Showing papers on "Benzopyran published in 1999"
Patent•
15 Oct 1999TL;DR: In this article, a class of benzopyrans, benzothiopyrans and dihydroquinolines, dihydronaphthalenes, and analogs thereof, are described for use in treating cyclooxygenase-2 mediated disorders.
Abstract: A class of benzopyrans, benzothiopyrans, dihydroquinolines, dihydronaphthalenes, and analogs thereof, is described for use in treating cyclooxygenase-2 mediated disorders. Compounds of particular interest are defined by Formula (I') wherein X, A?1, A2, A3, A4?, R, R'', R?1 and R2? are as described in the specification.
109 citations
TL;DR: A number of carbonyl and phenolic compounds efficiently couple with o-dibromobenzenes in the presence of a palladium catalyst and a base to give the corresponding oxygen-containing heterocycles or carbocyclic compounds.
Abstract: A number of carbonyl and phenolic compounds efficiently couple with o-dibromobenzenes in the presence of a palladium catalyst and a base to give the corresponding oxygen-containing heterocycles or carbocyclic compounds. Thus, from the reactions of benzyl phenyl ketones, 1-naphthols, and α,β-unsaturated aldehydes and ketones, benzofuran, benzopyran, benzocyclobutane, and indene derivatives, respectively, are produced selectively via the successive formation of C–C and C–O bonds or of two C–C bonds.
66 citations
TL;DR: 2-imino/oxo-2H-1-benzopyran-3-carboxamides 3a and b and 4a-h were further studied at graded doses for their acute toxicity in albino mice and were essentially non-toxic at the highest dose tested.
52 citations
TL;DR: Weinreb-α-aminoamides were prepared from 4-chlorocoumarin and α-amINOacid derivatives, and their reaction with organometallic compounds (RLi or RMgBr) and subsequent cyclization of ketones thus obtained, give [1]benzopyrano[4,3-b]pyrrol-4(1H)-ones as discussed by the authors.
23 citations
TL;DR: Biological studies showed L-enantiomer to be the active form, exhibiting a fivefold higher receptor affinity for the rat uterine cytosolic estrogen receptor, 100% contraceptive efficacy at 1.3 mg/kg dose in single day schedule and 89% inhibition of estradiol induced increase of uterine weight at its contraceptive dose.
19 citations
TL;DR: Synthesis and in vitro antimicrobial activity of some 3-(substituted phenacyl)-5-[4'(4H- 4-oxo-1-benzopyran-2-yl)-benzylidene]-2-4- thiazolidinedione derivatives are described.
Abstract: Synthesis and in vitro antimicrobial activity of some 3-(substituted phenacyl)-5-[4'(4H-4-oxo-1-benzopyran-2-yl)-benzylidene]-2-4- thiazolidinedione derivatives are described. These products were synthesized by the Knoevenagel reaction from 4'-flavone carboxaldehyde and 3-substituted phenacyl-2,4-thiazolidinediones.
18 citations
Patent•
14 Jun 1999
TL;DR: In this paper, a novel benzopyran derivative represented by formula (1): pharmaceutically acceptable salt or stereoisomer thereof, in which X, R1, R2, R3, R4 and A are defined as described in the specification, and to a process for preparation thereof and a pharmaceutical composition having anti-estrogenic activity which contains the compound (1) as an active component.
Abstract: The present invention relates to a novel benzopyran or thiobenzopyran derivative represented by formula (1): pharmaceutically acceptable salt or stereoisomer thereof, in which X, R1, R2, R3, R4 and A are defined as described in the specification, and to a process for preparation thereof and a pharmaceutical composition having anti-estrogenic activity which contains the compound (1) as an active component.
14 citations
TL;DR: Disubstituted isoquinolones 2 and 3 have affinity for GPIIb-IIIa and represent leads for further structural evaluation, and structure−activity studies centered on the bicyclic β-turn mimic contained in these molecules are focused on.
