- Identification of 8-O-4/8-5(Cyclic)- and 8-8(Cyclic)/5-5-Coupled Dehydrotriferulic Acids, Naturally Occurring in Cell Walls of Mono- and Dicotyledonous Plants
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Besides ferulate dimers, higher oligomers of ferulic acid such as trimers and tetramers were previously demonstrated to occur in plant cell walls. This paper reports the identification of two new triferulic acids. 8-O-4/8-5(cyclic)-triferulic acid was synthesized from ethyl ferulate under oxidative conditions using copper(II)-tetramethylethylenediamine [CuCl(OH)-TMEDA] as a catalyst, whereas 8-8(cyclic)/5-5-triferulic acid was isolated (preparative size exclusion chromatography, reversed-phase HPLC) from saponified insoluble maize fiber. Structures of both trimers were unambiguously elucidated by high-resolution LC-ToF-MS/MS and one- (1H) and two-dimensional (HSQC, HMBC, COSY, NOESY) NMR spectroscopy. The newly described trimers were identified by LC-MS/MS in alkaline hydrolysates of insoluble fibers from maize, wheat, and sugar beet, indicating that ferulic acid cross-links between cell wall polymers are more diverse than previously recognized. Saponification experiments also suggest that the newly identified 8-O-4/8-5(cyclic)-triferulic acid is the naturally occurring precursor of the previously identified 8-O-4/8-5(noncyclic)-triferulic acid in plant cell walls.
- Waterstraat, Martin,Bunzel, Diana,Bunzel, Mirko
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- Production of feruloylated lysophospholipids via a one-step enzymatic interesterification
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Incorporation of ferulic acid (FA) into egg-yolk phosphatidylcholine (PC) in a lipase-catalyzed acidolysis and interesterification process was studied using four commercially available immobilized lipases as catalysts and two acyl donors: ferulic acid (FA) and ethyl ferulate (EF). Novozym 435 and a binary solvent system of toluene/chloroform 9:1 (v/v) were found to be the most suitable biocatalyst and medium, respectively, and significantly increased the incorporation of FA into the phospholipid fraction. Subsequently response surface methodology (RSM) and Box-Behnken design were employed to evaluate the effects of substrate molar ratio, enzyme loading and time of the reaction on the process of interesterification. The selected optimized parameters were established as PC/EF molar ratio 1/15, enzyme load 30% (w/w) and incubation time 6 days. The process of interesterification at the optimized parameters carried out on a large scale afforded feruloylated lysophosphatidylcholine (FLPC) in high isolated yield of 62% (w/w).
- Rychlicka, Magdalena,Maciejewska, Gabriela,Niezgoda, Natalia,Gliszczyńska, Anna
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- Rapid syntheses of dehydrodiferulates via biomimetic radical coupling reactions of ethyl ferulate
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Dehydrodimerization of ferulates in grass cell walls provides a pathway toward cross-linking polysaccharide chains limiting the digestibility of carbohydrates by ruminant bacteria and in general affecting the utilization of grass as a renewable bioresource. Analysis of dehydrodiferulates (henceforth termed diferulates) in plant cell walls is useful in the evaluation of the quality of dairy forages as animal feeds. Therefore, there has been considerable demand for quantities of diferulates as standards for such analyses. Described here are syntheses of diferulates from ethyl ferulate via biomimetic radical coupling reactions using the copper(II)-tetramethylethylenediamine [CuCl(OH)-TMEDA] complex as oxidant or catalyst. Although CuCl(OH)-TMEDA oxidation of ethyl ferulate in acetonitrile produced mixtures composed of 8-O-4-, 8-5-, 8-8- (cyclic and noncyclic), and 5-5-coupled diferulates, a catalyzed oxidation using CuCl(OH)-TMEDA as catalyst and oxygen as an oxidant resulted in better overall yields of such diferulates. Flash chromatographic fractionation allowed isolation of 8-8- and 5-5-coupled diferulates. 8-5-Diferulate coeluted with 8-O-4-diferulate but was separated from it via crystallization; the 8-O-4 diferulate left in the mother solution was isolated by rechromatography following a simple tetrabutylammonium fluoride treatment that converted 8-5-diferulate to another useful diferulate, 8-5-(noncyclic) diferulate. Therefore, six of the nine (5-5, 8-O-4, 8-5-c, 8-5-nc, 8-5-dc, 8-8-c, 8-8-nc, 8-8-THF, 4-O-5) diferulic acids that have to date been found in the alkaline hydrolysates of plant cell walls can be readily synthesized by the CuCl(OH)-TMEDA catalyzed aerobic oxidative coupling reaction and subsequent saponification described here.
- Lu, Fachuang,Wei, Liping,Azarpira, Ali,Ralph, John
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- Peroxidase-catalyzed oligomerization of ferulic acid esters
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Valuable information about possible types of linkages, reaction mechanisms, and sequences for oxidative coupling of phenolic compounds in planta is available from in vitro model systems. Ferulate oligomers were generated in a system using ethyl ferulate, peroxidase, and hydrogen peroxide under various conditions. A molar ferulate/H2O2 ratio of 1:1, an ethanol level of 30% in an aqueous sodium phosphate buffer (pH 6.0), and a reaction time of 10 min were considered to be ideal to produce maximal proportions of ferulate trimers and tetramers from ethyl ferulate as starting material. The dominant trimer and tetramer were each isolated from the reaction mixture and identified as 8-O-4/8-5(cyclic)-dehydrotriferulic acid triethyl ester and 8-5(cyclic)/4-O-5/8-5(cyclic)-dehydrotetraferulic acid tetraethyl ester. The structure of the 8-O-4/8-5(cyclic)-dehydrotriferulic acid triethyl ester revealed that a third ferulate unit is bound to a preformed 8-O-4-diferulate dimer, a surprising reaction sequence considering the dominance of 8-5-coupled dimers among dehydrodiferulates in H2O2/peroxidase-based model reactions. As 4-O-5-coupling is not favored in the dimerization process of ferulates, the main tetramer isolated in this study is probably formed by 4-O-5-coupling of two preformed 8-5(cyclic)-diferulates, a logical step in analogy with reactions occurring in lignin biosynthesis.
