- Stereoselective Total Synthesis of (-)-(2 S,4 R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction
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The first stereoselective total synthesis of (-)-(2S,4R)-3′-methoxy citreochlorol and (-)-(2S,4S)-3′-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group.
- Sunnapu, Ranganayakulu,Banoth, Saikumar Naik,Reyno,Thomas, Aleena,Venugopal, Navyasree,Rajendar, Goreti
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p. 4103 - 4113
(2020/03/05)
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- Parallel in vitro and in silico investigations into anti-inflammatory effects of non-prenylated stilbenoids
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Stilbenoids represent a large group of bioactive compounds, which occur in food and medicinal plants. Twenty-five stilbenoids were screened in vitro for their ability to inhibit COX-1, COX-2 and 5-LOX. Piceatannol and pinostilbene showed activity comparable to the zileuton and ibuprofen, respectively. The anti-inflammatory potential of stilbenoids was further evaluated using THP-1 human monocytic leukemia cell line. Tests of the cytotoxicity on the THP-1 and HCT116 cell lines showed very low toxic effects. The tested stilbenoids were evaluated for their ability to attenuate the LPS-stimulated activation of NF-κB/AP-1. Most of the tested substances reduced the activity of NF-κB/AP-1 and later attenuated the expression of TNF-α. The effects of selected stilbenoids were further investigated on inflammatory signaling pathways. Non-prenylated stilbenoids regulated attenuation of NF-?B/AP-1 activity upstream by inhibiting the phosphorylation of MAPKs. A docking study used to in silico analyze the tested compounds confirmed their interaction with NF-?B, COX-2 and 5-LOX.
- Leláková, Veronika,?mejkal, Karel,Jakubczyk, Karolina,Vesely, Ond?ej,Landa, P?emysl,Václavík, Ji?í,Bobá?, Pavel,Pí?ová, Hana,Temml, Veronika,Steinacher, Theresa,Schuster, Daniela,Granica, Sebastian,Hanáková, Zuzana,Ho?ek, Jan
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p. 431 - 440
(2019/02/19)
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- Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-κB/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase
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Stilbenoids are important components of foods (e.g., peanuts, grapes, various edible berries), beverages (wine, white tea), and medicinal plants. Many publications have described the anti-inflammatory potential of stilbenoids, including the widely known trans-resveratrol and its analogues. However, comparatively little information is available regarding the activity of their prenylated derivatives. One new prenylated stilbenoid (2) was isolated from Artocarpus altilis and characterized structurally based on 1D and 2D NMR analysis and HRMS. Three other prenylated stilbenoids were prepared synthetically (9-11). Their antiphlogistic potential was determined by testing them together with known natural prenylated stilbenoids from Macaranga siamensis and Artocarpus heterophyllus in both cell-free and cell assays. The inhibition of 5-lipoxygenase (5-LOX) was also shown by simulated molecular docking for the most active stilbenoids in order to elucidate the mode of interaction between these compounds and the enzyme. Their effects on the pro-inflammatory nuclear factor-κB (NF-κB) and the activator protein 1 (AP-1) signaling pathway were also analyzed. The THP1-XBlue-MD2-CD14 cell line was used as a model for determining their anti-inflammatory potential, and lipopolysaccharide (LPS) stimulation of Toll-like receptor 4 induced a signaling cascade leading to the activation of NF-κB/AP-1. The ability of prenylated stilbenoids to attenuate the production of pro-inflammatory cytokines tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β) was further evaluated using LPS-stimulated THP-1 macrophages.
