cas 1486-48-2, 3,4,5-TRIS(BENZYLOXY)BENZOIC ACID

Articles about 1486-48-2Total 52 be found

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Mimic catechins to develop selective MMP-2 inhibitors
Abstract: Matrix metalloproteinase 2 (MMP-2) is a well-known anticancer target belonging to the MMP family. Because of the bilateral role of MMPs in cancer, developing highly selective MMP-2 inhibitors is a current challenge. In this paper, we investigated the binding modes of green tea polyphenols epigallocatechin gallate and epicatechin into the active site of the MMP-2 enzyme. The structure-based analysis allowed the optimization of these hits and hence led to a better lead candidate. Moreover, using a pharmacophore model, we screened FooDB compounds and selected food components as potential MMP-2 inhibitors. The search for food-derived compounds that target this enzyme may represent a strategy to identify new lead molecules with improved safety profiles and provide indications about possible functional foods. Graphical abstract: [Figure not available: see fulltext.].
Di Pizio, Antonella,Agamennone, Mariangela,Laghezza, Antonio,Loiodice, Fulvio,Tortorella, Paolo
p. 1293 - 1300
(2018)
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The Synthesized Plant Metabolite 3,4,5-Tri-O-Galloylquinic Acid Methyl Ester Inhibits Calcium Oxalate Crystal Growth in a Drosophila Model, Downregulates Renal Cell Surface Annexin A1 Expression, and Decreases Crystal Adhesion to Cells
The plant metabolite 3,4,5-tri-O-galloylquinic acid methyl ester (TGAME, compound 6) was synthesized, and its potential effect on calcium oxalate monohydrate (COM) crystal binding to the surface of Madin-Darby canine kidney cells type I (MDCKI) and crystal growth in a Drosophila melanogaster Malpighian tubule (MT) model were investigated. Membrane, cytosolic, and total annexin A1 (AxA1), α-enolase, and heat shock protein 90 (HSP90) amounts were examined by Western blot analysis after subcellular fractionation, then confirmed by immunofluorescence staining of cultured cells. Pretreatment of MDCKI cells with TGAME for up to 6 h significantly diminished COM crystal binding in a concentration-dependent manner. TGAME significantly inhibited AxA1 surface expression by immunofluorescence microscopy, whereas intracellular AxA1 increased. Western blot analysis confirmed AxA1 expression changes in the membrane and cytosolic fractions of compound-treated cells, whereas whole cell AxA1 remained unchanged. TGAME also significantly decreased the size, number, and growth of calcium oxalate (CaOx) crystals induced in a Drosophila melanogaster MT model and possessed a potent antioxidant activity in a DPPH assay.
Abd El-Salam, Mohamed,Bastos, Jairo Kenupp,Han, Jing Jing,Previdi, Daniel,Coelho, Eduardo B.,Donate, Paulo M.,Romero, Michael F.,Lieske, John
p. 1609 - 1621
(2018)
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Promotion of mitochondrial biogenesis by synthetic 1,2- or 1,3-digallates through activation of an energy sensing network
Based on the observations suggesting that a digallate functionality might serve as a novel scaffold for inducers of mitochondrial biogenesis, we prepared a series of digallates and evaluated their activity in an in vitro model widely used in PD research (
Chong, Youhoon,Kim, Mi Kyoung,Lee, Taegum
supporting information

(2022/01/08)

Cannabidiol derivative, preparation method and application thereof
The invention discloses a cannabidiol derivative, a preparation method and application thereof, and belongs to the technical field of medicinal chemistry, wherein the cannabidiol derivative is obtained by taking cannabidiol as a main body through a synthesis means, and an anti-tumor activity determination result shows that the cannabidiol derivative prepared by the invention has an inhibition effect on lung cancer cell strains, human breast cancer cell strains, nasopharynx cancer and drug-resistant strains thereof.
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Paragraph 0027; 0035; 0039; 0051-0053

(2021/07/28)

Synthesis and evaluation of new sesamol-based phenolic acid derivatives with hypolipidemic, antioxidant, and hepatoprotective effects
The objective of this study is to synthesize a series of sesamol-based phenolic acid derivatives, which were designed by combination principle. The hypolipidemic activity of all these compounds was preliminarily screened by acute hyperlipidemic mice model induced by Triton WR 1339, in which compound T6 exhibited more significant reducing plasma TG and TC than fenofibrate. Compound T6 was also found to obviously decrease TG and TC both in the plasma and hepatic tissue of high-fat-diet-induced hyperlipidemic mice. Moreover, T6 showed hepatoprotective effects, which remarkable amelioration in characteristic liver enzymes was examined and the histopathological observation displayed that compound T6 inhibited lipids accumulation in the hepatic. The levels of PPAR-α receptor related to lipids metabolism in hepatic tissue were upregulated after T6 treatment. Other potent effects of T6 such as antioxidant and anti-inflammatory activity were also observed. On the bases of these findings, compound T6 may serve as an effective hypolipidemic and hepatoprotective agent. [Figure not available: see fulltext.]
Xie, Yundong,Liu, Jiping,Shi, Yongheng,Bin Wang,Wang, Xiaoping,Wang, Wei,Sun, Meng,Xu, Xinya,He, Shipeng
p. 1688 - 1702
(2021/07/26)

Switchable Full-Color Reflective Photonic Ellipsoidal Particles
Full-color reflective photonic ellipsoidal polymer particles, capable of a dynamic color change, are created from dendronized brush block copolymers (den-BBCPs) self-assembled by solvent-evaporation from an emulsion. Surfactants composed of dendritic mono
He, Qilin,Ku, Kang Hee,Vijayamohanan, Harikrishnan,Kim, Bumjoon J.,Swager, Timothy M.
supporting information
p. 10424 - 10430
(2020/06/08)

