- Dicyanovinylcoumarin as a turn-on fluorescent sensor for cyanide ion
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Dicyanovinylcoumarin chemosensors (4a, 4b and 4c) were designed and synthesized by the Knoevenagel condensation reaction. The electronic absorption and emission spectra of the dicyanovinylcoumarin isomers exhibited red shifted absorption and less emission as compared to their precursor's coumarin aldehydes. The sensing behavior of dicyanovinylcoumarin isomers were studied for different anions. In these dicyanovinylcoumarin isomers, the 7-substituted isomer shows high selectivity towards CN? in the presence of other F?, Cl?, Br?, I?, ClO4?, HSO4? and NO2? ions. The effect of CN? on the structure of dicyanovinylcoumarin isomer was studied by performing DFT calculations. The theoretical calculations show strong agreement with the experimental results. The detection limit for CN? were found to be 1.14 × 10?8 M for 7-substitued dicyanovinylcoumarin isomer 4b.
- Reddy, T. Sheshashena,Choi, Myung-Seok
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Read Online
- A one-pot and convenient synthesis of coumarins in solventless system
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An efficient and facile preparation of simple coumarins via in situ Wittig reaction of salicylaldehydes, triphenylphosphine, and chloroethylacetate supported on MgO in satisfactory yields in solvent-free condition.
- Shockravi, Abbas,Valizadeh, Hassan,Heravi, Majid M.
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Read Online
- Synthesis of analogues of natural coumarins and coumarinolignans
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3-Aryl-4H-coumarins with the 1,3-benzodioxol, 1,4-benzodioxane, and 1,5-benzodioxepane moieties were synthesized by modified methods.
- Ismailova
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Read Online
- An expeditious coumarin synthesis via a "Pseudocycloaddition" between salicylaldehydes and ketene
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A variety of salicylaldehydes effected tandem nucleophilic addition onto ketene, leading to corresponding coumarins in good yields under mild conditions. This "pseudocycloaddition" represents a very mild variant of the historic Perkin synthesis of coumarin (which remains of key interest in both perfumery and several emerging areas).
- Chandrasekhar, Sosale,Kumar, Honnaiah Vijay
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Read Online
- Polyphosphoric acid-promoted synthesis of coumarins lacking substituents at positions 3 and 4
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Coumarins have recently emerged as a hot topic of research due to their diverse pharmacological properties. This work described a method for the synthesis of 3,4-diunsubstituted coumarins promoted by polyphosphoric acid (PPA) from salicylaldehydes and acetic anhydride. Various coumarins were produced in good to excellent yields.
- Yang, Li-Shou,Wang, Yu,Wang, En-Hua,Yang, Jan,Pan, Xiong,Liao, Xiu,Yang, Xiao-Sheng
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Read Online
- Synthesis method of coumarin derivatives
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The invention provides a synthesis method of coumarin derivatives. The synthesis method comprises the following steps: adding polyphosphoric acid PPA and a solvent N,N-dimethylformamide DMF, sequentially adding substituted salicylaldehyde and acetic anhydride, and carrying out a heating stirring reaction for 3-6 h under nitrogen protection; and after the reaction is finished, separating and purifying to obtain the coumarin derivative pure products. The synthesis method disclosed by the invention is disclosed for the first time, is short in reaction time, simple to operate, low in catalyst usage amount, cheap, easy to obtain and relatively good in derivative yield, not only provides a new method for synthesizing coumarin derivatives, but also provides more possibilities for large-scale production of products and improvement of production efficiency.
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Paragraph 0036-0038
(2020/09/23)
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- Fe(III)-Catalyzed Decarboxylative C3-Difluoroarylmethylation of Coumarins with α,α-Difluoroarylacetic Acids
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A facile Fe(III)-catalyzed oxidative decarboxylative radical coupling reaction of α,α-difluoroarylacetic acids with coumarins has been developed. This transformation, which provides a series of C-3 difluoroarylmethylated coumarins containing various functional groups in moderate-to-good yields, features easily accessible starting materials and operational simplicity.