- Ho?ek, Jan,Leláková, Veronika,Bobál, Pavel,Pí?ová, Hana,Gazdová, Markéta,Malaník, Milan,Jakubczyk, Karolina,Vesely, Ond?ej,Landa, P?emysl,Temml, Veronika,Schuster, Daniela,Prachyawarakorn, Vilailak,Pailee, Phanruethai,Ren, Gang,Zpurny, Filip,Oravec, Michal,?mejkal, Karel
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p. 1839 - 1848
(2019/08/20)
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- Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents
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A series of both novel and reported combretastatin analogues, including diarylpyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles, were synthesized via improved protocols to evaluate their antimitotic antitubulin activity using in vivo sea urchin embryo assay and a panel of human cancer cells. A systematic comparative structure-activity relationship studies of these compounds were conducted. Pyrazoles 1i and 1p, isoxazole 3a, and triazole 7b were found to be the most potent antimitotics across all tested compounds causing cleavage alteration of the sea urchin embryo at 1, 0.25, 1, and 0.5 nM, respectively. These agents exhibited comparable cytotoxicity against human cancer cells. Structure-activity relationship studies revealed that compounds substituted with 3,4,5-trimethoxyphenyl ring A and 4-methoxyphenyl ring B displayed the highest activity. 3-Hydroxy group in the ring B was essential for the antiproliferative activity in the diarylisoxazole series, whereas it was not required for potency of diarylpyrazoles. Isoxazoles 3 with 3,4,5-trimethoxy-substituted ring A and 3-hydroxy-4-methoxy-substituted ring B were more active than the respective pyrazoles 1. Of the azoles substituted with the same set of other aryl pharmacophores, diarylpyrazoles 1, 4,5-diarylisoxazoles 3, and 4,5-diaryl-1,2,3-triazoles 7 displayed similar strongest antimitotic antitubulin effect followed by 3,4-diarylisoxazoles 5, 1,5-diaryl-1,2,3-triazoles 8, and pyrroles 10 that showed the lowest activity. Introduction of the amino group into the heterocyclic core decreased the antimitotic antitubulin effect of pyrazoles, triazoles, and to a lesser degree of 4,5-diarylisoxazoles, whereas potency of the respective 3,4-diarylisoxazoles was increased.
- Semenova, Marina N.,Demchuk, Dmitry V.,Tsyganov, Dmitry V.,Chernysheva, Natalia B.,Samet, Alexander V.,Silyanova, Eugenia A.,Kislyi, Victor P.,Maksimenko, Anna S.,Varakutin, Alexander E.,Konyushkin, Leonid D.,Raihstat, Mikhail M.,Kiselyov, Alex S.,Semenov, Victor V.
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p. 700 - 721
(2019/01/03)
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- Preparation method of resveratrol
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The invention discloses a preparation method of resveratrol. The preparation method comprises that (1), 3, 5-dimethoxybenzhydrol is chloroformed under the action of triphosgene to form 3, 5-dimethoxybenzyl chloride, (2), 3, 5-dimethoxybenzyl chloride reacts with triphenylphosphine to produce phosphorus ylide, (3), phosphorus ylide and p-methoxybenzaldehyde form a cis-trans-isomer mixture of 3, 4',5-trimethoxydistyrene under the action of lithium hydroxide, (4), 3, 4', 5-trimethoxystilbene, aluminum and iodine are added to acetonitrile, the mixture is cooled to the room temperature so that yellow solids are separated, the yellow solids are filtered, the filtrate acetonitrile is directly recovered and recycled, 6N hydrochloric acid and ethyl acetate are added into the filter cake, the mixture is stood for layering, wherein the water layer contains ethyl acetate extract, the organic phases are mixed, the organic phases are washed through a saturated salt solution, anhydrous sodium sulfate is dried and filtered, the solvent is removed in vacuum through a water pump, and the organic phase is recrystallized through ethanol and water so that resveratrol is obtained. The preparation method utilizes easily available raw materials, is easy to operate and control, is environmentally friendly, produces easily purified products, has a high yield and is suitable for industrial production.
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-
Paragraph 0029-0031
(2018/11/03)
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- Preparation method for health product pterostilbene
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The invention provides a preparation method for a health product pterostilbene. According to the invention, 1, a deprotection method used in the invention is green, environment-friendly and pollution-free, the preparation method is almost free of production of waste gas, waste water and industrial residues, and the product 1,4-pentadiene has economic value; 2, a catalyst used in the invention has good cycle repeatability and can be cyclically used 50 times or more; 3, the preparation method is simple in operation requirements, mild in reaction conditions, good in specificity, simple in post-treatment and purification of the product, and suitable for industrial production; and 4, the pterostilbene prepared by using the method is free of impurities like 3-methoxy-4',5-dihydroxystilbene and resveratrol and has high purity.
