- Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst
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We have developed an efficient photocatalytic synthesis of coumarin derivativesviaa tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives dimerized lignan-type products.
- Zhao, Bin,Xu, Bo
-
supporting information
p. 568 - 573
(2021/02/06)
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- TRPV3 inhibitor and preparation method thereof
-
The invention discloses a TRPV3 inhibitor. The TRPV3 inhibitor is formed by sequentially connecting an R1 group, an R group and an R2 group, and the molecular structural general formula of the TRPV3 inhibitor is shown as a formula 1, wherein the structural formula of the R1 group is represented by a formula 2, R3 is selected from any one of -H, -OAc, -OH, a halogen group, -F3CO or a group containing a benzenesulfonyloxy group, and R4 is selected from any one of -H, -OAc or -OH; R1 and R2 are selected from alkyl or formula 3, R5 is selected from C or N, R6 is selected from any one of hydrogen, alkyl, halogen group or trifluoromethyl, R7 is selected from any one of hydrogen, halogen group, cyano group, nitro group or trifluoromethoxy group, and R8 is selected from hydrogen or halogen group. The invention also discloses a preparation method and application of the TRPV3 inhibitor. The TRPV3 inhibitor disclosed by the invention can specifically inhibit a TRPV3 ion channel and has huge scientific research and clinical values.
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Paragraph 0104; 0109-0110; 0116-0117; 0123-0124; 0131-0132
(2021/04/10)
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- Oat polyphenol avenanthramide-2c confers protection from oxidative stress by regulating the Nrf2-ARE signaling pathway in PC12 cells
-
Accumulating evidence has demonstrated that cellular antioxidant systems play essential roles in retarding oxidative stress-related diseases, such as Parkinson's disease. Because nuclear factor erythroid 2-related factor 2 (Nrf2) is a chief regulator of c
- Hou, Yanan,Peng, Shoujiao,Song, Zilong,Bai, Feifei,Li, Xinming,Fang, Jianguo
-
-
- Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
-
Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.
- Gao, Ang,Jiang, Run-Chuang,Liu, Chuang-Chuang,Liu, Qi-Le,Lu, Xiao-Yu,Xia, Ze-Jie
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supporting information
p. 8829 - 8842
(2021/06/30)
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- A polymer with mechanochemically active hidden length
-
Incorporating hidden length into polymer chains can improve their mechanical properties, because release of the hidden length under mechanical loads enables localized strain relief without chain fracture. To date, the design of hidden length has focused p
- Tian, Yancong,Cao, Xiaodong,Li, Xun,Zhang, Huan,Sun, Cai-Li,Xu, Yuanze,Weng, Wengui,Zhang, Wenke,Boulatov, Roman
-
supporting information
p. 18687 - 18697
(2020/11/17)
-
- Toward a Scalable Synthesis and Process for EMA401, Part II: Development and Scale-Up of a Pyridine- A nd Piperidine-Free Knoevenagel-Doebner Condensation
-
During route scouting for EMA401 (1), an angiotensin II type 2 antagonist, we identified the synthesis of key amino acid intermediate 2 via its cinnamic acid derivative 3 as a streamlined option. In general, cinnamic acids can be synthesized from the corresponding aldehydes by a Knoevenagel-Doebner condensation in pyridine with piperidine as an organocatalyst. We aimed to replace both of these reagents and found novel conditions involving toluene as the solvent and morpholine as the organocatalyst. Scale-up of the process allowed the production of 25 kg of cinnamic acid 3 that was of the quality required for process development of the subsequent phenylalanine ammonia lyase-catalyzed step. The modified conditions were found to be widely applicable to alternative aldehydes and thus are of relevance to practitioners of chemical scale-up.
- Hardegger, Leo A.,Humair, Roger,Sidler, Eric
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p. 1756 - 1762
(2020/10/26)
-
- Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids
-
A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed. Both β-monosubstituted and β-disubstituted unsaturated carboxylic acids, as well as conjugated diene unsaturated carboxylic acids are suitable reaction substrates. Substituted homoallylic alcohols were obtained in moderate to good yields. The product was obtained as a mixture of diastereomers favoring the anti diastereomer of the cyclic epoxides. This work provides a method for the modification of complex organic molecules containing α,β-unsaturated carboxylic acids.
