Showing papers on "Benzopyran published in 1991"

3-Methyl-2H-1-benzopyran potassium channel activators

Abstract: By aldol condensation of 4-chromanones with paraformaldehyde, 3-alkylenechromanones 10 were obtained which gave 3-alkylchromenes following reduction and dehydration. Subsequent 3-chloroperbenzoic acid oxidation produced the versatile epoxide intermediates 15, from which 3,4-epoxy-3,4-dihydro-2,2,3-trimethyl-2H-1-benzopyran-6-carbonitrile (15a) was resolved into its enantiomers by entrainment. In addition to the methyl group, the benzyl, alkyloxymethyl, and 2-nitroethyl residues could be introduced in the 3-position. Treatment of 15a with 2-pyridone simultaneously gave N- and O-substituted products 19a and 20. 19a easily gave 4-(1,2-dihydro-2-oxo-1-pyridyl)chromene 21 by treatment with base. The corresponding pyrrolidinone compounds 26 and 27 were obtained by a slightly modified procedure. Reaction with 2,4-dihydroxypyridine or 3,6-pyridazinediol resulted in the exclusive formation of 4-(heterocyclyloxy)chromanols (31 and 32). Treatment of 15a with 3-amino-6-pyridazinol gave 4-(3-amino-1,6-dihydro-6-oxo-1-pyridazinyl)chromanol derivative 34 lacking an NH bridge. This could be established after methylation of the ring-nitrogen atom (----35). Trans-configurated 3-methyl-4-pyridone compound 36 was obtained by addition of methyllithium to chromene 3. Hyperpolarizing and antispasmodic or relaxing effects of the compounds were determined in organ bath studies using pig coronary arteries precontracted with acetylcholine or rabbit main pulmonary arteries precontracted with noradrenaline. In the 3-methyl series the classical pyridone and pyrrolidinone structures (9, 21, 26, 27) were only weakly active or inactive, but the corresponding 4-(heterocyclyloxy) and 4-(heterocyclylamino) derivatives (31, 32, 35) were even more potent than the demethyl analogues. In conformation/activity investigations it was found that the activity of the 4-substituted benzopyran derivatives seems to be dependent on the relative orientation of their ring systems.

Photochromic chromene compounds

Abstract: Described are a series of novel photochromic benzopyran and naphthopyran compounds substituted with (1) a cyclopropyl group and (2) a phenyl, substituted phenyl, or 5-member aromatic heterocyclic group at the 2-position of the benzopyran or naphthopyran ring. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic or plano lenses that incorporate the novel pyran compounds or combinations of the novel pyran compounds with other complementary photochromic compounds are described.

Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones

Abstract: This invention relates to compounds of formula (I) which are useful in association with a pharmaceutical carrier as antiatherosclerotic agents. In addition, various compounds of formula (I) are useful inhibitors of cell proliferation.

Relaxant activity of 6-cyano-2,2-dimethyl-2H-1-benzopyran-4-carboxamides and -thiocarboxamides and their analogues in guinea pig trachealis.

Abstract: Structural modifications of the potassium channel activator cromakalim (1) are described in which the amide moiety at C-4 has been replaced by carboxamide and thiocarboxamide functions. Analogues in which the hydroxyl group at C-3 has been oxidized or removed are also disclosed. Such analogues display an interesting profile of smooth muscle relaxant activity in the guinea pig isolated trachea, not all of which appears to result from the opening of potassium channels, but few compounds retain useful in vivo activity. However, one compound in particular, 6-cyano-2,2-dimethyl-N-methyl-2H-1-benzopyran-4-thiocarboxamide (13) was shown to be a potent potassium channel activator in vitro and to provide prolonged protection to guinea pigs from the respiratory effects of inhaled histamine.