- Bunzel, Mirko,Heuermann, Birgit,Kim, Hoon,Ralph, John
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- First stereoselective and concise synthesis of rhoiptelol C
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The first concise stereoselective total synthesis of diarylheptanoid rhoiptelol C (1) was achieved from readily available vanillin. The synthesis involves Keck's asymmetric allylation, olefin cross metathesis, and Sharpless asymmetric dihydroxylation reaction as key steps. Copyright
- Purushotham Reddy, Sudina,Chinnababu, Baggu,Venkateswarlu, Yenamandra
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- Lipase-catalyzed preparation of mono- and diesters of ferulic acid
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Lipophilic and stable derivatives of ferulic acid are required to improve its efficacy in fatty foods and to optimize its use in cosmetic and pharmaceutical preparations. We report an improved synthesis of ferulic acid monoesters (ethyl ferulate and lauryl ferulate) using immobilized lipase from Candida antarctica B (CALB) in diisopropyl ether (DIPE). Maximum yields were 89% and 85% in 200 h for ethyl and lauryl ferulate, respectively. Ethyl ferulate was further acylated with vinyl esters to form ferulate diesters. 4-Acetoxy-ethyl ferulate was obtained with the immobilized lipase from Alcaligenes sp. (QLG) with 59% yield in 72 h, whereas 4-dodecanoyloxy-ethyl ferulate (a new compound) was synthesized with 52% yield in 72 h using CALB. DIPE was the best solvent for the transesterifications. Finally, the anti-inflammatory activity of the synthesized derivatives was evaluated in vitro; the compounds bearing a dodecyl chain showed improved anti-inflammatory activity compared with short-chain esters.
- Sandoval, Georgina,Quintana, Paula G.,Baldessari, Alicia,Ballesteros, Antonio O.,Plou, Francisco J.
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- Solvent role in the lipase-catalysed esterification of cinnamic acid and derivatives. Optimisation of the biotransformation conditions
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The esterification of cinnamic acid has been deeply investigated using ethanol as nucleophile and Candida antarctica lipase type B (CAL-B) as suitable biocatalyst. Special attention has been paid to the role that the solvent plays in the production of ethyl cinnamate. Therefore, volatile organic solvents and deep eutectic mixtures were employed in order to find optimal reaction conditions. Once that hexane was selected as the solvent of choice, other parameters that affect the enzyme activity were investigated in order to produce ethyl cinnamate with excellent yield. The CAL-B loading, nucleophile equivalents, temperature and reaction time have been identified as key parameters in the enzyme efficiency, and the potential of lipase-catalysed esterification has been finally exploited to produce a series of ethyl esters with different pattern substitutions on the aromatic ring.
- Suárez-Escobedo, Laura,Gotor-Fernández, Vicente
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- First total syntheses of four natural bioactive glucosides
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The efficient total syntheses of four biologically interesting natural glucosides Ethylconiferin, Butylconiferin, 2’-Butoxyethylconiferin and Balajaponin B, have been achieved for the first time starting from commercially available Vanilline via concise reaction sequence of 8–10 steps with the overall yield of 26–41%. This work definitely laid the foundation for the further pharmacological study of this kind of natural compounds. Meanwhile, currently developed approach could be used as a general synthetic strategy for the syntheses of other monolignol glucosides and their derivatives, and provides an opportunity for further study of the structure-activity relationship of this kind of glucosides.
- Xu, Guangya,Wu, Min,Yao, Zhongquan,Lou, Hongbin,Du, Weihong,Song, Mingwei,He, Yujiao,Dong, Hongbo
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supporting information
p. 1266 - 1271
(2021/02/06)
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- Structural Fine-Tuning of Desmuramylpeptide NOD2 Agonists Defines Their in Vivo Adjuvant Activity
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We report on the design, synthesis, and biological evaluation of a series of nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) desmuramylpeptide agonists with improved in vitro and in vivo adjuvant properties. We identified two promising compounds: 68, a potent nanomolar in vitro NOD2 agonist, and the more lipophilic 75, which shows superior adjuvant activity in vivo. Both compounds had immunostimulatory effects on peripheral blood mononuclear cells at the protein and transcriptional levels, and augmented dendritic-cell-mediated activation of T cells, while 75 additionally enhanced the cytotoxic activity of peripheral blood mononuclear cells against malignant cells. The C18 lipophilic tail of 75 is identified as a pivotal structural element that confers in vivo adjuvant activity in conjunction with a liposomal delivery system. Accordingly, liposome-encapsulated 75 showed promising adjuvant activity in mice, surpassing that of muramyl dipeptide, while achieving a more balanced Th1/Th2 immune response, thus highlighting its potential as a vaccine adjuvant.
- Guzelj, Samo,Nabergoj, Sanja,Gobec, Martina,Pajk, Stane,Klan?i?, Veronika,Slütter, Bram,Frkanec, Ru?a,?timac, Adela,?ket, Primo?,Plavec, Janez,Mlinari?-Ra??an, Irena,Jakopin, ?iga
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supporting information
p. 7809 - 7838
(2021/06/28)
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- Synthesis of Novel Antiviral Ferulic Acid-Eugenol and Isoeugenol Hybrids Using Various Link Reactions
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To develop novel antiviral agents, some novel conjugates between ferulic acid and eugenol or isoeugenol were designed and synthesized by the link reaction. The antiviral activities of compounds were evaluated using the half leaf dead spot method. Bioassay results showed acceptable antiviral activities of some conjugates against the tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Compounds A9, A10, E1, and E4 showed remarkable curative, protective, and inactivating effects on TMV and CMV at 500 μg mL-1. Notably, these compounds exhibited excellent protective effects on TMV and CMV. The EC50 values of compounds A9, A10, E1, and E4 against TMV were 180.5, 169.5, 211.4, and 135.5 μg mL-1, respectively, and those against CMV were 210.5, 239.1, 218.4, and 178.6 μg mL-1, respectively, which were superior to those of ferulic acid (471.5 and 489.2 μg mL-1), eugenol (456.3 and 463.2 μg mL-1), isoeugenol (478.4 and 487.5 μg mL-1), and ningnanmycin (246.5 and 286.6 μg mL-1). Then, the antiviral mechanisms of compound E4 were investigated by determining defensive enzyme activities and multi-omics analysis. The results indicated that compound E4 resisted the virus infection by enhancing defensive responses via inducing the accumulation of secondary metabolites from the phenylpropanoid biosynthesis pathway in tobacco.
- Gan, Xiuhai,Wang, Zhengxing,Hu, Deyu
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p. 13724 - 13733
(2021/11/23)
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- Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones
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We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.
- Au, Chi-Ming,Ling, Cho-Hon,Sun, Wenlong,Yu, Wing-Yiu
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supporting information
p. 3310 - 3314
(2021/05/29)
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- First total synthesis of mariamide A
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Mariamide A, a lignanamide isolated from the seeds of Silybum marianum, has demonstrated potential utility as an antioxidant and antidiabetic agent and possesses an 8-O-4′ neolignan skeleton. Herein, a first total synthesis of mariamide A is presented that proceeds in nine steps using vanillin as the starting material. The key steps for the preparation of mariamide A involve an I2-catalyzed bromomethoxylation of an alkene group, a nucleophilic substitution followed by a sequential elimination and a monoacylation reaction.
