cas 70424-94-1, METHYL 3,4,5-TRIS(BENZYLOXY)BENZOATE

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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)

A novel and reversible multifunction probe for Al3+and F? by fluorogenic and colorimetric method
A new highly selective and sensitive probe 2-hydroxy-1-formylnaphthalene trihydroxybenzoyl hydrazone (1) was designed and synthesized for sequential detection of Al3+ and F? ions with “OFF-ON-OFF” fluorescent signals. This probe 1 displays high selectivity towards Al3+ among 17 metal cations, the resultant complex [1-Al3+] formed by the coordination of 1 with Al3+ can be recognized as a sequential probe for sensing F?. Moreover, the formation of this 1-Al3+ complex with a 1:1 stoichiometry leads to a significant fluorescence enhancement at 505 nm with high selectivity, for that 1 shows “turn-on” fluorescence response to Al3+ with negligible interferences from other various metal cations, and the resultant sequential probe 1-Al3+ complex exhibits the nearly complete quenching of emission intensity with successive addition of F?, which is only specific for F?, without being hampered by the existence of other various anions. The lowest limit of detection (LOD) values of 1 and 1-Al3+ complex for separately sensing Al3+ and F? ions are determined to be 2.55 × 10?8 M and 1.48 × 10?7 M, respectively. In addition, 1 can severe as a highly selective probe towards Al3+ and F? ions by the “naked-eye” detection, for the solution color easily changing from colorless to yellow-green with the introduction of Al3+ and further to colorless upon subsequent addition of F?.
Fan, Long,Liu, Kui,Yang, Zheng-yin
(2022/03/27)

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; 0038; 0051-0053

(2021/07/28)

Preparation of isodehydrodigallic acid using Ullmann condensation
Isodehydrodigallic acid, which is an important component of several ellagitannin compounds, was easily synthesized using a classical Ullmann condensation reaction.
Imai, Haruka,Koyama, Ryo,Horino, Yoshikazu,Abe, Hitoshi
p. 298 - 301
(2021/03/08)

Understanding the regioselectivity in the oxidative condensation of catechins using pyrogallol-type model compounds
Catechins are found in many foods, including tea. These compounds are bioactive. Previous studies have shown that catechins form dimers on oxidation, and there seem to be distinct regioselective effects. However, the dimerization mechanism and regioselectivity are not well understood. Therefore, we investigated the oxidation of four pyrogallol-type model compounds of epigallocatechin (EGC) having various substituents with 1 equiv of copper chloride and 30% dioxane in water. Compounds having 2C-2C or 2C-4C bonds in the B-ring were obtained in different product ratios. Comparison of the oxidation rates of each compound revealed that the model compounds having an oxygen atom corresponding to the 1-position of the C-ring of EGC underwent slow oxidation. In addition, using density functional theory calculations, we found that the highest occupied molecular orbital energies of these compounds were higher than those of the others. Further, the 2C-2C-bonded oxidation product having an A-ring and an oxygen atom at the C-ring 1-position was confirmed to have the highest thermodynamic stability. From these results, it is suggested that the regioselective condensation reaction of the catechin B-ring is related to interactions between the A-rings, as indicated by earlier studies, and the presence of oxygen at the 1-position of the C-ring in EGC.
Yanase, Emiko,Ochiai, Yuto,Hirose, Sayumi
supporting information
p. 12359 - 12366
(2020/11/10)

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)

