Showing papers on "Benzopyran published in 2012"
TL;DR: The asymmetric domino reaction of various α,α-dicyano olefins to 3-nitro-2H-chromenes was studied employing readily available cinchona-derived bifunctional thioureas as organocatalysts as mentioned in this paper.
40 citations
TL;DR: This review covers the construction of drug-like 2H-benzopyrans and related libraries using solid-phase parallel synthesis and the preparation of substituted benzopyrants such as mono-, di- and trisubstituted Benzopyran derivatives and additional ring-fused benzopyrsans.
Abstract: This review covers the construction of drug-like 2H-benzopyrans and related libraries using solid-phase parallel synthesis. In this context, the preparation of substituted benzopyrans such as mono-, di- and trisubstituted benzopyran derivatives and additional ring-fused benzopyrans such as benzopyranoisoxazoles, benzopyranopyrazoles, six-membered ring-fused benzopyrans, and polycyclic benzopyrans are highlighted.
23 citations
TL;DR: In this paper, a short and simple synthesis of benzopyran derivatives was accomplished in good to excellent yields by the reaction of salicylaldehyde with 1,3-cyclohexanediones in aqueous media catalyzed by para-toluenesulfonic acid.
20 citations
TL;DR: N-(2,2-Dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-4H- 1,2,4 -benzothiadiazine-3-carboxamides 1,1-dioxides were prepared and evaluated on rat uterus, rat aortic rings and rat pancreatic β-cells as mentioned in this paper.
20 citations
TL;DR: An efficient synthesis of novel antifungal 3a,9a-dihydro- 1-ethoxycarbonyl-1-cyclopenteno[5,4-b]benzopyran-4-ones through 1,3-dipolar cycloaddition of all carbon 1, 3-dipole with substituted 3-formylchromones (8a-j) has been developed.
19 citations
TL;DR: It was found that the exchange of the carbonyl by a thiocarbonyl group enhanced the performance of the heterocyclic protecting group at 419 nm by improving the photolysis rates, making it an appropriate group for practical applications at long wavelengths.
Abstract: Aiming at the enhancement of the performance of (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl) methyl ester as photocleavable protecting group for the carboxylic acid function at long-wavelengths, 9-methoxy-3-thioxo-3H-benzo[f]benzopyran-l-valine and l-phenylalanine model conjugates were prepared through a thionation reaction of the corresponding oxo-benzobenzopyrans. These thioxobenzobenzopyran derivatives were subjected to photocleavage reactions in the same conditions as the parent oxo-benzobenzopyrans at different wavelengths of irradiation, and photocleavage data were obtained. It was found that the exchange of the carbonyl by a thiocarbonyl group enhanced the performance of the heterocyclic protecting group at 419 nm by improving the photolysis rates, making it an appropriate group for practical applications at long wavelengths.
18 citations
TL;DR: The synthesis of new 3-dithiocarbamic flavonoids has been accomplished by the reaction of the corresponding 2-hydroxyaryl dithiOCarbamates with aminals by the heterocyclization of these compounds.
Abstract: The synthesis of new 3-dithiocarbamic flavonoids has been accomplished by the reaction of the corresponding 2-hydroxyaryl dithiocarbamates with aminals. These flavonoids were obtained as a mixture of diastereoisomers, the anti isomer being the major one. The heterocyclization of these compounds provided novel tricyclic flavonoids bearing a 1,3-dithiolium-2-yl ring fused at the 3,4-carbon positions of the benzopyran moiety.
15 citations
TL;DR: In this article, a photochromic fused 2H-chromene that has a dehydropyran bridge between the pyran double bond and the benzene ring was prepared.
15 citations
TL;DR: In this paper, a light-triggered uncaging of butyric acid from the corresponding heterocyclic cages was achieved with complete release of the drug in short times.
12 citations
Patent•
17 Dec 2012
TL;DR: The OP-1074 as mentioned in this paper is a pure anti-estrogen when tested in the agonist mode and a complete anti -estrogen in the antagonist mode, which is the only compound known to have antiestrogenic activity.