- Xia, Yamu,Chen, Chenglong,Li, Mengying,Zhou, Weizeng,Sun, Shuyu,Chu, Shanpeng,Wang, Hui
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p. 114 - 120
(2019/12/12)
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- Br?nsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol
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An efficient conversion of biorenewable ferulic acid into bio-catechol has been developed. The transformation comprises two consecutive defunctionalizations of the substrate, that is, C?O (demethylation) and C?C (de-2-carboxyvinylation) bond cleavage, occurring in one step. The process only requires heating of ferulic acid with HCl (or H2SO4) as catalyst in pressurized hot water (250 °C, 50 bar N2). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.
- Bal, Mathias,Bomon, Jeroen,Liao, Yuhe,Maes, Bert U. W.,Sels, Bert F.,Sergeyev, Sergey,Van Den Broeck, Elias,Van Speybroeck, Veronique
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supporting information
p. 3063 - 3068
(2020/02/05)
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- METHOD FOR PRODUCING CINNAMIC ACID ESTER COMPOUND
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A method for producing a cinnamic acid ester derivative includes reacting a cinnamic acid derivative compound represented by the formula (1), wherein the symbols are as defined in the description, with an alcohol compound represented by the formula: R6OH, wherein the symbol is as defined in the description, in the presence of a strong acid resin catalyst without using a solvent. As the cinnamic acid derivative compound, cinnamic acid, ferulic acid, and caffeic acid are preferred, and as the alcohol compound, methanol, ethanol, propanol, butanol, pentanol, hexanol, ethylene glycol, glycerol, phenethyl alcohol, and a monosaccharide are preferred.
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Paragraph 0066-0067; 0068; 0075
(2020/05/06)
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- Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents
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Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.
- Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
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- Study on the formation of antihypertensive twin drugs by caffeic acid and ferulic acid with telmisartan
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Purpose: This study aimed to synthesize twin drugs from cinnamic acid compounds, caffeic acid (CFA) and ferulic acid (FLA), which can antagonize endothelin-1 (ET-1) with telmisartan through ester bonds. Moreover, the antihypertensive effect of telmisartan and its influence on blood pressure variability (BPV) were enhanced, and the bioavailability of caffeic acid and ferulic acid was improved. Methods: Six twin drugs, which were the target compounds, were synthesized. Hypertensive rats (SHR) and conscious sinoaortic-denervated (SAD) rats were spontaneously used as models for pharmacodynamic research to study the antihypertensive efficacy of these twin drugs. Wistar rats were employed as pharmacokinetic research models to investigate the pharmacokinetics of the target compounds via intragastric administration. Cellular pharmacodynamic research was also conducted on the antagonistic action on Ang II-AT1, ETA and ETB receptor. Results: Compound 1a was determined as the best antihypertensive twin drug and thus was further studied for its effect on BPV. Compared with that of telmisartan, the antihypertensive effect of compound 1a was improved (p50 of Lps-2 was still two orders of magnitude higher than that of the positive drug telmisartan. Hence, the twin drugs worked by metabolizing and regenerating telmisartan and caffeic acid or ferulic acid in the body. Conclusion: The synthesized twin drugs improved telmisartan’s antihypertensive effects, significantly decreased BPV in SAD rats and increased the bioavailability of caffeic acid and ferulic acid. This study serves as a basis for the development of new angiotensin receptor blocker (ARB) in the future and a reference for the development of new drugs to antagonize ET-1.
- Li, Pengshou,Li, Ziyong,Ma, Qixiang,Peng, Yingying,Zhang, Xiaohua
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p. 977 - 992
(2020/03/13)
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- Grafting Nature-Inspired and Bio-Based Phenolic Esters onto Cellulose Nanocrystals Gives Biomaterials with Photostable Anti-UV Properties
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New nature-inspired and plant-derived p-hydroxycinnamate esters and p-hydroxycinnamate diesters provide excellent protection against UV radiation when incorporated into a matrix. Herein, an efficient and sustainable pathway is reported to graft these phenolic compounds onto cellulose nanocrystals (CNCs) via click-type copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction. The successful grafting of the phenolic esters on CNC surface was evidenced by a range of chemical analyses, and the degrees of substitution (DS) of the CNC were found to depend on the structure of the phenolic ester grafted. Moreover, aqueous suspensions of the phenolic ester-grafted CNCs not only strongly absorb in both the UVA and UVB regions, but they also exhibit average to very high photostability. Their wide spectrum UV-absorbing properties and their stability upon exposure to UV are highly influenced by the structure of the phenolic ester, particularly by the extra ester group in p-hydroxycinnamate diesters. These findings demonstrate that cellulose nanocrystals decorated with such plant-derived and nature-inspired phenolic esters are promising sustainable nanomaterials for anti-UV applications.
- Allais, Florent,Browne, Christine,Garnier, Gil,Joram Mendoza, David,Mouterde, Louis M. M.,Simon, George P.,Singh Raghuwanshi, Vikram
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- Design, Synthesis, and Biological Evaluation of Novel Multifunctional Rolipram-Tranilast Hybrids As Potential Treatment for Traumatic Brain Injury
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Traumatic brain injury (TBI) is a prevalent public healthcare concern frequently instigated by mechanical shock, traffic, or violence incidents, leading to permanent nerve damage, and there is no ideal treatment for it yet. In this study, a series of Rolipram-Tranilast hybrids were designed and synthesized. The neuroprotective activities of the Rolipram-Tranilast hybrids were evaluated both in vitro and in vivo. Compound 5 has been identified as the strongest neuroprotective molecule among the series with robust anti-oxidant and anti-inflammatory potentials. Compound 5 significantly increased the heme oxygenase-1 (HO-1) levels and the phosphorylated cAMP response elements binding protein (p-CREB) while it down-regulated phosphodiesterase-4 B (PDE4B) expression in vitro. Furthermore, compound 5 remarkably attenuated TBI and had a good safety profile in mice. Taken together, our findings suggested that compound 5 could serve as a novel promising lead compound in the treatment of TBI and other central nervous system (CNS) diseases associated with PDE4B and oxidative stress.
- Chen, Chen,Deng, Xiaobing,Han, Yifan,He, Xixin,Liang, Jinhao,Lu, Junfeng,Maddili, Swetha K.,Mak, Marvin Sh,Pi, Rongbiao,Tsim, Karl W. K.,Zhu, Zeyu
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p. 2348 - 2360
(2020/09/02)
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- O -Hydroxycinnamate for sequential photouncaging of two different functional groups and its application in releasing cosmeceuticals
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We demonstrated a new approach for the sequential photouncaging of two different functional groups from o-hydroxycinnamate. The second caged molecule initially remains in the locked state and is released only after attaining its unlocked state upon in situ generation of the second phototrigger, i.e., coumarin, thereby leading to the sequential release of alcohol and carboxylic acid. We have utilised the above strategy for the controlled release of cosmeceutical agents.
