between the HIV-1 IN enzyme and the nuclear protein lens epithelium growth factor LEDGF/p75. A combined approach of docking and molecular dynamic simulations has been applied to clarify the activity of the new compounds. Specifically, the binding free energies by using the method of molecular mechanics-generalized Born surface area (MM-GBSA) was calculated, whereas hydrogen bond occupancies were monitored throughout simulations methods.
De Luca, Laura,Agharbaoui, Fatima E.,Gitto, Rosaria,Buemi, Maria Rosa,Christ, Frauke,Debyser, Zeger,Ferro, Stefania
p. 460 - 473
(2016/09/09)

Preparation and pharmacological effects of coumarin derivative and application of coumarin derivative to treatment on pruritus
The invention relates to preparation of a coumarin derivative 7,8-dihydroxy-4-trifluoromethyl-chromene-2H-chromen-2-one for treating the pruritus symptom, studies of pharmacodynamics on the aspects of a molecular pharmacology mechanism, a pruritus animal model and the like of the coumarin derivative, and a pharmaceutics study applicable to treatment on pruritus. The active compound is definite in pharmacological effect mechanism, is broad-spectrum and effective to treat the pruritus symptom, and can be used for clinical application to treatment on skin diseases.
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Paragraph 0070; 0071; 0072

(2016/11/17)

Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H14P5NaW30O110) (PA)
Escobar, Anglica M.,Ruiz, Diego M.,Autino, Juan C.,Romanelli, Gustavo P.
p. 10109 - 10123
(2016/01/12)

Multi-target tacrine-coumarin hybrids: Cholinesterase and monoamine oxidase B inhibition properties against Alzheimer's disease
A series of novel tacrine-coumarin hybrids were designed, synthesized and evaluated as multi-target agents against Alzheimer's disease. The biological assays indicated that most of compounds displayed potent inhibitory activity toward AChE and BuChE, and clearly selective inhibition for MAO-B. Among these compounds, 14c exhibited strong inhibitory activity for AChE (IC50 values of 33.63 nM for eeAChE and 16.11 nM for hAChE) and BuChE (IC50 values of 80.72 nM for eqBuChE and 112.72 nM for hBuChE), and the highest inhibitory activity against hMAO-B (IC50 value of 0.24 11/4M). Kinetic and molecular modeling studies revealed that 14c was a mixed-type inhibitor, binding simultaneously to catalytic, peripheral and mid-gorge sites of AChE. It was also a competitive inhibitor, which covered the substrate and entrance cavities of MAO-B. Moreover, 14c could penetrate the CNS and show low cell toxicity. Overall, these results suggested that 14c might be an excellent multi-target agent for AD treatment.
Xie, Sai-Sai,Wang, Xiaobing,Jiang, Neng,Yu, Wenying,Wang, Kelvin D.G.,Lan, Jin-Shuai,Li, Zhong-Rui,Kong, Ling-Yi
supporting information
p. 153 - 165
(2015/03/31)

Environmentally sustainable magnetic solid sulfonic acid: An efficient and reusable catalyst for the Pechmann reaction
Abstract An environmentally benign sulfonic acid nanocomposite based on Fe3O4@SiO2 core-shell magnetic nanoparticles, Fe3O4@SiO2@Et-PhSO3H, was prepared and the acidity and utility of the catalyst were explored for the synthesis of a diverse range of coumarin derivatives under solvent-free conditions. The catalyst shows potential for scale up in the synthesis of coumarins with high purity and was easily separated by using an external magnet. The recovered catalyst was reused in seven cycles without any significant loss of activity.
Mobaraki, Akbar,Yasham, Shahriar,Movassagh, Barahman
supporting information
p. 1263 - 1268
(2015/06/02)

