Showing papers on "Benzopyran published in 1994"
58 citations
Patent•
21 Feb 1994TL;DR: In this paper, a method for safening herbicides in crop plants by using substituted benzopyran or tetrahydronaphthalene compounds of formula I was provided.
Abstract: There is provided a method for safening herbicides in crop plants by using substituted benzopyran or tetrahydronaphthalene compounds of formula I ##STR1## Further provided are compounds of formula II and compositions comprising a herbicide and an antidotally effective amount of a substituted benzopyran or tetrahydronaphthalene compound of formula I.
52 citations
32 citations
TL;DR: In this paper, the synthesis and anti-hypertensive activity in spontaneously hypertensive rats (SHR) of a series of benzopyran potassium channel activators related to cromakalin where the pyrrolidinone at position 4 is replaced by a number of potential heterocyclic amide and ester bioisosteres is reported.
27 citations
Patent•
30 Aug 1994TL;DR: In this paper, the authors define a class of compounds having the formula "STR1## and pharmaceutically acceptable salts thereof" where X is alkyl, Y is a single bond.
Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein X is alkyl, Y is a single bond, --CH 2 --, --C(O)--, --O--, --S-- or --N(R 8 )-- where R 8 is hydrogen, alkyl, haloalkyl, aryl, arylalkyl, cycloalkyl or (cycloalkyl)alkyl, 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.
26 citations
25 citations
TL;DR: In this article, the structures of the final products 4, 10 and 15 have been assigned from their spectral data and their formation has been rationalized in terms of transformations available to the assumed primary products.
Abstract: 3-Amino-4-imino-4H-thieno[3,4-c][1]benzopyran 1 adds dimethyl maleate 2 and dimethyl acetylenedicarboxylate 6 in a [4 + 2] mode across the thiophene ring and reacts with 2,3-dichloro-1,4-naphthoquinone 12 by substitution of both chlorine atoms. All primary adducts, 3, 7 and 13, however, are unstable under the reaction conditions. The structures of the final products 4, 10 and 15 have been assigned from their spectral data and their formation has been rationalized in terms of transformations available to the assumed primary products.
21 citations
Journal Article•
TL;DR: Optically active and racemic 2-substituted-6-fluoro-2,3-dihydrospiro[4H-1-benzopyran-4, 4'-imidazolidine]-2-carboxamide showed the most potent in vitro and in vivo activity.
Abstract: Optically active and racemic 2-substituted-6-fluoro-2,3-dihydrospiro[4H-1-benzopyran-4, 4'-imidazolidine]-2',5'-diones were synthesized from (+)-, (-)-, and (+-)-6-fluoro-3,4-dihydro-4-oxo-2H-1-benzopyran-2-carboxylic acid. These compounds were then evaluated for in vitro and in vivo aldose reductase inhibitory activity. The 2S,4S isomers were found to be more potent aldose reductase inhibitors than the other corresponding stereoisomers. Among these compounds, (2S,4S)-6-fluoro-2,3-dihydro-2',5'-dioxospiro[4H-1-benzopyran-4, 4'-imidazolidine]-2-carboxamide ((+)-1b, SNK-860, CAS 105300-43-4) showed the most potent in vitro and in vivo activity.
20 citations
TL;DR: Optically active and racemic 2-substituted 6-fluoro-2, 3-dihydrospiro[4H-1-benzopyran-4, 4'-imidazolidine]-2', 5'-diones were synthesized stereoselectively from (+)-, (-)-, and (±)-6-fluor-3, 4-dhydro-4-oxo-2h-1boxo, 2H-2H-one-bensopyrans-
Abstract: Optically active and racemic 2-substituted 6-fluoro-2, 3-dihydrospiro[4H-1-benzopyran-4, 4'-imidazolidine]-2', 5'-diones were synthesized stereoselectively from (+)-, (-)-, and (±)-6-fluoro-3, 4-dihydro-4-oxo-2H-1-benzopyran-2-carboxylic acid [(+)-1, (-)-1, and (±)-1], respectively, for evaluation as new aldose reductase inhibitors. Among these compounds, the 2S, 4S compounds were found to be more potent inhibitors of aldose reductase in vitro and in vivo than the corresponding 2R, 4R enantiomers. The chloromethyl compound [(+)-5] showed highly potent activities in inhibiting cataract formation in the lenses and polyol accumulation in the sciatic nerve of rats.
18 citations
TL;DR: The steric course of catalytic hydrogenation of the trans-1,2-dihydronaphthalenes and the carboxylic acid 31 is controlled by the 1-phenyl and 1-carboxy group, respectively, rather than by the 2-substituent.