- Paul, Amrita,Bera, Manoranjan,Gupta, Prakhar,Singh, N. D. Pradeep
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p. 7689 - 7693
(2019/08/30)
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- One- and two-photon responsive sulfur dioxide (SO2) donors: a combinatorial drug delivery for improved antibiotic therapy
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One- and two-photon activated sulfur dioxide donors based on a 4,5-dimethoxy-2-nitrobenzyl phototrigger have been developed. The designed donors have the ability to release not only SO2 but also a hydroxy-compound in a simultaneous manner. Furthermore, we demonstrated their application in combinatorial therapy by the dual release of SO2 and an active drug, i.e. ferulic acid ethyl ester (FAEE) with self-monitoring ability. Next, we investigated the in vitro cellular uptake and the capability of SO2 generation from the donors using a well-known coumarin-hemicyanine fluorescent probe. Finally, we evaluated the antibacterial activity of the designed donors (5a, 5b and 6) by broth dilution and agar well diffusion methods on E. cloacae cells (MTCC 509). The results show that the donor 5a exhibits enhanced antibacterial efficacy compared to 5b and 6, due to the synergetic effect of dually released SO2 and FAEE.
- Venkatesh, Yarra,Kiran, Kumari Shanti,Shah, Sk. Sheriff,Chaudhuri, Amrita,Dey, Satyahari,Singh, N. D. Pradeep
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supporting information
p. 2640 - 2645
(2019/03/12)
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- Synthesis of phenolic components of Grains of Paradise
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Two vanilloids, (5E)-8-(4-hydroxy-3-methoxyphenyl)oct-5-en-4-one (1) and 4-[3-hydroxydecyl]-2-methoxyphenol (2), isolated from the dried seeds of Grains of Paradise (Aframomum melegueta), were synthesized; the latter compound was made as the S-enantiomer and the material derived from the seeds was found to be a 1:1.7 mixture of the R and S isomers. The synthetic route used should allow the preparation of analogs having extended alkyl chains and consequently different lipophilicity, and 3, a homolog of 2, was also prepared.
- Hattori, Hiroyuki,Mitsunaga,Clive, Derrick L.J.
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supporting information
p. 1989 - 1991
(2019/07/03)
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- Structure-based design and synthesis of new 4-methylcoumarin-based lignans as pro-inflammatory cytokines (TNF-α, IL-6 and IL-1β)inhibitors
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Suppression of pro-inflammatory cytokines (TNF-α, IL-1β and IL-6)along with nitric oxide reduction in RAW 264.7 cells by 7,8-dihydroxy-4-methylcoumarin, ethyl p-coumarate, ethyl caffeate and ethyl ferulate drove us to search structural-analogues of the aforementioned compounds through structure-based drug design. Docking studies revealed that substituted cinnamic acids and their ethyl esters (2-7c)showed higher GoldScore-fitness (GSF)and non-bonding interactions with target proteins than 7,8-dihydroxy-4-methylcoumarin (1a)and 7,8-dihydroxy-5-methylcoumarin (1b). With this background, the methylcoumarins (1a and 1b)and the cinnamic acid derivatives (2-7c)were fused in different permutations and combinations to generate sixty novel fused-cyclic coumarinolignans (FCLs)(8–13k). Docking studies on 8–13k indicated that several FCLs possess higher GSF, interesting active site interactions and distinctive π-π interactions compared to the standards (cleomiscosin A, diclofenac Na and prednisolone). Based on these findings, four novel FCLs (9d, 10d, 11d and 11e)were synthesized and tested for inhibition effect on TNF-α, IL-1β and IL-6 expressions in LPS and oxalate crystal-induced in-vitro models. Compound 10d exhibited significant effect (P 50 value of 8.5 μM against TNF-α. Compound 11e possessed IC50 values of 13.29 μM and 17.94 μM against IL-6 and IL-1β, respectively. Study on SAR corroborated the requirement of C-4-methyl substituent in the coumarin moiety, dihydroxyl groups in the phenyl ring, and esterification of lignans for potent activity. Additionally, the reported excellent anti-inflammatory activity of cleomiscosin-A-glucoside was corroborated by from the higher GSF and better hydrophobic interactions than cleomsicosin A in the docking study. As an outcome, some novel and potentially active FCLs acting through NFκB and caspase 1 signaling pathways have been discovered as multiple cytokine inhibitors.
- Santhosh Kumar,Sajeli Begum, Ahil,Hira, Kirti,Niazi, Sarfaraj,Prashantha Kumar,Araya, Hiroshi,Fujimoto, Yoshinori
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- Compound for treating or preventing hepatopathy (by machine translation)
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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 0122-0124
(2019/10/01)
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- Enantioselective total synthesis of ligraminol d and ligraminol e
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As a part of our ongoing research on the synthesis of bioactive constituents or molecules by using an organocatalytic approach, enantioselective total syntheses of ligraminol D and ligraminol E were achieved starting from a commercially available nonchiral aldehyde. Key steps in this synthesis were an asymmetric α-aminoxylation of an aldehyde and a Mitsunobu reaction.
- Kumbhar, D. D.,Mane, Baliram B.,Waghmode, Suresh B.
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supporting information
p. 2285 - 2289
(2019/12/11)
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- Modular synthesis and biological investigation of 5-hydroxymethyl dibenzyl butyrolactones and related lignans
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Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway.
- Davidson, Samuel J.,Pilkington, Lisa I.,Dempsey-Hibbert, Nina C.,El-Mohtadi, Mohamed,Tang, Shiying,Wainwright, Thomas,Whitehead, Kathryn A.,Barker, David
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- First total synthesis of quiquesetinerviusin A
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The first total synthesis of the dihydrobenzofuran neolignan quiquesetinerviusin A and its related structure have been described. Phenolic coupling is the key step to constructing the dihydrobenzofuran skeleton with vanillin as the raw material. The hydroxyl group was protected with dihydropyran (DHP) and the ester group was reduced with diisobutylaluminium hydride (DIBAL-H) in order to obtain the crucial intermediate diol, which was then condensed with an acid ligand to give the desired compounds following removal of the protecting groups.