Abstract: Benzopyran compounds with strong anti-estrogenic activity and essentially no estrogenic activity are provided, which are OP- 1038, which is 3-(4-hydroxyphenyl)-4-methyl-2-(4-{2-[(3R)-3-methylpyrrolidin-l-yl]ethoxy}phenyl)-2H-chromen-7-ol, and OP-1074, which is (2S)-3-(4-hydroxyphenyl)-4-methyl-2-(4-{2-[(3R)-3-methylpyrrolidin- 1 -yl]ethoxy}phenyl)-2H-chromen-7-ol. OP-1074 is a pure anti-estrogen when tested in the agonist mode and a complete anti-estrogen when tested in the antagonist mode. These compounds are useful for the treatment or prevention of a variety of conditions that are modulated through the estrogen receptor in mammals including humans.
11 citations
TL;DR: A novel class of 1'-cyclobutyl-6-(4-piperidyloxy)spiro[benzopyran-2,4'-piperidine] derivatives with low nanomolar affinity for the human and rat histamine-3 receptors (H(3)Rs) are described.
Patent•
01 Aug 2012
TL;DR: In this article, an isoflavone compound, its preparation method, and its application in the preparation of antiviral or antitumor drugs, and concretely relates to a compound with a structural formula represented by formula (I), in which R1 is hydrogen or C1-6 alkyl; X is -O-, -NH-, -CH=CH-, or ethinyl, or R2 is directly connected with benzopyran.
Abstract: The invention relates to an isoflavone compound, its preparation method, and its application in the preparation of antiviral or antitumor drugs, and concretely relates to a compound with a structural formula represented by formula (I). In the formula (I), R1 is hydrogen or C1-6 alkyl; X is -O-, -NH-, -CH=CH-, or ethinyl, or R2 is directly connected with benzopyran; R2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted heteroaryl, C1-16 alkyl, C1-16 alkyloxy, C1-16 alkyloxycarbonyl, or substituted or unsubstituted benzoyloxy; the heteroaryl is selected from groups derived from a five or six-membered heterocycle or a fused heterocycle containing one or two hetero atoms of N, O or S, and is selected but not limited to pyridyl, benzopyridyl, or groups derived from phenoxathiin, thiophene, oxazole and benzopyridine; and above substituent is selected from halogen, cyan, nitro, hydroxy, amino, C1-6 monosubstituted or disubstituted amino, C1-16 alkyl, halogenated C1-6 alkyl, C2-6 alkenyl, C6-12 arylalkenyl, C1-16 alkyloxy, C1-16 carboxyl, C1-16 alkyloxycarbonyl, C1-16 alkylcarbonyl, and substituted or unsubstituted phenoxyl. The invention also provides the preparation of the compound.
TL;DR: In this paper, the preparation of des-hydroxy stachybotrin C is described, and the efficiency of the intermolecular cyclization between the diethyl acetal 19 and phenol 12 leading to the benzopyran moiety 17 is discussed.
Abstract: The preparation of racemic des-hydroxy stachybotrin C is described. Different approaches have been studied. Observations made in the course of the synthesis show the efficiency of the intermolecular cyclization between the diethyl acetal 19 and phenol 12 leading to the benzopyran moiety 17.
TL;DR: In this paper, the Biginelli reaction was used to synthesize the title compounds of type (IV) in a one-pot procedure using benzopyran (I), urea (II), and aromatic aldehydes.
Abstract: First time, benzopyran (I), urea (II), and aromatic aldehydes are used in the Biginelli reaction to synthesize the title compounds of type (IV) in a one-pot procedure.
TL;DR: The title compound, 3-(D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one trihydrate, C22H22O12·3H2O, is a natural β-Dglucosylflavone (1) isolated from Argemone mexicana Linn. (Papaveraceae) as mentioned in this paper.
Abstract: The title compound, 3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one trihydrate, C22H22O12·3H2O, is a natural β-D-glucosylflavone (1) isolated from Argemone mexicana Linn. (Papaveraceae). The compound crystallizes in the monoclinic space group C2 with unit-cell parameters: a = 24.2721(9), b = 11.6227(4), c = 9.3193(4)A, β = 107.489(4)°, Z = 4. The crystal structure was refined to a final R-value of 0.0523 for 3733 observed reflections. The dihedral angle between the benzopyran moiety and the 4-hydroxy-3-methoxyphenyl ring is 9.95(8)°. The basal plane of the glucose moiety is nearly perpendicular to the benzopyran ring system. Molecules are held together in the crystal by O-H…O hydrogen bonds and C-H…π and π-π interactions.