- Chen, Zhiwei,Bai, Xiang,Sun, Jie,Xu, Yicheng
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supporting information
p. 7674 - 7682
(2020/07/15)
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- Unsymmetric Heteroleptic Ir(III) Complexes with 2-Phenylquinoline and Coumarin-Based Ligand Isomers for Tuning Character of Triplet Excited States and Achieving High Electroluminescent Efficiencies
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2-Phenylquinoline (PQ) and four coumarin-based ligand isomers with ease of synthesis have been selected to construct the unsymmetric heteroleptic [Ir(C1∧N)(C2∧N)(acac)]-type complex phosphors for organic light-emitting diodes (OLEDs). Six unsymmetric heteroleptic Ir(III) complexes have been obtained by employing four coumarin-based ligand isomers (L-C5/L-C6/L-C7/L-C8) in the [Ir(PQ)(C∧N)(acac)] structure due to two different coordinating carbon atoms in ligands L-C6 and L-C7 to form C-Ir bond. Through adopting unsymmetric heteroleptic [Ir(C1∧N)(C2∧N)(acac)] structure, these Ir(III) complexes can not only achieve impressive absolute quantum yield φp (ca. 0.5-1.0), higher than that of complex [Ir(PQ)2(acac)] (ca. 0.4), but also realize a dual modulation of both emission color from orange (AIrC6out, λ = 578 nm) to red (AIrC5, λ = 622 nm) and the character of the lowest triplet excited states (T1), showing both 3MLCT character and 3ILCT (intraligand charge transfer) character in their T1 states. AIrC5, AIrC7out, and AIrC7in show MLCT character from Ir(III) center to ligand L-C5 or L-C7 and ILCT character in ligand L-C5 or L-C7 in their T1 states, while AIrC6out, AIrC6in, and AIrC8 show MLCT character from Ir(III) center to ligand PQ and ILCT character in ligand PQ in their T1 states. Moreover, the color-tuning mechanism and the lowest triplet state characters are investigated in detail. AIrC6in and AIrC8 were selected as emitters to evaluate the electroluminescent (EL) performance due to their high φP of nearly up to unity. Optimal orange-emitting device B2 based on AIrC8 can give a maximum external quantum efficiency (ηext) of 23.9%, a maximum current efficiency (ηL) of 70.9 cd A-1, and a maximum power efficiency (ηP) of 60.7 lm W-1. All these impressive results can definitely demonstrate the effectiveness of our simple approach for tuning character of the triplet excited states and achieving high-performance Ir-based phosphors in OLEDs.
- Feng, Zhao,Wu, Yong,Wu, Zhaoxin,Yang, Xiaolong,Yu, Yue,Zhou, Guijiang
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supporting information
p. 12362 - 12374
(2020/09/15)
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- Visible-light-induced regioselective alkylation of coumarins via decarboxylative coupling with N-hydroxyphthalimide esters
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An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate to excellent yields. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance.
- Jin, Can,Yan, Zhiyang,Sun, Bin,Yang, Jin
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supporting information
p. 2064 - 2068
(2019/04/11)
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- Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
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A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.
- Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun
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supporting information
p. 1585 - 1591
(2019/08/07)
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- BIPHENYL COMPOUND AS CCR2/CCR5 RECEPTOR ANTAGONIST
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Provided is a CCR2/CCR5 receptor antagonist and the use thereof in the preparation of a drug for treating diseases associated with the CCR2/CCR5. In particular, disclosed are a compound represented by formula (I) and a pharmaceutically acceptable salt thereof
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Paragraph 0192
(2019/11/21)
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- Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions
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Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.
- Gulías, Moisés,Marcos-Atanes, Daniel,Mascare?as, José L.,Font, Marc
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supporting information
p. 1669 - 1673
(2019/09/04)
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- A coumarin type organic third-order nonlinear optical material and preparation and application thereof
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The invention relates to a coumarin type organic third-order nonlinear optical material. An arylamine derivative is connected to the 6 site of a core group that is coumarin, and includes N,N-dimethylbenzene, triphenylamine and carbazole phenyl. Preparatio
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Paragraph 0029-0033
(2019/06/07)
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- Organometallic iridium complex phosphorescent material containing coumarin skeleton and preparation method of phosphorescent material
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An organometallic iridium complex phosphorescent material containing a coumarin skeleton and a preparation method of the phosphorescent material are disclosed. The coumarin skeleton is introduced intoa traditional 2-phenylpyridine ligand, and through controlling the change of substitution positions and adopting an asymmetric structure type, double regulation and control of the luminescent wavelength and luminous efficiency of an obtained iridium complex is realized, so that the organic electrophosphorescent material having simple structure and excellent performance is obtained. By using the characteristics that the coumarin skeleton structure is highly rigid, simple, easy to synthesize, strong in luminescent property and the like, double regulation and control of the luminescent wavelength and luminous efficiency of the obtained iridium complex is realized.
