Studies on antianaphylactic agents—III
TL;DR: By the application of the Vilsmeier-Haack reaction to various o-hydroxyacetophenone derivatives, 4-oxo-4H-1-benzopyran-3-carboxaldehydes were synthesized in one step as discussed by the authors.
About: This article is published in Tetrahedron.The article was published on 1974-01-01. It has received 175 citations till now. The article focuses on the topics: Fragmentation (mass spectrometry) & Mass spectrum.
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TL;DR: This work was supported by the Foundation for Science and Technology (FCT), Portugal (projects PTDC/QUI-QUI/113687/2009 and PEst-C/QUI/UI0081/2013) and SFRH/BD/61262/2009.
Abstract: This work was supported by the Foundation for Science and Technology (FCT), Portugal (projects PTDC/QUI-QUI/113687/2009 and PEst-C/QUI/UI0081/2013). A.G. (SFRH/BD/43531/2008) and M.J.M. (SFRH/BD/61262/2009) thank FCT for grants.
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TL;DR: This review highlights the broad range of science that has arisen from the synthesis of coumarin-linked and fused heterocycle derivatives and their synthesis and biological activity.
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188 citations
TL;DR: It is proposed that inhibitors based on this chemical structure could serve as useful tools to probe the biological function of Cdc25 and modification of the bis-thioethanol moiety markedly decreased enzyme inhibitory activity, indicating its importance for bioactivity.
Abstract: Small molecules provide powerful tools to interrogate biological pathways but many important pathway participants remain refractory to inhibitors. For example, Cdc25 dual-specificity phosphatases regulate mammalian cell cycle progression and are implicated in oncogenesis, but potent and selective inhibitors are lacking for this enzyme class. Thus, we evaluated 10,070 compounds in a publicly available chemical repository of the National Cancer Institute for in vitro inhibitory activity against oncogenic, full-length, recombinant human Cdc25B. Twenty-one compounds had mean inhibitory concentrations of 75% were quinones and >40% were of the para-naphthoquinone structural type. Most notable was NSC 95397 (2,3-bis-[2-hydroxyethylsulfanyl]-[1,4]naphthoquinone), which displayed mixed inhibition kinetics with in vitro K(i) values for Cdc25A, -B, and -C of 32, 96, and 40 nM, respectively. NSC 95397 was more potent than any inhibitor of dual specificity phosphatases described previously and 125- to 180-fold more selective for Cdc25A than VH1-related dual-specificity phosphatase or protein tyrosine phosphatase 1b, respectively. Modification of the bis-thioethanol moiety markedly decreased enzyme inhibitory activity, indicating its importance for bioactivity. NSC 95397 showed significant growth inhibition against human and murine carcinoma cells and blocked G(2)/M phase transition. A potential Cdc25 site of interaction was postulated based on molecular modeling with these quinones. We propose that inhibitors based on this chemical structure could serve as useful tools to probe the biological function of Cdc25.
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TL;DR: Compounds 4b-c/5a-c and 9a demonstrated in vitro antitumor activity against P388 leukemia and Antineoplastic activity of the compounds 4b/5b and9a combined with methotrexate was showed using L1210 murine leukemia.
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83 citations
TL;DR: In 2-Stellung unsubstituierte 3-Acyl-chromone wurden aus 2-Hydroxy-ω-acyl-acetophenonen durch Reaktion with Orthoameisensaure-triathylester und Acetanhydrid oder aus 1-hydroxy-α-formylacetophenon and Acetanehydrid/Natriumacetat dargestellt as mentioned in this paper.
Abstract: In 2-Stellung unsubstituierte 3-Acyl-chromone wurden aus 2-Hydroxy-ω-acyl-acetophenonen durch Reaktion mit Orthoameisensaure-triathylester und Acetanhydrid oder aus 2-Hydroxy-ω-formyl-acetophenon und Acetanhydrid/Natriumacetat dargestellt. Strukturbeweise wurden mit Hilfe von UV-, IR- und NMR-Spektren gefuhrt.
37 citations
TL;DR: In this paper, the title compounds react with dimethylformamide in acetic anhydride to give dimethylamino-vinyl derivatives which, on treatment with base, yield benzochroman-4-ones.
29 citations
TL;DR: In this paper, Baicalin and Baicalein, components of the drug, were investigated on active anaphylactic reaction in guinea pig, and the results obtained were compared with those of rutin, methylhesperidin and quercetin.
Abstract: In the Chinese medicine, Scutellaria baicalensis GEORG has been used as a remedy for some of allergic diseases. Therefore, the authors investigated the effects of baicalin and baicalein, components of the drug, on active anaphylactic reaction in guinea pig, and the results obtained were compared with those of rutin, methylhesperidin and quercetin. 1) By the administration of baicalin, the onset of preconvulsion caused by the antigen-aerosol in actively sensitized guinea pig was delayed about 3 times in contrast to the control, and the effect of baicalin was more potent than that of rutin. 2) Baicalin and baicalein inhibited Schulz-Dale reaction in isolated ileum, and the intensity of inhibition was following order; in glycoside, baicalin>rutin>methylhesperidin, and in aglycon, baicalein>quercetin. Futhermore, the effect of aglycone was more potent than that of each glycoside. 3) As the antigen was added to the organ bath which placed sensitized and non-sensitized ileum, sensitized ileum strongly contracted followed by contraction of non-sensitized one. In this condition, baicalin decreased the contraction of non-sensitized ileum, while baicalein strongly decreased those of both ones. 4) Baicalin and baicalein slightly showed antihistaminic and anticholinergic effects on ileum of guinea pig. 5) The antigen-antibody combination was not affected by baicalin or baicalein in ring precipitation test. 6) The release of histamine and SRS-A from sinsitized guinea pig lung which perfused with antigen were decreased by baicalin, and the decreasing activity was more remarkable than that of rutin. 7) Baicalin and baicalein inhibited the anaphylactic release of histamine and SRS-A from chopped tissue of guinea pig lung. There was not much difference between the inhibitory activities of them in a equal molar concentration. However, they neither affected the destruction of mediator released nor inhibited contraction of ileum by mediator. The inhibitory action of baicalein on release of mediator was not affected by the addition of Ca++, but decreased by cysteine.
21 citations