Biological Characterization, Mechanistic Investigation and Structure-Activity Relationships of Chemically Stable TLR2 Antagonists
Toll-like receptors (TLRs) build the first barrier in the innate immune response and therefore represent promising targets for the modulation of inflammatory processes. Recently, the pyrogallol-containing TLR2 antagonists CU-CPT22 and MMG-11 were reported; however, their 1,2,3-triphenol motif renders them highly susceptible to oxidation and excludes them from use in extended experiments under aerobic conditions. Therefore, we have developed a set of novel TLR2 antagonists (1–9) based on the systematic variation of substructures, linker elements, and the hydrogen-bonding pattern of the pyrogallol precursors by using chemically robust building blocks. The novel series of chemically stable and synthetically accessible TLR2 antagonists (1–9) was pharmacologically characterized, and the potential binding modes of the active compounds were evaluated structurally. Our results provide new insights into structure-activity relationships and allow rationalization of structural binding characteristics. Moreover, they support the hypothesis that this class of TLR ligands bind solely to TLR2 and do not directly interact with TLR1 or TLR6 of the functional heterodimer. The most active compound from this series (6), is chemically stable, nontoxic, TLR2-selective, and shows a similar activity with regard to the pyrogallol starting points, thus indicating the variability of the hydrogen bonding pattern.
Bermudez, Marcel,Grabowski, Maria,Murgueitio, Manuela S.,Rademann, J?rg,Rudolf, Thomas,Tiemann, Markus,Varga, Péter,Weindl, Günther,Wolber, Gerhard
(2020/06/08)

Synthesis of B-ring-fluorinated (?)-epicatechin gallate derivatives
The synthesis of enantiomerically pure B-ring fluorinated catechin derivatives is presented. In a convergent approach the chromane was obtained by reaction of a lithiated fluoro-resorcine with an optically active epoxide. The latter was prepared from 3,4-
Baumgarten, Kai D.,Czekelius, Constantin,Michaelis, Carina S.,Thieltges, David D. S.
p. 4024 - 4028
(2020/06/09)

Synthesis, structure activity relationship and in vitro anti-influenza virus activity of novel polyphenol-pentacyclic triterpene conjugates
It is urgently necessary to develop more effective anti-influenza agents due to the continuous emergence of drug-resistant strains of influenza virus. Our earlier studies have identified that certain pentacyclic triterpene derivatives are effective inhibitors of influenza virus infection. In the present study, a series of C-28 modified pentacyclic triterpene derivatives via conjugation with a series of polyphenols were synthesized, and their antiviral activities against influenza A/WSN/33 (H1N1) virus in MDCK (Madin-Darby canine kidney) cells were evaluated. Four compounds 23m, 23o, 23q and 23s displayed robust anti-influenza potency with averaged IC50 values at the low-micromole level, surpassing the potency of oseltamivir. In addition, the in vitro cytotoxic activity of the four conjugates against MDCK cells showed no toxicity at 100 μM. Further mechanism studies of compound 23s, one of the best representative conjugates with IC50 value of 5.80 μM and a selective index (SI) value of over 17.2, by hemagglutination inhibition (HI), surface plasmon resonance and molecular modeling indicated that this conjugate bound tightly to the viral envelope hemagglutinin (KD = 15.6 μM), thus blocking the invasion of influenza viruses into host cells.
Li, Haiwei,Li, Man,Xu, Renyang,Wang, Shouxin,Zhang, Yongmin,Zhang, Lihe,Zhou, Demin,Xiao, Sulong
p. 560 - 568
(2019/01/03)

1,3-benzodioxole natural salvianolic acid ester compound and blood fat reduction application thereof
The invention discloses a 1,3-benzodioxole natural salvianolic acid ester compound and blood fat reduction application thereof. A sesamol structure is adopted as a functional fragment, a natural salvianolic acid type structure is introduced into the sesam
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(2019/10/17)

Optimization and anti-inflammatory evaluation of methyl gallate derivatives as a myeloid differentiation protein 2 inhibitor
Myeloid differentiation protein 2 (MD2) is a co-receptor of toll-like receptor 4 (TLR4) responsible for the recognition of lipopolysaccharide (LPS) and mediates a series of TLR4-dependent inflammatory responses in inflammatory lung diseases including acute lung injury (ALI). Targeting MD2 thus may provide a therapeutic strategy against these lung diseases. In this study, we identified a novel compound 4k with the potent anti-inflammatory activity among 39 methyl gallate derivatives (MGDs). MGD 4k exhibited a high binding affinity to MD2, which in turn prevented the formation of the LPS/MD2/TLR4 complex. In addition, MGD 4k significantly reversed the upregulation of LPS-induced inflammatory mediators such as tumor necrosis factor-α, interleukin-6, intracellular adhesion molecule-1, vascular cell adhesion molecule-1, and monocyte chemoattractant protein-1 in vitro and in vivo. Mechanistically, MGD 4k performed anti-inflammatory function by inactivating JNK, ERK and p38 signaling pathways. Taken together, our study identified MGD 4k as a novel potential therapeutic agent for ALI through inhibiting MD2, inflammatory responses, and major inflammation-associated signaling pathways.
Qiu, Yinda,Xiao, Zhongxiang,Wang, Yanyan,Zhang, Dingfang,Zhang, Wenxin,Wang, Guangbao,Chen, Wenbin,Liang, Guang,Li, Xiaokun,Zhang, Yali,Liu, Zhiguo
(2019/08/27)