TL;DR: In this article, tetraand penta-cyclic benzopyran derivatives, via direct intramolecular arylation of 2-iodophenoxymethylhetarenes and 3-chloromethylbenzo[4,5]imidazo[2,1-b]thiazole, are described.
Abstract: Syntheses of novel tetraand penta-cyclic benzopyran and pyridopyran derivatives, via direct intramolecular arylation of 2-iodophenoxymethylhetarenes and 3-(2-bromo-pyridin-3yloxymethyl)-benzo[4,5]imidazo[2,1-b]thiazole in the catalytic system Pd(OAc)2 / Xantphos / Cs2CO3 / Ag2CO3 in toluene, and a one-pot bicatalytic method for 12H[1]benzopyrano[3′,4′:4,5]thiazolo[3,2-a]benzimidazole directly from 3-chloromethylbenzo[4,5]imidazo[2,1-b]thiazole and 2-iodophenol, are described. This latter compound exhibits high cytotoxicity (MG-22A, 6 μg/mL) on the mouse hepatoma cancer cell line and low toxicity (LD50, 1058 mg/kg) on the mouse Swiss albino embryo fibroblasts 3T3.
TL;DR: In this article, the authors report the solid-phase library construction of a novel N-[alkyl sulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B derivatives.
Abstract: Center for Drug Discovery Platform Technology, Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea Received November 1, 2011, Accepted November 11, 2011We report the solid-phase library construction of 222 number of a novel N-[alkyl sulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B derivatives. The polymer-bound N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 9 and amine 10 derivativeswere obtained by first diversity generation with various acid chlorides and alkyl halides. Further reactions onthe resins 9 and 10 with substituted sulfonyl chlorides produced the desired N-[alkylsulfonamido-spiro(2H-1-benzopyran-2,4-piperidine)-6-yl] substituted amide 1A and amine 1B analogues.Key Words : Spiro(2H-1-benzopyran-2,4-piperidine)-6-yl derivatives, Solid-phase parallel synthesis, Drug-like benzopyran core skeleton IntroductionHeterocyclic compounds provide scaffolds on whichpharmacophores can be arranged to yield potent andselective drugs, and a variety of heterocycles have beensynthesized on solid support.
Patent•
17 Dec 2012
TL;DR: The OP-1074 is a pure anti-estrogen when tested in the agonist mode and a complete antiestrogen in the antagonist mode as mentioned in this paper, which is the only compound known to be effective in the presence of the estrogen receptor.
Abstract: Benzopyran compounds with strong anti-estrogenic activity and essentially no estrogenic activity are provided, which are OP-1038, which is 3-(4-hydroxyphenyl)-4-methyl-2-(4-{2-[(3R)-3-methylpyrrolidin-1-yl]ethoxy}phenyl)-2H-chromen-7-ol, and OP-1074, which is (2S)-3-(4-hydroxyphenyl)-4-methyl-2-(4-{2-[(3R)-3-methylpyrrolidin-1-yl]ethoxy}phenyl)-2H-chromen-7-ol. OP-1074 is a pure anti-estrogen when tested in the agonist mode and a complete anti-estrogen when tested in the antagonist mode. These compounds are useful for the treatment or prevention of a variety of conditions that are modulated through the estrogen receptor in mammals including humans.
01 Jan 2012
TL;DR: In this paper, the structures of the isolated products were established by elementary analysis and spectral data studies and most of the compounds were tested against sixteen different human cancer cell lines and the results showed that most of them were superior to the familiar comparative standards.