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Paragraph 0147; 0151-0153
(2019/04/26)
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- Exploring the Structure-Activity Relationship and Mechanism of a Chromene Scaffold (CXL Series) for Its Selective Antiproliferative Activity toward Multidrug-Resistant Cancer Cells
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Multidrug resistance (MDR) is one major barrier in cancer management, which urges for new drugs to help treat MDR malignancies and elucidate MDR mechanisms. A series of chromene compounds (the CXL series) demonstrate increased antiproliferative activity toward MDR acute-myeloid-leukemia (AML) cells. The structure-activity relationship (SAR) of the antiproliferative potency has been partly characterized, whereas the structural determinants contributing to selectivity have not been investigated. In this study, three series of CXL compounds were synthesized and evaluated in HL60 and HL60/MX2 leukemia cells. The results not only confirmed previous SAR studies but also, for the first time, provided structural insights into the selectivity for MDR HL60/MX2 cells. Using the lead compounds as probes, we demonstrated that their modulation of intracellular-calcium homeostasis results in their antiproliferative potency and selectivity. Three candidates also demonstrate excellent in vitro safety profiles between cancer cells and normal cells, which will be evaluated in vivo in future studies.
- Bian, Tengfei,Chandagirikoppal Vijendra, Kavitha,Wang, Yi,Meacham, Amy,Hati, Santanu,Cogle, Christopher R.,Sun, Haifeng,Xing, Chengguo
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supporting information
p. 6892 - 6903
(2018/07/21)
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- Synthesis of 7-Azido-3-Formylcoumarin – A Key Precursor in Bioorthogonally Applicable Fluorogenic Dye Synthesis
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Coumarins represent an important group of natural products and a common part of various drugs and fluorescent dyestuffs. Herein, we present the synthesis of a coumarin that can serve as a key starting material in the design and synthesis of bioorthogonally applicable fluorogenic dyes. The synthesis of 7-azido-3-formylcoumarin started from 7-diallylaminocoumarin. This allyl protected aminocoumarin is otherwise hard to obtain by conventional methods but was conveniently accessed in good yields by a sequential, Wittig-reaction–UV isomerization process. This sequential approach was studied in more details and applied for the synthesis of a series of substituted coumarins even in one-pot.
- Pünk?sti, Zoltán,Kele, Péter,Herner, András
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supporting information
p. 1183 - 1188
(2018/03/21)
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- A novel coumarin derivative, composition for detecting cyanide ion comprising the same and method for detecting cyanide ion using the same
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The present invention provides a novel dicyanovinyl coumarin compound, a composition for detecting cyanide containing the same, and a method for detecting cyanide using the same. The dicyanovinyl coumarin compound, the composition for detecting cyanide containing the same, and the method for detecting cyanide using the same of the present invention can be usefully used as a detecting technique for confirming human safety in a field of cyanide detection. The method for detecting cyanide comprises a step for measuring a light having a wavelength range of 360-380 nm.COPYRIGHT KIPO 2018
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Paragraph 0047; 0063; 0064; 0068; 0071; 0072
(2018/09/08)
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- Synthesis method for coumarins compound
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The invention discloses a synthesis method for a coumarins compound. The structural formula is shown in the specification, wherein R1 is selected from one or more of -H, -CH3, -OCH3, -F, -Cl, -Br, -OH, -NO2 and N(CH2CH3)2 and R2 is selected from one of -H, -CH3 or CH2CH3. According to the invention, a 2-hydroxy cinnamate compound is directly utilized as a raw material and the coumarins compound is synthesized in one step under the catalytic effect of visible light. Compared with the present synthesis method, the synthesis method for the coumarins compound disclosed by the invention has the characteristics of simple method, mild condition and high yield; the reaction is carried out under normal temperature; and the visible light is utilized as a reaction energy source and is green and pollution-free.