Synthesis and biological evaluation of novel gallic acid analogues as potential antimicrobial and antioxidant agents
A series of fifteen novel gallic acid esters (7a-o) was synthesized and structure was confirmed by spectral data. Antibiotic power of compounds was assessed against a panel of ten microbes while antioxidant activity was gauged by employing DPPH, ABTS and antilipid peroxidation assays. It was found that in comparison to lead, many of the synthesized derivatives implied much improved broad spectrum antimicrobial effect. Most effective compound found was 7c specifically against resistant gram-negative strains such as P.aeruginosa, E.coli and E.aerogenes. Potent antioxidant capacity was exhibited by7a and 7d in electron transfer assays while 7j and 7c provided maximum shielding against lipid peroxidation. Structure-activity analysis revealed that analogues with electron -withdrawing substituent particularly chloro group stand out as much better antibiotic agent. This study suggests that halogenated gallic acid analogues might be promising pharmacological candidates in view of further drug development.
Sherin, Lubna,Shujaat, Shahida,Sohail, Ayesha,Arif, Fatima
p. 551 - 565
(2019/04/17)

Methyl gallate analogue containing amide structure and application
The invention discloses a methyl gallate analogue containing an amide structure and application. The structure of the methyl gallate analogue is shown as a formula (I); in the formula (I), R1 is independently selected from various alkoxy, hydroxyl, various halogens and aromatic heterocycles. The invention does a lot of experiment researches aiming at the technical field of a methyl gallate analogue which takes a hydrolyzed methyl gallate ester bond as a parent nucleus structure, and a lot of design, synthesis and pharmacological activity screening of the methyl gallate analogue which takes thehydrolyzed methyl gallate ester bond as the parent nucleus structure are carried out to obtain one type of the methyl gallate analogue which takes the hydrolyzed methyl gallate ester bond as the parent nucleus structure; the methyl gallate analogue provided by the invention has high-efficiency and broad-spectrum anti-inflammatory application. The formula I is shown in the description.
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Paragraph 0034; 0037

(2018/12/13)

Double-gallic acid ester derivative in the preparation of the use in the medicament for treating hyperuricemia
The invention discloses application of a digallate derivative which has a formula (I) and a pharmaceutically acceptable salt thereof to preparation of a medicine for treating hyperuricemia. The digallate derivative has a strong effect of inhibiting xanthi
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Paragraph 0088-0095

(2017/08/25)

Synthesis of tyrosyl-DNA phosphodiesterase i inhibitors
The first report for the synthesis of tyrosyl-DNA phosphodiesterase I inhibitors 3,4-dimethoxyphenol-1-β-d-(6′-O-galloyl)glucopyranoside 3 and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol 2-β-d-(6′-O-galloyl) glucopyranoside 5 has been accomplished starting from readily available d-glucose as a starting material. An efficient and general approach has been reported for the synthesis of compounds 3 and 5 with an overall yield of 26% and 27%, respectively.
Nale, Sagar D.,Jadhav, Vrushali H.
supporting information
p. 2652 - 2654
(2016/06/01)

π-Stacking assisted redox active peptide-gallol conjugate: Synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles
In this study, we describe the rational design and synthesis of a redox-active petide-gallol conjugate and explore its application in the preparation of antimicrobial silver nanoparticles. Increase in acidity and redox activity of peptide-gallol compounds
Das, Manisit,Senapati, Kalyan,Panda, Sayak Subhra,Bhattacharya, Prabuddha,Jana, Saibal,Mandal, Santi M.,Basak, Amit
p. 85254 - 85260
(2016/10/12)

Active component having synergistic effect together with hyperuricemia treatment medicine, and febuxostat composition of active component
The invention discloses an active component having a synergistic effect together with a hyperuricemia treatment medicine. The active component is plant polyphenol with the structure represented by formula (I) and a pharmaceutically acceptable salt of the plant polyphenol. The invention also provides a febuxostat composition. The febuxostat composition comprises febuxostat and the active component having a synergistic effect together with the hyperuricemia treatment medicine. The active component having a synergistic effect together with the hyperuricemia treatment medicine, and acts together with the hyperuricemia treatment medicine in the prior art in order to reduce the toxic and side effects of the hyperuricemia treatment medicine and keep an ideal uric acid reduction effect, and the active component has a synergistic medicine effect in the treatment process of hyperuricemia and hyperuricemia induced gouts or gout complications.
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Paragraph 0055; 0057; 0058

(2017/01/31)

Multifunctional diamine AGE/ALE inhibitors with potential therapeutical properties against Alzheimer's disease
An important part of pathogenesis of Alzheimer's disease (AD) is attributed to the contribution of AGE (Advanced Glycation Endproducts) and ALE (Advanced Lipid peroxidation Endproducts). In order to attenuate the progression of AD, we designed a new type of molecules that consist of two trapping parts for reactive carbonyl species (RCS) and reactive oxygen species (ROS), precursors of AGE and ALE, respectively. These molecules also chelate transition metals, the promoters of ROS formation. In this paper, synthesis of the new AGE/ALE inhibitors and evaluation of their physicochemical and biological properties (carbonyl trapping capacity, antioxidant activity, Cu2+-chelating capacity, cytotoxicity and protective effect against in?vitro MGO-induced apoptosis in the model AD cell-line PC12) are described. It is found that compounds 40b and 51e possess promising therapeutic potentials for treating AD.
Lohou, Elodie,Sasaki, N. André,Boullier, Agnès,Sonnet, Pascal
p. 702 - 722
(2016/07/26)