Abstract: Disubstituted isoquinolones 2 and 3 have affinity for GPIIb-IIIa and represent leads for further structural evaluation. Structure-activity studies centered on the bicyclic beta-turn mimic contained in these molecules indicated that this moiety could accommodate a variety of modifications. Specifically, monocyclic, 6, 5-bicyclic, and 6,7-bicyclic structures provide compounds with affinity for GPIIb-IIIa. Within the 6,6-series, isoquinoline, tetralin, tetralone, and benzopyran nuclei yield potent antagonists that are specific for GPIIb-IIIa. Attachment of the arginine isostere (benzamidine) to the supporting nucleus can be accomplished with an ether or amide linkage, although the latter enhances activity. Several compounds in this series provided measurable blood levels after oral dosing. Conversion of the acid moiety in these molecules to an ester generally provided compounds which gave greater systemic exposure after oral administration. Absolute bioavailabilities in the rat for the ethyl ester prodrug derivatives of the tetralin, tetralone, and benzopyran analogues of 3 were 28%, 23%, and 24%, respectively.
11 citations
Patent•
14 Jun 1999
TL;DR: In this paper, the authors provided novel benzopyran compounds, pharmaceutically acceptable salts thereof and stereoisomers thereof, where the compounds of the invention are compounds according to Formula I.
Abstract: The present invention provides novel benzopyran compounds, pharmaceutically acceptable salts thereof and stereoisomers thereof where the benzopyran compounds of the invention are compounds according to Formula I: The present invention further provides pharmaceutical compositions which possess anti-estrogenic activity and comprise at least one benzopyran compound of the invention and a method of treating breast cancer by administration of an effective amount of a benzopyran compound provided by the present invention.
8 citations
TL;DR: The 4-oxospiro[benzopyran-2,4′ piperidine] ring system is contained within potent class III antiarrhythmic agents.
8 citations
TL;DR: The structures of two isomeric compounds, (E)-3-{[2-(dimethoxythiophosphoryl)-2-methylhydrazino]-methylidene}-3,4-dihydro-2H-1-benzopyran-2, 4-dione, C 13 H 15 N 2 O 5 PS, have been determined from X-ray data and compared as discussed by the authors.
Abstract: The structures of two isomeric compounds, (E)-3-{[2-(dimethoxythiophosphoryl)-2-methylhydrazino]-methylidene}-3,4-dihydro-2H-1-benzopyran-2,4-dione, C 13 H 15 N 2 O 5 PS, and 3-{[2-(dimethoxythiophosphoryl)-2-methylhydrazino]carbonyl}-3,4-dihydro-4H-1-benzopyran-4-one, C 13 H 15 N 2 O 5 PS, have been determined from X-ray data and compared. The benzopyran moieties of both molecules are planar. Extra six-membered rings are formed by N-H...O hydrogen bonds. The geometry around the P atoms is tetrahedral, slightly deformed to trigonal pyramidal.
TL;DR: The title aldehyde as discussed by the authors gives the bischromones 2, 3, 3 and disalicyloylbenzene 5 with sodium naphthalenide; a mixture of 3 and chromanone 22 with zinc in methanol; 3, carbinol 6 and diol 8 with zinc ion in acetic acid; and acetates 7 and 9 with Zn-Ac2O-AcONa.
Abstract: The title aldehyde 1 gives the bischromones 2, 3 and disalicyloylbenzene 5 with sodium naphthalenide; a mixture of 3 and chromanone 22 with zinc in methanol; 3, carbinol 6 and diol 8 with zinc in acetic acid; and acetates 7 and 9 with Zn–Ac2O–AcONa.
Journal Article•
TL;DR: The synthesis of new flavonoid derivatives, which possess a 1,4-dihydropyridine moiety on the phenyl ring of flavone were realized by the Hantzsch method.
Abstract: In this study, the synthesis of new flavonoid derivatives, which possess a 1,4-dihydropyridine (1,4-DHP) moiety on the phenyl ring of flavone were realized. 3' or 4'-Formyl-flavones were synthesized, then the aldehyde groups of these compounds were converted to the 1,4-DHP moiety by the Hantzsch method. A series of 23 new derivatives having different substituents at C-3 and C-5 of the 1,4-DHP ring were prepared. Two compounds (8a, 8b) were tested for their calcium channel blocker activity and 8b exhibited the best result.