Synthesis of osthole derivatives with grignard reagents and their larvicidal activities on mosquitoes
The structure of osthole has been modified to improve its larvicidal activity against mosquitoes. A new efficient synthesis of osthole derivatives with Grignard reagents has been developed, which employs CuI and LiCl as promoters and covers a broad range of substrates to afford the corresponding products in mild to good yields (up to 83%). Bio-activity evaluation showed that several products exhibited better activities than osthole. CuI and LiCl promoted efficient synthesis of osthole derivatives with Grignard reagents has been developed. Bio-activity evaluation showed that several products exhibited far better larvicidal activities against mosquitoes than osthole.
Liu, Ming,Liu, Yang,Hua, Xuewen,Wu, Changchun,Zhou, Sha,Wang, Baolei,Li, Zhengming
supporting information
p. 1353 - 1358
(2016/02/18)

Synthesis of 4-arylcoumarins via palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamates with diaryliodonium salts
The palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamate ester derivatives by using diaryliodonium(III) salts has been developed. With this method, 4-arylcoumarins were easily prepared in good to excellent yields under base-free conditions
Yang, Yang,Han, Jianwei,Wu, Xunshen,Xu, Shujia,Wang, Limin
supporting information
p. 3809 - 3812
(2015/06/08)

Synthesis of the coumarins via pechmann method in the presence of environmentally friendly Y(NO3)3×6H2O
Several substituted coumarins can be prepared in high yield and purity by direct reaction of β-keto esters and phenol derivatives in the presence of a catalytic amount Y(NO3)3×6H2O as Lewis acid and at ambient temperature under solvent-free conditions. Several substituted coumarins can be prepared in high yield and purity by direct reaction of β-keto esters and phenol derivatives in the presence of a catalytic amount Y(NO3)3×6H2O as Lewis acid and at ambient temperature under solvent-free conditions. This method that is based on Pechmann condensation is very easy and rapid reaction for the synthesis of coumarin derivatives. Copyright
Karami, Bahador,Kiani, Mahtab
p. 213 - 216
(2014/05/06)

BENZOPYRONE DERIVATIVE AND USE THEREOF
The present invention relates to the field of pharmaceutical chemistry, and in particular, to a benzopyrone derivative and a use thereof. The benzopyrone derivative is compound having a structure of formula (I) or a pharmaceutically acceptable salt thereof. It has been found by experiments that, this type of compounds is useful in prevention or treatment of neuropsychical diseases.
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Paragraph 0025; 0048

(2014/03/22)

BENZOPYRONE DERIVATIVE AND USE THEREOF
The present invention relates to the field of pharmaceutical chemistry, and in particular, to a benzopyrone derivative and a use thereof. The benzopyrone derivative is compound having a structure of formula (I) or a pharmaceutically acceptable salt thereof. It has been found by experiments that, this type of compounds is useful in prevention or treatment of neuropsychical diseases.
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Paragraph 0123

(2014/05/07)

Magnesium bis(trifluoromethane)sulfonimide: An efficient catalyst for the synthesis of coumarins under solvent-free conditions
Magnesium bis(trifluoromethane)sulfonimide [Mg(NTf2) 2] is an efficient catalyst for the synthesis of coumarins via the Pechmann condensation reaction of phenols and β-ketoesters under solvent-free conditions.
Wang, Hongshe
p. 411 - 414
(2013/05/21)

Design, synthesis and biological evaluation of novel 7-mercaptocoumarin derivatives as α1-adrenoceptor antagonists
Study on the pharmacophore model of α1-adrenoceptor (α1-AR) antagonists led to design a series of novel 7-mercaptocoumarin derivatives as α1-AR antagonists. All designed compounds have been synthesized and biologically eva
Xie, Sai-Sai,Wang, Xiao-Bing,Li, Jiang-Yan,Kong, Ling-Yi
p. 16 - 24
(2013/02/23)