NOVEL GLYCOSYLTRANSFERASE, NOVEL GLYCOSYLTRANSFERASE GENE, AND NOVEL GLYCOSYL DONOR COMPOUND
An object of the present invention is to provide a sugar donating reagent comprising a sugar donor compound other than a sugar nucleotide and an enzyme capable of catalyzing a glycosyl transfer reaction using a sugar donor compound other than a sugar nucleotide. The present invention provides the following: a sugar donating reagent containing a compound of formula (A): wherein R 1 is independently selected from hydrogen, or C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl in which each of the groups is unsubstituted or substituted with one or more groups selected from OH, F, Cl, Br, I, CN, NO 2 , and SO 2 , n is 0, 1, 2, 3, 4 or 5, m is 0 or 1, and X represents a monosaccharide bound via a 2 bond on its anomeric carbon; a glycosyltransferase capable of catalyzing a glycosyl transfer reaction using the sugar donor; and a glycosyltransferase gene comprising DNA encoding the glycosyltransferase.
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(2015/09/22)

The synthesis and antitumor activity of twelve galloyl glucosides
Twelve galloyl glucosides 1-12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-?±-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-?±-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-?2-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-?2-D-glucopyranose (1), 1,4,6-tri-O-galloyl-?2-D-glucopyranose (2), 1,2-di-O-galloyl-?2-D-glucopyranose (3), 1,3-di-O-galloyl-?2-D-glucopyranose (4), 1,2,3-tri- O-galloyl-?±-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-?±-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1-12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 ??g/mL, and their IC50 values were determined to be varied in 17.2-124.7 ??M on the tested three human cancer cell lines. In addition, compounds 1-12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 ??g/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control.
Li, Chang-Wei,Dong, Hua-Jin,Cui, Cheng-Bin
p. 2034 - 2060
(2015/03/05)

COMPOUNDS REDUCING THE PRODUCTION OF SORBITOL IN THE EYE AND METHODS OF USING THE SAME
Methods of inhibiting the progression of or treating secondary complications of diabetes, especially a diabetic eye disease, in a mammal by inhibiting the production of sorbitol in the mammal. Small molecule inhibitors of sorbitol production in the eye useful in the methods of the invention and pharmaceutical compositions containing the compounds, and methods of using the same.
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Page/Page column 23; 24

(2014/02/16)

A synthetic strategy toward branched oligomesogenic phosphonic acids: Comparison of alternative pathways
This work is devoted to the elaboration of a practical scheme for the synthesis of dendritic derivatives of gallic acid containing a carboxylate-ω-alkylphosphonic acid group and three terminal promesogenic substituents. Two synthetic strategies toward the
Prodanov, Maksym F.,Vashchenko, Olga V.,Vashchenko, Valerii V.
supporting information
p. 275 - 278
(2014/01/06)

Structure-activity relationships for vitamin D3-based aromatic a-ring analogues as hedgehog pathway inhibitors
A structure-activity relationship study for a series of vitamin D3-based (VD3) analogues that incorporate aromatic A-ring mimics with varying functionality has provided key insight into scaffold features that result in potent, selective Hedgehog (Hh) pathway inhibition. Three analogue subclasses containing (1) a single substitution at the ortho or para position of the aromatic A-ring, (2) a heteroaryl or biaryl moiety, or (3) multiple substituents on the aromatic A-ring were prepared and evaluated. Aromatic A-ring mimics incorporating either single or multiple hydrophilic moieties on a six-membered ring inhibited the Hh pathway in both Hh-dependent mouse embryonic fibroblasts and cultured cancer cells (IC50 values 0.74-10 μM). Preliminary studies were conducted to probe the cellular mechanisms through which VD3 and 5, the most active analogue, inhibit Hh signaling. These studies suggested that the anti-Hh activity of VD3 is primarily attributed to the vitamin D receptor, whereas 5 affects Hh inhibition through a separate mechanism.
Deberardinis, Albert M.,Madden, Daniel J.,Banerjee, Upasana,Sail, Vibhavari,Raccuia, Daniel S.,De Carlo, Daniel,Lemieux, Steven M.,Meares, Adam,Hadden, M. Kyle
p. 3724 - 3736
(2014/05/20)

Synthetic studies of fisetin, myricetin and nobiletin analogs and related probe molecules
We synthesized a series of analogs of fisetin, myricetin and nobiletin, as well as related fluorescein- and biotin-based flavone-probe molecules, on a suitable scale for biological and structure-activity relationship studies.
Hiza, Aiki,Tsukaguchi, Yuta,Ogawa, Takahiro,Inai, Makoto,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki
p. 1371 - 1396
(2016/10/12)

ANTAGONISTS OF THE TOLL-LIKE RECEPTOR 1/2 COMPLEX
Provided are compounds, compositions and methods for treating Toll-like receptor 1/2 complex (TLRI/2) related inflammatory disorders. Small molecules, based on the benzotropolone scaffold, capable of influencing downstream signaling are dislcosed as well as methods of making and modifying these molecules. Also provided are methods for treating a subject for a clinical condition associated with Toll? like receptor complex 1/2 activation, comprising administering to the subject an effective amount of a benzotropolone compound.
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Page/Page column 29

(2014/02/16)

Highly ordered dielectric mirrors via the self-assembly of dendronized block copolymers
Dendronized block copolymers were synthesized by ruthenium-mediated ring-opening methathesis polymerization of exo-norbornene functionalized dendrimer monomers, and their self-assembly to dielectric mirrors was investigated. The rigid-rod main-chain confo
Piunova, Victoria A.,Miyake, Garret M.,Daeffler, Christopher S.,Weitekamp, Raymond A.,Grubbs, Robert H.
p. 15609 - 15616
(2013/11/06)

TRYPTAMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN GASTROPATHY
The synthesis and evaluation of gastroprotective effect of different tryptamine derivatives. Tryptamine derivatives have been synthesized by formation of amide or ester with some known anti oxidant molecules. These derivatives show excellent antioxidant property in vitro. Among all the derivatives the compound SEGA (3a), that was prepared by the combination of serotonin with gallic acid shows the greater antioxidant property than the other synthesized compounds both in vivo and in vitro. SEGA(3a) shows the gastroprotective effect against NSAIDs (indomethacin or diclofenac)-induced gastropathy in dose dependent manner and also accelerates the healing from injury. It prevents the NSAIDs-induced mitochondrial oxidative stress in vivo. This derivative prevents NSAID-induced mitochondrial oxidative stress-mediated apoptosis in vivo by preventing the activation of caspase 9 and caspase-3 and restores NSAIDs-mediated collapse of mitochondroial transmembrane potential and dehydrogenase activity. SEGA (3a) plays an important role as an iron chelator as well as intra mitochondrial ROS scavenger. Thus, SEGA (3a) is a potent antioxidant antiapototic molecule, which efficiently prevents NSAID-induced gastropathy and stress or alcohol-mediated gastric damage.
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(2013/08/14)

Synthesis and HIV-1 inhibitory activities of dicaffeoyl and digalloyl esters of quinic acid derivatives
Twenty analogues of the anti-HIV-1 integrase (IN) inhibitors dicaffeoylquinic acids (DCQAs) were prepared. Their IC50 values for 3'-end processing and strand transfer against recombinant HIV-1IN were determined in vitro, and their cell toxiciti
Junior,Verde,Rezende,Caneschi,Couri,McDougall,Robinson Jr.,De Almeida
p. 724 - 733
(2013/07/28)

Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity
A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cel
Zheng, Shaojun,Laraia, Luca,O'Connor, Cornelius J.,Sorrell, David,Tan, Yaw Sing,Xu, Zhaochao,Venkitaraman, Ashok R.,Wu, Wenjun,Spring, David R.
supporting information; experimental part
p. 2590 - 2593
(2012/04/23)

Synthesis of poly(3,4,5-trihydroxybenzoate amide) and poly(3,4,5- trihydroxybenzoate ester) dendrimers from polyphenols and their chemiluminescence
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Lee, Yong-Gyun,Song, Ju-Hyun,Lee, Eon-Jin,Lee, Do-Hun,Jung, Dai-Il,Hahn, Jung-Tai
experimental part
p. 2051 - 2054
(2012/09/21)

Synthetic studies toward c-glucosidic ellagitannins: A biomimetic total synthesis of 5-O-desgalloylepipunicacortein A
C-glucosidic ellagitannins constitute a subclass of bioactive polyphenolic natural products with strong antioxidant properties, as well as promising antitumoral and antiviral activities that are related to their capacity to interact with both functional and structural proteins. To date, most synthetic efforts toward ellagitannins have concerned glucopyranosic species. The development of a synthetic strategy to access C-glucosidic ellagitannins, whose characteristic structural feature includes an atropoisomeric hexahydroxydiphenoyl (HHDP) or a nonahydroxyterphenoyl (NHTP) unit that is linked to an open-chain glucose core by a C-aryl glucosidic bond, is described herein. The total synthesis of the biarylic HHDP-containing 5-O- desgalloylepipunicacortein A (1 β) was achieved by either using the natural ellagic acid bis-lactone as a precursor of the requested HHDP unit or by implementing an atroposelective intramolecular oxidative biarylic coupling to forge this HHDP unit. Both routes converged in the penultimate step of this synthesis to enable a biomimetic formation of the key C-aryl glucosidic bond in the title compound.
Malik, Ga?lle,Natangelo, Anna,Charris, Jaime,Pouységu, Laurent,Manfredini, Stefano,Cavagnat, Dominique,Buffeteau, Thierry,Deffieux, Denis,Quideau, Stéphane
supporting information; experimental part
p. 9063 - 9074
(2012/10/07)

Synthesis and antitumor activity of ellagic acid peracetate
Ellagic acid (1) was synthesized for the first time from methyl gallate through α-pentagalloylglucose (α-PGG), and ellagic acid peracetate (3,4,3′,4′-tetra-O-acetylellagic acid, 2) was derived from 1 by acetylation. Oral administration of 2 suppressed melanoma growth significantly in C7BL/6 immunocompetent mice without having any effect on natural killer (NK) cell activity. Comparison of the immunoenhancing activities of 1 and 2 indicated that the latter compound increased white blood cell quantities in peripheral blood and immune cells enriched from the bone marrow and liver of mice. Therefore, both the antitumor efficacy and the immunity enhancement by 2 were greater than those by 1. In addition, on oral administration, neither 1 nor 2 resulted in whole body, liver, or spleen weight changes of normal, tumor-free mice, indicating that these compounds are potentially nontoxic to mice. It was shown that ellagic acid peracetate (2) inhibits B16 melanoma cell growth in vitro and induces B16 cell apoptosis, corresponding to BCL-2 down-regulation. Collectively, the present data imply that 2 can suppress tumor growth by enhancing mouse immunity and inducing tumor cell apoptosis without apparent side effects.
Ren, Yulin,Still, Patrick C.,Kinghorn, A. Douglas,Wei, Min,Chen, Xiaozhuo,Himmeldirk, Klaus,Yuan, Shunzong,Deng, Youcai,Yu, Jianhua
supporting information
p. 631 - 636,6
(2020/08/31)