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Paragraph 0072; 0073; 0074; 0076; 0077; 0078; 0079
(2017/08/29)
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- Development of 6-arylcoumarins as nonsteroidal progesterone antagonists. Structure–activity relationships and fluorescence properties
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Progesterone is involved in multiple physiological processes, including female reproduction, via binding to the progesterone receptor (PR). We have developed 6-arylcoumarins such as 5 and 6 as non-steroidal PR antagonists with receptor-binding-dependent f
- Kinoshita, Marie,Negishi, Mai,Sakai, Haruka,Hirano, Tomoya,Mori, Shuichi,Fujii, Shinya,Kagechika, Hiroyuki,Tanatani, Aya
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p. 5602 - 5610
(2016/10/24)
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- Rh-Catalyzed Synthesis of Coumarin Derivatives from Phenolic Acetates and Acrylates via C-H Bond Activation
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An efficient annulation strategy involving the reaction of phenolic acetates with acrylates in the presence of [Rh2(OAc)4] as catalyst and formic acid as reducing agent, leading to the high yield synthesis of coumarin derivatives, has been developed. The addition of NaOAc as a base increased the yield of the products. The reaction is quite successful for both electron-rich as well as electron-deficient phenolic acetates, affording coumarins with excellent regioselectivity, and proceeds via C-H bond activation proven by deuterium incorporation studies.
- Gadakh, Sunita K.,Dey, Soumen,Sudalai, Arumugam
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p. 11544 - 11550
(2015/12/04)
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- Cp?Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives
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Cp?Co(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C-H activation is the turnover limiting step. Furthermore, the efficiency of this reaction was demonstrated by the rapid total synthesis of three natural products herniarin, xanthyletin, and seselin.
- Liu, Xu-Ge,Zhang, Shang-Shi,Jiang, Chun-Yong,Wu, Jia-Qiang,Li, Qingjiang,Wang, Honggen
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supporting information
p. 5404 - 5407
(2015/11/18)
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- Derivatization of coumarins at the benzenoid ring in aqueous medium
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Some 6-disubstituted, 8-disubstituted, and/6,8-disubstituted compounds have been prepared from coumarin, 7-methylcoumarin, and 3,4-benzocoumarin. The Reimer-Tiemann reaction, Lederer-Manasse reaction, bromination using molecular bromine as well as 2,4,4,6-tetrabromocyclohex-2,5-dien-1-one, Elbs reaction, and diazocoupling have been carried under controlled conditions to obtain various derivatives. Further, several reactions of aldehyde derivatives of these coumarins have been carried on to prepare important functional compounds including some heterocycles. It is noteworthy that these aldehydes behave as phenolic aldehydes under alkaline conditions to undergo the Dakin reaction. The reactions are mostly carried in aqueous media involving a dianionic intermediate and hence fulfill one important criterion of green chemistry.
- Bhunia, Sankar C.,Pal, Sutanuka,Patra, Gopal C.,Pal, Sudhir C.
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p. 1679 - 1688
(2015/02/02)
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- A practical one-pot synthesis of coumarins in aqueous sodium bicarbonate via intramolecular Wittig reaction at room temperature
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An efficient, simple and relatively inexpensive method for the synthesis of coumarins in aqueous sodium bicarbonate at ambient temperature has been developed. It features an intramolecular Wittig reaction of substituted 2-formylphenyl 2-bromoacetate in saturated aqueous sodium bicarbonate. Its advantages include benign reaction conditions, easy work-up and good overall yield with short reaction time. Various substituted coumarins have been synthesized by utilizing this methodology. This journal is
- Belavagi, Ningaraddi S.,Deshapande, Narahari,Sunagar, Manjunath G.,Khazi, Imtiyaz Ahmed M.
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p. 39667 - 39671
(2014/12/11)
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- Design, synthesis, and biological and crystallographic evaluation of novel inhibitors of plasmodium falciparum enoyl-ACP-reductase (pf fabi)
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Malaria, a disease of worldwide significance, is responsible for over one million deaths annually. The liver-stage of Plasmodium's life cycle is the first, obligatory, but clinically silent step in malaria infection. The P. falciparum type II fatty acid biosynthesis pathway (PfFAS-II) has been found to be essential for complete liver-stage development and has been regarded as a potential antimalarial target for the development of drugs for malaria prophylaxis and liver-stage eradication. In this paper, new coumarin-based triclosan analogues are reported and their biological profile is explored in terms of inhibitory potency against enzymes of the PfFAS-II pathway. Among the tested compounds, 7 and 8 showed the highest inhibitory potency against Pf enoyl-ACP-reductase (PfFabI), followed by 15 and 3. Finally, we determined the crystal structures of compounds 7 and 11 in complex with PfFabI to identify their mode of binding and to confirm outcomes of docking simulations.