Synthetic Ellagic Acid Glycosides Inhibit Early Stage Adhesion of Streptococcus agalactiae Biofilms as Observed by Scanning Electron Microscopy
Ellagic acid derivatives possess antimicrobial and antibiofilm properties across a wide-range of microbial pathogens. Due to their poor solubility and ambident reactivity it is challenging to synthesize, purify, and characterize the activity of ellagic acid glycosides. In this study, we have synthesized three ellagic acid glycoconjugates and evaluated their antimicrobial and antibiofilm activity in Streptococcus agalactiae (Group B Streptococcus, GBS). Their significant impacts on biofilm formation were examined via SEM to reveal early-stage inhibition of cellular adhesion. Additionally, the synthetic glycosides were evaluated against five of the six ESKAPE pathogens and two fungal pathogens. These studies reveal that the ellagic acid glycosides possess inhibitory effects on the growth of gram-negative pathogens.
Chambers, Schuyler A.,Gaddy, Jennifer A.,Townsend, Steven D.
supporting information
p. 9923 - 9928
(2020/04/28)

Polytopic carriers for platinum ions: From digalloyl depside to tannic acid
A novel dinuclear platinum(ii) complex, namely [Pt2m-GG(Me2SO-S)4] (8, GG = deprotonated methyl digallate), was easily synthesized under solvent-free conditions by grinding a solid m/p digalloyl depside with the Pt precursor [PtCO3(Me2SO-S)2]. Similarly, platinum nuclei were introduced into the galloyl chains of tannic acid (TA). In particular, three complexes A, B and C were prepared by reacting TA as a polytopic ligand with an increasing amount of [PtCO3(Me2SO-S)2]. The antiproliferative activity of complexes 8, A, B and C together with the corresponding ligands GG and TA was tested in vitro and compared with that of cisplatin on two human tumor cell lines, A2780 (ovarian cisplatin-sensitive) and A2780cis (ovarian cisplatin-resistant), and one non-tumoral cell line, HaCat. The experiments focusing on their pro-apoptotic activity indicated that the antiproliferative activity of the most active Pt(II) complexes is associated with the induction of apoptosis. This journal is
Fogagnolo, Marco,Bergamini, Paola,Marchesi, Elena,Marvelli, Lorenza,Gambari, Roberto,Lampronti, Ilaria
p. 12227 - 12235
(2020/07/30)

Compound for treating or preventing hepatopathy (by machine translation)
The invention discloses a compound, an optical isomer or a pharmaceutically acceptable salt, an optical isomer or a pharmaceutically acceptable salt thereof for treating or preventing hepatopathy, and the compound, optical isomer or pharmaceutically acceptable salt thereof can be applied to the preparation of a medicine for treating or preventing liver diseases. (by machine translation)
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Paragraph 0191-0192; 0194

(2019/10/01)

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)

Novel coumarin-based containing denrons selective fluorescent chemosesor for sequential recognition of Cu2+ and PPi
In this study, we have successfully synthesized a novel coumarin-based dendrons derivative CD and its chemical structure was characterized by 1H NMR, 13C NMR and ESI-HR-MS. The sensor CD showed an obvious “on-off” fluorescence quenching response toward Cu2+ with a maximum quenching efficiency of 99.8%. The CD-Cu2+ complex showed an “off-on” fluorescence enhancement response toward PPi over many competitive anions. The detection limit of the sensor CD was 0.29 × 10?6 M to Cu2+ and 2.39 × 10?9 M to PPi. In addition, the sensor CD showed a 1:1 binding stoichiometry to Cu2+ and the sensor CD-Cu2+ showed a 2:1 binding stoichiometry to PPi in CH3CN/HEPES buffer medium (9:1 v/v, pH = 7.2). The stable pH range of sensor CD to Cu2+ and CD-Cu2+ to PPi was from 3 to 8.
Zhao, Chongyang,Chen, Jian,Cao, Duanlin,Wang, Jianlong,Ma, Wenbing
p. 1997 - 2003
(2019/02/24)

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
(2018/06/14)

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
(2018/03/08)

PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED ISOXAZOLINE COMPOUNDS - CRYSTALLINE TOLUENE SOLVATE OF (S)-AFOXOLANER
This invention relates to processes for the preparation of antiparasitic isoxazoline compounds enriched in an enantiomer using quinine- based chiral phase transfer catalysts. The invention also relates to novel quinine-based phase transfer catalysts and t
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Page/Page column 117; 118; 121