Synthesis and antiviral activity of substituted quercetins
Influenza viruses are important pathogens that cause respiratory infections in humans and animals. In addition to vaccination, antiviral drugs against influenza virus play a significant role in controlling viral infections by reducing disease progression and virus transmission. Plant derived polyphenols are associated with antioxidant activity, anti-carcinogenic, and cardio- and neuro-protective actions. Some polyphenols, such as resveratrol and epigallocatechin gallate (EGCG), showed significant anti-influenza activity in vitro and/or in vivo. Recently we showed that quercetin and isoquercetin (quercetin-3-β-d-glucoside), a glucoside form of quercetin, significantly reduced the replication of influenza viruses in vitro and in vivo (isoquercetin). The antiviral effects of isoquercetin were greater than that of quercetin with lower IC50 values and higher in vitro therapeutic index. Thus, we investigated the synthesis and antiviral activities of various quercetin derivatives with substitution of C3, C3′, and C5 hydroxyl functions with various phenolic ester, alkoxy, and aminoalkoxy moieties. Among newly synthesized compounds, quercetin-3-gallate which is structurally related to EGCG showed comparable antiviral activity against influenza virus (porcine H1N1 strain) to that of EGCG with improved in vitro therapeutic index.
Thapa, Mahendra,Kim, Yunjeong,Desper, John,Chang, Kyeong-Ok,Hua, Duy H.
p. 353 - 356
(2012/02/15)

TRYPTAMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN GASTROPATHY
The present invention concerns the synthesis and evaluation of gastroprotective effect of different tryptamine derivatives. Tryptamine derivatives have been synthesized by formation of amide or ester with some known anti oxidant molecules. These derivatives show excellent antioxidant property in vitro. Among all the derivatives the compound SEGA (3 a), that was prepared by the combination of serotonin with gallic acid shows the greater antioxidant property than the other synthesized compounds both in vivo and in vitro. SEGA(3a) shows the gastroprotective effect against NSAIDs (indomethacin or diclofenac)-induced gastropathy in dose dependent manner and also accelerates the healing from injury. It prevents the NSAIDs-induced mitochondrial oxidative stress in vivo. This derivative prevents NSAID-induced mitochondrial oxidative stress-mediated apoptosis in vivo by preventing the activation of caspase 9 and caspase-3 and restores NSAIDs-mediated collapse of mitochondroial transmembrane potential and dehydrogenase activity. SEGA (3 a) plays an important role as an iron chelator as well as intra mitochondrial ROS scavenger. Thus, SEGA (3 a) is a potent antioxidant antiapototic molecule, which efficiently prevents NSAID-induced gastropathy and stress or alcohol -mediated gastric damage.
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(2012/04/04)

Discovery of small-molecule inhibitors of the TLR1/TLR2 complex
An important regulator of innate immunity, the protein complex of Toll-like receptors 1 and 2 (TLR1/TLR2) provides an attractive target for the treatment of various immune disorders. The novel compound CU-CPT22 can compete with the binding of the specific lipoprotein ligand to TLR1/TLR2 (see picture) with high inhibitory activity and specificity. Repression of downstream signaling from TNF-α and IL-1β was also observed. Copyright
Cheng, Kui,Wang, Xiaohui,Zhang, Shuting,Yin, Hang
supporting information
p. 12246 - 12249
(2013/02/23)

Luminescent micro and nanogel formation from AB3 type poly(aryl ether) dendron derivatives without conventional multi-interactive gelation motifs
We report the synthesis, gelation and photophysical properties of luminescent AB3 type poly(aryl ether) dendron derivatives in the absence of conventional multi-interactive gelation motifs. The gelation process is controlled through employing partial polar solvent milieu, which significantly enhances the propensity of π-π interaction between the aryl units present in the system. The self-assembly leads to unprecedented gelation through entrapping solvent molecules in the fibrillar arrangement of poly(aryl ether) units. The strategy was further utilized to prepare an excimer based photoluminescent gel through incorporating anthracene units in the dendrons. The close proximity between the anthracene units in the gel renders the formation of anthracene excimers at room temperature, resulting in the emission of bright green light from the gel, upon UV excitation. The study suggests that the size and packing of the self-assembled fibre can be controlled by the generation and functional groups present in the dendron. Furthermore, the strategy envisages an easy approach to generate fluorescent Low Molecular-mass Organic Gelator (LMOG) through incorporating poly cyclic aromatic hydrocarbon units to the poly(aryl ether) dendrons, since the self-assembly is largely guided by π-π interactions. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Rajamalli,Prasad, Edamana
experimental part
p. 1541 - 1548
(2011/09/20)

Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli
A series of 33 novel divanillates and trivanillates were synthesized and found to possess promising cytostatic rather than cytotoxic properties. Several compounds under study decreased by >50% the activity of Aurora A, B, and C, and WEE1 kinase activity at concentrations 50 growth inhibitory ones, accounting, at least partly, for their cytostatic effects in cancer cells and to a lesser extent in normal cells. Compounds 6b and 13c represent interesting starting points for the development of cytostatic agents to combat cancers, which are naturally resistant to pro-apoptotic stimuli, including metastatic malignancies.
Lamoral-Theys, Delphine,Pottier, Laurent,Kerff, Frédéric,Dufrasne, Fran?ois,Proutière, Fabien,Wauthoz, Nathalie,Neven, Philippe,Ingrassia, Laurent,Antwerpen, Pierre Van,Lefranc, Florence,Gelbcke, Michel,Pirotte, Bernard,Kraus, Jean-Louis,Nève, Jean,Kornienko, Alexander,Kiss, Robert,Dubois, Jacques
experimental part
p. 3823 - 3833
(2010/08/19)

