Showing papers on "Benzopyran published in 2016"
TL;DR: Of the seven compounds evaluated for antiproliferative activities, 3k and 3r were the most active, inhibiting leukaemia K562 cell proliferation by 50% after 72 h at concentrations of 4.5 and 7.9 mu M, whereas normal peripheral blood mononuclear cells were not affected.
28 citations
TL;DR: The most promising molecule, 16c, was further analyzed for its effect on cell cycle and apoptosis of estrogen receptor positive cancer cells (MCF- 7 cells) which showed that 16c triggered apoptosis in MCF-7 cells and arrested cells population at sub-G0 (apoptotic) and G2M phase.
15 citations
TL;DR: A small library of glycofused tricyclic compounds with a central pyran ring chemically modified in the position para to the ring oxygen has been synthesised and the influence of the chemical modification on the structural conformation and their ability to bind Aβ peptide has been evaluated.
Abstract: A small library of glycofused tricyclic compounds with a central pyran ring chemically modified in the position para to the ring oxygen has been synthesised. The influence of the chemical modification on the structural conformation of the compounds and on their ability to bind Aβ peptide has been evaluated respectively using molecular mechanics (MM) and molecular dynamics (MD) simulations, and STD NMR spectroscopy. The introduction of particularly polar/charged groups leads to the loss of binding ability, without a significant change in the conformation, whilst other substitutions does not significantly affect either the structural conformation or the binding.
15 citations
TL;DR: In this paper, a new spirobenzopyranindoline containing a rhodamine fragment bonded by an azomethine spacer was synthesized based on 6-formyl-7-hydroxy-substituted spiropyran; the new compound exhibited complexation properties in solutions
Abstract: A new spirobenzopyranindoline containing a rhodamine fragment bonded by an azomethine spacer with the benzopyran fragment was synthesized based on 6-formyl-7-hydroxy-substituted spiropyran; the new compound exhibited complexation properties in solutions
6 citations
TL;DR: The Oxa-Pictet-Spengler reaction of methyl 3-hydroxy-4-phenylbutanoate was explored to obtain novel σ receptor ligands to yield spirocyclic compounds that show high ρ1 affinity and σ1/σ2 selectivity.
5 citations
TL;DR: Total syntheses of teadenols A and B, isolated from fermented tea, were accomplished in a highly stereocontrolled manner, utilizing the different conformational preferences of cyclic and acyclic carbonate precursors to obtain cis- and trans-fused benzopyran rings, respectively, via intramolecular etherification.
Abstract: Total syntheses of teadenols A and B, isolated from fermented tea, were accomplished in a highly stereocontrolled manner. Key steps were an organocatalytic asymmetric α-aminoxylation reaction of an aldehyde and a palladium-catalyzed intramolecular allylic substitution with phenol. In the latter reaction, we utilized the different conformational preferences of cyclic and acyclic carbonate precursors to obtain cis- and trans-fused benzopyran rings, respectively, via intramolecular etherification.
4 citations
TL;DR: In this article, the E-isomer of alcohol Me2CHCH(OH) CH2CH2CH=C(Me)CH2Ch2Ph with CF3SO3H was shown to give a substituted tetrahydropyrano-[3,2-c][1]-benzopyran.
Abstract: Decarboxylation of α-allyl-substituted acetoacetic esters afforded α-allyl ketones that were reduced with L-selectride [LiBH(s-Bu)3] in alcohols RCH(OH)CH2CH2CH=C(Me)CH2R'. The latter reacted with methyl 4-hydroxy-3-formylbenzoate and methyl orthoformate in the presence of p-toluenesulfonic acid to provide trans-tetrahydropyrano[3,2-с][1]benzopyran. In reaction of the E-isomer of alcohol Me2CHCH(OH) CH2CH2CH=C(Me)CH2CH2Ph with CF3SO3H a stereoselective cyclization occurred with the formation of 2,6-disubstituted tetrahydropyran; Prins reaction with 4-bromobenzaldehyde and salicylaldehyde in the presence of boron trifluoride etherate also proceeded stereoselectively giving a substituted tetrahydropyrano-[3,2-c][1]-benzopyran.
4 citations
Patent•
10 Feb 2016
TL;DR: In this article, a coumarin compound N'-(quinoiline-2-methylene)-7-diethylamine (NQM)-7D-Coumarin-3-formylhydrazine with metal ion recognizing groups and a preparation method and application was presented.
