Showing papers on "Pyran published in 1977"
133 citations
TL;DR: Macrophage “activation” to inhibit MBL-2 leukemia cell growth was sharply dose-dependent and required >24 hr after exposure to pyran, while similar activation was observed for poly(I)·poly(C) and to a lesser extent for dextran sulfate.
62 citations
Journal Article•
TL;DR: Results from both in vivo and in vitro studies support the concept that pyran enhances host resistance to neoplasia by mobilization and activation of the reticuloendothelial elements of the host's defense.
Abstract: Summary Pyran copolymer (NSC 46015) therapy markedly enhanced host resistance to a murine lung carcinoma (M109) implanted s.c. Multiple dose schedules were not significantly better than single doses at increasing lifespan. Although tumor necrosis was much more extensive in the lesions of pyran-treated mice, pyran copolymer was not directly toxic to M109 cells in vitro . A comparative histopathological study revealed an intense histiocytic reaction in the connective tissue surrounding the primary tumor in mice receiving pyran as compared to 0.9% NaCl solutiontreated controls. Macrophages were often associated with necrobiotic tumor cells. Morphologically activated macrophages were recovered from pyran-treated animals which potently inhibited DNA synthesis of M109 tumor cells in vitro . This response peaked 6 days after drug treatment and was to a large extent specific for neoplastic cells. Our results from both in vivo and in vitro studies support the concept that pyran enhances host resistance to neoplasia by mobilization and activation of the reticuloendothelial elements of the host9s defense.
56 citations
51 citations
36 citations
TL;DR: The structure-activity data generated indicate that, in general, a change of the 1-hydroxy group to an amine results in a retention of pharmacological activity but that a change to sulfur results in loss of Pharmacological activity.
Abstract: A series of 1-amino- and 1-mercapto-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyrans was synthesized and subsequently evaluated in three rodent test systems for CNS activity. The structure-activity data generated indicate that, in general, a change of the 1-hydroxy group to an amine results in a retention of pharmacological activity but that a change to sulfur results in loss of pharmacological activity. Derivatization of the 1-amino group with various functions decreased the activity of the parent compound. For optimum potency, in all series, the 3-position alkyl side chain should be either 1,1- or 1,2-dimethylheptyl. With either the 1-hydroxy- or 1-amino-7,8,9,10-tetrahydro-3-(1,1-dimethylheptyl)-6,6,9-trimethyl-6H-dibenzo[b,d]pyran (4c or 10c), preparation of the optically active antipodes did not lead to any great degree of spearation of activity. Both of the antipodes possess pharmacological activity as measured in these rodent test systems.
36 citations
TL;DR: In this paper, it was shown that ortho-Alkenyl phenols react rapidly with PhSeCl to produce derivatives of 2,3-dihydrobenzofuran or 3,4-dhydro-2H-benzo[b]pyran in a process shown to belong to the general class of cyclofunctionalisations.
Abstract: ortho-Alkenyl phenols react rapidly with PhSeCl to produce derivatives of 2,3-dihydrobenzofuran or 3,4-dihydro-2H-benzo[b]pyran (depending on the nature of the ortho-substituent) in a process shown to belong to the general class of cyclofunctionalisations.
34 citations
Patent•
18 Oct 1977
TL;DR: In this paper, an aluminum halide in an unreactive organic solvent effects complete epimerization to provide the corresponding trans-1-hydroxy-3-substituted-6,6-dimethyl, 6,6a,7,8,10,10a-hexahydro-9 H-dibenzo[b,d]pyran-9-one.
Abstract: Reaction of cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H- dibenzo[b,d]pyran-9-ones with an aluminum halide in an unreactive organic solvent effects complete epimerization to provide the corresponding trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9 H-dibenzo[b,d]pyran-9-one.
25 citations
15 citations
TL;DR: In this article, a synthesis of 4,4-diphenylγ-pyran from diphenylmethane was elaborated, which was shown to yield trans-endo-5,6-dipsyl-2-oxabicyclo[3.1.0]-hexene.
Abstract: A synthesis of 4,4-diphenyl-γ-pyran (1) was elaborated from diphenylmethane. Prolonged irradiation of pyran 1 in tert-butyl alcohol led to: trans-endo-5,6-diphenyl-2-oxabicyclo[3.1.0]-hexene (18), ...
15 citations
TL;DR: In this paper, the reactions of cis-and trans-2-tert-butyl-4,5-epoxytetrahydropyran with HBr and with LAH have been examined as a model for the nucleophilic step of the reaction of the corresponding olefin with NBA in aqueous dioxane.
TL;DR: Tachrosin [8-(2,3-dihydro-2,2-dimethyl-3-oxo-4-furyl)-5,7-dimethoxyflavone]-1] has been synthesized by oxidative rearrangement of a 1-aryl 4-hydroxypent-1-en-3)-one with thallium(III) nitrate followed by cyclisation to a 4-aryl 2,2,dimethylfuran-3(2H)-one as the key step as discussed by the authors.
Abstract: Tachrosin [8-(2,3-dihydro-2,2-dimethyl-3-oxo-4-furyl)-5,7-dimethoxyflavone](1) has been synthesized by oxidative rearrangement of a 1-aryl-4-hydroxypent-1-en-3-one with thallium(III) nitrate followed by cyclisation to a 4-aryl-2,2-dimethylfuran-3(2H)-one as the key step. A multi-stage transformation of the flavone (1) gave 8-(3-hydroxy-3-methyl-2-oxobutyl)-5-methoxy-7-methoxycarbonylmethoxyflavone (29), which afforded in one step the furo[2,3-c]pyran (30). Reduction of (30) with borohydride and reoxidation yielded (±)-stachyoidin (2), and treatment of (2) with lead tetra-acetate gave (±)-tephrodin (3). Sodium alkoxides are shown to catalyse the transacetalisation of α-aryl-α-aroylacetaldehyde acetals.