Novel inhibitors of basal glucose transport as potential anticancer agents
Cancer cells commonly show increased levels of glucose uptake and dependence. A potential strategy for the treatment of cancer may be the inhibition of basal glucose transport. We report here the synthesis of a small library of polyphenolic esters that inhibit basal glucose transport in H1299 lung and other cancer cells. These basal glucose transport inhibitors also inhibit cancer cell growth in H1299 cells, and these two activities appear to be correlated.
Zhang, Weihe,Liu, Yi,Chen, Xiaozhuo,Bergmeier, Stephen C.
scheme or table
p. 2191 - 2194
(2010/06/15)

Synthesis, radical scavenging activity, protection during storage, and frying by novel antioxidants
Novel antioxidants, derivatives of trolox, and selected phenolic acids have been prepared in good yields and fully characterized by 1H NMR, 13C NMR, and MS. Their antioxidant activities have been assessed by DPPH and ORAC assays, and during frying and accelerated storage tests. Novel phenolic compounds exhibited higher radical scavenging activities than both trolox and R-tocopherol. Trolox hydroxybenzoate showed a significantly higher protection than R-tocopherol under storage conditions. All new antioxidants performed better than R-tocopherol under frying conditions. Moreover, their outstanding thermal stability makes them more valuable than R-tocopherol for frying applications.
Catel, Yohann,Aladedunye, Felix,Przybylski, Roman
scheme or table
p. 11081 - 11089
(2011/06/21)

The first total synthesis of galloyl tyramine
The first total synthesis of galloyl tyramine, an inhibitor of Pim2 kinase was accomplished in an overall high-yield reaction sequence.
Ullah, Nisar
experimental part
p. 464 - 466
(2009/08/08)

Structure-activity relationship of bis-galloyl derivatives related to (-)-epigallocatechin gallate
Green tea and (-)-epigallocatechin gallate (EGCG: one of main components of green tea) are well known to have preventive activities against human cancers. Previously, using a galloyl group as a core structure derived from EGCG, we developed alkyl gallate and gallamide derivatives, which showed strong antiproliferative activity towards human leukemia HL-60 cells by inducing apoptosis. Here, as a further structural development study, we planned to introduce an additional galloyl group into alkyl gallates and gallamides. According to this strategy, various bisgallate and bisgallamide derivatives were synthesized and tested for antiproliferative activity towards HL-60 cells. In gallamide derivatives having a short alkyl chain, the additional galloyl group enhanced the antiproliferative activity. In contrast, in the gallate derivatives, the additional galloyl group had no effect on the antiproliferative activity.
Dodo, Kosuke,Minato, Taro,Hashimoto, Yuichi
scheme or table
p. 190 - 194
(2009/11/30)

Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (-)-epigallocatechin gallate
Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate and gallamide derivatives and evaluated their antiproliferative effects on human leukemia HL-60 cells. Dodecyl 3,4,5-trihydroxybenzoate (6c) showed the most potent activity, being more potent than EGCG. To clarify the molecular mechanism of the antiproliferative action, we investigated the effects of 6c on various factors. Compound 6c was found to induce apoptosis mediated by endoplasmic reticulum (ER)-stress-related caspase-12. Upregulation of gadd-153, an ER-stress marker protein, was also observed. These results indicate that 6c induced apoptosis via the ER-stress-related pathway.
Dodo, Kosuke,Minato, Taro,Noguchi-Yachide, Tomomi,Suganuma, Masami,Hashimoto, Yuichi
p. 7975 - 7982
(2008/12/23)

Synthesis of 7-O-galloyl-d-sedoheptulose
A facile synthetic approach to 7-O-galloyl-d-sedoheptulose (1), a natural product with notable immunosuppressant activity, was developed. The starting material, 2,7-anhydro-d-sedoheptulose (2), was converted in three steps into 1,3,4,5-tetra-O-benzyl-d-se
Xie, Yupeng,Zhao, Yimin
p. 1510 - 1513
(2008/02/08)

METHOD FOR THE SYNTHESIS OF ANTHOCYANINS
The present invention relates to methods of preparing anthocyanins, and methods of preparing precursors of anthocyanins. The methods utilise a coupling reaction between a sugar and a suitable electrophilic precursor to form Eastern half intermediates, that are then reacted with Western half intermediates to form the target anthocyanins. Some Eastern half intermediates and electrophilic precursors also form part of the invention.
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Page/Page column 18;26-27

(2008/06/13)

First chemical synthesis of three natural depsides involved in flavonol catabolism and related to quercetinase catalysis
We report here the first chemical synthesis of three depsides related to quercetinase-catalyzed degradation of kaempferol, quercetin, and myricetin. The three depsides were constructed through the coupling of suitably protected phloroglucinol carboxylic acid and hydroxy-perbenzylated, derivatives of gallic, protocatechuic, and 4-hydroxy benzoic acids. The three synthesized target compounds proved to be identical to their natural counterparts, arising from quercetinase action on corresponding flavonols. Copyright Taylor & Francis Group, LLC.
Tranchimand, Sylvain,Tron, Thierry,Gaudin, Christian,Iacazio, Gilles
p. 587 - 597
(2007/10/03)