- Belluti, Federica,Perozzo, Remo,Lauciello, Leonardo,Colizzi, Francesco,Kostrewa, Dirk,Bisi, Alessandra,Gobbi, Silvia,Rampa, Angela,Bolognesi, Maria Laura,Recanatini, Maurizio,Brun, Reto,Scapozza, Leonardo,Cavalli, Andrea
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p. 7516 - 7526
(2013/11/06)
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- Palladium-catalyzed synthesis of benzofurans and coumarins from phenols and olefins
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Triple C-H functionalization: Palladium-catalyzed synthesis of benzofurans and coumarins by reacting phenols and unactivated olefins is described. The reaction comprises sequential C-H functionalization and shows diverse functional group compatibility. Preliminary mechanistic studies shed light into the possible mechanisms. Copyright
- Sharma, Upendra,Naveen, Togati,Maji, Arun,Manna, Srimanta,Maiti, Debabrata
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supporting information
p. 12669 - 12673
(2013/12/04)
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- Amine-catalyzed cascade synthesis of 3,4-diunsubstituted coumarins
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We disclose an efficient route to synthesize 3,4-diunsubstituted coumarins through a cascade organocatalytic reaction. The reaction is catalyzed by using of a combination of benzylamine (10 mol-%) and triethylamine (10 mol-%). Various salicylaldehydes were tested, and the corresponding coumarin products were obtained in good to high yields under mild and metal-free reaction conditions. We disclose an efficient route to synthesize 3,4-diunsubstituted coumarins through a cascade organocatalytic reaction. The reaction is catalyzed by using of a combination of benzylamine (10 mol-%) and triethylamine (10 mol-%). Various salicylaldehydes are tested, and the corresponding coumarin products are obtained in good to high yields under mild and metal-free reaction conditions. Copyright
- Wei, Jia,Wang, Pengcheng,Jia, Qianfa,Huang, Jiaoyao,Du, Zhiyun,Zhang, Kun,Wang, Jian
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supporting information
p. 4499 - 4502
(2013/07/26)
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- Tandem aldehyde-alkyne-amine coupling/cycloisomerization: A new synthesis of coumarins
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Cu-catalyzed A3 coupling of ethoxyacetylene, pyrrolidine and salicylaldehydes led to a concomitant cycloisomerization followed by hydrolysis of the resultant vinyl ether to afford coumarins in a cascade process. The reaction proceeded through exclusive 6-endo-dig cyclization and is compatible with halo and keto groups giving coumarins in good to moderate yields.
- Reddy, Maddi Sridhar,Thirupathi, Nuligonda,Haribabu, Madala
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supporting information
p. 180 - 184
(2013/03/14)
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- Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
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(E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 °C. We find that the use of tri-nbutylphosphane (20 mol %) as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60-70 °C). Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph3P=CHCO2Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.
- Boeck, Florian,Blazejak, Max,Anneser, Markus R.,Hintermann, Lukas
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supporting information
p. 1630 - 1636,7
(2020/09/14)
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- Structure-activity relationship (SAR) study of ethyl 2-amino-6-(3,5- dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (CXL017) and the potential of the lead against multidrug resistance in cancer treatment
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Multidrug resistance (MDR) against standard therapies poses a serious challenge in cancer treatment, and there is a clinical need for new anticancer agents that would selectively target MDR malignancies. Our previous studies have identified a 4H-chromene system, CXL017 (4) as an example, that can preferentially kill MDR cancer cells. To further improve its potency, we have performed detailed structure-activity relationship (SAR) studies at the 3, 4, and 6 positions of the 4H-chromene system. The results reveal that the 3 and 4 positions prefer rigid and hydrophobic functional groups while the 6 position prefers a meta or para-substituted aryl functional group and the substituent should be small and hydrophilic. We have also identified and characterized nine MDR cancer cells that acquire MDR through different mechanisms and demonstrated the scope of our new lead, 9g, to selectively target different MDR cancers, which holds promise to help manage MDR in cancer treatment.
- Aridoss, Gopalakrishnan,Zhou, Bo,Hermanson, David L.,Bleeker, Nicholas P.,Xing, Chengguo
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scheme or table
p. 5566 - 5581
(2012/08/29)
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- Synthesis of substituted coumarins and 2-quinolinones by cycloisomerisation of (hydroxy/aminophenyl)propargyl alcohols
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A new cycloisomerization strategy for the synthesis of coumarins and quinolinones is described. The addition of ethoxyacetylide to 2-hydroxyacetophenones directly resulted in 4-substituted coumarins by 6-endo-dig cycloisomerisation of the intermediate 3-ethoxy-1-(2-hydroxyphenyl)- 2-propyn-1-ols. Under similar conditions, 2-aminoacetophenone produced 2-ethoxyquinoline, a masked quinolinone, which was converted into the quinolinone by acid treatment. N-Protected intermediate 8 was isolated and converted into the quinolinone [with In(OTf)3 or H2SO 4] or the 3-iodo-2-quinolinone (with I2 and H +).