Abstract: The invention belongs to the technical field of chemical sensing, particularly relates to a coumarin compound N'-(quinoiline-2-methylene)-7-diethylamine coumarin-3-formylhydrazine with metal ion recognizing groups and a preparation method and application of the coumarin compound, and aims at providing the coumarin compound N'-(quinoiline-2-methylene)-7-diethylamine coumarin-3-formylhydrazine high in sensitivity, selectivity and water solubility. The compound is obtained by introducing a diethylamino group to the 7th site of a coumarin mother nucleus benzopyran structure to serve as the electron donating group and introducing an aldehyde quinoline structure with copper iron specificity combining capacity to the 3rd site of the coumarin mother nucleus benzopyran structure through the Schiff's base reaction. The compound can be used as a fluorescent agent for fluorescent detection of metal ions and particularly used for fluorescent detection of Cu2+.
3 citations
3 citations
Patent•
07 Dec 2016
TL;DR: In this article, a method for synthesizing a chiral spirocyclo-oxindole-benzopyran-ketone-3,4-dihydro-pyran compound is presented.
Abstract: The invention discloses a method for synthesizing a chiral spirocyclo-oxindole-benzopyran-ketone-3,4-dihydro-pyran compound. The method comprises the following steps: using an isatin derivative beta, gama-unsaturated alpha-keto ester and 3-hydroxy-4-hydrogen-chromene-4-ketone as reactants, and synthesizing in a solvent under the catalysis of chiral multifunctional chiral quinine thiourea to obtain a product. The method provided by the invention has the advantages of simple and easy obtaining of raw materials, mild reaction conditions, simple and convenient post-treatment, wide range of suitable substrates, high yield and high enantioselectivity, and the synthesized product can be used for synthesizing intermediates of drugs, insecticides and photoelectric materials.
3 citations
Patent•
18 May 2016TL;DR: In this article, a 4-sulfur pentafluoride phenol compound, a preparing method and a preparation method for a SPMB substituted benzopyran compound are presented.
Abstract: The invention provides a 4-sulfur pentafluoride phenol compound, a preparing method and a preparing method for a sulfur pentafluoride substituted benzopyran compound. Sulfur pentafluoride phenol is used as a raw material, sulfur pentafluoride sulfur pentafluoride with multiple substituent groups is synthesized through multi-step synthesis, and then the sulfur pentafluoride substituted benzopyran compound is synthesized on the basis. The method is simple and low in cost, has wide industrial application prospects and overcomes the defects that at present, the number of types of sulfur pentafluoride phenol is small, and the requirement for synthesizing various sulfur pentafluoride substituted benzopyran compounds cannot be met.
Patent•
06 Apr 2016
TL;DR: In this paper, diethylin was introduced as an electron donating group into the 7-site of a coumarin mother nucleus benzopyran structure, activating carboxyl at the 3-site through a chloroformylation reaction and reacting with hydroxy on 7-hydroxycoumarin.
Abstract: The invention belongs to the technical field of coumarin compounds containing heterocyclic rings and specifically relates to 7-N,N-diethylamino-coumarin-3-carboxylic acid-7-benzopyrone and its preparation method and application By introducing diethylin as an electron donating group into the 7-site of a coumarin mother nucleus benzopyran structure, activating carboxyl at the 3-site through a chloroformylation reaction and reacting with hydroxy on 7-hydroxycoumarin, 7-N,N-diethylamino-coumarin-3-carboxylic acid-7-benzopyrone is generated The compound is a fluorescent reagent with high sensitivity and good selectivity and can be used in fluorescence detection of metal ions
Journal Article•
TL;DR: In this paper, a Schiff-base ligand, 2p-hydroxy benzoic-4p-tolyl imino-5,7-two hydroxy benzopyran, C22H17O4N (Mr = 359.1) has been synthesized by the condensation reaction of p-methyl-anilin and apigenin.
