Showing papers on "Benzopyran published in 2004"
••
TL;DR: Three unique pyrano-1,6-dione derivatives and a new furo[3,2-c]pyran-4-one, named phelligridins C-F (2-5), together with hispolon (8), (E)-4-(3,4-dihydroxyphenyl)but-3-en-2-one (9), 4-hydroxybenzaldehyde, protocatechualdehyde,
Abstract: Three unique pyrano[4,3-c][2]benzopyran-1,6-dione derivatives and a new furo[3,2-c]pyran-4-one, named phelligridins C−F (2−5), together with hispolon (8), (E)-4-(3,4-dihydroxyphenyl)but-3-en-2-one (9), 4-hydroxybenzaldehyde, protocatechualdehyde, syringic acid, protocatechuic acid, caffeic acid, isoergosterone, and octadecyl ferulate were isolated and identified from the ethanolic extract of Phellinus igniarius. Their structures were determined by spectroscopic methods including IR, MS, and 1D and 2D NMR experiments. The structures of the new compounds were characterized as 3-(4-hydroxystyryl)-8,9-dihydroxypyrano[4,3-c]isochromene-4-one (2), 3-(3,4-hydroxystyryl)-8,9-dihydroxypyrano[4,3-c]isochromene-4-one (3), 8,9-dihydroxy-3-{5‘,6‘-dihydroxy-5‘ ‘-methyl-3‘ ‘-oxo-spiro[fural-2‘ ‘(3‘ ‘H),1‘-indene]-2‘-yl}-1H,6H-pyrano[4,3-c][2]benzopyran-1,6-dione (4), and (3Z)-3-(3,4-dihydroxybenzylidene)-6-(3,4-dihydroxystyryl)-2,3-dihydro-2-methoxy-2-(2-oxo-propyl)furo[3,2-c]pyran-4-one (5), respectively. Some compound...
161 citations
••
TL;DR: The reaction of aromatic aldehyde, malononitrile and 1,3-cyclohexanediones in water in the presence of triethylbenzyl-ammonium chloride (TEBA) provides an efficient access to 3-cyano-substituted 2-...
Abstract: The reaction of aromatic aldehyde, malononitrile and 1,3-cyclohexanediones in water in the presence of triethylbenzyl-ammonium chloride (TEBA) provides an efficient access to 3-cyano-substituted 2-...
60 citations
••
47 citations
••
TL;DR: In this article, a three-component condensation involving reactive phenols, aldehydes, and active methylene substrates is described under BF3.Et2O catalysis to afford benzopyranyl products in satisfactory yields.
Abstract: A three-component condensation involving reactive phenols, aldehydes, and active methylene substrates is described under BF3.Et2O catalysis to afford benzopyranyl products in satisfactory yields.
45 citations
••
TL;DR: In this paper, the synthesis of 1-benzopyrano[3,4d]isoxazole-4-one has been studied using 3-(alkyl-/aryl-aminomethylene)chroman-2,4-dione depending upon the reaction medium.
27 citations
•
26 Mar 2004TL;DR: The subject of as discussed by the authors concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders, and the compounds of particular interest are benzopyrans and their analogs defined by formula (1).
Abstract: The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula (1). Wherein Z, X, R1, R2, R3, and R4 are as described in specification.
22 citations
••
TL;DR: The synthesis, binding affinity for estrogen receptor subtypes (ER alpha and ER beta) and pharmacological activity on rat uterus of a new class of potent ligands, characterized by a 3-phenylbenzopyran scaffold with a basic side chain in position 4, are reported.
22 citations
••
TL;DR: Of all the compounds of this series, spirobipyridopyran (1) inhibited specifically the growth of human melanoma (HBL) cells but not the grow of normal fibroblasts (WI38), and Indolinospirobenzopyrans showed significant cytostatic activities against all tumor cell lines.
19 citations
••
TL;DR: In this paper, thermal thio-Claisen rearrangement of 4-allylthio[1]benzopyran-2-ones in refluxing quinoline for 0.5-8.0 h was performed.
Abstract: A number of thieno[3,2-c][1]benzopyran-4-ones, potential antiinflamatory, antipyretic, and antiallergic drugs, are synthesized in 65–80% yield by thermal thio-Claisen rearrangement of 4-allylthio[1]benzopyran-2-ones in refluxing quinoline for 0.5–8.0 h. The 4-allylthio[1]benzopyran-2-ones are in turn prepared in 75–85% yield from 4-mercaptocoumarin and different allylic halides by phase-transfer-catalysed alkylation with TBAB or BTEAC catalyst in chloroform-aq. NaOH at room temperature.