- Sridhar Reddy, Maddi,Thirupathi, Nuligonda,Babu, Madala Hari
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p. 5803 - 5809
(2012/11/07)
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- Synthesis of structural fragments of natural 3-phenoxycoumarins
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The synthesis of substituted and unsubstituted 3-phenoxycoumarins is described. Pleiades Publishing, Ltd., 2012.
- Ismailova,Mavlyanov,Kamaev
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p. 435 - 437
(2012/10/29)
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- Catalytic asymmetric conjugate addition of Grignard reagents to coumarins - Synthesis of versatile chiral building blocks
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A new protocol for the Cu-catalysed asymmetric conjugate addition of Grignard reagents to coumarins has been developed. The corresponding products are formed in high yields and enantioselectivities. Through a sequential protocol involving conjugate addition followed by nucleophilic ring opening of the chiral enolate, chiral esters and amides are readily accessible.
- Teichert, Johannes F.,Feringa, Ben L.
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supporting information; experimental part
p. 2679 - 2681
(2011/04/27)
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- Synthesis and biological evaluation of (6- and 7-Phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1
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17β-Hydroxysteroid dehydrogenase type 1 (17β-HSD1) is an enzyme that catalyzes NADPH-dependent reduction of the weak estrogen, estrone, into the most potent estrogen, estradiol, which exerts proliferative effects via the estrogen receptors. Overexpression of 17β-HSD1 in estrogen-responsive tissues is related to the development of hormone-dependent diseases, such as breast cancer and endometriosis; thus, 17β-HSD1 represents an attractive target for the development of new therapies. We have discovered that simple coumarines 1 and 2 significantly inhibit 17β-HSD1 in a recombinant enzyme assay, with high selectivity against 17β-HSD2. We postulated that the introduction of various p-substituted phenyl moieties to position 6 or 7 of the coumarin core using the Suzuki-Miyaura cross-coupling reaction would provide mimetics of steroidal structures with improved inhibition of 17β-HSD1. The best inhibitor in the series proved to be 6a, with an IC50 of 270 nM, and with exceptional selectivity for 17β-HSD1 over 17β-HSD2 and against the α and β estrogen receptors.
- Star?evi?, ?tefan,Bro?i?, Petra,Turk, Samo,Cesar, Jo?ko,Lani?nik Ri?ner, Tea,Gobec, Stanislav
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experimental part
p. 248 - 261
(2011/03/22)
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- 6-arylcoumarins as novel nonsteroidal type progesterone antagonists: An example with receptor-binding-dependent fluorescence
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Various 6-arylcoumarin derivatives were designed and synthesized as candidate nonsteroidal type progesterone antagonists. 6-Bromocoumarin derivatives were prepared from the corresponding 4-substituted 2-acetoxy-5-bromobenzaldehyde by employing the Still-Gennari modification of the Horner-Wadsworth-Emmons olefination reaction and were converted to 6-arylcoumarins by means of Suzuki-Miyaura cross-coupling reactions. The biological activities of these coumarin derivatives were evaluated by means of alkaline phosphatase assay in the T47D human breast carcinoma cell line. Among the synthesized compounds, 36 (IC50 = 0.12 μM) and 38 (IC 50 = 0.065 μM), bearing a five-membered heterocycle, showed potent PR antagonist activity. Competitive binding assay showed that compounds 8 and 34 have potent PR binding affinity. The fluorescence of compound 8 was dependent on the solvent properties and was increased in the presence of PR ligand binding domain. This property might be applicable to the development of fluorescence probes for studies on PR.
- Sakai, Haruka,Hirano, Tomoya,Mori, Shuichi,Fujii, Shinya,Masuno, Hiroyuki,Kinoshita, Marie,Kagechika, Hiroyuki,Tanatani, Aya
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experimental part
p. 7055 - 7065
(2011/12/04)
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- A single precatalyst tandem RCM-allylic oxidation sequence
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Ring closing metathesis of allyloxy styrenes and a subsequent Ru-catalyzed allylic oxidation can be combined to a tandem sequence that makes coumarins accessible using less active but more conveniently available first generation catalysts.