Patent•
24 Aug 1999
TL;DR: In this paper, the problem of obtaining the subject material capable of highly luminant and highly efficient light emission by lowvoltage drive, excellent in stability when repeatedly used, and capable of uniform planar light emission, by including a specific benzopyran compound was solved by incorporating a compound of formula I.
Abstract: PROBLEM TO BE SOLVED: To obtain the subject material capable of highly luminant and highly efficient light emission by low-voltage drive, excellent in stability when repeatedly used, and capable of uniform planar light emission by including a specific benzopyran compound. SOLUTION: This material is obtained by incorporating a compound of formula I [R1 to R8 are each H or a substitutent; X is O, S or a group NR; R is H, an aliphatic hydrocarbon or the like; Y is O, S, or a group CQ1(Q2); Q1 and Q2 are each H or a substitutent, and at least one of them is an electron attractive group or they form a ring by being bound to each other; Z is a group OM or the like; M is a heterocyclic ring, cation or the like] (e.g. a compound of formula II). The compound of formula I is obtained, for instance, by formylation of a compound of formula III followed by reaction of the product with a compound of formula IV (e.g. 2-benzimidazolyl acetonitrile) in the presence of a base such as piperidine to be cyclized, and then by reacting the product with a compound of formula V (L1 and L2 are each an eliminable group) (e.g. phenyl chloroformate) in the presence of a base such as pyridine to be cyclized.
TL;DR: In this article, 3,4-dibromo-2,2,6,8-tetramethyl-2H-[1]benzopyran with either organolithium reagents or magnesium generates the novel strained alkyne, 3, 4-didehydro-2h-[1], 2H-[2]b.
Patent•
01 Jul 1999
TL;DR: In this paper, the activity of particular benzofuran derivatives as inhibitors of the recapture of biogenic amines such as noradrenalin, dopamine and serotonin and their consequent use as active ingredients for the preparation of new antidepressant drugs is described.
Abstract: Benzofuran, dihydrobenzofuran, dihydrobenzopyran and benzopyran derivatives as antidepressant agents. The activity of particular benzofuran, dihydrobenzofuran, dihydrobenzopyran and dibenzopyran derivatives corresponding to the general formula as inhibitors of the recapture of biogenic amines such as noradrenalin, dopamine and serotonin and their consequent use as active ingredients for the preparation of new antidepressant drugs is described. Some of these derivatives show greater specificity as inhibitors of serotonin recapture. Some of the derivatives described are new to the literature.
TL;DR: The synthesis of the title compound via the Hantzsch method from 4'-flavone carboxaldehyde is described, and its molecular structure was determined by X-ray crystallography.
Abstract: The synthesis of the title compound via the Hantzsch method from 4′-flavone carboxaldehyde is described, and its molecular structure was determined by X-ray crystallography. The 1,4-dihydropyridine (1,4-DHP) ring adopts a boat conformation. The phenyl ring of the flavone is not exactly perpendicular to the DHP ring. Calcium antagonistic activity of this compound was evaluated in vitro by using BaCl2-stimulated rat ileum.
Journal Article•
TL;DR: The surface of alumina is polar and contains immobile catalytic Bronsted and Lewis acid as well as base sites; the composition and nature of these sites can be altered by heating, and hydroxy groups on oxide surfaces are much weaker nucleophiles than the lattice oxide anions as mentioned in this paper.
Abstract: The surface of alumina is polar and contains immobile catalytic Bronsted and Lewis acid as well as base sites; the composition and nature of these sites can be altered by heating, and hydroxy groups on oxide surfaces are much weaker nucleophiles than the lattice oxide anions}. That is why alumina not only functions as a solid support for interacting reagents but also mediates several types of reactions e.g. Cannizzaro reaction. , Meerwein-Pondorf-Verley type reduction 7 including internal redox reaction of some ketols, epimerisation, Favorskii rearrange10 I . II . 12 I 11 ment, acy om , OXlrane, cyc opropylketone . rearrangements, skeletal rearrangement of quadri cyclanone l4 , spifting of ethylenic linkages l5 , selfcondensation of methylene aldehydes, methylene ketones l 6 and 3-acetylchromone I7 , deacetalisation and subsequent deformylation 18 and conversion of benzyl halide to dibenzyl ether l9 . Alumina mediated reactions of chloroacetone with 4-oxo-4H-I-benzopyran3-carbaldehyde, -3-c.arbonitrile and -3-carboxylate give the products different from those . ari sing from the respective reactions conducted ' in acetone containing anhydrous potassium carbonate The transformation of the title 4-oxo-4H-I-benzopyran (chromone) derivati ves 1-4, each containing three electropositive centres (namely C-2, formylor
Patent•
14 Jul 1999
TL;DR: In this article, a process for the synthesis of benzopyran-based compounds represented by Formula (1) and Formula (2) is described, as well as two novel compounds, Formula (E), Formula (G), and Formula(G).