18 citations
••
TL;DR: The reaction of substituted cinnamonitriles with 4-hydroxycoumarin in water in the presence of triethylbenzyl-ammonium chloride affords 2amino-4-aryl-4H,5H-pyrano [3,2-c] [1]benzopyran-5-one deriv...
Abstract: The reaction of substituted cinnamonitriles with 4-hydroxycoumarin in water in the presence of triethylbenzyl-ammonium chloride affords 2-amino-4-aryl-4H,5H-pyrano [3,2-c] [1]benzopyran-5-one deriv...
17 citations
••
TL;DR: In this paper, a highly catalytic method for the synthesis of dihydrobenzopyrans from salicylaldehydes has been developed, and an extension of this method to pyrano[2,3, b ]benzopsopyran has also been achieved.
••
TL;DR: On the other hand, this paper showed that on heating under reflux in dry MeOH, aliphatic nitrones 2a−d produce corresponding carboxylic acids 4 but aromatic nitrones 1a−D give aldehyde 1.
Abstract: On hydrolysis with 70% H2SO4, aliphatic nitrones 2a–d produce the corresponding carboxylic acids 4 but aromatic nitrones 2e, f give aldehyde 1. On heating under reflux in dry MeOH, 2a–d rearrange t...
••
TL;DR: X-ray diffraction studies carried out on single crystals of the monomeric and dimeric forms of pimpinellin have revealed that the carbonyl groups are head-to-head with respect to one another following cyclodimerization.
Abstract: X-ray diffraction studies carried out on single crystals of the monomeric, viz. 5,6-dimethoxy-2H-furo[2,3-h][1]benzopyran-2-one, C(13)H(10)O(5), and dimeric, viz. 5,5',6,6'-tetramethoxy-3,3',4,4'-tetrahydro-2H,2'H-3,3':4,4'-bi(furo[2,3-h][1]benzopyran)-2,2'-dione, C(26)H(20)O(10), forms of pimpinellin have revealed that, following cyclodimerization, the carbonyl groups are head-to-head with respect to one another. In the monomer, the heterocyclic ring is planar, but it exhibits a twisted-boat conformation in the dimer. Both the monomer and the dimer interact through C-H...O interactions.
••
TL;DR: A series of 2-amino-3-ethoxycarbonyl-4-aryl-4H,5H-pyrano-[3,2-c]benzopyran-5-ones have been synthesized by the reaction of 4-hydroxycoumarin, an aromatic aldehyde and ethyl cyanoacetate under microwave irradiation with short times and high yields.
Abstract: A series of 2-amino-3-ethoxycarbonyl-4-aryl-4H,5H-pyrano-[3,2-c]benzopyran-5-ones have been were synthesised by the reaction of 4-hydroxycoumarin, an aromatic aldehyde and ethyl cyanoacetate under microwave irradiation with short times and high yields.
••
TL;DR: The first unambiguous observation of an oxepin-2,3-oxide was reported in this paper, where it was shown that 2,3oxides of monocyclic oxepins rearrange to stable, ring-opened dialdehydes or diketones.
••
TL;DR: Novel tricyclic 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2]benzopyran (TFB) derivatives were synthesized, and their herbicidal activities were elucidated.
Abstract: Novel tricyclic 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2]benzopyran (TFB) derivatives were synthesized, and their herbicidal activities were elucidated. They were synthesized from D-glucose as a natural chiral source. The formation of the TFB skeleton was achieved by a Friedel-Crafts type intramolecular cyclization of methyl 5-deoxy-2,3-O-dibenzyl-5-C-methyl-D-xylofranosides. The intramolecular cyclization was dependent upon the electronic effects of the substituents at the C-2 benzyloxy group of methyl xylofranosides. Some TFBs exhibited a remarkable herbicidal activity to annual paddy weeds, such as Echinochloa sp, without injury to the rice.
•
16 Mar 2004
TL;DR: In this article, the subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders, and compounds of particular interest are benzopyrans and their analogs defined by formula 1.
Abstract: The subject invention concerns methods and compounds that have utility in the treatment of a condition associated with cyclooxygenase-2 mediated disorders. Compounds of particular interest are benzopyrans and their analogs defined by formula 1
Wherein Z, X, R 1 , R 2 , R 3 , and R 4 are as described in the specification.
••
TL;DR: PhosphorHydrazines and phosphorohydrazones of benzopyran-2,4-dione as well as the phosphorhydrazone of 4-hydroxycoumarine were tested for antitumor activity in lymphatic leukemia L1210 bearing mice.