Design, synthesis and evaluation of novel tacrine-coumarin hybrids as multifunctional cholinesterase inhibitors against Alzheimer's disease
A series of tacrine-coumarin hybrids (8a-t) were designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit ChE and self-induced β-amyloid (Aβ) aggregation, and to act as metal chelators. Especially, 8f displayed the greatest ability to inhibit acetylcholinesterase (AChE, IC50 = 0.092 μM) and Aβ aggregation (67.8%, 20 μM). It was also a good butyrylcholinesterase inhibitor (BuChE, IC50 = 0.234 μM) and metal chelator. Besides, kinetic and molecular modeling studies indicated that 8f was a mixed-type inhibitor, binding simultaneously to active, peripheral and mid-gorge sites of AChE. These results suggested that 8f might be an excellent multifunctional agent for AD treatment.
Xie, Sai-Sai,Wang, Xiao-Bing,Li, Jiang-Yan,Yang, Lei,Kong, Ling-Yi
p. 540 - 553
(2013/07/27)

Synthesis of coumarins and 2,3-dihydroquinazolin-4(1H)-ones using trichloroacetic acid as a catalyst
Trichloroacetic acid was used as an efficient catalyst for the synthesis of coumarins from phenols and β-ketoesters and in an efficient synthesis of 2,3-dihydroquinazolin-4(H)-ones through the condensation of 2-aminobenzamide with aldehydes or ketones under solvent-free conditions. The remarkable advantages offered by this method are short reaction times, simple procedure, and an easy work-up without using any chromatographic methods.
Karimi-Jaberi, Zahed,Zarei, Leila
p. 178 - 183
(2013/06/27)

Rational design, synthesis, evaluation and enzyme - Substrate structures of improved fluorogenic substrates for family 6 glycoside hydrolases
Methylumbelliferyl-β-cellobioside (MUF-G2) is a convenient fluorogenic substrate for certain β-glycoside hydrolases (GH). However, hydrolysis of the aglycone is poor with GH family 6 enzymes (GH6), despite strong binding. Prediction of the orientation of the aglycone of MUF-G2 in the +1 subsite of Hypocrea jecorina Cel6A by automated docking suggested umbelliferyl modifications at C4 and C6 for improved recognition. Four modified umbelliferyl-β-cellobiosides [6-chloro-4-methyl- (ClMUF); 6-chloro-4-trifluoromethyl- (ClF3MUF); 4-phenyl- (PhUF); 6-chloro-4-phenyl- (ClPhUF)] were synthesized and tested with GH6, GH7, GH9, GH5 and GH45 cellulases. Indeed the rate of aglycone release by H. jecorina Cel6A was 10-150 times higher than with MUF-G2, although it was still three orders of magnitude lower than with H. jecorina Cel7B. The 4-phenyl substitution drastically reduced the fluorescence intensity of the free aglycone, while ClMUF-G2 could be used for determination of kcat and KM for H. jecorina Cel6A and Thermobifida fusca Cel6A. Crystal structures of H. jecorina Cel6A D221A mutant soaked with the MUF-, ClMUF- and ClPhUF-β-cellobioside substrates show that the modifications turned the umbelliferyl group 'upside down', with the glycosidic bond better positioned for protonation than with MUF-G2. 2012 The Authors Journal compilation
Wu, Miao,Nerinckx, Wim,Piens, Kathleen,Ishida, Takuya,Hansson, Henrik,Sandgren, Mats,Stahlberg, Jerry
p. 184 - 198
(2013/03/28)

Synthesis and biological investigation of coumarin piperazine (piperidine) derivatives as potential multireceptor atypical antipsychotics
The discovery and synthesis of potential and novel antipsychotic coumarin derivatives, associated with potent dopamine D2, D3, and serotonin 5-HT1A and 5-HT2A receptor properties, are the focus of the present article. The most-promising derivative was 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl)butoxy) -4-methyl-8-chloro-2H-chromen-2-one (17m). This derivative possesses unique pharmacological features, including high affinity for dopamine D2 and D3 and serotonin 5-HT1A and 5-HT2A receptors. Moreover, it possesses low affinity for 5-HT2C and H1 receptors (to reduce the risk of obesity associated with chronic treatment) and hERG channels (to reduce the incidence of torsade des pointes). In animal models, compound 17m inhibited apomorphine-induced climbing behavior, MK-801-induced hyperactivity, and the conditioned avoidance response without observable catalepsy at the highest dose tested. Further, fewer preclinical adverse events were noted with 17m compared with risperidone in assays that measured prolactin secretion and weight gain. Acceptable pharmacokinetic properties were also noted with 17m. Taken together, 17m may constitute a novel class of drugs for the treatment of schizophrenia.
Chen, Yin,Wang, Songlin,Xu, Xiangqing,Liu, Xin,Yu, Minquan,Zhao, Song,Liu, Shicheng,Qiu, Yinli,Zhang, Tan,Liu, Bi-Feng,Zhang, Guisen
supporting information
p. 4671 - 4690
(2013/07/19)

