Showing papers on "Benzopyran published in 1995"

Mesoporous aluminosilicate MCM-41 as a convenient acid catalyst for Friedel–Crafts alkylation of a bulky aromatic compound with cinnamyl alcohol

Abstract: Owing to its large molecular size, alkylation of 2,4-di-tert-butylphenol with cinnamyl alcohol does not take plAcc using HY zeolite (pore opening 7.4 A) as catalyst even after controlled steaming treatment to increase its mesoporosity; by contrast, novel mesoporous aluminosilicate MCM-41 catalyses this reaction giving rise to 6,8-di-tert-butyl-2-phenyl-2,3-dihydro[4H]benzopyran (arising from intramolecular cyclization of the primary cinnamylphenol) together with 4-tert-butylphenol and small amounts of 6-tert-butyl-2-phenyl-2,3-dihydro[4H]benzopyran.

2-(2-amino-3-methoxyphenyl)-4-oxo-4h-[1]benzopyran for treating proliferative disorders

Abstract: 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran inhibits MEK and, as such, is effective in treating cancer and other proliferative diseases such as psoriasis and restenosis.

N-(3-hydroxy-4-piperidinyl) dihydrobenzofuran, (dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives

Abstract: N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives, their N-oxide forms and pharmaceutically acceptable salts having gastrointestinal motility stimulating properties, compositions containing these compounds as active ingredient and methods of treating warm-blooded animals suffering from the decreased peristalsis of the gastrointestinal system.

Synthetic reactions of 2-(2-amino-3-cyano-4H-[1]benzopyran-4-yl)propane-1,3-dinitrile with reactive methylene compounds

Abstract: Derivatives of dibenzo [b,d]pyran, [1]benzopyrano[2,3-b]pyridine, [1]benzopyron[3,4-c]pyridine and [1]benzopyrano[4,3,2-de][1,6]naphthyridine are obtained from the reaction of 2-(2-amino-3-cyno-4H-[1]benzopyran-4-yl)propane-1,3-dinitrile with compounds containing a reactive methylene group. Consideration of these reactions suggests that the dicyanomethyl group is released from the 4-position of the starting material, and that it mean reacts at the 2-position of the newly formed iminium ion. The 4-position is now available for Michael addition of a compound containing a reactive methylene group, but the nature of the final product depends on the substituents on the methylene group.

Benzopyran and benzo-fused compounds, their preparation and their use as leukotriene b4' (ltb4) antagonists

Abstract: This invention relates to novel benzopyran and other benzo-fused leukotriene B4 (LTB4) antagonists of formula (I), and the pharmaceutically acceptable salts thereof wherein A1 is O, CH?2?, S, NH or N(C1-C6)alkyl; A?2? is (a), (b) or (c); R1 is selected from the group consisting of tetrazolyl, carboxyl, cis or trans -(CH?2?)m-CX?1 = CX2-CO?2H, -(CH2)mCX3X4X5, -CO-NG1G2, (d), and a substituted five or six-membered aromatic ring optionally having one or two heteroatoms where the heteroatoms are independently selected from the group consisting of O, S and N; R2 is hydrogen, fluoro, chloro, (C?1?-C6)alkyl, (C1-C6)alkoxy, (C1-C4)perfluoroalkyl, (C1-C4)perfluoroalkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, phenylsulfinyl, (C1-C6)alkylsulfonyl or phenylsulfonyl; and to the corresponding intermediates of formula (1A), and to pharmaceutical compositions containing such compounds, and to a method of using such compounds as LTB4 antagonists. The compounds of this invention inhibit the action of LTB4 and are therefore useful in the treatment of LTB4 induced illnesses such as inflammatory disorders including rheumatoid arthritis, osteoarthritis, inflammatory bowel disease, psoriasis and other skin disorders such as eczema, erythema, pruritus and acne, stroke and other forms of reperfusion injury, graft rejection, autoimmune diseases, asthma, and other conditions where marked neutrophil infiltration occurs.

6-Chloro-2,3-dihydro-4H-1-benzopyran carboxylic acids: Synthesis, optical resolution and absolute configuration

Abstract: 6-Chloro-2,3-dihydro-4H-1-benzopyran-2-carboxylic acid, a rigid analogue of clofibric acid, the active metabolite of the antilipidemic drug clofibrate, has been prepared together with two isomers, 6-chloro-2,3-dihydro-4H-1-benzopyran-3- and 4-carboxylic acids. The three acids have been resolved into their optical antipodes and the absolute configuration established by chemical correlation.