- Xia, Yamu,Mo, Zhen,Sun, Lin,Zou, Lijia,Zhang, Wen,Zhang, Jiahong,Wang, Lihong
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p. 296 - 300
(2017/06/19)
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- Novel trans-Ferulic Acid Derivatives Containing a Chalcone Moiety as Potential Activator for Plant Resistance Induction
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A series of novel trans-ferulic acid derivatives containing a chalcone moiety were designed and synthesized to induce plant resistance. Antiviral activities of the compounds were evaluated. Bioassay results demonstrated that compounds F3, F6, F17, and F27 showed remarkable curative, protective, and inactivating activities against tobacco mosaic virus (TMV). With a 50% effective concentration (EC50) value of 98.78 μg mL-1, compound F27 exhibited the best protective activity compared with trans-ferulic acid (328.6 μg mL-1), dufulin (385.6 μg mL-1), and ningnanmycin (241.3 μg mL-1). This protective ability was associated with potentiation of defense-related enzyme activity and activation of photosynthesis of tobacco at an early stage. This notion was confirmed by up-regulated expression of stress responses and photosynthesis regulating proteins. This work revealed that F27 can induce resistance and enhance plant tolerance to TMV infection. Hence, F27 can be considered as a novel activator for inducing plant resistance.
- Gan, Xiuhai,Hu, Deyu,Wang, Yanjiao,Yu, Lu,Song, Baoan
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p. 4367 - 4377
(2017/06/13)
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- Efficient synthesis of functionalized olefins by Wittig reaction using Amberlite resin as a mild base
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A convenient procedure for the synthesis of olefins by the reaction of stabilized, semistabilized, and nonstabilized phosphorous ylides with various aldehydes or ketone using Amberlite resin as a mild base is described. Our developed method offers facile and racemization-free synthesis of α,β-unsaturated amino esters and chiral allylic amine. The developed methodology offers mild reaction conditions, high efficiency, and facile isolation of the final products, a practical alternative to known procedures.
- Valkute, Tushar R.,Aratikatla, Eswar K.,Bhattacharya, Asish K.
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p. 581 - 589
(2017/03/15)
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- Novel ferulic amide derivatives with tertiary amine side chain as acetylcholinesterase and butyrylcholinesterase inhibitors: The influence of carbon spacer length, alkylamine and aromatic group
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Based on our recent investigations on chalcone derivatives as AChE inhibitors, a series of ferulic acid (FA) tertiary amine derivatives similar to chalcone compounds were designed and synthesized. The results of bioactivity evaluation revealed that most of new synthesized compounds had comparable or more potent AChE inhibitory activity than the control drug Rivastigmine. The alteration of carbon chain linking tertiary amine groups and ferulic acid scaffold markedly influenced the inhibition activity against AChE. Among them the inhibitory activity of compound 6d (IC50: 0.71 ± 0.09 μmol/L) and 6e (IC50: 1.11 ± 0.17 μmol/L) was equal to 15-fold and 9-fold than that of Rivastigmine against AChE (IC50: 10.54 ± 0.86 μmol/L), respectively. Moreover, compound 6d shows the highest selectivity for AChE over butyrylcholinesterase(BuChE) (ratio: 18.3). The kinetic study suggested that compound 6d revealed a mixed-type inhibition against AChE. The result of molecular docking showed that compound 6d combines to AChE with three amino acid sites(Trp84, Tyr334 and Trp279), while combines to BuChE with two amino acid sites (Tyr67 and Gly66) in enzyme domains, respectively. Compound 6d might act as a potential agent for the treatment of Alzheimer's diseases (AD).
- Liu, Haoran,Liu, Linbo,Gao, Xiaohui,Liu, Yingzi,Xu, Wanjun,He, Wei,Jiang, Hong,Tang, Jingjing,Fan, Haoqun,Xia, Xinhua
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p. 810 - 822
(2016/12/18)
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- Exploration of phenylpropanoic acids as agonists of the free fatty acid receptor 4 (FFA4): Identification of an orally efficacious FFA4 agonist
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The long chain free fatty acid receptor 4 (FFA4/GPR120) has recently been recognized as lipid sensor playing important roles in nutrient sensing and inflammation and thus holds potential as a therapeutic target for type 2 diabetes and metabolic syndrome. To explore the effects of stimulating this receptor in animal models of metabolic disease, we initiated work to identify agonists with appropriate pharmacokinetic properties to support progression into in vivo studies. Extensive SAR studies of a series of phenylpropanoic acids led to the identification of compound 29, a FFA4 agonist which lowers plasma glucose in two preclinical models of type 2 diabetes.
- Sparks, Steven M.,Aquino, Christopher,Banker, Pierette,Collins, Jon L.,Cowan, David,Diaz, Caroline,Dock, Steven T.,Hertzog, Donald L.,Liang, Xi,Swiger, Erin D.,Yuen, Josephine,Chen, Grace,Jayawickreme, Channa,Moncol, David,Nystrom, Christopher,Rash, Vincent,Rimele, Thomas,Roller, Shane,Ross, Sean
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p. 1278 - 1283
(2017/06/19)
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- Bioactivity and structure-activity relationship of cinnamic acid esters and their derivatives as potential antifungal agents for plant protection
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A series of cinnamic acid esters and their derivatives were synthesized and evaluated for antifungal activities in vitro against four plant pathogenic fungi by using the mycelium growth rate method. Structure-activity relationship was derived also. Almost all of the compounds showed some inhibition activity on each of the fungi at 0.5 mM. Eight compounds showed the higher average activity with average EC50 values of 17.4-28.6 μg/mL for the fungi than kresoxim-methyl, a commercial fungicide standard, and ten compounds were much more active than commercial fungicide standards carbendazim against P. grisea or kresoxim-methyl against both P. grisea and Valsa Mali. Compounds C1 and C2 showed the higher activity with average EC50 values of 17.4 and 18.5 μg/mL and great potential for development of new plant antifungal agents. The structure-activity relationship analysis showed that both the substitution pattern of the phenyl ring and the alkyl group in the alcohol moiety significantly influences the activity. There exists complexly comprehensive effect between the substituents on the phenyl ring and the alkyl group in the alcohol moiety on the activity. Thus, cinnamic acid esters showed great potential the development of new antifungal agents for plant protection due to high activity, natural compounds or natural compound framework, simple structure, easy preparation, low-cost and environmentally friendly.
- Zhou, Kun,Chen, Dongdong,Li, Bin,Zhang, Bingyu,Miao, Fang,Zhou, Le
-
-
- Anti selective glycolate aldol reactions of (: S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one: application towards the asymmetric synthesis of 8-4′-oxyneolignans
-
The anti selective glycolate aldol reactions of (S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one auxiliary have been standardized with high yields and excellent diastereoselectivities on various substituted aryl, allyl and alkyl aldehydes. The optimized reaction conditions were employed for the stereoselective synthesis of oxyneolignans.
- Gangar, Mukesh,Ittuveetil, Avinash,Goyal, Sandeep,Pal, Anang,Harikrishnan,Nair, Vipin A.