(2017/11/06)

POLYCATENAR LIGANDS AND HYBRID NANOPARTICLES MADE THEREFROM
Described herein are polycatenar ligand compounds and their use in the production of hybrid nanoparticles, typically nanocrystals. The present disclosure also relates to films containing the hybrid nanoparticles described herein and their use.
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Page/Page column 35; 36

(2017/10/13)

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)

Aryl ethers coupled pyridoxal as supramolecular gelator for selective sensing of F?
Aryl ethers coupled pyridoxal Schiff base 1 has been synthesized and its gelation properties have been examined. The gelator 1 forms colorless gels from various solvents such as DMSO, DMF, DMSO/H2O and DMF/H2O. The gel matrix obtained from DMSO shows ribbon-like fibrous morphology and has been utilized for efficient ‘naked eye’ detection of fluoride ion through a reversible gel-sol transition, which is associated with color change from almost colorless to yellow. In DMSO, the Schiff base 1 has also been observed to sense F?ion more efficiently over the basic ions AcO?and CN?. Though few examples of anion sensing in solution with pyridoxal-based Schiff bases are known, anion recognition utilizing pyridoxal-based gelators is unexplored in the literature.
Ghosh, Kumaresh,Pati, Chiranjit
supporting information
p. 5469 - 5474
(2016/11/19)

Polycatenar Ligand Control of the Synthesis and Self-Assembly of Colloidal Nanocrystals
Hydrophobic colloidal nanocrystals are typically synthesized and manipulated with commercially available ligands, and surface functionalization is therefore typically limited to a small number of molecules. Here, we report the use of polycatenar ligands d
Diroll, Benjamin T.,Jishkariani, Davit,Cargnello, Matteo,Murray, Christopher B.,Donnio, Bertrand
supporting information
p. 10508 - 10515
(2016/09/04)

Poly(aryl ether) Dendrons with Monopyrrolotetrathiafulvalene Unit-Based Organogels exhibiting Gel-Induced Enhanced Emission (GIEE)
A series of poly(aryl ether) dendrons with a monopyrrolo-tetrathiafulvalene unit linked through an acyl hydrazone linkage were designed and synthesized as low molecular mass organogelators (LMOGs). Two of the dendrons could gelate the aromatic solvents an
Liu, Yucun,Lei, Wenwei,Chen, Tie,Jin, Longyi,Sun, Guangyan,Yin, Bingzhu
supporting information
p. 15235 - 15245
(2015/11/02)

Complex columnar hexagonal polymorphism in supramolecular assemblies of a semifluorinated electron-accepting naphthalene bisimide
Simple synthetic methods for a strongly electron-accepting naphthalene bisimide (NBI) derivative functionalized with a new environmentally friendly chiral racemic semifluorinated alkyl group and with AB3 minidendrons containing the same semifluorinated group are reported. The semifluorinated dendron was attached to the imide groups of the NBI via one, two, and three (m = 1, 2, 3) methylenic units. The NBI-containing semifluorinated groups and the dendronized NBI with m = 1 and 2 self-organize into lamellar crystals. The dendronized NBI with m = 3 self-assembles into an unprecedentedly complex and ordered column that self-organizes in a columnar hexagonal periodic array. This array undergoes a continuous transition to a columnar hexagonal superlattice that does not display a first-order phase transition during analysis by differential scanning calorimetry at heating and cooling rates of 10 and 1 °C/min. These complex columnar hexagonal periodic arrays with intramolecular order could be elucidated only by a combination of powder and fiber X-ray diffraction studies and solid-state NMR experiments. The lamellar crystals self-organized from m = 1 and the two highly ordered columnar hexagonal periodic arrays of m = 3 are assembled via thermodynamically controlled processes. Since strongly electron-accepting derivatives are of great interest to replace fullerene acceptors in organic photovoltaics and for other supramolecular electronic materials, the multitechnique structural analysis methodology elaborated here must be taken into consideration in all related studies.
Wu, Yu-Chun,Leowanawat, Pawaret,Sun, Hao-Jan,Partridge, Benjamin E.,Peterca, Mihai,Graf, Robert,Spiess, Hans W.,Zeng, Xiangbing,Ungar, Goran,Hsu, Chain-Shu,Heiney, Paul A.,Percec, Virgil
supporting information
p. 807 - 819
(2015/01/30)