N-(4-piperidinyl) (dihydrobenzofuran or dihydro-2h-benzopyran) carboxamide derivatives

Abstract: Piperidine derivatives of formula (SEE FORMULA) wherein A is a radical of formula -CH2-CH2- (a-1), -CH2-CH2-CH2- (a-2), or -CH2-CH2-CH2-CH2- (a-3), wherein one or two hydrogen atoms in said radicals (a-1) to (a-3) may be replaced by a C1-6alkyl radical; R1 is hydrogen or halo; R2 is hydrogen, amino, mono or di(C1-6alkyl)amino or C1-6alkylcarbonylamino; R3 is hydrogen or C1-6alkyl; L is C3-6cycloalkyl, C5-6cycloalkanone, C3-6alkenyl optionally substituted with aryl, or L is a radical of formula -Alk-R4 (b-1), -Alk-X-R5 (b-2), -Alk-Y-C(=O)-R7 (b-3), or -Alk-Y-C(=O)NR9R10 (b-4), the N-oxide foams, addition salts and stereochemically isomeric form thereof, said compounds having gastrointestinal motility stimulating properties pharmaceutical compositions containing these compounds as active ingredient, and a method of preparing said compounds and pharmaceutical compositions.

Benzopyran derivatives and heterocyclic analogs thereof as antiischemic agents

Abstract: A new method for the treatment of ischemia conditions and arrhythmia is disclosed. The method uses compounds of the formula ##STR1## wherein A can be --CH 2 --, --O--, --NR 9 --, --S--, --SO--, --SO 2 --; X can be oxygen or sulfur; Y can be --NR 8 , --O--, --S--, --CH 2 -- and the R groups are as defined herein. Novel compounds within the definition of formula I are also disclosed.

Synthesis and antihypertensive activity of pyran oxygen and amide nitrogen replacement analogues of the potassium channel activator cromakalim

Abstract: The synthesis and oral antihypertensive activity in conscious spontaneously hypertensive rats of two new series of compounds related to the prototype potassium channel activator cromakalim (1) are described. In the first series, replacement of the benzopyran oxygen atom by nitrogen or methylene led to the 1,2,3,4-tetrahydroquinoline 12 and 1,2,3,4-tetrahydronaphthalene 13, which were both less active than 1. However, in contrast to the equivalent activity found previously for 1 and its dehydrated analogue 28, the dihydronaphthalene 27 was found to be more active than 13. In the second series, replacement of the C(4) amide nitrogen atom in acyclic amides related to cromakalim by methylene gave ketone 16 that was less active than the corresponding amide 15. However, replacement of the 4-acetonyl substituent in 16 by N,N-dimethylacetamido as in compound 22 resulted in a marked enhancement in activity. The compounds described in this paper thus illustrate the importance of the benzopyran oxygen and C(4) substituent on antihypertensive activity in the cromakalim series of potassium channel activators.

Synthesis and characterization of 3-phenyl-4[H]-4-[one]-benzopyran (isoflavone) derivatives as potential mesogens

Abstract: With few mesogenic chromone derivatives in the literature the synthesis of 7-[4′-n-alkyloxybenzoyloxy) isoflavones was carried out. The resulting homologous series was characterized by elemental an...

Novel benzopyran derivative

Abstract: A benzopyran derivative represented by general formula (I), which has a K+ channel activating effect and so is widely applicable for treating, for example, asthma and epilepsy, wherein X represents =O, =S, =N-Z (wherein Z represents lower alkyl, etc.), or =CHNO?2?; Y represents substituted amino, alkoxy, alkylthio, etc.; and R1 to R7 represent each hydrogen, lower alkyl, etc.

A rapid synthesis of substituted 4-hydroxymethyl-3-chromene from 2'-hydroxyacetophenone and phenyl vinyl sulfoxide

Abstract: A two-step synthesis of 6-alkyl-4-hydroxymethyl-3-chromene (6-alkyl-4-hydroxymethyl-2H-1 -benzopyran) from addition of phenyl vinyl sulfoxide carbanion to 5'-alkyl-2'-hydroxyacetophenone is described. Application to the synthesis of 4-methyl-3-chromene (4-methyl-2H-1-benzopyran) and 4,4-dimethylchroman (3,4-dihydro-4,4-dimethyl-2H-1-benzopyran) is also presented

Chemistry of phosphorus ylides 9.1 reactions with phosphacumulenes iii.2 synthesis of benzodipyrans from the reaction of ketenylidene- and thioketenylidenetriphenylphosphorane with formyl benzopyran derivatives

Abstract: When 6-formyl-7-hydroxy-5-methoxy-2-methylbenzopyran-4-one (1a), was reacted with ketenylidene(2a) and thioketenylidenetriphenylphosphorane (2b), the corresponding 5-methoxy-8-methyl-2,6-dioxo 2H, 6H-benzo[1,2-b:5,4-b′]dipyran (4a) and its thio analogue (4b), were obtained respectively. The structure of the new benzodipyrans (4) were confirmed on the basis of elemental analysis and spectral studies. Moreover, the pyrazole derivatives (5), were obtained when compounds (4) were allowed to react with hydrazine hydrate.