Abstract: Phosphorohydrazines and phosphorohydrazones of benzopyran-2,4-dione as well as the phosphorohydrazone of 4-hydroxycoumarine were tested for antitumor activity in lymphatic leukemia L1210 bearing mice.
•
14 Feb 2004
TL;DR: In this article, a method for preparing the compound of the formula(I) comprises reacting epoxide compounds of formula(II) with imidazole containing secondary amine compounds, in the presence of metal salt and a solvent.
Abstract: PURPOSE: Benzopyran derivatives substituted by secondary amine containing imidazole and a method for preparing the same are provided. The compounds are useful for treatment of cancer, diabetic retinopathy and external brain wound. CONSTITUTION: Benzopyran derivatives substituted by secondary amine containing imidazole represented by the formula(1), partial stereo isomers thereof and pharmaceutically acceptable salts thereof are provided, wherein R1 is H, CN, NO2 or NH2; R2 is CH3, CHORaRa or CHOOZ; Ra is C1-C4 linear or branched chain alkyl; Z is C2-C6 linear or branched chain alkyl; R3 and R4 are independently H, Cl, Br, F, C1-C3 linear or branched chain alkyl, ORb, CF3, OCF3, NO2 or CO2Rb; Rb is H or C1-C3 alkyl; and * is chiral carbon. A method for preparing the compound of the formula(I) comprises reacting epoxide compounds of the formula(II) with imidazole containing secondary amine compounds of the formula(III) in the presence of metal salt and a solvent, wherein the metal salt is selected from Mg(ClO4)2, COCl2, LiClO4, NaClO4, CaCl2, ZnCl2, LiBF4 and Zn(Tf)2; and the solvent is selected from acetonitrile, tetrahydrofuran and dimethylformamide.
•
TL;DR: On heating a mixture of 3-formylchromone 1, active methylene compound 2 or 3 and urea (4) in AcOH produces dihydropyrimidinones 10 or 11, whereas use of thiourea in place of urea produces 1,3-thiazine derivative 14 or 15 and the above reactions pass through the Knoevenagel condensate 5 or 6.
••
TL;DR: In this article, the authors proposed an isomeric compound, C18H18O5, which was solved by direct methods and refined to R = 0.056 for 1719 observations.
Abstract: Claisen rearrangement of ethyl-2,4-diallyloxy-α-carbethoxycinnamate (1) in refluxing DMA afforded ethyl-9-allyl-2-methyl-2,3-dihydrofuro(2,3-h)benzopyran-5H-one-6-carboxylate (2) in a single step. Dehydrogenation with Pd/C (10%) in DPE furnished an unexpected isomeric compound, 9-(1,2-propenyl)-6-carbethoxy-2-methyl-2,3-dihydrofuro[2,3-h]-benzopyran-5H-one (3). This compound, C18H18O5, crystallizes in the monoclinic space group P21/n with unit cell parameters, a = 7.346(1), b = 16.482(3), c = 12.653(2),A, and β = 92.71(1)°. The structure has been solved by direct methods and refined to R = 0.056 for 1719 observed reflections. The coumarin nucleus is planar. The five-membered ring is in envelope-conformation. The crystal structure is stabilized by intra- and intermolecular C―H⋯O hydrogen bonds.
••
TL;DR: In this paper, thermal thio-Claisen rearrangement of 4-allylthio[1]benzopyran-2-ones in refluxing quinoline for 0.5-8.0 h was performed.
Abstract: A number of thieno[3,2-c][1]benzopyran-4-ones, potential antiinflamatory, antipyretic, and antiallergic drugs, are synthesized in 65–80% yield by thermal thio-Claisen rearrangement of 4-allylthio[1]benzopyran-2-ones in refluxing quinoline for 0.5–8.0 h. The 4-allylthio[1]benzopyran-2-ones are in turn prepared in 75–85% yield from 4-mercaptocoumarin and different allylic halides by phase-transfer-catalysed alkylation with TBAB or BTEAC catalyst in chloroform-aq. NaOH at room temperature.
•
TL;DR: In this article, the authors tested for antitumor activity in lymphatic leukemia L1210 bearing mice using benzopyran-2,4-dione and 4-hydroxycoumarine.
Abstract: Phosphorohydrazines and phosphorohydrazones of benzopyran-2,4-dione as well as the phosphorohydrazone of 4-hydroxycoumarine were tested for antitumor activity in lymphatic leukemia L1210 bearing mice.