- Schmidt, Bernd,Krehl, Stefan
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supporting information; experimental part
p. 5879 - 5881
(2011/06/23)
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- Facile and efficient synthesis of simple coumarins via the Pd(II)/KHC03 catalyzed heck reaction under MW-Assisted neat conditions
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An efficient and fast Pd(II)-catalyzed cross-coupling of aryl halides with olefins has been developed. In the presence of Pd(OAc)2 and PdCI 2 cross-coupling of various aryl halides with olefins underwent smoothly to afford the corresponding products in moderate to high yields under MW mediated neat conditions. Simple coumarins were synthesized in good yields using 2-halophenoles in this procedure. Furthermore no solvent, solid support, expensive or/and toxic ligand is required.
- Valizadeh, Hassan,Vaghefi, Sevil
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experimental part
p. 113 - 120
(2011/06/25)
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- Structure-activity relationship and molecular mechanisms of ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4H-chromene-3-carboxylate (sHA 14-1) and its analogues
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Rapid development of multiple drug resistance against current therapies is a major barrier in the treatment of cancer. Therefore, anticancer agents that can overcome acquired drug resistance in cancer cells are of great importance. Previously, we have demonstrated that ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6- phenyl-4H-chromene-3-carboxylate (5a, sHA 14-1), a stable analogue of ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (6, HA 14-1), mitigates drug resistance and synergizes with a variety of cancer therapies in leukemia cells. Structure-activity relationship (SAR) studies of 5a guided the development of ethyl 2-amino-6-(3′,5′-dimethoxyphenyl)- 4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (5q, CXL017), a compound with low micromolar cytotoxicity against a wide-range of hematologic and solid tumor cells. More excitingly, our studies of 5q in camptothecin (CCRF-CEM/C2) and mitoxantrone (HL-60/MX2) resistant cancer cells highlight its ability to selectively kill drug-resistant cells over parent cancer cells. 5q inhibits tumor cell growth through the induction of apoptosis, with detailed mechanism of its selectivity toward drug-resistant cancer cells under investigation. These results suggest that 5q is a promising candidate for treatment of cancers with multiple drug resistance. 2009 American Chemical Society.
- Das, Sonia G.,Doshi, Jignesh M.,Tian, Defeng,Addo, Sadiya N.,Srinivasan, Balasubramanian,Hermanson, David L.,Xing, Chengguo
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experimental part
p. 5937 - 5949
(2010/03/24)
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- One-Pot wittig and knoevenagel reactions in ionic liquid as convenient methods for the synthesis of coumarin derivatives
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Efficient synthesis of a variety of 3-substituted coumarins via NaOMe-catalyzed Knoevenagel condensation and one-pot preparation of 3,4-unsubstituted coumarins in the presence of NaOMe via Wittig reaction in room-temperature ionic liquids are described. Knoevenagel condensation of 2-hydroxybenzaldehyde with dimethyl- and diethylmalonate was performed with excellent yields in room-temperature ionic liquids. Although diethyl- and dimethylchloromalonates were mostly recovered unchanged in Knoevenagel condensation, higher conversions were observed via Wittig reaction of these compounds with 2-hydroxybenzaldehyde derivatives and triphenylphosphine. Other 2-hydroxybenzaldehyde derivatives, methyl- and ethylchloroacetates, were reacted in ionic liquids to afford simple coumarins in good yields. These reactions widen the applicability of ionic liquid in organic synthesis. Copyright Taylor & Francis Group, LLC.
- Valizadeh, Hassan,Vaghefi, Sevil
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experimental part
p. 1666 - 1678
(2009/10/02)
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- Task-specific ionic liquid as reagent and reaction medium for the one-pot Horner-Wadsworth-Emmons-type reaction under microwave irradiation
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A task-specific imidazolium-based phosphinite ionic liquid (IL-OPPh2) was used as the dual solvent-reagent for the synthesis of E-cinamates and coumarin derivatives via the one-pot Horner-Wadsworth-Emmons-type reaction. The ionic liquid containing its cor
- Valizadeh, Hassan,Shockravi, Abbas
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experimental part
p. 4341 - 4349
(2010/04/26)
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- THERAPEUTIC COMPOUNDS
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The invention provides compounds of Formula (I) and (IV): as described herein, as well as salts thereof. The compounds have anti-cancer properties and/or chemosensitization properties.