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p. 102116 - 102126
(2016/11/09)
-
- COMPOUNDS AND METHODS FOR THE TREATMENT OF MICROBIAL INFECTION(S)
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The present invention relates to compounds useful in methods of treating at least one microbial infection, such methods and uses of said compounds, pharmaceutical formulations comprising said compounds, and/or synthetic processes. The compounds have the general formula (I) wherein R1 is H, N02, Br, I, NHC2H4OH, NHC(=NH)NH2; NH2; R2 is H, CH(CH3)2) S02-4-C6H4F or SO2-4-C6H4-OCH3; R3 is H or NO2; and R4 is CHO or CH=CHC(0)OR5, wherein R5 is CH2CH2CH2CH3, or more preferably H, CH3, CH2CH3 or CH2CH2CH3.
- -
-
Page/Page column 30; 31; 32
(2016/02/29)
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- Compositions for the prevention or treatment of neurodegenerative disease containing alkoxyphenylpropenone derivatives or pharmaceutically acceptable salts thereof as an active ingredient
-
PURPOSE: An alkoxyphenylpropenone derivative is provided to efficiently use as a pharmaceutical composition for preventing or treating a degenerative brain disease; or pharmaceutical composition for protecting a brain cell by having an excellent protecting effect of the brain cell. CONSTITUTION: An alkoxyphenylpropenone derivative or a pharmaceutically acceptable salt thereof is indicated as below chemical formula 1; and R^1 is hydrogen or O-R^4; R^2 is hydrogen or O-R^5; R^3 is hydroxy, O-R^6 or -NR^7R^8; R^4, R^5 and R^6 are C_1-C_12 straight chain or a side chain alkyl, C_2-C_12 straight chain or a side chain alkenyl, and unsubstituted or C_5-C_6 aryl which is substituted as C_1-C_4 straight chain, or a side chain alkoxy, C_5-C_6 aryl C_1-C_4 alkyl; R^7 is hydrogen, C_1-C_4 straight chain, or a side chain alkyl; R^8 is hydrogen, the C_1-C_4 straight chain or the side chain alkyl, and the C5-C6 aryl which is unsubstituted or hydroxy-substituted, the C1-C4 alkyl or the C5-C6.
- -
-
Paragraph 0350-0354
(2021/05/28)
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- Structure property relationships of biobased: N -alkyl bisferulate epoxy resins
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In this work, a series of bio-based chemically recyclable epoxy resins were synthesized from n-alkyl bisferulate esters that do not activate human estrogen receptor alpha (ERα). Viscosities of corresponding glycidyl ether n-alkyl bisferulate resins, determined by steady shear rheology, range from 12-9.4 Pa s. Activation energies of flow range from 83-96 kJ mol-1 and are similar to the diglycidyl ether bisphenol A (DGEBA). Thermomechanical properties of diglycidyl ether n-alkyl bisferulate resins cured with isophorone diamine were governed by the length of α,ω-diols that link glycidyl ether ferulate units. That is, the glassy phase modulus and alpha transition temperatures range from 3400-2400 MPa (at 25 °C) and 40-53 °C (peak of E′′), respectively. Furthermore, the onset of thermal degradation (Td5%) varied from 331-300 °C. Chemical recycling of cured epoxy resins was performed by static immersion in 10 w/w sodium hydroxide aqueous solutions at 60 °C. Times required for complete conversion of cured resins to water-soluble degradation products was also α,ω-diol length dependent and varied from 5 to 65 h. Thus, diglycidyl ether of n-alkyl bisferulate resins provides a viable biobased alternative to BPA epoxy resins as well as the option of chemical degradability and recovery of fillers in composite applications.
- Maiorana, Anthony,Reano, Armando F.,Centore, Robert,Grimaldi, Marina,Balaguer, Patrick,Allais, Florent,Gross, Richard A.
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p. 4961 - 4973
(2016/10/25)
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- Mesomorphism dependence on molecular flexibility
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A novel ester homologous series of liquid crystals with a highly polar laterally substituted –OCH3 group is synthesized and studied with a view to understanding and establishing the effects of molecular structure involving lateral substitution on liquid crystal behavior. The novel series RO·C6H4·COO·C6H3·OCH3(ortho)CH=CH·COO·C2H5 consists of 12 homologs of which C7, C8, C10 are nematogenic and C12, C14, C16 homologs are smectogenic. The rest of the homologs are nonliquid crystals. The textures of nematic phase are threaded and the smectic phase is of the type A or C. Transition temperatures and the textures of mesophases were determined by an optical polarizing microscope equipped with a heating stage. Analytical and spectral data support the molecular structures. The N-I and Sm-I transition curves behave in normal manner without exhibition of an odd-even effect. Average thermal stability for smectic and nematic are 127.3°C and 129°C, respectively. The total mesophase length ranges from 17°C to 57°C and series is of a middle ordered melting type with transition temperatures varying between 82°C and 148°C. The liquid crystal properties of present novel series are compared with, structurally similar known homologous series.
- Travadi,Vadodaria,Ladva,Doshi
-
-
- Dimerization of ferulic acid and structure determination of phenylindane derivatives
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Ferulic acid dimers with phenylindane skeletons were obtained from ferulic acid 1 in an acidic ethanol solution. The reaction conditions used to prepare the dimers or the ester were examined in detail, and the stereochemistries of the dimers were determined. The structural features of the dimers and the diastereoselective formation mechanisms involved in forming the two types of dimers (the racemic diastereomer 8α, which was a major product, and the racemic diastereomer 8γ, which was a minor product) were characterized.
- Nomura, Eisaku,Kakimoto, Yasuhiro,Yamamoto, Tomoya,Noda, Takumi,Miyake, Yasuhito,Mori, Hajime
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p. 3567 - 3577
(2016/04/05)
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- Synthesis and anticancer activities of glycyrrhetinic acid derivatives
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A total of forty novel glycyrrhetinic acid (GA) derivatives were designed and synthesized. The cytotoxic activity of the novel compounds was tested against two human breast cancer cell lines (MCF-7, MDA-MB-231) in vitro by the MTT method. The evaluation results revealed that, in comparison with GA, compound 42 shows the most promising anticancer activity (IC50 1.88 ± 0.20 and 1.37 ± 0.18 μM for MCF-7 and MDA-MB-231, respectively) and merits further exploration as a new anticancer agent.
- Li, Yang,Feng, Ling,Song, Zhi-Fang,Li, Hai-Bei,Huai, Qi-Yong
-
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- 4-cycloaminoalkoxy-3-methoxycinnamates, and preparation method and application thereof
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The invention relates to 4-cycloaminoalkoxy-3-methoxycinnamates, and a preparation method and application thereof. The preparation method is characterized by comprising the following steps: 1. preparing ferulic acid acyl chlorides from the initial raw material ferulic acid under the conditions of a first solvent and an acylating agent; 2. carrying out reaction on the ferulic acid acyl chlorides and alcohol or phenol in a second solvent under the first alkaline condition to obtain corresponding ferulates; and 3. carrying out reaction on the ferulates and 1-substituted-4-chloroalkylpiperidine in a third solvent under the second alkaline condition to generate the 4-cycloaminoalkoxy-3-methoxycinnamates. The compounds have favorable effects on treating and/or preventing neurodegeneration related diseases, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV (human immunodeficiency virus) related dementia, multilocular sclerosis, progressive lateral spinal sclerosis, neuropathic pains, glaucoma and the like.