Visual detection of fluoride ions
Dendrimer-hydrazides are coupled to polycyclic aromatic hydrocarbons for use in the visual detection of the presence of low levels of fluoride in a sample. The dendrimers can have a phenyl core, a first generation of aralkyl ethers, and an optional second generation of aralkyl ethers. The compounds form gels with solvents. In the presence of fluoride ion, the gels undergo color changes and/or gel to liquid phase change.
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Page/Page column 18-19

(2015/12/18)

Design, synthesis and characterization of novel inhibitors against mycobacterial β-ketoacyl CoA reductase FabG4
We report the design and synthesis of triazole-polyphenol hybrid compounds 1 and 2 as inhibitors of the FabG4 (Rv0242c) enzyme of Mycobacterium tuberculosis for the first time. A major advance in this field occurred only a couple of years ago with the X-ray crystal structure of FabG4, which has helped us to design these inhibitors by the computational fragment-based drug design (FBDD) approach. Compound 1 has shown competitive inhibition with an inhibition constant (Ki) value of 3.97 ± 0.02 μM. On the other hand, compound 2 has been found to be a mixed type inhibitor with a Ki value of 0.88 ± 0.01 μM. Thermodynamic analysis using isothermal titration calorimetry (ITC) reveals that both inhibitors bind at the NADH co-factor binding domain. Their MIC values, as determined by resazurin assay against M. smegmatis, indicated their good anti-mycobacterial properties. A preliminary structure-activity relationship (SAR) study supports the design of these inhibitors. These compounds may be possible candidates as lead compounds for alternate anti-tubercular drugs. All of the reductase enzymes of the Mycobacterium family have a similar ketoacyl reductase (KAR) domain. Hence, this work may be extrapolated to find structure-based inhibitors of other reductase enzymes. The Royal Society of Chemistry.
Banerjee, Deb Ranjan,Dutta, Debajyoti,Saha, Baisakhee,Bhattacharyya, Sudipta,Senapati, Kalyan,Das, Amit K.,Basak, Amit
p. 73 - 85
(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)

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)

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)

Transformation from kinetically into thermodynamically controlled self-organization of complex helical columns with 3d periodicity assembled from dendronized perylene bisimides
The dendronized perylene 3,4:9,10-tetracarboxylic acid bisimide (PBI), (3,4,5)12G1-1-PBI, was reported by our laboratory to self-assemble into complex helical columns containing dimers of dendronized PBI with one molecule in each stratum, with different intra- and interdimer rotation angles but identical intra- and interdimer distance of 3.5 ?, exhibiting a four-strata 2 1 helical repeat. A thermodynamically controlled 2D columnar hexagonal phase with short-range intracolumnar order represents the thermodynamic product at high temperature, while a kinetically controlled monoclinic columnar array with 3D periodicity is the thermodynamic product at low temperature. With heating and cooling rates higher than 10 C/min to 1 C/min, at low temperature the 2D columnar periodic array is the kinetic product for this dendronized PBI. Here the synthesis and structural analysis of a library of (3,4,5)nG1-m-PBI with n = 12 to 6 and m = 1 are reported. A combination of differential scanning calorimetry, X-ray diffraction on powder and orientated fibers, including pattern simulation and electron density map reconstruction, and solid-state NMR, all as a function of temperature and heating and cooling rate, was employed for their structural analysis. It was discovered that at low temperature the as-prepared n = 12 to 10 exhibit a 3D layered array that transforms irreversibly into columnar periodicities during heating and cooling. Also the kinetically controlled 3D columnar phase of n = 12 becomes thermodynamically controlled for n = 10, 9, 8, 7, and 6. This unprecedented transformation is expected to facilitate the design of functions from dendronized PBI and other self-assembling building blocks.
Percec, Virgil,Sun, Hao-Jan,Leowanawat, Pawaret,Peterca, Mihai,Graf, Robert,Spiess, Hans W.,Zeng, Xiangbing,Ungar, Goran,Heiney, Paul A.
supporting information
p. 4129 - 4148
(2013/04/23)