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Page/Page column 24
(2008/12/04)
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- Resin-bound (succinimid-1-yloxycarbonylmethyl)triphenylphosphonium ylide - A synthon for rapid access to diverse heterocycles under microwave heating
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The synthesis of a novel and versatile resin-bound (succinimid-1- yloxycarbonylmethyl)triphenylphosphonium ylide is described. The use of this resin to the synthesis of several diverse heterocycles, whilst allowing for ease of workup, is reported. Georg Thieme Verlag Stuttgart.
- Henkel, Bernd
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p. 355 - 358
(2008/09/16)
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- Synthesis of coumarins by Pt-catalyzed hydroarylation of propiolic acids with phenols
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Synthesis of coumarins from phenols and propiolic acids was examined by using a Pt catalyst such as PtCl2/AgOTf, K2PtCl4/AgOTf, and K2PtCl4/AgOAc. Propiolic acid reacted even with less reactive phenols in trifluoroacetic acid to give coumarins and dihydrocoumarins. In the case of substituted propiolic acids, phenylpropiolic acid and 2-octynoic acid, the reactions proceeded selectively to afford coumarins in good to high yields.
- Oyamada, Juzo,Kitamura, Tsugio
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p. 6918 - 6925
(2007/10/03)
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- Simple synthesis of versatile coumarin scaffolds
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We describe an approach using ring-closing metathesis (RCM) to synthesize versatile coumarin derivatives that present appropriate substitutions both at the aromatic and at the α,β-unsaturated lactone ring. The obtained compounds can be used as molecular scaffolds suitable for further diversifications through a combinatorial approach. Copyright Taylor & Francis Group, LLC.
- Polito, Laura,Cravini, Massimiliano,Poletti, Laura,Lay, Luigi
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p. 2203 - 2209
(2007/10/03)
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- Microwave-induced in situ Wittig reaction of salicylaldehydes with ethyl chloroacetate and triphenylphosphine in solventless system
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A variety of coumarins was prepared by an in situ Wittig reaction of salicylaldehydes, triphenylphosphine and ethyl chloroacetate using sodium methoxide/molecular sieves (3A) under solvent-free conditions.
- Valizadeh,Shockravi,Heravi,Ghadim, H. Abbasi
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p. 718 - 720
(2007/10/03)
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- Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent. IV: Improved synthetic method of substituted coumarins
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The reaction of salicylaldehydes (2) with Horner-Wadsworth-Emmons (HWE) or Ando-HWE reagents was attempted to afford intramolecular phosphonate derivatives (6). A new synthetic method for coumarins (1) was achieved by using protected 2.
- Takeuchi, Yasuo,Ueda, Norihiro,Uesugi, Koji,Abe, Hitoshi,Nishioka, Hiromi,Harayama, Takashi
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p. 217 - 224
(2007/10/03)
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- An efficient large scale synthesis of coumarins by a dealkylative boron- mediated ring closure of 3-(ortho-methoxyaryl)propenoic esters
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Various substituted coumarins 3 were prepared via a dealkylative boron- mediated ring closure of ortho-methoxycinnamates 2.
- Dubuffet,Loutz,Lavielle
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p. 929 - 936
(2007/10/03)
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- Convenient synthesis of a simple coumarin from salicylaldehyde and Wittig reagent. II: Synthesis of bromo- and methoxycarbonylcoumarins
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Reaction of salicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in diethylaniline under reflux gave coumarins (3) in moderate to high yield except 3-methoxycarbonylsalicylaldehyde (1e). The substituent effects are discussed. A substituent at C6 on 1 usually facilitated the formation of the coumarin ring regardless of its electronic character.
- Harayama,Nakatsuka,Nishioka,Murakami,Hayashida,Ishii
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p. 2170 - 2173
(2007/10/02)
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- Synthesis of Coumarins by Nucleophilic Denitrocyclization Reaction
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2-propanedioic acids(2a-c) were denitrocyclized to coumarins (3a-c) by heating in quinoline in the presence of copper powder. 2-(4-Methoxiphenyl)-3-(2-nitrophenyl)-(Z)-2-propenoic acids (6a,b,d,e) were also similarly denitrocycli
- Oda, Noriichi,Yoshida, Yukio,Nagai, Shin-ichi,Ueda, Taisei,Sakakibara, Jinsaku
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p. 1796 - 1802
(2007/10/02)
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