- -
-
Paragraph 0020; 0050; 0059; 0060; 0061
(2016/10/09)
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- 4-amine alkoxy-3-methoxyl cinnamic acid ester compound, preparation method and application of compound
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The invention relates to a 4-amine alkoxy-3-methoxyl cinnamic acid ester compound, a preparation method and application of the compound.The preparation method of the compound comprises the following steps that 1, a ferulic acid acyl chloride compound is obtained by taking ferulic acid as a staring material under the condition of in first solvent under the condition of an acylating agent; 2, the ferulic acid acyl chloride compound reacts with alcohol or phenol in second solvent under a first alkaline condition to obtain a corresponding cinnamic acid ester compound; 3, the cinnamic acid ester compound reacts with a dihalogen alkyl compound in third solvent under a second alkaline condition to generate a corresponding halogen compound; 4, the halogen compound reacts with an organic amine compound in fourth solvent to obtain the 4-amine alkoxy-3-methoxyl cinnamic acid ester compound.Accordingly, the compound has the significant inhibiting effect on acetylcholinesterase, the inhibiting activity on acetylcholinesterase is greatly higher than the inhibiting activity on butyrylcholine esterase, and the certain selective inhibiting effect on acetylcholinesterase is achieved.
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-
Paragraph 0060; 0070
(2016/10/09)
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- Discovery of neurotrophic agents based on hydroxycinnamic acid scaffold
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The number of people affected by neurodegenerative disorders such as Alzheimer's disease and Parkinson's disease is rapidly increasing owing to the global increase in life expectancy. Small molecules with neurotrophic effects have great potential for management of these neurological disorders. In this study, different (C1–C12) alkyl ester derivatives of hydroxycinnamic acids (HCAs) were synthesized (a total of 30 compounds). The neurotrophic capacity of the test compounds was examined by measuring promotion of survival in serum-deprived conditions and enhancement of nerve growth factor (NGF)-induced neurite outgrowth in PC12 neuronal cells. p-Coumaric, ferulic, and sinapic acids and their esters did not alter cell survival, while caffeic acid and all its alkyl esters, especially decyl and dodecyl caffeate, significantly promoted neuronal survival at 25?μm. Methyl, ethyl, propyl, and butyl caffeate esters also significantly enhanced NGF-induced neurite outgrowth, among which the most effective ones were propyl and butyl esters, which at 5?μm led to 25- and 22-fold increases in the number of neurites, respectively. The findings of the docking study suggested phosphatidylinositol 3-kinase (PI3K) as the potential molecular target. In conclusion, our findings demonstrate that alkyl esters of caffeic acid can be useful as scaffolds for the discovery of therapeutic agents for neurodegenerative diseases.
- Hosseini, Razieh,Moosavi, Fatemeh,Rajaian, Hamid,Silva, Tiago,Magalh?es e Silva, Diogo,Soares, Pedro,Saso, Luciano,Edraki, Najmeh,Miri, Ramin,Borges, Fernanda,Firuzi, Omidreza
-
p. 926 - 937
(2016/11/11)
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- First stereo selective synthesis of 5-O-feruloyl-2-deoxy-D-ribono-γ-lactone
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The first stereo selective synthesis of 5-O-feruloyl-2-deoxy-D-ribono-γ-lactone was achieved by coupling reaction of substituted ferulic acid and hydroxy methyl ribono lactone and followed by deprotection of O-PMB. The spectroscopic data were compared with the reported values and a clear indication to the absolute stereochemistry of the natural 5-O-feruloyl-2-deoxy-D-ribono-γ-lactone.
- Ganesh, K. Ravi,Rao, K. Raghavendra,Pratap,Raghunadh,Kumar, S. Praveen,Basaveswara Rao,Murthy,Meruva, Suresh Babu
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supporting information
p. 4734 - 4736
(2016/09/28)
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- Novel multifunctional dopamine D2/D3receptors agonists with potential neuroprotection and anti-alpha synuclein protein aggregation properties
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Our ongoing drug development endeavor to design compounds for symptomatic and neuroprotective treatment of Parkinson's disease (PD) led us to carry out a structure activity relationship study based on dopamine agonists pramipexole and 5-OHDPAT. Our goal was to incorporate structural elements in these agonists in a way to preserve their agonist activity while producing inhibitory activity against aggregation of α-synuclein protein. In our design we appended various catechol and related phenol derivatives to the parent agonists via different linker lengths. Structural optimization led to development of several potent agonists among which (?)-8a, (?)-14 and (?)-20 exhibited potent neuroprotective properties in a cellular PD model involving neurotoxin 6-OHDA. The lead compounds (?)-8a and (?)-14 were able to modulate aggregation of α-synuclein protein efficiently. Finally, in an in vivo PD animal model, compound (?)-8a exhibited efficacious anti-parkinsonian effect.
- Luo, Dan,Sharma, Horrick,Yedlapudi, Deepthi,Antonio, Tamara,Reith, Maarten E.A.,Dutta, Aloke K.
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p. 5088 - 5102
(2016/10/22)
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- Ferulic acid ester derivative containing quinazoline, as well as preparation method and purpose of ferulic acid ester derivative
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The invention discloses a ferulic acid ester derivative containing quinazoline, as well as a preparation method and a purpose of the ferulic acid ester. A structural general formula (I) of the ferulic acid ester derivative containing the quinazoline is as follows: R1 is methyl, ethyl, n-propyl, isopropyl and normal-butyl; R2 is hydrogen, 6,7-dimethoxy and 6,7-bis-methoxyethoxy. The ferulic acid ester derivative containing the quinazoline can resist the cucumber mosaic virus, the tobacco mosaic virus, the southern rice black-streaked dwarf virus and the rice stripe virus.The structural general formula (I) is shown in the specification.
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-
Paragraph 0013; 0017
(2016/10/09)
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- Total synthesis of a lignanamide from Aptenia cordifolia
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(E,E)-N,N-Dityramin-4,4'-dihydroxy-3,5'-dimethoxy-ss,3'-bicinnamamide, a lignanamide isolated from Aptenia cordifolia, was synthesised from vanillin and tyramine. The key 8-5'-neolignan intermediate diacid was formed efficiently using oxidative coupling of the ferulic acid derivatives and the ring-opening reaction of a dihydrobenzofuran.