Intramolecular 1,3-dipolar cycloaddition at the periphery of heterocyclic systems. Part 1. Facile oxime–nitrone isomerisation at the periphery of pyran and 1-benzopyran

Abstract: 4-(Alk-2-enylamino)-2-oxo-2H-1-benzopyran-3-carbaldehyde oximes 5 underwent thermally induced 1,3-dipolar cycloaddition under mild conditions giving isoxazolo[3,4-d][1]benzopyrano[4,3-b]pyridine derivatives 6 in good yields. The features of the oxime–nitrone isomerisation and nitrone–olefin cycloaddition are discussed.

Sulfonamido substituted benzopyran derivatives

Abstract: ##STR1## and pharmaceutically acceptable salts thereof wherein Y is a single bond, --CH 2 --, --C(O)--, --O--, --S-- or --N(R 14 )--; and R 1 to R 7 are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.

Stereoselective acetylation of 3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Abstract: The chiral intermediate diol (3 S ,4 R )-trans-3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2 H -1-benzopyran-6-carbonitrile 2 . was prepared for the total synthesis of a potassium channel opener drug candidate. The stereoselective acetylation of racemic 1 was carried out with various lipases among which the lipases from Candida cylindraceae and Pseudomonas cepacia catalyzed the acetylation of the undesired enantiomer of racemic 1 to yield monoacetylated product and unreacted desired (+)-trans diol 2 . A reaction yield of >40% and an optical purity >90% were obtained using each lipase.

Process for preparing benzopyran compounds

Abstract: A process for preparing substituted benzopyran derivatives which comprises a final step cyclisation of the corresponding open-chain intermediates.

Benzopyran compounds as 5HT2C receptor antagonists

Abstract: Compounds of formula (I): ##STR1## in which: n represents 1 or 2, R1 represents hydrogen or alkyl, benzyl, acetyl, benzoyl, allyl, pyridinecarbonyl, pyridinemethyl, acylaminoalkyl (optionally substituted), pyridineaminocarbonyl, phthalimidoalkyl, thiochromanyloxyalkyl or (benzodioxanyloxy)alkyl, R2, R3 or R4, which may be identical or different, represent hydrogen or halogen or alkyl, alkoxy, hydroxyl, acetyl, aminocarbonyl, aminomethyl, cyano, nitro, amino, phenyl (which may or may not be substituted), furyl, pyridinyl, thienyl or pyridyl, or alternatively, when they are located on adjacent carbons, R2 and R3 form, with the carbon atoms which bear them, a furan or phenyl ring, the isomers thereof and the addition salts thereof with a pharmaceutically acceptable acid, and medicinal products containing the same are useful for the treatment of diseases requiring a ligand to the 5-HT2C receptors.

Phenylglycine and phenylalaninen amido benzopyran derivatives

Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein a, b and d are all carbon atoms or one of a, b and d is a nitrogen atom or --N(O)-- and the others are carbon atoms; Y is a single bond, --CH 2 --, --C(O)--, --O--, --S-- or --N(R 8 )--; and R 1 to R 7 are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.

C-4 amide substituted compounds and their use as therapeutic agents

Abstract: The invention provides certain 5 and/or 8 substituted benzopyran, pyranopyridine or tetrahydroquinaline compounds having a C-4 amide substituent and processes for making them. The compounds described are useful in treating and/or preventing certain disorders.

Phosphinic ester substituted benzopyran derivatives

Abstract: ##STR1## and pharmaceutically acceptable salts thereof wherein Y is a single bond, --CH2 --, --C(O)--, --S-- or --N(R11)--; and R1 to R6 are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.