TL;DR: The experimental results suggest a mechanism for microsphere formation that is consistent with a hypothesized mechanism of pharmacologie action of pyran-divalent cation complexes.
TL;DR: In this article, the effect of the replacement of ring and carbonyl oxygens with sulphur on the chemical shift of the H-3 proton was studied, from the 1 H nmr data of the pyran derivatives.
TL;DR: In this paper, the reaction of 4 and 5-aryl-3-methylthio-1,2-dithiolylium iodides with 4-hydroxy-6-methyl-2 H -pyran-2-one and 4hydroxycoumarin has been studied.
TL;DR: The 1,4-cycloaddition of dichloroketene to N,N-disubstituted 6-aminomethylene-b,7,8,9-tetra-hydro-5H-benzocyclohepten-5-ones was shown in this article to give a 4-amino-3,4,6,7-Tetrahydroid-5 H-benzo.
Patent•
30 Jun 1977
TL;DR: In this article, a 5-substituted resorcinol with a 1-alkoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a suitable catalyst to provide the corre-sponding d1-6a,10a-cis- 1-hydroxyl-3-substantituted-6,6-dimethyl.
Abstract: of the Disclosure This invention provides a novel process which comprises the reaction of a 5-substituted resorcinol with a 1-alkoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a suitable catalyst to provide the corre-sponding d1-6a,10a-cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.
TL;DR: The Knoevenagel condensation of phthalic anhydride with ethyl Cyanoacetate gives (Z)-ethyl 2-carbamoyl- 8-cyano-3-hydroxybenzofulvene-8-carboxylate in good yield.
Abstract: The Knoevenagel condensation of phthalic anhydride with ethyl Cyanoacetate gives (Z)-ethyl 2-carbamoyl-8-cyano-3-hydroxybenzofulvene-8-carboxylate (2) in good yield. This compound provides a ready entry into the 2H-indeno[2,1-c]pyridine-1,9-dione, 2H-indeno[2,1-c]pyridine-3,9-dione, 2H-indeno[2,1-c]pyridazine-3,9-dione, and indeno[2,1-c]pyran-1,9-dione systems.
Patent•
08 Sep 1977TL;DR: In this paper, a 5-substituted resorcinol with a 1-alkoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a suitable catalyst affords the corresponding dl-cis 1-hydroxymethyl-3.6-dimethyl-6,6a,7,8,10,10-10a-hexahydro-9H-dibenzo[b,d]pyran-9-
Abstract: Reaction of a 5-substituted resorcinol with a 1-alkoxy-4-(1-hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a suitable catalyst affords the corresponding dl-cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.
TL;DR: In this article, 4-Morpholinomethyl-2H-pyran-3(6H)-one and its epoxide were obtained by treatment with morpholine and aqueous 37% formalin in methanol in 70-88% yield.
Abstract: 4-Morpholinomethyl-2H-pyran-3(6H)-ones 3 and 8 were prepared directly from 6-methoxy-2H-pyran-3(6H)-one (1) and its epoxide 4 by treatment with morpholine and aqueous 37% formalin in methanol in 70–88% yield. The mechanisms of the reaction have been discussed on the basis of the intermediates 5,6-dimethoxytetrahydropyran-3-one (2), 2,6-dimethoxy-5-hydroxytetrahydropyran-3-one (5), 2,6-dimethoxy-2H-pyran-3(6H)-one (6), and 2,5,6-trimethoxytetrahydropyran-3-one (7).
Patent•
30 Aug 1977
TL;DR: In this paper, the authors proposed a novel process which involves the cyclization of the corresponding aryl(methylsulfinyl)methyl ketones, which is useful in the treatment of hyperacidity and for alleviating allergic manifestations.
Abstract: The invention relates to novel compounds having the formulas I and III: wherein, in formula I, X is -O- or -N-COR wherein R is lower alkyl or aryl, and Z is WHEREIN R' is hydrogen, halogen or alkoxy. the compounds of this invention are prepared by a novel process which involves the cyclization of the corresponding aryl(methylsulfinyl)methyl ketones. The compounds of this invention having formulas I and III are useful in the treatment of hyperacidity and for alleviating allergic manifestations.
Journal Article•
TL;DR: Under suitable conditions the reaction of phenol and N,N-dialkylethoxycarbonylacetamides, in the presence of phosphorus oxychloride, resulted in the formation of 2-dialkylaminochromones, which markedly affect the CNS.
Abstract: Under suitable conditions the reaction of phenol and N,N-dialkylethoxycarbonylacetamides, in the presence of phosphorus oxychloride, resulted in the formation of 2-dialkylaminochromones. In a similar manner, variously substituted phenols afforded 2-dialkylaminochromones with substituents in different positions of the benzene ring. Pharmacological screening of all these compounds showed that they markedly affect the CNS, activity being mainly excitatory. Decreased activity was shown by compounds with particular substituents in the positions 6,7,8 among which two products [(V e) - K 12440, (V s) - K 12420] have weak but clear anticonvulsant effect.