Showing papers on "Benzopyran published in 2007"
TL;DR: The first direct organocatalytic asymmetric domino oxa-Michael/aldol condensation reaction is presented, which proceeds with high chemo- and enantioselectivities to give the corresponding chromene-3-carbaldehyde derivatives in high yields and with ee values of 83-98%.
Abstract: Catalytic enantioselective domino oxa-Michael/aldol condensations: asymmetric synthesis of benzopyran derivatives : -
190 citations
TL;DR: In this paper, a new bifunctional compound C31H26N3O16CrMn has been synthesized, which exhibits ferromagnetic (Tk −5.1 K) and photochromic properties in the solid state.
65 citations
TL;DR: The complex bioactive natural and unnatural benzopyran congeners have been synthesized using one-/two-step approaches in very good yields from the reactions of two different dihydroxyphthalides, natural resorcyclic acid derivative, and trihydroxybenzophenone through the phenol-driven intramolecular diastereoselective thermal/base-catalyzed dipolar [2+2] cycloaddition reactions.
Abstract: The complex bioactive natural and unnatural benzopyran congeners have been synthesized using one-/two-step approaches in very good yields from the reactions of two different dihydroxyphthalides, natural resorcyclic acid derivative, and trihydroxybenzophenone with citral and/or farnesal, via the phenol-driven intramolecular diastereoselective thermal/base-catalyzed dipolar [2 + 2] cycloaddition reactions and three different thermal intramolecular cyclization reactions. The effects of the nature and the position of phenolic groups in the starting materials on the course of these cycloaddition reactions have also been described. Depending upon the absence or presence of intramolecular hydrogen bonding of the phenolic group with the carbonyl moiety in the starting materials, these phenol-driven intramolecular thermal/base-catalyzed dipolar [2 + 2] cycloaddition reactions either furnished the kinetically controlled products or directly formed the thermodynamically controlled rearranged products, respectively.
56 citations
TL;DR: Modification of the C-ring disrupts binding to ERalpha, thus improving ERbeta selectivity up to 100-fold, and syntheses of cyclopentanone and cyclohexanone intermediates for SAR studies of theC-ring on the benzopyran scaffold are described.
46 citations
TL;DR: In this paper, a substitution at the 8-position of the benzopyran A-ring was proposed to disrupt binding to ERα, thus improving ERβ subtype selectivity.
41 citations
TL;DR: Two new compounds, a cyclopenta[bc]benzopyran, ponapensin (1), and an aglaialactone, 5,6-desmethylenedioxy-5-methoxy-aglalactone (2), together with nine known compounds were isolated from the CHCl(3) soluble extract of the leaves and twigs of Aglaia p onapensis.
35 citations
TL;DR: X-ray crystal structures of 5b and a non-selective analog 5c in ERalpha help explain the observed selectivity of the benzopyran platform.
35 citations
TL;DR: Five new flavagline derivatives were isolated from the leaves of Aglaia foveolata collected in Indonesia and has an unprecedented cyclic amide moiety in its cyclopenta[b]benzopyran skeleton, while compound 6 is a novel benzo[ b]oxepine derivative in which the oxepine ring is cleaved.
33 citations
TL;DR: 2-oxo-2H-1-benzopyran derivatives, characterized by a 2-ethyl-2'-oxoacetamide)-5'-chlorophenyl ester side chain, was shown to be a good THR inhibitor, displaying an excellent selectivity profile against other serine proteases such as factor Xa, trypsin, and alpha-CT.
Abstract: New 2-oxo-2H-1-benzopyran derivatives were prepared to optimize 2a,b, initially developed as mechanism-based alpha-chymotrypsin (alpha-CT) inhibitors, into potent and selective thrombin (THR) inhibitors. From this study, 22, characterized by a 2-(N-ethyl-2'-oxoacetamide)-5'-chlorophenyl ester side chain, was shown to be a good THR inhibitor (ki/KI = 3455 M(-1) x s(-1)), displaying an excellent selectivity profile against other serine proteases such as factor Xa, trypsin, and alpha-CT. Docking analysis of this compound into the different protein structures revealed the molecular basis responsible for its potency and selectivity.
32 citations
TL;DR: In this article, the formation of a complex with BAA in water was reported for the first time, which may provide a potential application for in situ recognition of BAA, and its formation with MC was shown to be stable in water.