Abstract: 1-Phenyl-2-benzopyran-3-one 2 adds to a series of unsymmetrically substituted dienophiles (methyl acrylate, ethyl crotonate, methyl ω-bromocrotonate, and crotonaldehyde) with regioselectivity largely determined by the phenyl group but with little endo-exo-selectivity. Addition of 2 to dimethyl fumarate results in preferred exo-addition adjacent to the phenyl group. The stereochemistry of hydrogenolysis of the endo15 and exo16 maleate adducts of 2 appears to be governed by steric effects rather than the nature of the catalyst (Pd or Ni). Catalytic hydrogenation of the cis dihydronaphthalenes 23 and 24 gave 18 and 25, respectively, which were different from the products obtained by addition of the o-quinodimethanes 11 and 12 to dimethyl maleate in agreement with preferred exo-addition in both Diels–Alder reactions. The steric course of catalytic hydrogenation of the trans-1,2-dihydronaphthalenes 26 and 28 and the carboxylic acid 31 is controlled by the 1-phenyl and 1-carboxy group, respectively, rather than by the 2-substituent.
12 citations
TL;DR: Directed lithiation of chroman-4-ols occurs predominantly at C-5 under kinetic control, but at c-8 at higher temperatures as mentioned in this paper, where chroman 4-ols are converted into pyrano[4,3,2-de] phthalazines.
Abstract: Directed lithiation of chroman-4-ols occurs predominantly at C-5 under kinetic control, but at C-8 at higher temperatures. Dehydration and oxidation of the products provides viable routes to 5-substituted 2H-chromenes and chroman-4-ones, respectively. The chroman-4-ones have been converted into novel pyrano[4,3,2-de] phthalazines. 2,2,5,7-Tetramethylchroman-4-ol is preferentially lithiated at the 5-methyl group and leads to the pyrano[2,3,4-de][1]benzopyran system.
TL;DR: The chromone derivatives 1, 2, and 4 give with N -phenylmaleimide the cycloadducts 5, 12, and 13 which are converted by palladised charcoal into 2-azaxanthone 6, xanthones 14 and 15, respectively as mentioned in this paper.
TL;DR: In this article, 6-substituted benzopyran-4-(N-cyano)amidines and their analogs have been synthesized and some of these compounds, 1a, 1e, and 1f exhibited selective activity for guinea pig trachealis.
TL;DR: In this paper, the presence of six compounds, i.e., the epimeric hydroxyfuro[2,3-b]benzofurans 4, a pair of diastereomers of the hydroxylated tetrahydrofuran 6 and the diastereric pair of benzopyran aldehydes 8, was identified in the equilibrium mixture established when hemiacetals 4 were in solution.
TL;DR: A new compound, 9-hydroxy-2,2,6,7-tetramethyl-2H-[1]-benzopyran-(1-phenylethylene-10-yl)-[3,2-b]-dihydropyran-4-one, has been isolated from the leaves of Calophyllum tomentosum.
Journal Article•
TL;DR: In this article, the synthesis of hippuric acid in acetic anhydride with ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates, and 2-dymethylhexanediones, respectively, is described.
Abstract: The synthesis of ethyl or methyl 6-substituted 3-(benzoylamino)-2-oxo-2H-pyran-5-carboxylates 2 and 3-(benzoylamino)-7,8-dihydro-2H-1-benzopyran-2,5(6H)-diones 4 by reaction of hippuric acid in acetic anhydride with ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates and 2-dimethylaminomethylene-1,3-cyclohexanediones, respectively, is described. Some compounds 2 and 4 showed a strong local anesthetic activity in mice and a platelet antiaggregating activity in vitro comparable to that of acetylsalicylic acid, as well as moderate analgesic, antiinflammatory and antiarrhythmic activities in rats and mice.
Patent•
10 Feb 1994TL;DR: Spirocycles of general structural formula (I) or a pharmaceutically acceptable salt, hydrate or crystal form thereof (II) which are Class III antiarrhythmic agents as mentioned in this paper.
Abstract: Spirocycles of general structural formula (I) or a pharmaceutically acceptable salt, hydrate or crystal form thereof wherein: R1 = H3CSO2NH-, H3CO-, alkylSO2-, alkylCONH-, NO2-; R2 = H, -OCH?3?; R?3 and R4? taken together are =O; or R3 = H and R4 = OH; R5 = R6 taken together are -CH?2?-CH2- or =CH2; R?7? is (II) which are Class III antiarrhythmic agents.
TL;DR: The crystal and molecular structure of the title compound has been determined by direct methods, and refined to a finalR of 0.070 for 1466 observed reflections as mentioned in this paper. The compound crystallizes in space group P2l/n with cell dimensionsa=10.706(8),b=21.127(11),c=12.038(10) A, Z=4.
Abstract: The crystal and molecular structure of the title compound has been determined by direct methods, and refined to a finalR of 0.070 for 1466 observed reflections. The compound crystallizes in space group P2l/n with cell dimensionsa=10.706(8),b=21.127(11),c=12.038(10) A, Z=4.1,4-dihydropyridine ring adopts a boat shaped conformation. The flavon molecule is planar and it's phenyl ring is almost perpendicular to the 1,4-DHP. The C36 atom of the allyl group shows disorder.