2-Benzopyran-3-ones stabilised by alkoxy substituents

Abstract: In contrast to the corresponding compounds lacking alkoxy substituents, the 2-benzopyran-3-ones 5, 6, 7 and 9 are stable and easily isolated. In contrast to the 6-methoxy derivative 7, the 7-methoxy isomer 8 cannot be isolated; the stabilising effect of the 6,7-methylenedioxy group in 5 and 9 is therefore due to the alkoxy group at C-6. This is consistent with a donor-acceptor interaction involving the C-6 alkoxy group and the pyrone carbonyl which decreases reactivity towards nucleophilic attack by water.

New benzopyran and benzothio- pyran derivatives

Abstract: The invention relates to the compounds of the formula wherein each R independently represents hydrogen, lower alkyl, halogen, trifluoromethyl, lower alkoxy, carbocyclic or heterocyclic aryl, carbocyclic or heterocyclic aryloxy, carbocyclic or heterocyclic aryl-lower alkyloxy, carbocyclic or heterocyclic aryl-lower alkyl, C3-C7-cycloalkyl-lower alkyloxy, or C3-C7-cycloalkyloxy; R1 represents hydrogen, lower alkyl or carbocyclic aryl; R2 represents hydrogen or lower alkyl; Y represents oxygen (O), sulfur (S), sulfinyl or sulfonyl; n represents 1, 2 or 3; A represents a direct bond or lower alkylene; Z represents wherein R3 represents hydrogen or acyl; R4 represents lower alkyl, C3-C7-cycloalkyl, carbocyclic or heterocyclic aryl, carbocyclic or heterocyclic aryl-lower alkyl, or C3-C7-cycloalkyl-lower alkyl; or Z represents wherein X represents oxygen or sulfur, R3 represents hydrogen or acyl; R5 represents lower alkyl, lower alkoxycarbonyl-lower alkyl, C3-C7-cycloalkyl, carbocyclic or heterocyclic aryl, carbocyclic or heterocyclic aryl-lower alkyl, C3-C7-cycloalkyl-lower alkyl, amino, mono- or di-lower alkylamino, lower alkenylamino, lower alkynylamino, carbocyclic or heterocyclic aryl-lower alkylamino, carbocyclic or heterocyclic arylamino, C3-C7-cycloalkylamino, C3-C7-cycloalkyl-lower alkylamino, lower alkoxycarbonyl-lower alkylamino, or lower alkoxy; R6 and R7 independently represent hydrogen or lower alkyl; and pharmaceutically acceptable salts thereof; which are useful as 5-lipoxygenase inhibitors.

Benzopyran phenol derivatives for use as antibacterial agents

Abstract: A method of inhibiting microorganisms, including bacteria, using benzopyran phenol derivates from propolis. Propolis is extracted with an alcohol, and the resulting compounds are effective as antibacterial, antiviral or immunostimulating agents.

Structure of 7-methoxy-2-(2-methoxyphenyl)-4h-1-benzopyran-4-one (2',7-dimethoxyflavone)

Abstract: C17H14O4, M(r) = 282.30, monoclinic, P2(1)/c, a = 12.498 (4), b = 9.490 (2), c = 12.184 (2) angstrom, beta = 107.87 (2)degrees, V = 1375.4 (6) angstrom 3, Z = 4, D(x) = 1.36 g cm-3, Cu K-alpha, lambda = 1.54178 angstrom, mu = 7.98 cm-1, F(000) = 592, T = 291 K, R = 0.042 for 1848 observed reflections. The benzopyran heterocycle is planar within experimental errors (max. deviation from the best mean plane through the ten atoms 0.031 angstrom). The dihedral angle between the heterocycle and the phenyl ring is 23.5 (5)degrees. The methoxy groups are nearly coplanar with their aromatic rings (torsion angles about C(arom)-O are 4-6-degrees).