Abstract: The present invention provides a process for the synthesis of benzopyran based compounds represented by Formula (1). Also disclosed are novel benzopyran based compounds represented by Formula (E) and Formula (3).
TL;DR: The structure of clusifoliol isolated from whole plants of Peperomia clusiifolia has been established as 3,4-dihydro-2,7-dimethyl-6-(3-methyl-2-butenyl)-2-(4methyl-1,3-pentadienyl)2H-1-benzopyran-5-ol by spectroscopic methods.
Abstract: The structure of a new compound, clusifoliol, isolated from whole plants of Peperomia clusiifolia has been established as 3,4-dihydro-2,7-dimethyl-6-(3-methyl-2-butenyl)-2-(4-methyl-1,3-pentadienyl)-2H-1-benzopyran-5-ol by spectroscopic methods.
TL;DR: The 4-oxospiro[benzopyran-2,4′ piperidine] ring system is contained within potent class III antiarrhythmic agents as mentioned in this paper.
Abstract: The 4-oxospiro[benzopyran-2,4′-piperidine] ring system is contained within potent class III antiarrhythmic agents. We highlight how these agents can be chemically transformed into a new class of potent ( 25-fold) α 1a -receptor subtype adrenergic tagonists.
TL;DR: Several acetoacetanilides were trilithiated in excess lithium diisopropylamide, and the resulting polylithiated intermediates were regioselectively condensed with lithiated methyl salicylates followed by acid cyclization to substituted 4-oxo-N-aryl-4H-1-benzopyran-2-acetamides as mentioned in this paper.
Abstract: Several acetoacetanilides were trilithiated in excess lithium diisopropylamide, and the resulting polylithiated intermediates were regioselectively condensed with lithiated methyl salicylates followed by acid cyclization to substituted 4-oxo-N-aryl-4H-1-benzopyran-2-acetamides (benzopyranone-2-acetamides).
TL;DR: The title racemic compound, C 20 H 20 O 5, was obtained from the condensation reaction of 2-cyclohexenecarboxaldehyde and 4-hydroxy-6-(3,4-dimethoxyphenyl)-2-pyrone in the presence of L-proline as mentioned in this paper.
Abstract: The title racemic compound, C 20 H 20 O 5 , an antitumor agent, was obtained from the condensation reaction of 2-cyclohexenecarboxaldehyde and 4-hydroxy-6-(3,4-dimethoxyphenyl)-2-pyrone in the presence of L-proline. The X-ray structure (173K) shows a linear tricyclic skeleton in which the cyclohexane ring has a chair conformation, with the junction H atom axially oriented on the lone asymmetric C atom. The structure is disordered, such that the two enantiomers lie on the same site. The dimethoxyphenyl ring is virtually coplanar with the 2-pyrone ring, the angle between these two planes being 4.56 (11)°.
TL;DR: In this article, a boat conformation of the 1,4-dihydropyridine ring was shown for diethyl 2,6-dimethyl-4-(2-phenyl-4-oxo-4H-1-benzopyran-6-yl)-1, 4-diamethyl-3,5-dicarboxylate.
Abstract: In the title compound, diethyl 2,6-dimethyl-4-(2-phenyl-4-oxo-4H-1-benzopyran-6-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C 28 H 27 NO 6 , the 1,4-dihydropyridine ring exhibits a boat conformation. The benzopyran moiety of the flavone is nearly planar, and is approximately perpendicular to the 1,4-dihydropyridine ring [dihedral angle 87.1(1)°]. The phenyl ring is twisted 10.7(1)° from the plane of the benzopyran ring system.