Supramolecular design for two-component hydrogels with intrinsic emission in the visible region
We report, for the first time, an in situ formation of two-component hydrogels from pyridine derivatives of poly(aryl ether) dendrons and tartaric acid. The two-component system (dendron + acid) undergoes J-type aggregation, leading to fibrillar type self-assembly in THF-water mixture along with blue (470 nm) and green (500 nm) intrinsic emissions. The Royal Society of Chemistry 2013.
Rajamalli,Atta, Supriya,Maity, Sandeepan,Prasad, Edamana
supporting information
p. 1744 - 1746
(2013/03/14)

Glucose-cored poly(aryl ether) dendron based low molecular weight gels: PH controlled morphology and hybrid hydrogel formation
We designed poly(aryl ether) dendron based transparent hydrogels containing glucose moiety, which undergoes in situ transition from nanofibers to spherical aggregates, upon pH variation. The process is reversible and the assembled structures have been characterized by DLS and SEM. More importantly, efficient dispersion of graphene oxide results in lower CGC (0.08 wt%) value and higher mechanical strength, compared to the native gel.
Rajamalli,Sheet, Partha Sarathi,Prasad, Edamana
supporting information
p. 6758 - 6760
(2013/07/26)

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)

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 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)

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)

Decorating the lanthanide terminus of self-assembled heterodinuclear lanthanum(iii)/gallium(iii) helicates
Arylacylhydrazones of 2,3-dihydroxybenzaldehyde are appropriate ligands for the preparation of heterodinuclear triple-stranded helicates involving high coordinated lanthanide(iii) ions. In the present study, three different kinds of substituents are intro
Albrecht, Markus,Latorre, Irene,Mehmeti, Gent,Hengst, Konstantin,Oppel, Iris M.
scheme or table
p. 12067 - 12074
(2012/01/14)

COMPOSITIONS AND METHODS FOR GLUCOSE TRANSPORT INHIBITION
Glucose deprivation is an attractive strategy in cancer research and treatment. Cancer cells upregulate glucose uptake and metabolism for maintaining accelerated growth and proliferation rates. Specifically blocking these processes is likely to provide new insights to the role of glucose transport and metabolism in tumorigenesis, as well as in apoptosis. As solid tumors outgrow the surrounding vasculature, they encounter microenvironments with a limited supply of nutrients leading to a glucose deprived environment in some regions of the tumor. Cancer cells living in the glucose deprived environment undergo changes to prevent glucose deprivation-induced apoptosis. Knowing how cancer cells evade apoptosis induction is also likely to yield valuable information and knowledge of how to overcome the resistance to apoptosis induction in cancer cells. Disclosed herein are novel anticancer compounds that inhibit basal glucose transport, resulting in tumor suppression and new methods for the study of glucose deprivation in animal cancer research.
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Page/Page column 27-28

(2011/10/13)

Low molecular weight fluorescent organogel for fluoride ion detection
The design, synthesis, and the photophysical properties of a Low Molecular Weight Gel (LMWG) based on AB3 and AB2 type poly(aryl ether) dendrons with an anthracene chromophore attached through an acylhydrazone linkage are described. The gel is utilized for an efficient 'naked eye' detection of fluoride ions (as low as 0.1 equiv with respect to the gelator concentration), through a reversible gel-sol transition, which is associated with a color change from deep yellow to bright red.
Rajamalli,Prasad, Edamana
supporting information; experimental part
p. 3714 - 3717
(2011/09/12)