Synthesis and structure-activity relationship study of antidiabetic penta-O-galloyl-D-glucopyranose and its analogues
The rapid increase of obesity-associated diabetes has created urgent demands for more effective antidiabetic therapies and pharmaceuticals that are able to address the problems of hyperglycemia and weight gain simultaneously. Our previous studies indicated that the α- and β-anomers of penta-O-galloyl-D-glucopyranose (PGG), 2 and 3, act as insulin mimetics that bind to and activate the insulin receptor, stimulate glucose transport in adipocytes, and reduce blood glucose and insulin levels in diabetic and obese animals. In addition, they inhibit differentiation of preadipocytes into adipocytes. These activities suggest that 2 and 3 may reduce blood glucose without increasing adiposity. To investigate the structure-activity relationship of 2 and 3, four series of novel compounds were prepared and their glucose transport stimulatory activities were measured using a radioactive glucose uptake bioassay. The assay results indicate that both the glucose and the galloyl groups are critical to the activity of 2 and 3. It appears that the glucose core provides an optimal scaffold to present the galloyl groups with the correct spatial orientation to induce activity. Moreover, the galloyl groups linked to the 1, 2, 3, and 4 positions of glucose are essential, while the galloyl group connected to the 6 position of 2 is unnecessary for the induction of activity. The discovery that two related novel compounds, 6-deoxytetra-O-galloyl-α-D-glucopyranose (43) and tetra-O-galloyl-α- D-xylopyranose (59), also possess glucose transport stimulatory activity suggests that 2 may be further modified around position 6 to modulate and enhance its efficacy. To test this hypothesis, we developed a new synthetic method that allows for the stereoselective preparation of derivatives of 2 that are modified on C-6. We found that 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl- α-D-glucopyranose (80) exhibits a significantly higher glucose transport stimulatory activity than 2. Its activity is comparable to that of insulin.
Ren, Yulin,Himmeldirk, Klaus,Chen, Xiaozhuo
p. 2829 - 2837
(2007/10/03)

Depigmenting activity and low cytotoxicity of alkoxy benzoates or alkoxy cinnamte in cultured melanocytes
To obtain effective and safe topical depigmenting agents, we synthesized hydroxybenzoates, alkoxybenzoates, and 3,4,5-trimethoxycinnamate containing a thymol moiety and screened then for high-level inhibitory activity against melanin synthesis in cultured melanocytes. Eight compounds were tested for their depigmenting effect and cytotoxicity using a murine melanocyte cell line. We found that 3,4,5-trialkoxybenzoates and 3,4,5-trimethoxycinnamate, synthesized by conjugating 3,4,5-trialkoxybenzoic acids and 3,4,5-trimethoxycinnmic acid with thymol, showed a potent depigmenting effect and low cytotoxicity. Compound 4h, 5-methyl-2-(methylethyl)phenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate, showed the most potent depigmenting effect (IC50=10 μM) with low cytotoxicity (IC50=200 μM).
Kang, Hak Hee,Rho, Ho Sik,Hwang, Jae Sung,Oh, Seong-Geon
p. 1085 - 1088
(2007/10/03)

Synthetic gallic acid derivatives as models for a comprehensive study of antioxidant activity
The synthesis and antioxidant efficiencies of amphiphilic gallic acid derivatives are reported. To specify the impact of chemical structure on the antioxidant efficiency, several structural modifications of gallic acid were performed. The following structural features were chosen: i) introduction of hydrophobic or hydrophilic residues on the gallic acid and the type of their linkage, ii) the hydrophilic and/or lipophilic character of the whole molecule. The physico-chemical studies of the different series prepared revealed that the antioxidant efficiency of this polyphenol depends clearly on the nature of the linkage with both hydrophilic and hydrophobic parts. A push-pull effect is always necessary, and ester or amide bonds seem well adapted to increase the antioxidant efficiency. Second, under the oxidation conditions applied, it was observed that the hydrophilic and/ or lipophilic character affects drastically the antioxidant activity of gallic acid derivatives. The results obtained are in accordance with the polar paradox, hydrophobic derivatives inhibit oxidation in an aqueous phase, whereas hydrophilic products are not efficient.
Belin, Florence,Barthelemy, Philippe,Ruiz, Karine,Lacombe, Jean Michel,Pucci, Bernard
p. 247 - 265
(2007/10/03)

Synthesis and biological activity of polygalloyl-dendrimers as stable tannic acid mimics
Inspired by the structure of tannic acid, first- to third-generation dendrimers containing two, four, and eight galloyl moieties were synthesized. Stability, antioxidant activity and collagen cross-linking activity of the natural product and its dendrimer analogues were compared. The experimental results indicate that polygalloyl dendrimers might be used as new lead compounds to improve the long-term healing characteristics of burn wounds.
Halkes,Vrasidas, Ioannis,Rooijer, Gilbert R.,Van den Berg,Liskamp, Rob M.J.,Pieters, Roland J.
p. 1567 - 1570
(2007/10/03)

Synthesis of poly (3,4,5-trihydroxybenzoate ester) dendrimers and their chemiluminescence
Gallic acid (GA) and gallic acid methyl ester (GM), polyphenol chemiluminescence (CL) compounds, produces light in the presence of alkali and hydrogen peroxide. We synthesized first-generation polyphenol dendrimers with GA units in the periphery and measured their CL for developing a polyphenol compound which has a strong CL intensity. The CL intensities of the poly (3,4,5-trihydroxybenzoate ester) dendrimers 4 and 8 in MeOH are approximately 400- and 600-fold stronger than that of GA, respectively.
Nakazono, Manabu,Ma, Li,Zaitsu, Kiyoshi
p. 8185 - 8189
(2007/10/03)