Structure of 2'-hydroxy flavone1

Abstract: The title compound [C 15 H 10 O 3 , Mw = 238] crystallises in the monoclinic space group P2 1 /a with a = 25.684(2) A, b = 5.173(2) A, c = 18.014(3) A and β = 110.44(4)°, V = 2245.7(2) A 3 , Dx = 1.411 Mgm −3 , Z = 8, F(000) = 992, μ = 0.77 mm −1 , T = 293 K. The structure was solved by direct methods to a final R = 0.082 and Rw = 0.084 for 1715 observed reflections. There are two molecules in the asymmetric unit. They are similar in conformation. The benzopyran and phenyl rings are planar and the phenyl ring is rotated by 6.9(3)° and 9.5(3)° from the plane of the benzopyran ring in the two molecules, respectively. The molecules in the unit cell are stabilised by hydrogen bonds across the centre of inversion

Benzopyrane derivatives, process for their preparation and pharmaceutical compositions containing them

Abstract: Benzopyran derivs of formula (I), their isomers and acid addn salts, are new n = 1 or 2; R1 = H, 1-6C alkyl, benzyl, acetyl, benzoyl, allyl, pyridinecarbonyl, pyridine-methyl, pyridine-aminocarbonyl, phthalimido(1-6C)alkyl, (thiochroman-8-yl-oxy)-(1-4C)alkyl, (benzo-dioxanyl-oxy)(1-4C)alkyl, acylamino(1-6C)alkyl; acyl (in acylamino) = benzoyl, naphthylcarbonyl, thienylcarbonyl, (1-6C)alkyl-carbonyl, furylcarbonyl, pyrrolylcarbonyl, pyridinylcarbonyl or (3-7C)cycloalkylcarbonyl, all opt substd by one or more halo, trihalomethyl, alkoxy or hydroxy; R2, R3, R4 = H, halo, (1-6C)alkyl, (1-6C)alkoxy, hydroxy, acetyl, aminocarbonyl, aminomethyl, cyano, nitro, amino; phenyl opt substd by one or more halo, hydroxy, (1-6C)alkoxy, (1-6C)alkyl or trihalomethyl; furyl, pyridinyl, thienyl or pyrrolyl; or R2+R3 on adjacent C atoms form furan or phenyl

Crystal Structure of 5,7‐Dimethoxy‐8‐(2‐oxo‐3‐methylbutyl)‐2 H‐1‐benzopyran‐2‐one (Isosibiricin)

Abstract: The title compound, C 16 H 18 O 5 , a simple coumarin crystallizes in the monoclinic space group P2 1 /c with unit cell parameters a = 7.321(3), b = 21.111(9), c = 11.649(3)A ; β = 123.14(2)°. The structure has been solved by direct methods. The coumarin ring system is planar. The methoxy groups at C5 and C7 are almost coplanar with the coumarin mean plane. The crystal structure is stabilized by C-H... O hydrogen bonds.

Synthesis and Enantiodifferentiation of Isomeric 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-ones (3,4-Dihydro-3-oxoedulans)

Abstract: The benzopyran derivatives 1a-d were prepared in a biomimetic type reaction from their presumed natural precursor 3-oxo-retro-α-ionol, which was available from α-ionone by tert-butyl chromate oxidation, reduction with NaBH 4 , and subsequent rearrangement of the 7,8 double bond. The so-obtained geometrical isomers of 3-oxo-retro-α-ionol (4a/b) were separated by preparative and analytical multilayer coil countercurrent chromatography. Racemic 3-oxo-retro-α-ionol (4a) was esterified with (R)-(-)-2-phenylpropionic acid, and the resulting diastereomeric esters (5a/b) were isolated in pure form by preparative HPLC. Configuration at C-9 was determined by 1 H NMR spectroscopy. The isomeric ketols 6a/b obtained from esters 5a/b by enzymatic hydrolysis were subjected to thermal treatment (simultaneous distillation extraction, pH 1), yielding two pairs of diastereomeric 3,4-dihydro-3-oxoedulans (1a/b and 1c/d). The absolute configuration at C-8a was established by NOE experiments. Using on-line coupled multidimensional gas chromatography-mass spectrometry [DB-Wax/octakis(2,6-di-O-methyl-3-O-pentyl)-γ-cyclodextrin] with selected ion monitoring mode, enantiodifferentiation of 1a-d in a number of natural sources was carried out.

3,4-dihydro-2,5,7,8-tetramethyl-benzopyran-6-ol derivatives for use as drugs

Abstract: Compounds of general formula (I), as defined in the description, salts, hydrates, solvates and therapeutically acceptable prodrugs thereof, as well as racemic forms and enantiomers thereof, are disclosed. A method for preparing the compounds, and pharmaceutical compositions containing said compounds as the active principle for treating and/or preventing acute or chronic inflammatory diseases, are also disclosed.