- Xia, Yamu,Li, Chenchen,Zhang, Huaizheng,Lin, Jiao,Chai, Chen
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p. 535 - 538
(2015/11/27)
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- ANTIMICROBIAL FERULIC ACID DERIVATIVES AND USES THEREOF
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Antimicrobial diferulates, compositions containing same, and uses of same for inhibiting growth of microorganisms. The antimicrobial diferulates can be used alone or in combination with other antimicrobial agents to inhibit growth of microorganisms such as fungi, oomycetes, and other microorganisms having a glucan-containing cell wall. The antimicrobial diferulates can be included in pharmaceutical compositions for treatment of animals or included in agricultural compositions for treatment of plants, crops, and soils.
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Paragraph 0104
(2015/11/27)
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- Design, synthesis, and in vitro antiplatelet aggregation activities of ferulic acid derivatives
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In order to discover new compounds with antiplatelet aggregation activities, some ferulic acid (FA) derivatives were designed and synthesized. The in vitro antiplatelet aggregation activities of these compounds were assessed by turbidimetric test. The results showed that the target compound 7f had potent antiplatelet aggregation activity with its IC50 27.6 μmol/L, and 7f can be regarded as a novel potent antiplatelet aggregation candidate.
- Zhang, Peng-Xuan,Lin, Hang,Qu, Cheng,Tang, Yu-Ping,Li, Nian-Guang,Kai, Jun,Shang, Guanxiong,Li, Baoquan,Zhang, Li,Yan, Hui,Liu, Pei,Duan, Jin-Ao
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- Ethyl cinnamate derivatives as promising high-efficient acaricides against Psoroptes cuniculi: Synthesis, bioactivity and structure-activity relationship
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This paper reported the synthesis, structure-activity relationship (SAR) and acaricidal activity in vitro against Psoroptes cuniculi, a mange mite, of 25 ethyl cinnamate derivatives. All target compounds were synthesized and elucidated by means of MS, 1H- and 13C-NMR analysis. The results showed that 24 out of 25 tested compounds at 1.0 mg/mL demonstrated acaricidal activity in varying degrees. Among them, 6, 15, 26, 27 and 30 showed significant activity with median lethal concentration values (LC50) of 89.3, 119.0, 39.2, 29.8 and 41.2 μg/mL, respectively, which were 2.1- to 8.3-fold the activity of ivermectin (LC50=247.4 μg/mL), a standard drug in the treatment of Psoroptes cuniculi. Compared with ivermectin, with a median lethal time value (LT50) of 8.9 h, 27 and 30 showed smaller LTM50 values of 7.9 and 1.3 h, respectively, whereas 6, 15 and 26 showed slightly larger LT50 values of 10.6, 11.0 and 10.4 h at 4.5 μmol/mL. SARs showed that the presence of o-NO2 or m-NO2 on the benzene ring significantly improved the activity, whereas the introduction of a hydroxy, methoxy, acetoxy, methylenedioxy, bromo or chloro group reduced the activity. (E)-Cinnamates were more effective than their (Z)-isomer. Nevertheless, the carbon-carbon double bond in the acrylic ester moiety was proven not to be essential to improve the activity of cinnamic acid esters. Thus, the results strongly indicate that cinnamate derivatives, especially their dihydro derivatives, should be promising candidates or lead compounds for the development of novel acaricides for the effective control of animal or human acariasis.
- Zhang, Bingyu,Lv, Chao,Li, Weibo,Cui, Zhiming,Chen, Dongdong,Cao, Fangjun,Miao, Fang,Zhou, Le
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p. 255 - 262
(2015/04/22)
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- A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism
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Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.
- Sirasani, Gopal,Tong, Liuchuan,Balskus, Emily P.
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supporting information
p. 7785 - 7788
(2014/08/05)
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- Synthesis of neolignans as microtubule stabilisers
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Tubulin is a well established target for anticancer drug development. Lignans and neolignans were synthesized as tubulin interacting agents. Neolignans 10 and 19 exhibited significant anticancer activity against MCF-7 and MDAMB-231 human breast cancer cell lines. Both the compounds effectively induced stabilization of microtubule at 4 and 20 μM concentrations respectively. Neolignan 10 induced G2/M phase arrest in MCF-7 cells. Docking experiments raveled that 10 and 19 occupied the same binding pocket of paclitaxel with some difference in active site amino acids and good bioavailability of both the compounds. In in vivo acute oral toxicity 10 was well tolerated up to 300 mg/kg dose in Swiss-albino mice.
- Sathish Kumar,Singh, Aastha,Kumar, Amit,Singh, Jyotsna,Hasanain, Mohammad,Singh, Arjun,Masood, Nusrat,Yadav, Dharmendra K.,Konwar, Rituraj,Mitra, Kalyan,Sarkar, Jayanta,Luqman, Suaib,Pal, Anirban,Khan, Feroz,Chanda, Debabrata,Negi, Arvind S.
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p. 1342 - 1354
(2014/03/21)
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- NEUROPROTECTIVE AGENTS FOR TREATMENT OF NEURODEGENERATIVE DISEASES
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A compound having formula I is useful for treating a neurodegenerative disease: I, R1 is an C1-12 organyl group; is a C1-12 heterocyclic ring system containing 5 to 12 ring atoms and up to three heteroatoms individually selected from the group consisting of N, O, S, and Se; R2 are C1-12 organyl groups; R7, R8 are each independently, hydrogen (H), hydroxyl, oxo (i.e., carbonyl), C1-8 alkyl, C1-8 alkoxyl, C2-8 alkenyl, C2-10 alkynyl, C5-7 cycloalkyl, C5-7 cycloalkenyl, halo, C1-4 aldehyde, or -NR4q where R4 is H, C1-8 alkyl, C2-8 alkenyl, C4-8 cycloalkyl, C4-8 cycloalkenyl, or C6-10 aryl; o is 0, 1, 2, 3, or 4; A is a C6-12 aryl group, C5-12 heteroaryl group, or an optionally substituted 3-hydroxypyridin- 4(1H)-one; p is an integer from 1 to 6; and Zm is absent or a divalent linking moiety; and m is an integer representing the number of time Z is repeated.
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-
Paragraph 00088-00090; 000137
(2014/06/23)
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- The first stereoselective total synthesis of a new antitumour and anti-inflammatory neolignan, surinamensinol A
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The stereoselective total synthesis of an antitumour and anti-inflammatory 8-O-4′-neolignan, surinamensinol A has been accomplished starting from two aldehydes, 3,4,5-trimethoxy benzaldehyde and vanillin. The key steps involve an asymmetric reduction using a chiral oxazaborolidine complex, a Sharpless asymmetric dihydroxyllation and a Mitsunobu reaction. This is the first report of the total synthesis of surinamensinol A.
- Reddy, Parigi Raghavendar,Das, Biswanath
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p. 7432 - 7434
(2014/02/14)
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