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)

Design and synthesis of two aromatic amines with dendritic structure
The design and synthesis of two aromatic amines with dendritic structures, i.e. 3,4,5-tribenzyloxyaniline (3,4,5-G1-NH2) and 2,5-dibenzyloxyaniline (2,5-G1-NH2), were conducted. A coupling reaction of three or two equivalents of benzyl bromide to one equivalent of methyl hydroxybenzoate generated methyl 3,4,5-tribenzyloxybenzoate (3,4,5-G1-COOCH3), methyl 2,5-dibenzyloxybenzoate (2,5-G1-COOCH3) and 2,6-dibenzyloxybenzoate (2,6-G1-COOCH3) in high yields. All G1-COOCH3 derivatives were studied by X-ray analysis. The results show that these dendrons have sufficient volume to be used as the fine ligands for certain catalysts. The amide intermediates (benzamide, G1-CONH2) were obtained by reaction between ammonia and G1-COOCH3. Interestingly, 2,6-dibenzyloxybenzamide (2,6-G1-CONH2) can not be prepared in the same condition, which may be due to the overlarge steric block. Sodium hypochlorite was an effective oxidant to generate methyl carbamates G1-NHCO2CH3.
Luo, Zhenghong,Cheng, Hua,Xu, Wei
experimental part
p. 303 - 308
(2010/10/21)

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
scheme or table
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)

Total synthesis of sanguiin H-5
(Chemical Equation Presented) Using an atropdiastereoselective oxidative biaryl coupling as the key step, the total synthesis of the ellagitannin natural product sanguiin H-5 is reported. Both organomagnesium and organozinc based metalation methodologies
Su, Xianbin,Surry, David S.,Spandl, Richard J.,Spring, David R.
supporting information; experimental part
p. 2593 - 2596
(2009/05/26)

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)

OPTICALLY ACTIVE QUATERNARY AMMONIUM SALT HAVING AXIAL ASYMMETRY AND PROCESS FOR PRODUCING -AMINO ACID AND DERIVATIVE THEREOF WITH THE SAME
The present invention provides a chiral phase-transfer catalyst of the following formula (I): The compound (I) can be produced by reacting a 2,2'-dimethylene bromide-1,1'-biphenyl derivative, which can be produced through comparatively small number of steps, with an easily available secondary amine.
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Page/Page column 95

(2008/06/13)

Gallotannins and ellagitannins as regulators of cytokine release
A means and method for increasing or inhibiting the secretion of cytokines using gallotannins and ellagitannins is described. The preferred cytokine release inhibiting compounds are dimeric gallotannins having a linker molecule that misaligns the carbohydrate cores of the compounds. The preferred cytokine release promoting gallotannins and ellagitannins include a diaryl ether linker unit. In comparison to the more structurally complex ellagitannins, the compounds of this invention are structurally simpler, easier to synthesize, and more potent.
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Page/Page column 38

(2010/11/28)

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)

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

(2008/06/13)

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)

Analogs of green tea polyphenols as chemotherapeutic and chemopreventive agents
Novel compounds useful as chemotherapeutic and chemopreventive agents are provided. The compounds are analogs of polyphenol catechins that occur in green tea, such as epigallocatichin-3-gallate (EGCG), and have the structure of formula (I) wherein R1 through R11 are defined herein. Preferred R4 moieties are selected from O, S, NH and CH2, and in exemplary compounds, R4 is O and R5 is a tri-substituted aroyloxy substituent, such as a 3,4,5-substituted benzoyloxy group. Pharmaceutical compositions are provided as well, as are methods of chemotherapy and chemoprevention.
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(2010/02/07)