•
10 Mar 2004
TL;DR: In this article, a method for synthesizing 2,2'-disubstituted-3,4-dihydro-7,8-dis-substitized-6-amino benzopyran derivative using a solid-phase synthetic method simplifies the treatment and purification procedures after the reaction, which makes possible to efficiently construct numerous drug-like libraries.
Abstract: When a multi-step process reaction is carried out in a solution, it generally requires several treatments and purification procedures to go through with after the reaction, however, the inventive method for preparing 2,2'-disubstituted-3,4-dihydro-7,8-disubstituted-6-amino benzopyran derivative using a solid-phased synthetic method simplifies the treatment and purification procedures after the reaction, which makes possible to efficiently construct numerous drug-like libraries. In particular, since the inventive method of the present invention comprises the steps of introducing a carbonate linker of formula 2 into Wang resin used as a common solid support (Step 1); synthesizing various benzopyran in a carbamate form of formula 3 as a key intermediate by reacting various amino benzopyran derivatives with the carbamate resin of formula 2 (Step 2); synthesizing 2,2'-disubstituted-3,4-2H-6-substituted benzopyran resin of formula 4 (Step 3); and synthesizing 2,2'-disubstituted-3,4-2H-6-alkylamino benzopyran derivative of formula 1 using a dichloromethane solution containing TFA or an organic solvent containing an organic acid, the inventive method is capable of efficiently synthesizing various 2,2'-disubstituted-3,4-2H-6-alkylamino benzopyran derivatives. Consequently, the present invention has developed a new technique for constructing 2,2'-disubstituted-3,4-2H-6-alkylamino benzopyran library using a solid-phase parallel synthetic method and makes increased the applicability of combinatorial chemical synthetic method. Further, 2,2'-disubstituted-3,4-2H-6-alkylamino benzopyran derivative prepared by the inventive method has a high inhibitory effect to 5-lipoxygenase (5-LO) activity, and therefore, can be effectively used for developing a new propylactic or therapeutic drug for leukotriene activation-related diseases such as chronic inflammation, rheumatic arthritis, colitis, asthma and psoriasis.
••
TL;DR: In this paper, the linear (65-81%) and angular (51-60%) bioactive natural and unnatural benzopyran derivatives are produced exclusively in one step and described via phenol-keto resonance.
Abstract: Remarkably tuned regioselectivities are obtained in the condensation of 3,5-dihydroxyphthalide (1) with several α,β-unsaturated aldehydes using DBU and neutral conditions. The linear (65-81%) and angular (51-60%) bioactive natural and unnatural benzopyran derivatives are produced exclusively in one step and are described via phenol-keto resonance.
••
TL;DR: In this article, the enantiomeric purities of the final aminochroman derivatives were determined by capillary electrophoresis using β-cyclodextrins as a chiral selector.
Abstract: Enantiomerically pure 5-acetyl-3-amino-3,4-dihydro-2H-1-benzopyran and methyl 3-amino-3,4-dihydro-2H-1-benzopyran-5-carboxylate were successfully synthesized starting from d- or l-serine. The formation of the benzopyran ring involved a radical cyclization step. The enantiomeric purities of the final aminochroman derivatives were determined by capillary electrophoresis using β-cyclodextrins as a chiral selector.
•
TL;DR: The title compounds are synthesized from the corresponding 4-hydroxy-benzopyran-2[H]-ones 5a,b.2, 4-Dihydroxyacetophenone la,b on condensation with 2-bromocyclohexanone, followed by linear cyclisation and then on reaction with diethyl carbonate in presence of pulverised sodium gives 6, 7, 8, 9-tetrahydro-4-hydroxymethylbenzofuro [3, 2-g]-4-
Abstract: The title compounds are synthesized from the corresponding 4-hydroxy-benzopyran-2[H]-ones 5a,b .2, 4-Dihydroxyacetophenone la,b on condensation with 2-bromocyclohexanone, followed by linear cyclisation and then on reaction with diethyl carbonate in presence of pulverised sodium gives 6, 7, 8, 9-tetrahydro-4-hydroxy-benzofuro [3, 2-g]-2H-1-benzopyran-2-one 5a,b, which on reaction with aniline, followed by dehydrogenation with palladised charcoal gives benzofuro[3, 2-g]-4-anilino-2H-1-benzopyran-2-one 7a,b. 5a,b on condensation with benzalacetone followed by dehydrogenation with palladised charcoal furnishes 2-methyl-4-phenyl-4-hydro-pyrano[3, 2-c]-benzofuro[3, 2-g]-5H-benzopyran-5-one 9a,b.
•
TL;DR: The chalcones of 4-hydroxycoumarin have been shown to possess significant antibacterial activities as mentioned in this paper, and the structures of all the compounds have been confirmed on the basis of spectral and analytical data.