TL;DR: Some compounds 2 and 4 showed a strong local anesthetic activity in mice and a platelet antiaggregating activity in vitro comparable to that of acetylsalicylic acid, as well as moderate analgesic, antiinflammatory and antiarrhythmic activities in rats and mice.
Abstract: The synthesis of ethyl or methyl 6-substituted 3-(benzoylamino)-2-oxo-2H-pyran-5-carboxylates 2 and 3-(benzoylamino)-7,8-dihydro-2H-1-benzopyran-2,5(6H)-diones 4 by reaction of hippuric acid in acetic anhydride with ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates and 2-dimethylaminomethylene-1,3-cyclohexanediones, respectively, is described. Some compounds 2 and 4 showed a strong local anesthetic activity in mice and a platelet antiaggregating activity in vitro comparable to that of acetylsalicylic acid, as well as moderate analgesic, antiinflammatory and antiarrhythmic activities in rats and mice.
Patent•
11 Apr 1994TL;DR: In this article, the authors defined a set of compounds having the formula a, b, d, A and R¹ to R Ω(n) where n is the number of nodes in the channel.
Abstract: Compounds having the formula
and pharmaceutically acceptable salts thereof wherein a, b, d, A and R¹ to R⁹ are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.
TL;DR: The 2-benzopyran-3-ones 7a and 7c undergo intramolecular Diels-Alder addition, via preferred endo-addition of the connecting chain, whereas for 7d and 7e (X = SO2Ph), exo-ADDITION of the chain is preferred; the main adducts from the latter additions (9d and 9e), give the diterpene-related products 12(R = H, Y = OMe) as mentioned in this paper.
Abstract: The 2-benzopyran-3-ones 7a and 7c undergo intramolecular Diels–Alder addition, via preferred endo-addition of the connecting chain, whereas for 7d and 7e(X = SO2Ph), exo-addition of the chain is preferred; the main adducts from the latter additions (9d and 9e), give the diterpene-related products 12(R = H, Y = OMe) and 12(R = Me, Y = OMe) upon treatment with sodium amalgam.
TL;DR: In this article, a new synthesis of the title compound using aryllithium salts as key intermediates is described, mainly based on a cyclization reaction that mimics the process by which it is believed benzopyran rings are formed in nature.
Journal Article•
TL;DR: This paper showed that the highest levels of immunotropic activity were associated with polymeric derivatives of benzopyran-2-one (see Scheme 1, Scheme 2) and polymeric copolymers with N-vinylpyrrolidone using a radical mechanism.
Abstract: Much attention has been paid to synthetic immunomodulators of the benzopyran series because of their ability to act on different branches of the immune system. Many of our studies [1-13] indicate that a number of benzopyran-2-one derivatives have potential as immunomodulators; depending on the initial immune status, doses and regimes of administration, these agents stimulate immune reactivity [1, 4, 6, 9-13]. Immunotropic activity is seen both with monomeric benzopyran-2ones and with their copolymers (CP) with N-vinylpyrrolidone [1, 6-13]. During these studies, it was shown that the highest levels of immunotropic activity were associated with polymeric derivatives of benzopyran-2-one (see Scheme 1), in which the benzopyran-2-one molecule is combined with other heterocyclic compounds, such as imidazole (II), benzimidazole (I), and maleimide (IV), and then polymerized with N-vinylpyrrolidone using a radical mechanism [1, 6, 14, 15].
TL;DR: In this article, the synthesis and vasorelaxant activity of N-imino-2-(benzopyran-4-yl)pyridines are described.
TL;DR: In this paper, the formation of tetrahydroindeno[1,2-b]indol-10-ones by reaction of ninhydrin with substituted anilines is described.
Abstract: The formation of tetrahydroindeno[1,2-b]indol-10-ones 1 by reaction of ninhydrin with substituted anilines is described. The tetrahydroindeno[1,2-b]indol-10-ones 1 rearrange to form 5,11-dihydro-[2]benzopyran[4,3-b]indol-5-ones 8 when heated under acid conditions. Reaction of ninhydrin with 3-hydroxyaniline gave a benzo[b]indeno[2,1-d]furan 4
TL;DR: The title molecule of as mentioned in this paper consists of two six-membered condensed rings, with a Cl atom at position 4 and a dimethoxyphosphoryl(dimethoxy phosphoryloxy)methylene group at position 2.
Abstract: The title molecule, C 14 H 17 ClO 8 P 2 , consists of two six-membered condensed rings, with a Cl atom at position 4 and a dimethoxyphosphoryl(dimethoxyphosphoryloxy)methylene group at position 2. Both rings are aromatic. The best planes of the two rings form a dihedral angle of 178.5 (1) o . The Cl atom lies 0.012 (2) A out of the plane defined by the ring. The molecule is the E isomer. The torsion angle O4-C3-C11-P19 is -174.2 (2) o
Journal Article•