Abstract: Treatment of 4-(5,9-dimethoxy -4H-furo(3,2-g)(1)benzopyran)methylene-2-thiohydantoin 1 with different alkylhalid gave 2-alkyl mercapto derivatives 2a,b, which on 2a,b reaction with antharnilic acid yielded (2Z)-2-((4,9-dimethoxy-5-oxo-5H-furo(3,2-g)chromen-6-yl)methylene) imidazo-(2,1-b) quinazoline-3,5(2H, 10H)-dione 3. Reaction of compound 1 with acryolnitrile in pyridine gave compound 5, in which compound 5 was hydrolyses with acetic-hydrochloric acid mixture to give the corresponding acid 6. Cyclization of 6 with acetic anhydride yielded the imidazothiazine derivative 7. Several new imidazothiazine derivatives 10a-c, 13a-c and 16a-c were synthesized via the reaction of compound 1 with α, β- unsaturated nitriles. The structures of the isolated products were established by elementary analysis and spectral data studies. Compounds 1, 2a, 3, 5, 6, and 7 were tested against sixteen different human cancer cell lines and most of the compounds were superior to the familiar comparative standards.
TL;DR: The ligand-free Pd-mediated reaction between styrene and a 6bromo-2,2-diaryl-2H-[1]benzopyran proceeded anomalously to give a 2-(diary lmethyl)-5-styrylbenzofuran via a tandem Heck coupling.
Patent•
10 Aug 2012TL;DR: In this paper, a deuterated benzopyran compound having a structure feature in the formula (I), a pharmaceutically acceptable salt or stereoisomer thereof, or a pre-drug molecule thereof is disclosed.
Abstract: Disclosed is a deuterated benzopyran compound having a structure feature in the formula (I), a pharmaceutically acceptable salt or stereoisomer thereof, or a pre-drug molecule thereof. The compound has excellent anti-inflammatory and analgesic effects, can inhibit growth of tumor cells, and is a novel COX-2 selective inhibitor. The compound and pharmaceutically acceptable salt thereof can be applied to prepare anti-inflammatory and analgesic drugs and drugs for treating or preventing tumors.
Patent•
27 Jan 2012TL;DR: The use of benzopyran compounds of formula I, for example, pomiferin-3′,4′-dimethyl ether, and compositions thereof to modulate melanogenesis and pigmentation is discussed in this paper.
Abstract: Provided are benzopyran compounds of formula I, for example, pomiferin-3′,4′-dimethyl ether, and the use of such compounds and compositions thereof to modulate (e.g., inhibit) melanogenesis and pigmentation. wherein R3, R4, R5, R6, R7 and R8 are described herein. Also provided are plant extracts containing a compound of formula I, and the use of such a plant extract to modulate (e.g., inhibit) melanogenesis and pigmentation. The compound or plant extract may be prepared as pharmaceutical and cosmetic compositions, and may be used for the prevention and treatment of conditions that are related to aberrant melanogenesis activity.
TL;DR: Condensation of cyclic 1,3-diones with alkylidene cyanoacetates in the presence of the quinine-based thiourea renders possible the preparation of various biologically interesting benzopyran structures as mentioned in this paper.
Abstract: Condensation of cyclic 1,3-diones with alkylidene cyanoacetates in the presence of the quinine-based thiourea renders possible the preparation of various biologically interesting benzopyran structures.
01 Jan 2012
TL;DR: In this paper, the synthesis of 6-chloro-4-(furan-2-ylmethyleneamino)-2,2-dimethyl-2H-chromen-3-ol was achieved.
Abstract: The synthesis of 6-chloro-4-(furan-2-ylmethyleneamino)-2,2-dimethyl-2H-chromen-3-ol was achieved. These compounds were synthesized from different substituted phenols as starting material. The phenols acetylated in the first step and undergone Fries rearrangement in the second step to afford ortho hydroxyl acetophenone moiety 3a-e. These further treated with acetone in toluene in the presence of piperidine to afford benzopyaranone 4a-e. The compound 4a-e was further reduced by sodium borohydrate in methanol to obtain 4hydroxy benzopyran 5a-e. The compound 5a-e was refluxed under Dean Stack condition using p-toluene sulphonic acid to afford benzopyrans 6a-e. These compounds were converted to epoxide 7a-e by treating with sodium hyphochloride in the presence of phosphate buffer and DCM- water as solvent. In the next step the ring opening reaction is done by treating with ammonia and methanol at 50-60 o C to afford 8a-e. The amino alcohol functional group is treated with different substituted furfuraldehyde to afford the target compound 9a-j. All the target compounds 9a-j were characterized by IR, NMR and Mass spectral data and tested for in vivo antihypertensive activity.