Abstract: The chalcones of 4-hydroxycoumarin such as 4-hydroxy-2-oxo-3-(1'-oxo-3'-phenylprop-2'-enyl)-2H-[1]-benzopyran 1 and 4-hydroxy-2-oxo-3-(3'-oxo-3'-phenylprop-1'-enyl)-2H-[1]-benzopy-ran 2 are separately refluxed with phenacyl pyridinium bromide and ammonium acetate in acetic acid to give 2,4-diaryl-6-[2'H-[1']-4'-hydroxy-2'-oxo-benzopyran-3'-yl]pyridines 3 and 2,6-diaryl-4-[2'H-[1']-4'-hydroxy-2'-oxo-benzopyran-3'-yl]pyridines 4 respectively. The structures of all the compounds have been confirmed on the basis of spectral and analytical data. All the above compounds have been screened for their antimicrobial activity and are found to possess significant antibacterial activities.
••
TL;DR: In this article, the thermochromic properties of ferrocenyl benzopyrans have been investigated and correlations between the structure of the compounds investigated and their thermochrome properties are discussed.
Abstract: The synthesis and the photochromic behaviour of a series of benzopyrans (otherwise called 2H-chromenes), substituted in the 2-position by a metallocene, have been previously described. Some of these compounds also present thermochromic properties. As the thermochromism has been scarcely studied in the benzopyran series, we describe here a study of the thermochromic properties of ferrocenyl benzopyrans. The correlations between the structure of the compounds investigated and their thermochromic properties are discussed. Copyright © 2004 John Wiley & Sons, Ltd.
•
TL;DR: A new syythesis of chromonyl based on the reaction of formylfurochromone (4,9-dimethoxy -5-oxo- 5H-furo[3,2-g][1] benzopyran-6-yl)- aryliminoethyl derivatives was obtained by refluxing compound 1 with 1 2 -diketone in presence of ammonium acetate reaction of compound 4d with different amines afforded 3- (4 9-diphenyl-2-(4, 9-dimethyl
Abstract: A new syythesis of chromonyl based on the reaction of formylfurochromone (4,9-dimethoxy -5-oxo- 5H-furo[3,2-g][1] benzopyran -6- carbaldehyde) 1 with semicarbazide hydrochloride and thiosemicarbazide afforded 4,9-dimethoxy -5-oxo- 5H-furo[3,2-g] ][1] benzopyran - 6- yl- (1-aminovinyl) hydrazone derivatives 2a,b Also 4,5-Diphenyl-2- (4,9-dimethoxy -5-oxo-5H-furo[3,2-g][1] benzopyran - 6- yl)- imidazole 3 was obtained by refluxing compound 1 with 1,2- diketone in presence of ammonium acetate Reaction of compound 1 with different amines afforded 3- (4,9-dimethoxy -5-oxo- 5H-furo[3,2-g][1] benzopyran-6-yl)- aryliminoethyl derivatives 4a-g Condensation reaction of compounds 4a-d to C-Hacid compounds were given 4-aminosubstituted -5- (6-hydroxy - 4,7 -dimethoxy -5-oxo-5H-benzofuranyl)- pyrano]2,3-b] cyclohexa2,3-diene 5a-d and 2- methyl -3-methoxy -4-(4-methoxyphenylamine)- 5- (6-hydroxy- 4,7- dimethoxy-5-oxo-5H-benzofuranyl) 6 Refluxing compound 4d with thiosemicarbazide formed 6-methanimine- (4,9-dimethoxy-5-oxo- 5H-furo[3,2-g][1] benzopyran-6-yl)-(1E)-1-phenylethan-1-one thiosemicarbazide 7 Also, the reaction of compound 4d with p-aminoacetophenone gave the aryliminehtyl compound 8 The reaction of compound 4d with different aldehydes were given 3-(4,9-dimethoxy -5-oxo- 5H-furo[3,2-g][1] benzopyran)- iminomethyl- (1-aryl-1-oxo-3-proponyl substituted) 9a-d Condensation of formyl fuorochromone 1 with phenolic compounds yielded 3-(4,9-dimethoxy -5-oxo- 5H-furo[3,2-g][1] benzopyran-6-yl)- derivatives 10a-dAll the tested compounds a significant increase in PT & APTT when compared with that of the control group Only the compound IIa treated rats induced significant increaseAst, alkaline phosphatase and urea during experimental period, while other tested compounds did not cause any significant changes in liver and kidney function Concomitantly, all the tested compound caused a significant decrease in serum cholesterol and triglyaside levels