- Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) in Vitro
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Background: In order to identify potential activities against periodontal diseases, eighteen dihydrochalcones and structurally related compounds were tested in an established biological in vitro cell model of periodontal inflammation using human gingival fibroblasts (HGF-1 cells). Methods: Subsequently to co-incubation of HGF-1 cells with a bacterial endotoxin (Porphyromonas gingivalis lipopolysaccharide, pgLPS) and each individual dihydrochalcone in a concentration range of 1 μM to 100 μM, gene expression of interleukin-8 (IL-8) was determined by qPCR and cellular interleukin-8 (IL-8) release by ELISA. Results: Structure–activity analysis based on the dihydrochalcone backbone and various substitution patterns at its aromatic ring revealed moieties 20,4,40,60-tetrahydroxy 3-methoxydihydrochalcone (7) to be the most effective anti-inflammatory compound, reducing the pgLPS-induced IL-8 release concentration between 1 μM and 100 μM up to 94%. In general, a 2,4,6-trihydroxy substitution at the A-ring and concomitant vanilloyl (4-hydroxy-3-methoxy) pattern at the B-ring revealed to be preferable for IL-8 release inhibition. Furthermore, the introduction of an electronegative atom in the A,B-linker chain led to an increased anti-inflammatory activity, shown by the potency of 4-hydroxybenzoic acid N-vanillylamide (13). Conclusions: Our data may be feasible to be used for further lead structure designs for the development of potent anti-inflammatory additives in oral care products.
- Hans, Joachim,Ley, Jakob P.,Pfeiffer, Stefanie,Schueller, Katharina,Somoza, Veronika,Walker, Jessica
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- Identification of novel quinoline analogues bearing thiazolidinones as potent kinase inhibitors for the treatment of colorectal cancer
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In this investigation, a novel series of quinoline analogues bearing thiazolidinones were designed and synthesized based on our previous study. Among them, the most potent compound 11k, 4-((4-(4-(3-(2-(2,6-difluorophenyl)-4-oxothiazolidin-3-yl)ureido)phen
- Zhou, Yuting,Xu, Xingwei,Wang, Fei,He, Huan,Gong, Guowei,Xiong, Li,Qi, Baohui
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- CARBAMATE AND UREA COMPOUNDS AS MULTIKINASE INHIBITORS
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The present disclosure describes carbamate and urea compounds as novel multikinase inhibitors and methods for preparing them. The pharmaceutical compositions comprising such multikinase inhibitors and methods of using them for treating cancer, infectious diseases, and other disorders associated with kinases are also described.
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Paragraph 068; 091
(2019/07/13)
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- Design, synthesis and biological evaluation of 6-substituted quinolines derived from cabozantinib as c-Met inhibitors
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Based on the cabozantinib scaffold, novel c-Met inhibitors were rationalized from the limited knowledge of structure-activity relationships for the quinoline 6-position. Emphasis was given to modifications capable of engaging in additional polar interacti
- Lien, Vegard Torp,Pettersen, Solveig,Haugen, Mads Haugland,Olberg, Dag Erlend,M?landsmo, Gunhild M.,Klaveness, Jo
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- Synthesis of N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C–N Cross-coupling
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A number of β-enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β-diketones. Two general protocols for their palladium-catalyzed intramolecular C–N cross-coupling were established to give corresponding N-substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.
- Dou?ová, Hana,R??i?ková, Zdeňka,?im?nek, Petr
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p. 670 - 684
(2018/01/22)
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- Substituent effects at the benzyl position and aromatic ring of silane-coupling agents containing 2-nitrobenzyl esters on photosensitivity and hydrophobic surface of a self-assembled monolayer (SAM)
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Silane-coupling agents with 2-nitrobenzyl esters containing alkyl substituents at the benzyl position and alkoxy and/or fluoroalkoxy groups of the aromatic ring were synthesized to prepare a self-assembled monolayer (SAM) on quartz glass, silicon wafer and thermally oxidized silicon wafer. The resulting photosensitive SAMs before and after photoirradiation were characterized by contact angle measurement, UV spectroscopy, X-ray photoelectron spectroscopy (XPS), and X-ray reflectivity (XRR). Photosensitivity of the SAM was influenced by substituents at the benzyl position and aromatic ring as well as the irradiation conditions in air or solution and substrates employed. Silane-coupling agents with bulky substituent at the benzyl position and double fluoroalkoxy chains are preferable in terms of the photosensitivity and hydrophobic surface.
- Konishi, Tsubasa,Hashimoto, Teppei,Sato, Naoya,Nakajima, Kazuki,Yamaguchi, Kazuo
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p. 125 - 134
(2016/01/27)
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- An intramolecular C-N cross-coupling of β-enaminones: A simple and efficient way to precursors of some alkaloids of Galipea officinalis
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2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date.