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-
Paragraph 0041; 0042
(2017/12/05)
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- Synthesis method of piceatannol
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The present invention provides a synthesis method of piceatannol. The method comprises the following steps: reacting 3,5-dimethoxybenzyl alcohol with phosphorus oxychloride to obtain 3,5-dimethoxybenzyl chloride; adding the obtained 3,5-dimethoxybenzyl ch
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Paragraph 0021; 0023; 0024
(2016/10/10)
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- Oxyresveratrol synthesis method
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The invention provides an oxyresveratrol synthesis method which comprises the following steps: firstly performing a reflux reaction between raw materials 3,5-dimethoxybenzyl alcohol and phosphorus oxychloride; after the reaction is complete, pressurizing and recycling the solvent; filtering, washing to neutrality and drying to obtain 3,5-dimethoxybenzyl chloride; performing a reflux reaction between the obtained 3,5-dimethoxybenzyl chloride and trimethyl phosphite in a solvent DMF (dimethyl formamide); after the reaction is complete, adding a catalyst sodium methylate solution, and adding a mixed solution of 2,4-dimethoxy benzaldehyde and DMF to obtain tetramethoxy diphenyl ethylene; and finally, performing a reflux reaction between the obtained tetramethoxy diphenyl ethylene and aluminum trichloride and xylene, wherein oxyresveratrol is obtained after the reaction is complete. According to the method provided by the invention, a Witting-Homer reaction is adopted, the raw materials are easily available, the yield is high, the cost is low, and the method is suitable for industrial production.
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-
Paragraph 0019; 0020
(2016/10/17)
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- Phosphine functionalized polyphosphazenes: soluble and re-usable polymeric reagents for highly efficient halogenations under Appel conditions
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In this paper we present the preparation and application of a novel soluble phosphine functionalized polyphosphazene (poly[3-(diphenylphosphino)propylamino]phosphazene) and investigate its application as a polymeric reagent. Upon chlorination of the pendant phosphine groups, the polymer was found to facilitate the rapid and efficient transformation of alcohols to the corresponding chlorides and bromides under Appel-type conditions. Reaction times followed by 31P NMR spectroscopy are shown to be rapid (several minutes) and the yields for the transformation of alcohols to the corresponding halides are in the range 80–99?%. The facile recovery of the oxidized polymeric agent by precipitation is also described, offering a significant advantage over notoriously difficult to remove small molecule phosphine oxide by-products. Furthermore the regeneration of the reactive phosphine chloride pendant groups is demonstrated, which could be efficiently re-used in a further chlorination reaction. Graphical abstract: [Figure not available: see fulltext.]
- K?nig, Michael,Linhardt, Anne,Brüggemann, Oliver,Teasdale, Ian
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p. 1575 - 1582
(2016/08/16)
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- Method for preparing resvertrol (by machine translation)
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The invention discloses method for preparing resvertrol, in order to 3,5-dimethoxy-methanol as the raw material, through chloropivaloyl, to obtain 3,5-dimethoxy oxygen radical chlorine animal pen, through the 3,5-dimethylbenzaldehyde by oxygen radical chlorine animal pen 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works. This invention, through the triphosgene 3,5-dimethoxy-methanol chloropivaloyl, instead of ethanol using sodium hydride and sodium, synthetic 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works, preparation method has high yield, low cost. (by machine translation)
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Paragraph 0021; 0022; 0023; 0024; 0033
(2016/10/31)
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- A scalable process for the synthesis of (E)-pterostilbene involving aqueous Wittig olefination chemistry
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A synthetic approach toward the pharmacologically active (E)-stilbene pterostilbene is described using a Wittig reaction conducted under mildly basic, aqueous conditions. A surprising, non-intuitive difference in (E)/(Z) stereoselectivity was observed comparing the two possible isomeric Wittig routes, allowing for the development of a highly efficient process to access the title stilbene derivative through a one-pot olefination deprotection sequence.
- McNulty, James,McLeod, David
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supporting information
p. 6303 - 6306
(2013/11/06)
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- Ultrasound promoted Barbier reactions and Csp3-Csp2 Stille coupling for the synthesis of diarylmethanes and substituted benzophenones
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Here we present the preparation of a variety of diarylmethanes obtained via ultrasound Stille coupling under palladium catalysis between some substituted aryl compounds and benzyltributyltin compounds generated through sonicated Barbier reaction in a very short time reaction and excellent yield. The study reported below compares different methods to optimize the synthesis of usually unstable benzyltin derivatives and is another contribution to the investigation of Csp3-Csp2 coupling process involving benzyl-aryl reagents. Substituted carboxylated benzophenones were easily prepared in a very good yield by oxidation of some diarylmethanes.