Abstract: Apigenin as a natural flavonoid shows limited antioxidant activities as new drug. The natural flavonoid derivatives as drug have been a hot topic to achieve effective drug innovation. In the paper, a novel Schiff-base ligand, 2-p-hydroxy benzoic-4-p-tolyl imino-5,7-two hydroxy benzopyran, C22H17O4N (Mr = 359.1) has been synthesized by the condensation reaction of p-methyl-anilin and apigenin. The above ligand and its copper (II) complex, [C44H32O8N2Cu] has been synthesized and characterize by IR, UV, MS, HNMR, DSC-TGA, etc. The ligand and metal complex exhibit yellow fluorescence under UV light. In addition, the antioxidant activity of the apigenin and its Schiff base metal complex were determined by superoxide and hydroxyl radical scavenging methods in vitro. The metal complex was found to process potent antioxidant activity and be better than apigenin.
Patent•
21 Sep 2016
TL;DR: In this paper, a benzopyran-thiophane derivative with antibacterial activity and a synthesis method and application of the derivative were described. But they did not specify a structural formula for the derivative.
Abstract: The invention discloses a benzopyran-thiophane derivative with antibacterial activity and a synthesis method and application of the benzopyran-thiophane derivative. A structural formula (I) of the benzopyran-thiophane derivative is as shown in the specification, wherein R1 is selected from hydrogen, chlorine, bromine or methoxyl, and R2 is selected from hydrogen, chlorine, bromine, methyl, methoxyl or trifluoromethyl. The benzopyran-thiophane derivative has an excellent antibacterial effect and can be used as a potential antibacterial agent.
Patent•
10 Feb 2016
TL;DR: The application of a benzopyran derivative represented as the formula (I) and a pharmaceutically acceptable salt thereof in preparation of drugs for treating hyperuricaemia is discussed in this paper.
Abstract: The invention discloses an application of a benzopyran derivative represented as the formula (I) and a pharmaceutically acceptable salt thereof in preparation of drugs for treating hyperuricaemia. The benzopyran derivative not only has strong in-vitro inhibition effect on xanthine oxidase but also can significantly reduce the serum uric acid level of mice suffered from the hyperuricaemia. The benzopyran derivative has dose-dependent, is free of toxic and side effects, is good in safety and can be used as a potential xanthine oxidase inhibitor and a uric acid reducing medicine for treating the hyperuricaemia and gout or gout complications caused by the hyperuricaemia.
Patent•
30 Jun 2016
TL;DR: In this paper, a method to prepare a benzopyran compound and its use for treating pulmonary fibrosis was presented. But this method requires the extraction, separation, and purification of a broth of Streptomyces xiamenensis CGMCC No. 5675.
Abstract: The present invention opens to the public a method to prepare a benzopyran compound and its use for treating pulmonary fibrosis. A benzopyran compound has a structure (I): in which: R1 represents hydrogen, C1-C4 alkyl, or various remaining amino acid moieties after removal of an amino group; R2 represents hydrogen, C1-C4 alkyl, or various remaining amino acid moieties after removal of an amino group; R3 represents hydrogen, or C1-C4 alkyl; and n is any integer of 1-4, wherein the benzopyran compound is derived from a broth of Streptomyces xiamenensis CGMCC No. 5675 by extraction, separation and purification. The derivatives of xiamenmycin made from the present invention have a higher bioactivity to suppress the proliferation of normal human lung fibroblast, and medicinal products containing the same are useful in the treatment of pulmonary fibrosis.
TL;DR: In this paper, a = 9.3751(2) Å, b = 17.3340(3)Å, c = 13.3828(2), β = 98.460(1)°, V = 2151.15(7) ǫ Å3, Z = 8, Rgt(F) = 0.0381, wRref(F2) =0.1065, T = 150 (2) K.
Abstract: Abstract C13H10O4, monoclinic, P21/n (no. 14), a = 9.3751(2) Å, b = 17.3340(3) Å, c = 13.3828(2) Å, β = 98.460(1)°, V = 2151.15(7) Å3, Z = 8, Rgt(F) = 0.0381, wRref(F2) = 0.1065, T = 150(2) K.
TL;DR: In this article, the authors investigate the activities of benzopyran (chromones) and benzofuranones (coumaranones) derivatives against Steinernema feltiae (S. feltiae).