Benzopyran derivative, production thereof, and pharmaceutical composition containing the same

Abstract: A benzopyran derivative represented by general formula (I), a pharmaceutically acceptable salt thereof, and an ACAT inhibitor, an antihyperlipemic agent and an antiarteriosclerotic composition each containing the same as the active ingredient; formula (I) wherein one of X and Y represents the group (1) and the other of X and Y and R?1 to R10? represent each a substituent.

Smooth generation of 3H-2-benzopyran-3-ones and their Diels–Alder reactions with olefinic dienophiles

Abstract: The generation of methoxy-substituted 3H-2-benzopyran-3-ones from o-acylphenylacetic acid derivatives in acetic anhydride at 140 °C and their in situ Diets–Alder reactions being inefficient in the synthesis of some carbocyclic compounds, alternative reagents have been used. It is shown that, e.g. 1,3-dicyclohexylcarbodiimide (DCC) with 2-hydroxypyridine, disuccinimidyl carbonate (DSC), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) of 2-isobutoxy-N-isobutoxycarbonyl-1,2-dihydroquinoline (IIDQ) are much more efficient reagents.Using these alternative reagents the formation of side-products from the benzopyranone, e.g. chrysene, can be avoided; with the modified DCC-method the 6,7-dimethoxy-1 -methyl-2-benzopyran3-one intermediate 8a can be identified spectroscopically. An exemplified procedure with IIDQ is proposed, opening new prespectives for Diets–Alder reactions of unstable or less reactive dienophiles with problematic benzopyranones.

N-(4-piperodinyl)(dihydrobenzofuran or dihydro-2h-benzopyran) carboxamide derivatives

Abstract: Piperidine derivatives of formula ##STR1## wherein A is a radical of formula ##STR2## wherein one or two hydrogen atoms in said radicals (a-1) to (a-3) may be replaced by a C 1-6 alkyl radical; R 1 is hydrogen or halo; R 2 is hydrogen, amino, mono or di(C 1-6 alkyl)amino or C 1-6 alkylcarbonylamino; R 3 is hydrogen or C 1-6 alkyl; L is C 3-6 cycloalkyl, C 5-6 cycloalkanone, C 3-6 alkenyl optionally substituted with aryl, or L is a radical of formula ##STR3## the N-oxide forms, addition salts and stereochemically isomeric forms thereof, said compounds having gastrointestinal motility stimulating properties. Pharmaceutical compositions containing these compounds as active ingredient, and a method of preparing said compounds and pharmaceutical compositions.

Certain 2-oxo-tetrahydro-cycloalkyl-benzopyran-3yl ureas having acyl-CoA-cholesterol acyl transferase inhibitory activity

Abstract: Novel heterocyclic compound of the general formula: ##STR1## wherein ring A and ring B each means a benzene ring which is substituted or unsubstituted; X means a group of the formula: ##STR2## wherein R2 is hydrogen, an alkyl or an alkoxy; m is 0 or 1, the formula: ##STR3## wherein R3 is hydrogen or an alkyl, or the formula: --O--CO--; Y means a bond, --NH--, an C1 or 2 alkylene group or --CH═CH--; R1 means a hydrocarbon group which is substituted or unsubstituted; and n means a whole number of 3 through 6, or a salt thereof, having excellent acyl-CoA:cholesterol acyltransferase inhibitory activity, and a method for preparing it and its use.

4(2-(4-sub-piperidinyl/piperazinyl)-ethyl)-3,4- dihydrobenzopyrans as pharmaceuticals

Abstract: New benzopyran derivatives of formula: (I) in which R1 is hydrogen, halogen, hydroxy, alkoxy, nitro, amino, alkylsulphonamido, bis(alkylsulphonyl) amino or acylamino, X is nitrogen or a >CH-radical R is a radical of formula: in which A denotes a single bond or methylene or, when X is nitrogen, A may denote carbonyl, and R2 and R3, which are identical or different, are hydrogen, halogen, hydroxy, alkyl, alkoxy, nitro, amino, alkylsulphonamido, bis(alkylsulphonyl)amino, acylamino, sulphamoyl or cyano, or, when they are adjacent, together form a methylenedioxy or ethylenedioxy radical, or else R is pyridyl or 2(2H)-benzimidazolonyl if X denotes >CH-, and R' and R'' are identical and are hydrogen or alkyl, their isomeric forms and mixtures thereof, and their acid addition salts, can be used as antiarrhythmic and antifibrillation agents.