- Ocampo, Romina A.,Koll, Liliana C.,Mandolesi, Sandra D.
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- Synthesis and biological evaluation of resveratrol-coumarin hybrid compounds as potential antitumor agents
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Eighteen resveratrol-coumarin hybrid compounds (6 or 7-styryl-3- phenylcoumarin) were designed, synthesized and thirteen compounds were evaluated for their antitumor activities against MCF-7, HCT-28, and K562 tumor cell lines. Among them, compounds 2Z, 2E, 5E, and 7E showed varying degrees of growth inhibition of the above cell lines (IC50: 3.78-19.16 μmol/L). On the basis of the biological results, structure-activity relationships were obtained and discussed.
- Shen, Wei,Mao, Jianfeng,Sun, Juan,Sun, Minjie,Zhang, Can
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p. 1630 - 1640
(2013/07/26)
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- Dimerization of resveratrol trimethyl ether by phosphotungstic acid, structure confirmation of resformicol A and B
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Dimerization of the trimethyl ether of resveratrol catalyzed by phosphotungstic acid gave two tetralins and a naphthalene derivative. The structure of the tetralins was obtained by X-ray crystallography and confirms the reported stereochemical configuration of resformicol A and B.
- Davis, Matthew C.,Groshens, Thomas J.
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supporting information; experimental part
p. 3521 - 3523
(2012/08/29)
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- Practical preparation of resveratrol 3-O-β-D-glucuronide
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A practical synthesis of resveratrol 3-Oβl-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large-scale preparation of resveratrol is also reported.
- Jungong, Christian S.,Novikov, Alexei V.
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p. 3589 - 3597,9
(2020/08/31)
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- Complete NMR data of methoxylated cis- and trans-stilbenes as well as 1,2-diphenylethanes
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Resveratrol is a polyphenol isolated from many natural sources including grapes, mulberries, eucalyptus, spruce, lilies, and peanuts. The hydroxyl groups in polyphenols can be substituted with various functional groups, allowing production of multiple derivatives. NMR spectroscopy is used to identify new derivatives. Since the complete NMR data of the known derivatives can be useful for identification of the newly isolated derivatives, here, we report the synthesis of 14 methoxylated stilbenes and four 1,2-diphenylethanes and their NMR data.
- Jo, Geunhyeong,Hyun, Jiye,Hwang, Doseok,Lee, Young Han,Koh, Dongsoo,Lim, Yoongho
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scheme or table
p. 374 - 377
(2011/12/04)
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- A practical method to stereospecifically synthesize trans-stilbene derivatives
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A practical method to stereospecifically synthesize trans-stilbenes was developed via the one-pot benzylation-dehydration reaction of aromatic aldehydes with benzyltrimethylsilane (BTMS), which was driven by tetrabutylammonium fluoride (TBAF) in THF. At the same time a plausible description of the whole process was proposed and the effects of substituted groups on the reaction were investigated. Also this method was employed to synthesize three precursors of natural products with excellent yields, which demonstrated that this method is much efficient and practical in the synthesis of some natural products. A practical method to stereospecifically synthesize trans-stilbenes was developed via the one-pot benzylation-dehydration reaction of aromatic aldehydes with benzyltrimethylsilane, which was driven by tetrabutylammonium fluoride in THF. A plausible description of the whole process was proposed and the effects of substituted groups on the reaction were investigated. This method was employed to synthesize three precursors of natural products with excellent yields. Copyright
- Jian, Yujuan,Sun, Gaojun,Li, Jiaming,Su, Dan,Li, Chuanrun,Zhong, Guochen
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scheme or table
p. 1423 - 1428
(2011/10/31)
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- Pentiptycene-derived light-driven molecular brakes: Substituent effects of the brake component
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Five pentiptycene-derived stilbene systems (1R; R = H, OM, NO, Pr, and Bu) have been prepared and investigated as light-driven molecular brakes that have different-sized brake components (1Hrot = 108-109 s-1) with little interaction with the brake component in the trans form ((E)-1R), which corresponds to the brake-off state. When the brake is turned on by photoisomerization to the cis form ((Z)-1R), the pentiptycene rotation can be arrested on the NMR spectroscopic timescale at temperatures that depend on the brake component. In the cases of (Z)-1NO, (Z)-1Pr, and (Z)-1Bu, the rotation is nearly blocked (krot = 2-6 s-1) at 298 K. It is also demonstrated that the rotation is slower in [D6]DMSO than in CD2Cl 2. A linear relationship between the free energies of the rotational barrier and the steric parameter A values is present only for (Z)-1H, (Z)-1OM, and (Z)-1NO, and it levels off on going from (Z)-1NO to (Z)-1Pr and (Z)-1Bu. DFT calculations provide insights into the substituent effects in the rotational ground and transition states. The molar reversibility of the E-Z photoswitching is up to 46%, and both the E and Z isomers are stable under the irradiation conditions.