TL;DR: In the title compound, C26H12FNO6, the central pyran ring and both benzopyran systems are nonplanar, having total puckering amplitudes of 0.139, 0.050, and 0.112 (2) Å, respectively.
Abstract: In the title compound, C26H12FNO6, the central pyran ring and both benzopyran systems are nonplanar, having total puckering amplitudes of 0.139 (2), 0.050 (1) and 0.112 (2) A, respectively. The central pyran ring adopts a boat conformation. The crystal structure is stabilized by C—H⋯O, N—H⋯O, N—H⋯F and C—H⋯π interactions.
TL;DR: In this article, the synthesis of hitherto unknown pyridyl-substituted benzopyran derivatives is achieved in moderate to high yields involving the introduction of a pyridisyl moiety in the system as the key step.
Abstract: The synthesis of hitherto unknown pyridyl-substituted benzopyran derivatives is achieved in moderate to high yields involving the introduction of a pyridyl moiety in the benzopyran system as the key step.
Patent•
11 Jul 2012
TL;DR: In this paper, a 2-(4-fluorine phenyl)-3-nitryl-8-ethyoxyl-2H-benzopyran chiral compound and a preparation method and the application thereof are discussed.
Abstract: The invention relates to a 2-(4-fluorine phenyl)-3-nitryl-8-ethyoxyl-2H-benzopyran chiral compound and a preparation method and the application thereof and specifically discloses a ((R)-XM002S (formula I)) and an (S)-XM002S (formula II) of the chiral compound and the preparation method of the chiral compound. The application of the chiral compound in preparation of anti-tumor medicine is further disclosed.
TL;DR: In this article, ten title compounds of type (III) were prepared by 1,3-dipolar cycloaddition reaction and tested as antifungal agents, and the results showed that they were effective in the presence of yeast.
Abstract: Ten title compounds of type (III) are prepared by 1,3-dipolar cycloaddition reaction and tested as antifungal agents.
TL;DR: The asymmetric unit of the title compound, C26H12ClNO6, consists of two independent molecules and the central pyran rings and both the 1-benzopyran ring systems are nearly planar in both molecules.
Abstract: The asymmetric unit of the title compound, C26H12ClNO6, consists of two independent molecules. The central pyran rings and both the 1-benzopyran ring systems are nearly planar in both molecules [r.m.s. deviations of pyan rings = 0.0264 (1) and 0.0326 (1) A for molecules A and B, respectively; r.m.s. deviations of benzopyran rings = 0.0439 (1) and 0.0105 (1) for molecule A, 0.0146 (1) and 0.0262 (1) A for molecule B]. In the crystal, the molecules are linked by C—H⋯O, N—H⋯O and C—H⋯π interactions.
Patent•
04 Jul 2012
TL;DR: The 2,2-dimethyl benzopyran compound has an excellent inhibition function on various cancer cells so as to be applied to treatment of tumors as discussed by the authors, which has the advantages of simple operation, convenience for post-treatment and higher yield.
Abstract: The invention discloses a 2,2-dimethyl benzopyran compound and a preparation method and application thereof, belonging to the technical field of medicines. The structure of the 2,2-dimethyl benzopyran compound is shown in a figure described in the specification. The preparation method of the 2,2-dimethyl benzopyran compound comprises the following steps of: with 2-methyl-butyl-3-alkyne-2 alcohol as a starting raw material, carrying out four-step reactions comprising chlorination, Williamson etherification, cyclization and Aldol condensation to obtain the 2,2-dimethyl benzopyran compound. The preparation method of the 2,2-dimethyl benzopyran compound, disclosed by the invention, has the advantages of simple operation, convenience for post-treatment and higher yield. The 2,2-dimethyl benzopyran compound has an excellent inhibition function on various cancer cells so as to be applied to treatment of tumors. A formula is described in the specification, wherein R' represents H and C1-6 alkyl and R represents substituted or unsubstituted aromatic ring or heteroaromatic ring.