Abstract: Basic amino acids (BAA) induced 1-(β-carboxyethyl)-3,3-dimethyl-6′-nitrospiro(indoline-2,2′[2H-1]benzopyran) (SP) isomerization to its open form, i.e.merocyanine (MC), and the formation of its complex with BAA in water was reported for the first time, which may provide a potential application for in situ recognition of BAA.
32 citations
TL;DR: These compounds underwent a cascade sequence of reactions, deprotection-halogenation-annulation, to afford polyoxygenated tetracyclic 6H,11H-[2]benzopyrano-[4,3-c] [1]benZopyran-11-ones in good yields and showed a moderate cytotoxicity against human epithelial mammary HBL100 cells.
Abstract: 2-(methoxymethoxymethyl)aryllead triacetates, obtained in situ from the corresponding arylboronic acids, reacted with 4-hydroxycoumarins, leading to 3-(2-methoxymethoxymethyl)aryl-4-hydroxycoumarin derivatives in good to high yields. These compounds underwent a cascade sequence of reactions, deprotection-halogenation-annulation, to afford polyoxygenated tetracyclic 6H,11H-[2]benzopyrano-[4,3-c] [1]benzopyran-11-ones in good yields. Some compounds showed a moderate cytotoxicity against human epithelial mammary HBL100 cells.
Patent•
23 Apr 2007
TL;DR: In this article, the present invention relates to compounds having pharmacological activity towards the sigma (σ) receptor, and more particularly to spiro[benzopyran] or spiro [benzofuran] derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and their use in therapy and prophylaxis, in particular for the treatment of psychosis.
Abstract: The present invention relates to compounds having pharmacological activity towards the sigma (σ) receptor, and more particularly to spiro[benzopyran] or spiro[benzofuran] derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy and prophylaxis, in particular for the treatment of psychosis.
TL;DR: In this article, the insecticidal tetrahydroisocoumarin (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4, 4a,5-tetrahedro-1H-2-benzopyran-1-one, was synthesized as a racemate and as an optically active form using one-pot esterification.
Patent•
09 Mar 2007
TL;DR: In this paper, the authors proposed an efficient process for producing an optically active chromene oxide compound which is an important intermediate for a benzopyran compound effective in the treatment of arrhythmia.
Abstract: [PROBLEMS] To provide an efficient process for producing an optically active chromene oxide compound which is an important intermediate for a benzopyran compound effective in the treatment of arrhythmia. [MEANS FOR SOLVING PROBLEMS] The process for producing an optically active chromene oxide compound comprises using an optically active titanium complex represented by, e.g., the formula (1) or (2) as a catalyst to asymmetrically oxidize an optically active chromene compound with high enantioselectivity in high chemical yield.
TL;DR: Improved synthetic method affording 4-chlorocoumarin-3-sulfonyl chloride in very good yield (ca. 85%) is reported and it is shown that these fused heterocycles are not stable and decompose with opening of the 1,2,4-thiadiazine ring.
Abstract: An improved synthetic method affording 4-chlorocoumarin-3-sulfonyl chloride (4) in very good yield (ca. 85 %) is reported. This compound was reacted with various bidentate nucleophiles such as 2-aminopyridines and 2-aminothiazoles in order to obtain substituted pyrido- and thiazino-1,2,4-thiadiazino-benzopyranone dioxides (potential anticancer and anti-HIV agents). These reactions occurred rapidly at room temperature giving yellowish precipitates, which are insoluble in common organic solvents, making the purification process challenging. Further investigation has shown that these fused heterocycles are not stable and decompose with opening of the 1,2,4-thiadiazine ring.
Patent•
21 May 2007TL;DR: In this paper, a process for the production of a compound of formula (I), where Y is selected from CH3, CH2OH, CH 2CH2OH and CH2Br, is described.
Abstract: The invention provides a process for the production of a compound of formula (I), wherein Y is selected from CH3, CH2OH, CH2CH2OH, CH2Br and Br; comprising the steps of: (i) reacting a compound of formula (II), wherein OX is hydroxy or O- M+, in which M+ is a cation selected from Li+, Na+ and K+, and Y is as defined above; with trans-cinnamaldehyde (III), in the presence of a secondary amine compound; then (ii) treating the product of the preceding step with acid to afford the compound of formula (I). The above process may be used in the production of tolterodine and fesoterodine, which are useful in the treatment of overactive bladder.