- Sun, Wei-Ting,Huang, Yau-Ting,Huang, Guan-Jhih,Lu, Hsiu-Feng,Chao, Ito,Huang, Shou-Ling,Huang, Shing-Jong,Lin, Ying-Chih,Ho, Jinn-Hsuan,Yang, Jye-Shane
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experimental part
p. 11594 - 11604
(2010/12/18)
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- Modified approach for preparing (E)-Stilbenes related to resveratrol, and evaluation of their potential immunobiological effects
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Resveratrol and closely related stilbenoids belong to the most intensively studied biologically active compounds. This interest evoked several attempts to prepare such compounds in a convenient synthetic way. Our approach allowed obtaining largely methoxystilbenes, formed as E-isomers only (using Wittig-Horner synthesis as the key step), which were further demethylated by boron tribromide. The hydroxymethoxystilbenes (e.g. pterostilbene) were prepared using isopropyl protection, later selectively deprotected by boron trichloride. The method is suitable for preparing such compounds in a large amount. Effects of the obtained stilbene derivatives on immunobiological responses triggered by lipopolysacharide and interferon-a were tested under in vitro conditions. Namely production of nitric oxide (NO) was investigated, and relation between the molecular structure and immunobiological activity was assessed.
- Smidrkal, Jan,Harmatha, Juraj,BudiSinsky, Milo,Vokae, Karel,ZIDEKc, Zdenik,Kmoniekova, Eva,Merkl, Roman,Filip, Vladimir
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scheme or table
p. 175 - 186
(2010/07/10)
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- Inhibitory effect of a novel resveratrol derivative on nitric oxide production in lipopolysaccharide-activated microglia
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Excessive nitric oxide (NO) production by activated microglial cells has been implicated in various neurodegenerative diseases. In the present study, we found that a new resveratrol derivative, (E)-5-(3-nitrostyryl)benzene-1,3-diol (RV06), has a more potential inhibitory effect on the production of NO in LPS-activated N9 microglial cells, and the result was confirmed on primary rat microglial cells. Further studies showed that RV06 inhibited LPS-induced iNOS expression in N9 microglial cells, with no activity on direct scavenging nitric oxide radical in a cell-free environment. The results suggest that RV06 might be a potential anti-inflammatory agent or leading compound which can inhibit inflammatory responses of microglia.
- Meng,Chen,Yang,Wang,Wu, Chun Fu,Wang
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experimental part
p. 671 - 675
(2009/04/07)
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- The design, synthesis, and anti-tumor mechanism study of N-phosphoryl amino acid modified resveratrol analogues
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A novel series of trans-N-phosphoryl amino acid modified resveratrol analogues were synthesized and evaluated in vitro for their cytotoxic effects against CNE-1 and CNE-2 cell lines. These analogues showed good anti-proliferative activity, among which 8d, 8e, 8j, and 9d displayed much stronger inhibition effect than resveratrol and 8d showed the most potent activity with IC50 value at 3.45 ± 0.82 μM. The anti-tumor effects of 8d, 8e, 8j, and 9d were due to the induction of apoptosis, confirmed by the DNA fragmentation and flow cytometry analysis using PI (propidium iodide) staining and Annexin-V-FITC/PI staining assay. The PI staining assay also showed that 8d, 8e, 8j, and 9d caused cell cycles arrest at G0-G1 phase which finally led to cell apoptosis. Further mechanism study on compound 8d against CNE-2 cells has shown the PARP cleavage, which is a hallmark of caspase-3 activation, as well as the activation of caspase-9, and the intracellular ROS generation. These results all suggest that 8d induced a mitochondrial-dependent apoptosis pathway.