Alternative two-step route to khellactone analogues using silica tungstic acid and sodium hydrogen phosphate
A series of coumarins was synthesised via the silica tungstic acid-catalysed Pechmann reaction; some of these were employed for known three-component reactions with aromatic aldehydes and malononitrile in the presence of sodium hydrogen phosphate (Na2HPO4) as a basic catalyst, affording a variety of potentially anti-HIV active khellactone analogues.
Karami, Bahador,Khodabakhshi, Saeed,Eskandari, Khalil
p. 1474 - 1478
(2013/07/26)

Diversity-oriented general protocol for the synthesis of privileged oxygen scaffolds: Pyrones, coumarins, benzocoumarins and naphthocoumarins
A new general methodology for the synthesis of various functionalized privileged oxygen heterocyclic scaffolds, viz. pyrones, coumarins, and benzannulated coumarins, is developed. The synthesis proceeds through carbanion-induced ring transformation of lactones with various methylene carbonyl compounds followed by DDQ-mediated unprecedented oxidative cleavage of oxaylidenes intermediates. Studies of the mechanism of the conversions of oxaylidene intermediates into corresponding carbonyl compounds in the presence of DDQ revealed that the reactions took place via the formation of a Michael adduct instead of an intermolecular charge transfer complex. The methodology offers the fabrication of diverse privileged scaffolds with tolerance for many functional groups onto the oxygen heterocyclic molecular framework.
Goel, Atul,Taneja, Gaurav,Raghuvanshi, Ashutosh,Kant, Ruchir,Maulik, Prakas R.
p. 5239 - 5253
(2013/08/23)

An environmentally friendly, chemoselective, and efficient protocol for the preparation of coumarin derivatives by Pechman condensation reaction using new and reusable heterogeneous Lewis acid catalyst polystyrene-supported GaCl 3
An environmentally benign Pechman protocol for the one-pot synthesis of 4-substituted coumarins through the condensation reactions of phenol substrates with β-ketoesters using polystyrene-supported GaCl3 (PS-GaCl3) as a highly active and reusable solid Lewis acid catalyst under mild and heterogeneous conditions in good to excellent yields is described. This new protocol is easy, simple, cost-effective, chemoselective, and in addition has the advantages of easy availability, stability, reusability and eco-friendly character of the catalyst, high to excellent yields, simple experimental and work-up procedure.
Rahmatpour, Ali,Mohammadian, Sara
p. 271 - 278
(2013/05/08)

Xanthan sulfuric acid: An efficient and recyclable solid acid catalyst for Pechmann condensation
In this report, substituted coumarins are formed via Pechmann condensation using various substituted phenols and ethyl acetoacetates in the presence of xanthan sulfuric acid as a solid acid catalyst under solvent-free conditions. This method is very simple, costeffective, and has shorter reaction times, and the catalyst could be reused. Copyright Taylor & Francis Group, LLC.
Kuarm, B. Suresh,Madhav, J. Venu,Rajitha
experimental part
p. 1770 - 1777
(2012/04/23)

Tetrakis(acetonitrile)copper(I) hexafluorophosphate catalyzed coumarin synthesis via pechmann condensation under solvent-free condition
Tetrakis(acetonitrile)copper(I) hexafluorophosphate (Cu(CH 3CN)4PF6) is used as an efficient catalyst in the Pechmann condensation reaction of phenols with ethyl acetoacetate leading to the formation of coumarin derivatives in excellent yields under solvent free conditions at ambient temperature. The method is simple, solvent-free and gives excellent yields in a short reaction time. Copyright
Soleimani, Ebrahim,Khodaei, Mohammad Mehdi,Batooie, Nasim,Samadi, Saadi
experimental part
p. 409 - 412
(2012/06/04)