Patent•
30 Apr 2007
TL;DR: In this article, the field of aryl hydrocarbon receptor (Ah receptor; AhR) antagonists has been studied and a compound of formula (lII) or (V) in which R1 to R10 independently of one another can be hydrogen, hydroxyl, C1-C10-alkyl, and R5 can be replaced by a double bond as a drug, which is intended for reducing or preventing a translocation of the AhR into a cell nucleus.
Abstract: The invention relates to the field of aryl hydrocarbon receptor (Ah receptor; AhR) antagonists and to a compound of formula (lII) or (V) in which R1 to R10 independently of one another can be hydrogen, hydroxyl, C1-C10-alkyl, C1-C10-alkenyl, C1-C10-alkoxy, prenyl or O-glycosyl, and two radicals R1 to R10 can be joined via a methylenedioxy group -O-CH2-O-, and R5 can be replaced by a double bond, as a drug, which is intended for (a) reducing or preventing a translocation of the AhR into a cell nucleus, (b) reducing or preventing a UVB-induced or UVB-inducible gene expression, (c) reducing or preventing a gene expression induced or inducible by polycyclic aromatic hydrocarbons, preferably TCDD, and/or (d) reducing or preventing UVB-induced or UVB-inducible skin damage, especially skin cancer, skin ageing, skin inflammations and sunburn; as well as to process for the preparation of a drug, comprising the extraction of wood.
TL;DR: In this paper, the β1-adrenergic antagonist (S,R, R,R)-α,α′-iminobis(methylene)bis(6-fluoro-3H,4H-dihydro-2H-1-benzopyran-2methanol) was synthesized from natural chiral pool starting materials through an efficient, convergent synthetic strategy.
Abstract: The β1-adrenergic antagonist (S,R,R,R)-α,α′-iminobis(methylene)bis(6-fluoro-3H,4H-dihydro-2H-1-benzopyran-2-methanol) was synthesized from natural chiral pool starting materials through an efficient, convergent synthetic strategy. The cyclization mechanism of the key step was investigated using computer modeling and is discussed.
TL;DR: In this article, the synthesis of (+)-scyphostatin was performed in >98% ee. Key synthetic steps were (i) the oxidative dearomatization of an l -tyrosine derived phenol, (ii) the transformation of the resulting p -quinol acetate to the corresponding resorcinol upon exposure to Thiele reaction conditions and, (iii) the direct formation of the benzopyran ring upon treatment of an N -Boc protected 4-(2-acetoxybenzyl)oxazolidin-
TL;DR: The key of the heterocyclic carbene formation is the activation of the carbonyl group by alkylation with alkyl trifluoromethanesulfonate reagent as mentioned in this paper.
TL;DR: Condensation of 8.formyl, 7.methoxy, 2.7methoxyl, 3.3methioxyl, 4.5methoxide, and 3.1methylbenzopyran-4.4.1.
TL;DR: X-ray diffraction studies were carried out on single crystals of two flavonoids, viz. 5-hydroxy-6,7,4′-trimethoxyflavone, C18H16O6, (I) and 5-Hydroxy-3, 7, 4′-thimethylhexyl-hexylhexyl hexylhexynylhexethylhexynoylhexynycloenoxyflaxynoyluoxynoyle (C18H 16O6), (II) as mentioned in this paper.
Abstract: X-ray diffraction studies were carried out on single crystals of two flavonoids, viz. 5-hydroxy-6,7,4′-trimethoxyflavone, C18H16O6, (I) and 5-hydroxy-3,7,4′-trimethoxyflavone, C18H16O6, (II). Crystal structures of both the flavonoids were solved by direct methods and refined by full-matrix least-squares procedures. In both the molecules, the benzopyran moiety is planar. The dihedral angle between the phenyl ring and the benzopyran portion is 5.50(4)° in (I) and 29.11(5)° in (II). In (I), the crystal packing is influenced by O-H…O hydrogen bonds, and weak C-H…O and π…π interactions whereas in (II) the crystal structure is stabilized by the presence of four intermolecular short contacts of the type C-H…O. There is also one C-H…π hydrogen bond with H… centroid distance of <2.7 A. The molecules are further stabilized by π-π interactions.
TL;DR: The results suggest that the inhibitory effect of NM-3 on gastric cancer growth is mediated through decreased angiogenesis and the increased induction of apoptosis, andNM-3 in combination with carboplatin may be effective in the treatment of Gastric cancer.