- Liu, Huachen,Dong, Aijun,Gao, Chunmei,Tan, Chunyan,Liu, Hongxia,Zu, Xuyu,Jiang, Yuyang
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experimental part
p. 10013 - 10021
(2009/04/06)
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- Synthetic study for two 2H-chromenic acids, 8-chlorocannabiorcichromenic acid and mycochromenic acid
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Two 2H-chromenes having a fully substituted benzene ring, 8-chlorocannabioreichromene (1) and mycochromenic acid (2), were synthesized by a condensation of salicylaldehydes with isopropylidenemalonate or the thermal cyclization of corresponding propargyl ethers.
- Yamaguchi, Seiji,Nedachi, Masahiro,Maekawa, Mikiko,Murayama, Yohei,Miyazawa, Masahiro,Hirai, Yoshiro
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- Synthesis and anti-inflammatory activity of resveratrol analogs
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Seventeen novel resveratrol derivatives were synthesized. Their anti-inflammatory activities were tested on xylene-induced mouse ear edema. The pharmacological results showed that some compounds have potent anti-inflammatory activities.
- Chen, Guoliang,Shan, Wei,Wu, Yingliang,Ren, Lixiang,Dong, Jinhua,Ji, Zhizhong
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p. 1587 - 1590
(2007/10/03)
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- Mutasynthesis of Glycopeptide Antibiotics: Variations of Vancomycin's AB-Ring Amino Acid 3,5-Dihydroxyphenylglycine
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In the mutasynthetic approach, the ΔdpgA mutant of the vancomycin-type glycopeptide antibiotic producer Amycolatopsis balhimycina, which is deficient in the synthesis of 3,5-dihydroxyphenylglycine (DPg), was supplemented with synthetic DPg analogues to obtain the corresponding modified glycopeptides. Sterically more demanding 3,5-disubstituted methoxy derivatives as well as monosubstituted DPg analogues were accepted as substrates. These facts indicate that steric and electronic requirements suffice in several cases for the oxidative closure of the AB ring, thus leading to the generation of novel antibiotically active glycopeptide derivatives. The results represent a further step in evaluating the potential of mutasynthesis for peptidic secondary metabolites. Copyright
- Weist, Stefan,Kittel, Claudia,Bischoff, Daniel,Bister, Bojan,Pfeifer, Volker,Nicholson, Graeme J.,Wohlleben, Wolfgang,Suessmuth, Roderich D.
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p. 5942 - 5943
(2007/10/03)
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- COMPOUNDS
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This invention relates to novel carboxylic acid indole compounds and compositions for use in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).
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- SYNTHESIS OF (+/-)-DIMETHYL CURVULARIN BASED ON THE PALLADIUM-CATALYZED CARBONYLATION OF 3,5-DIMETHOXYBENZYL CHLORIDE USING A BUTADIENE TELOMER AS A BUILDING BLOCK
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Palladium -catalyzed carbonylation of 3,5-dimethoxybenzyl chloride (13) with benzyl 7-hydroxyoctanoate (12) afforded benzyl 7-(3,5-dimethoxyphenylacetoxy)octanoate (6) in 70percent yield, which is the precursor of Curvularin (4).The ester (12) was easily prepared from the butadiene telomer obtained by the palladium-catalyzed reaction of butadiene with acetic acid.
- Takahashi, Takashi,Ikeda, Hiroshi,Tsuji, Jiro
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p. 3885 - 3888
(2007/10/02)
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- 1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor
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Compounds of the formula STR1 wherein R1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH2)p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group; R2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl; R3 is selected from hydrogen, methyl and ethyl; R4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl; Z is selected from: (a) alkylene having from one to nine carbon atoms; (b) --(alk1)m --X--(alk2)n -- wherein each of (alk1) and (alk2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk1) plus (alk2) is not greater than 9; m and n are each 0 or 1; X is selected from O, S, SO, and SO2 ; and W is selected from hydrogen, methyl, pyridyl, piperidyl, phenyl, monochlorophenyl, monofluorophenyl and STR2 wherein W1 is selected from hydrogen, phenyl, monochlorophenyl and monofluorophenyl; a is an integer from 1 to 5 and b is 0 or an integer from 1 to 4, with the proviso that the sum of a and b is not greater than 5. Compounds I and II are useful as analgesics. Compound III is useful as an intermediate for the preparation of Compounds I and II. Intermediates for the preparation of I, II and III are disclosed. A process for the use of compounds I and II to produce analgesia is also described.
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