- Douov, Hana,Hork, Radim,Ruikov, Zdeka,imunek, Petr
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p. 884 - 892
(2015/08/24)
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- FLUORINE-CONTAINING COMPOUND, PATTERN FORMING SUBSTRATE, PHOTODEGRADABLE COUPLING AGENT, PATTERN FORMING METHOD, COMPOUND, AND ORGANIC THIN FILM TRANSISTOR
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PROBLEM TO BE SOLVED: To provide a compound that has a big difference in contact angle before and after light irradiation and is useful as a coupling agent, and an organic thin film transistor prepared by using the compound. SOLUTION: A fluorine-containin
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Paragraph 0188; 0189; 0190
(2016/10/08)
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- QUINOLINE DERIVATIVES AND QUINAZOLINE DERIVATIVES INHIBITING AUTOPHOSPHORYLATION OF Flt3 AND MEDICINAL COMPOSITIONS CONTAINING THE SAME
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An objective of the present invention is to provide compounds and pharmaceticals useful for the treatment of disease where the inhibition of autophosphorylation of FMS-like tyrosine kinase 3(Flt3) is therapeutically effective. The present invention relates to a pharmaceutical composition for use in the treatment or prevention of diseases where the inhibition of autophosphorylation of Flt3 therapeutically or prophylactically effective, which comprises a compound represented by formula (I) or a pharmaceutically acceptable salt or solvate thereof: wherein X represents CH or N; Z represents O or S; R1, R2, and R3 represent H, OH, or optionally substituted alkoxy; R4 represents H; R5, R6, R7, and R8 represent H, Hal, alkyl or the like; and R9 represents, e.g., alkyl substituted by t-butyl or the like.
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Page/Page column 21
(2010/02/13)
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- QUINOLINE OR QUINAZOLINE DERIVATIVES INHIBITING AUTO-PHOSPHORYLATION OF FIBROBLAST GROWTH FACTOR RECEPTORS
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An objective of the present invention is to provide novel compounds which have inhibitory activity against autophosphorylation of an FGF receptor family and, when orally or intraveneously administered, can suppress the growth of cancer cells. The compounds of the present invention are represented by formula (I) or a pharmaceutically acceptable salt or solvate thereof: wherein X represents CH or N; Z represents 0 or S; Q represents NR10, CR11R12, carbonyl, O, S(=O)m, wherein m is 0 to 2, or urea; R1 to R3 each independently represent H, OH, halogen, nitro, amino, alkyl, alkoxy or the like in which the alkyl and alkoxy groups are optionally substituted; R4 represents H; R5 to R8 each independently represent H, halogen, alkyl, or alkoxy; and R9 represents an optionally substituted carbocyclic or heterocyclic group.
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- A formal new access to the benzo[c]phenanthridine alkaloids, synthesis of Nitidine and O-Methyl Fagaronine analogues
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Previously unreported 2-aryl-1-naphthylamines were obtained in good yields from 2-aryl-1-tetraloneoximes by using the Semmler-Wolf reaction but omitting the acetic anhydride usually present in the reaction mixture. From these amines, through the thermal cyclization of their corresponding ethyl carbamates, a new access to the benzo[c]phenanthridin-6(5H)-ones was found. Preparation of water-soluble Nitidine and O-Methyl Fagaronine analogues bearing an alkylamino side chain on the C-6 position was achieved from these compounds.
- Janin,Bisagni
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p. 10305 - 10316
(2007/10/02)
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- SYNTHESIS OF 4-PHENYLCOUMARINS FROM DALBERGIA VOLUBILIS AND EXOSTEMA CARIBAEUM
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Two isomeric 4-phenyl coumarins, 3',7-dihydroxy-4',5-dimethoxy-4-phenylcoumarin (seshadrin) from Dalbergia volubilis and 3',5-dihydroxy-4',7-dimethoxy-4-phenylcoumarin from Exostema caribaeum have been synthesized.However, the spectral properties of the f
- Bose, P.,Banerji, J.
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p. 2438 - 2439
(2007/10/02)
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- An Unambiguous Synthesis of Melannein
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Melannein (6-hydroxy-7-methoxy-4-(3'-hydroxy-4'-methoxyphenyl)coumarin, I) and its O,O-diethyl ether (II) have been synthesised.The steps involved in the synthesis of I and II are the respective condensation of o-methoxyhydroquinone with ethyl m-benzyloxy-p-methoxybenzoylacetate (XI) and ethyl m-ethoxy-p-methoxybenzoylacetate (III) in absolute ethyl alcohol in the presence of dry hydrogen chloride gas.The isomeric O,O-diethyl ether of melannein, viz. 6-ethoxy-7-methoxy-4(4'-ethoxy-3'-methoxyphenyl)coumarin (VI) has also been prepared by the condensation of o-methoxyhydroquinone with ethyl p-ethoxy-m-methoxybenzoylacetate (VII).The esters (III), (VII) and (XI) have been prepared by the reaction of the appropriate acetophenone derivatives with diethyl carbonate in the presence of sodium hydride.
- Ahluwalia, V. K.,Kapur, Kanchan,Manchanda, Saroj
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p. 186 - 188
(2007/10/02)
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