Regioselective palladium-catalyzed direct cross-coupling of coumarins with simple arenes
An efficient method for the C4-regiocontrolled C-H functionalization of coumarins to enable facile oxidative cross-couplings with simple arene components is disclosed.
Min, Minsik,Hong, Sungwoo
supporting information
p. 9613 - 9615
(2012/10/29)

Palladium-catalyzed oxidative heck coupling reaction for direct synthesis of 4-arylcoumarins using coumarins and arylboronic acids
An efficient protocol for the direct synthesis of 4-arylcoumarins via palladium-catalyzed oxidative Heck coupling reaction of coumarins and arylboronic acids was developed. 4-Arylcoumarins were obtained in moderate to excellent yields, and the reaction also showed tolerance toward functional groups such as hydro, methoxy, diethylamino, nitro, and chloro groups.
Li, Yaming,Qi, Zisong,Wang, Huifeng,Fu, Xinmei,Duan, Chunying
supporting information; experimental part
p. 2053 - 2057
(2012/04/04)

A facile route to flavone and neoflavone backbones via a regioselective palladium catalyzed oxidative Heck reaction
A straightforward and atom-economical base-free palladium-catalyzed regioselective direct arylation of coumarins and chromenones is devised. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and allows construction of various biologically important flavone and neoflavone backbones.
Khoobi, Mehdi,Alipour, Masoumeh,Zarei, Samaneh,Jafarpour, Farnaz,Shafiee, Abbas
supporting information; experimental part
p. 2985 - 2987
(2012/04/04)

Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives
A number of 7-hydroxycoumarins have been synthesised by Pechmann cyclisation using differently substituted resorcinols employing perchloric acid as the condensing agent. All the compounds have been characterised by analytical and spectroscopic methods. The anti-inflammatory properties were tested with LPS-induced inflammation in J774 macrophages. Expression of iNOS and COX-2 was determined by Western blot, NO by nitrite assay and IL-6 by ELISA analyses. Fifteen of the tested 7-hydroxycoumarins also inhibited IL-6 production but none of them had any major inhibitory effect on COX-2 expression.
Timonen, Juri M.,Nieminen, Riina M.,Sareila, Outi,Goulas, Antonis,Moilanen, Lauri J.,Haukka, Matti,Vainiotalo, Pirjo,Moilanen, Eeva,Aulaskari, Paula H.
supporting information; experimental part
p. 3845 - 3850
(2011/11/13)

ZrOCl2.8H2O/SiO2: An efficient and recyclable catalyst for the preparation of coumarin derivatives by Pechmann condensation reaction
Silica gel supported zirconyl chloride octahydrate was found to be an efficient and recyclable catalyst for the synthesis of a series of biologically important molecules in high turnover numbers and rates. Several substituted coumarins can be prepared in high yield and purity by direct reaction of β-keto esters and phenol derivatives in the presence of a catalytic amount of ZrOCl2.8H2O/SiO2 as Lewis acid and at ambient temperature under solvent-free conditions. This method which is called Pechmann condensation is a very easy and a rapid reaction for the synthesis of coumarin derivatives.
Karami, Bahador,Kiani, Mahtab
experimental part
p. 62 - 67
(2012/01/15)

Synthesis of coumarins and neoflavones through zinc chloride catalyzed hydroarylation of acetylenic esters with phenols
Acetylenic esters react with oxygenated phenols under solvent-free conditions in the presence of only 5 mol% of zinc chloride as a catalyst to give coumarins and neoflavones in reasonable-to-good yields. Georg Thieme Verlag Stuttgart. New York.
Leao, Raquel A. C.,Def.demoraes, Paula,Pedro, Marcella C. B. C.,Costa, Paulo R. R.
experimental part
p. 3692 - 3696
(2011/12/16)