Abstract: This study was purposed to inquire the activities of benzopyran (chromones) and benzofuranones (coumaranones) derivatives against Steinernema feltiae (S. feltiae). The toxicity assay against S. feltiae showed that benzopyran derivatives 2, 3, 4, 6, and 9 have the highest activity on S. feltiae with viabilities percentage of <50%. The compound 9 demostrated the highest activity with LD 50 and LD values, 7.2 and 52.2 μM, respectively. The activities of compound 7 and 10 showed the lowest toxicity. Interestingly, the activity of benzofuranone derivatives showed significant activities against S. feltiae. Compare to benzopyran derivatives, the benzofuranone derivatives has the highest toxicity, in particular compound 13 with LD 5.45 μM. The nematicidal assay showed that benzofuranones (coumaranones) derivatives revealed higher activities than benzopyran (chromones) derivatives. Key words: chromones, benzopyran, coumaranones, benzofuranone, and Steinernema feltiae
Patent•
14 Jun 2016
TL;DR: In this article, the authors disclosed deuterated benzopyran compounds having structure features as shown in Formula (I), or pharmaceutically acceptable salts or stereoisomers thereof, or prodrug molecules thereof.
Abstract: The present invention discloses deuterated benzopyran compounds having structure features as shown in Formula (I), or pharmaceutically acceptable salts or stereoisomers thereof, or prodrug molecules thereof. With excellent anti-inflammatory and analgesic effects and the capability to inhibit growth of tumor cells, such compounds are novel COX-2 selective inhibitors. The compounds and pharmaceutically acceptable salts thereof disclosed by the present application can be applied in preparing anti-inflammatory and analgesic drugs and drugs for treating or preventing tumors.
01 Jan 2016
TL;DR: In this article, 3-methyl-1H-2-benzopyran-1-one was synthesized in excellent yields by the reaction of homophthalic anhydride with acetyl chloride using pyridine as a catalyst.
Abstract: 3-methyl-1H-2-benzopyran-1-one was synthesized in excellent yields by the reaction of homophthalic anhydride with acetyl chloride using pyridine as a catalyst, followed by rearrangement of 4-acetyl-1H-2-benzopyran-1,3(4H)- dione with Conc. Sulphuric acid at high temperature.
Patent•
21 Dec 2016
TL;DR: The 2-H benzopyran derivative has a structural formulashown in formula (1), the preparation method is as follows: in a reactor, adding an alkynyl ether, an olefine acid ester and a solvent, adding a palladium salt catalyst and an oxidant, stirring for reacting for 3 to 48 hours at 20 to 150 DEG C, at the end of the reaction, cooling to room temperature, removing the solvent by vacuum evaporation to obtain a crude product, purifying by column chromatography to obtain the 2H benz
Abstract: The invention belongs to the technical field of organic synthesis, and discloses a 2-H benzopyran derivative and a synthesis method thereof The 2-H benzopyran derivative has a structural formulashown in formula (1), the preparation method is as follows: in a reactor, adding an alkynyl ether, an olefine acid ester and a solvent, adding a palladium salt catalyst and an oxidant, stirring for reacting for 3 to 48 hours at 20 to 150 DEG C, at the end of the reaction, cooling to room temperature, removing the solvent by vacuum evaporation to obtain a crude product, purifying by column chromatography to obtain the 2-H benzopyran derivative The synthesis method has the advantages of simple and safe operation, easily available raw materials, cheap price, good functional group adaptability, wide substrate adaptability and environment friendliness, and is conducive to industrial production, can be widely used in synthesis of pesticides, pharmaceuticals and natural products
TL;DR: A tandem one pot reaction involving gem-dichlorination, hydrolysis and nitrile oxide generation from 7-alkoxy-4-chloro-2,2-dimethyl-2H-chromene-6-carbaldehyde oxime followed by olefin/alkyne cycloaddition has been carried out in good yield at ambient temperature using open flask chemistry as discussed by the authors.
Abstract: A tandem one pot reaction involving gem-dichlorination, hydrolysis and nitrile oxide generation from 7-alkoxy-4-chloro-2,2-dimethyl-2H-chromene-6-carbaldehyde oxime followed by olefin/alkyne cycloaddition has been carried out in good yield at ambient temperature using open flask chemistry. The synthesized 4-chromanone derivatives show conformational isomerism as determined by VT 1H-NMR, confirmed by X-ray crystallography and explained by DFT calculations. This can be a general method for C-3 electrophilic chlorination of benzopyran derivatives.
TL;DR: A comprehensive survey of the synthesis and chemistry of the title nitrile covering the literature published during 2005-2014 is given in this article, with a focus on the synthesis process.
Abstract: Review: comprehensive survey of the synthesis and chemistry of the title nitrile covering the literature published during 2005-2014; 70 refs.