Abstract: Effect of 2-(8-hydroxy-6-methoxy-1-oxo-1H-2-benzopyran-3-yl) propionic acid in combination with carboplatin on gastric carcinoma growth in vivo
TL;DR: The first efficient synthesis of biologically interesting biologically interesting nigrolineabenzopyran A, blandachromene II, and daurichromene D with the benzopyrans moiety has been accomplished using ethylenediamine diacetate-catalyzed reaction as a key step.
Abstract: The first efficient synthesis of biologically interesting nigrolineabenzopyran A, blandachromene II, and daurichromene D with the benzopyran moiety has been accomplished using ethylenediamine diacetate-catalyzed reaction as a key step. The key step in these synthetic strategies involves the formation of benzopyran moiety via an electrocyclization reaction.
Journal Article•
TL;DR: Substituted 4-oxo-4H-1-benzopyran-3-carboxaldehydes 2a-h have been synthesized in good yields under microwave irradiation using Vilsmeier reagent over silica gel in solvent free conditions.
Abstract: Substituted-4-oxo-4H-1-benzopyran-3-carboxaldehydes 2a-h have been synthesised in good yields under microwave irradiation using Vilsmeier reagent over silica gel in solvent free conditions. The reaction takes place within 2-3.5 min.
TL;DR: In this article, an effective approach for the synthesis of epicatechin derivatives based on sequential one-pot multi-step reactions is described, where the disulfanyl derivative was promoted with a catalytic amount of TfOH, providing the cis-substituted benzopyran derivative in a stereoselective manner.
Abstract: An effective approach for the synthesis of epicatechin derivatives based on sequential one-pot multi-step reactions is described. Reductive etherification of the disulfanyl derivative was promoted with a catalytic amount of TfOH, providing the cis-substituted benzopyran derivative in a stereoselective manner.
Patent•
22 Aug 2007
TL;DR: In this article, the synthesis process of 6-fluoro-3, 4-dihydro-2H-1-benzopyran -2-formaldehyde has been described.
Abstract: The present invention discloses synthesis process of 6-fluoro-3, 4-dihydro-2H-1-benzopyran -2-formaldehyde. The material 6-fluoro-3, 4-dihydro-2H-1-benzopyran-2-methanol is oxidized by using PCC supported oxidant prepared with inorganic adsorbent to obtain 6-fluoro-3, 4-dihydro-2H-1-benzopyran-2-formaldehyde. The synthesis process has yield over 90 %, easy industrial application, and no change in the stereo form of the reaction substrate, and the prepared 6-fluoro-3, 4-dihydro-2H-1-benzopyran-2-formaldehyde has optical activity.
Journal Article•
TL;DR: The coupling reaction of the diazonium solution of the 6-aminocoumarins (la-c) with malononitrile affords the corresponding 2]-(4,7-dimethyl-2-oxo-2H-benzopyran-6-yl)-hydrazono]-malononionitrile (2a-c), which on refluxing with morpholine and piperidine separately yields the corresponding 3-amino-2-(4, 7-dimmethyl-2.5)-dimethyl 2
Abstract: The coupling reaction of the diazonium solution of the 6-aminocoumarins (la-c) with malononitrile affords the corresponding 2-[(4,7-dimethyl-2-oxo-2H-benzopyran-6-yl)-hydrazono]-malononitrile (2a-c) which on refluxing with morpholine and piperidine separately yields the corresponding 3-amino-2-(4,7-dimethyl-2-oxo-2H-benzopyran-6-ylazo)-3-morpholin-4-yl-acrylonitrile (3a-c) and 3-amino-2-(4,7-dimethyl-2-oxo-2H-benzopyran-6-ylazo)-3-piperidin-1-yl-acrylonitrile (3d-f) respectively. The enaminonitrile derivatives (3a-f) on heating with acetic anhydride give the corresponding 5-(4,7-dimethyl-2-oxo-2H-benzopyran-6-ylazo)-2-methyl-6-morpholin-4-yl-2,3-dihydro-3H-pyrimidin-4-one and 5-(4,7-dimethyl-2-oxo-2H-benzopyran-6-ylazo)-2-methyl-6-piperidin-1-yl-2,3-dihydro-3H-pyrimidin-4-one (4a-f). The structures of the compounds (2a-c), (3a-f) and (4a-f) have been established on the basis of spectral and analytical data. All the above compounds have been screened for their antimicrobial activities and arc found to possess significant antibacterial activities.