- Lu, Xiao-Yu,Li, Jin-Song,Wang, Shi-Qun,Zhu, Yu-Jing,Li, Yue-Ming,Yan, Lu-Yu,Li, Jia-Mei,Wang, Jin-Yu,Zhou, Hai-Pin,Ge, Xiu-Tao
-
supporting information
p. 11123 - 11126
(2019/09/20)
-
- Antifungal Polyamides of Hydroxycinnamic Acids from Sunflower Bee Pollen
-
The aim of the bioassay-guided fractionation was the selection of the most potent group of compounds responsible for the protection of sunflower bee pollen grains. Synthesis of prospective antifungal polyamides of hydroxycinnamic acids was based on previo
- Kyselka, Jan,Bleha, Roman,Dragoun, Miroslav,Bialasová, Kristyna,Horá?ková, ?árka,Sch?tz, Martin,Sluková, Marcela,Filip, Vladimír,Synytsya, Andriy
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p. 11018 - 11026
(2018/10/24)
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- Novel piperazine amides of cinnamic acid derivatives as tyrosinase inhibitors
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Background: A series of novel cinnamic acid piperazine amide derivatives has been designed and synthesized, and their biological activities were also evaluated as potential tyrosinase inhibitors. Methods: Compounds 9, 11 and 17 showed the most potent biological activity (IC50 = 66.5, 61.1 and 66 μM, respectively). In silico docking simulation was performed to position compound 11 into the Agaricus bisporus mushroom tyrosinase’s active site to determine the putative binding interactions. Results and Conclusion: The results indicated that compound 11 could serve as a promising lead compound for further development of potent tyrosinase inhibitors.
- Gür, Zehra Tu??e,?enol, Fatma Sezer,Shekfeh, Suhaib,Orhan, ?lkay Erdo?an,Bano?lu, Erden,?ali?kan, Burcu
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- Synthesis of a series of benzothiazole amide derivatives and their biological evaluation as potent hemostatic agents
-
A series of benzothiazole amide derivatives were synthesized through a facile and efficient method via a nucleophilic acyl substitution reaction between 2-aminobenzothiazole and various cinnamic acid compounds. The obtained products exhibited good thermal stabilities. All compounds were evaluated for their in vitro hemostatic activities using the commercially available standard drug etamsylate as a positive control. The results showed that compound Q2 had a significant partial coagulation activity, reduced capillary permeability at 5, 10 and 50 μmol L-1, activated thrombin activity, and a more potent platelet aggregation activity than the positive control group (etamsylate, up to 1283.9 times in the nanomole range). A molecular modeling study revealed that compound Q2 was a competitive thrombin activator. Therefore, Q2 may be a potential lead for further biological screening and for the generation of drug molecules. Moreover, the structure-activity relationship of the prepared compounds is also discussed herein.
- Nong, Wenqian,Zhao, Anran,Wei, Jinrui,Cheng, Hui,Luo, Xuan,Lin, Cuiwu
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p. 6231 - 6241
(2018/02/19)
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- Enantioselective Organocatalytic Intramolecular Aza-Diels–Alder Reaction
-
A highly efficient catalytic enantioselective intramolecular Povarov reaction was developed with primary anilines as 2-azadiene precursors. A wide variety of angularly fused azacycles were obtained without column chromatography in high to excellent yields and with excellent diastereo- and enantioselectivity (d.r.>99:1 and up to e.r. 99:1). Furthermore, the catalyst loading could be lowered to 1 mol %, and the obtained azacycles could be used as key intermediates for further transformations to generate additional molecular diversity.
- Jarrige, Lucie,Blanchard, Florent,Masson, Géraldine
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supporting information
p. 10573 - 10576
(2017/08/22)
-
- Long pepper amide analogs, preparation method and application thereof
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The invention relates to the pharmaceutical chemistry field, and concretely relates to a piplartine analogue (I) or (II), a preparation method therefor and pharmaceutical compositions containing the piplartine analogue (I) and (II). The pharmacodynamic experiments prove that piplartine analogue can be used for treating or preventing thromboembolism diseases. The structural formulas of the piplartine analogue (I) and (II) are shown in the specification.
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-
Paragraph 0109; 0110; 0111
(2017/08/25)
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- COMPOUND APPLICABLE TO PHOTOALIGNMENT METHOD AND ITS PHOTOSENSITIVE POLYMER
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PURPOSE: A photosensitive polymer prepared by polymerizing a compound which is proper for photoalignment is provided to prevent static electricity and to manufacture liquid crystal alignment film with high optical uniformity. CONSTITUTION: A compound which is proper to photoalignment is denoted by chemical formula 1. A photosensitive polymer is used by polymerizing the compound of chemical formula 1. A liquid crystal alignment film is manufactured using the photoalignment agent. A liquid crystal display device is manufactured using the photoalignment agent.
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Paragraph 0203-0205; 0208-0209
(2017/09/29)
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- Synthesis and biological evaluation of a new series of cinnamic acid amide derivatives as potent haemostatic agents containing a 2-aminothiazole substructure
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Ten new cinnamic acid derivatives containing a 2-aminothiazole substructure were designed and synthesized. This series of compounds exhibited good thermostabilities as demonstrated by thermogravimetric analysis. In coagulation assays (prothrombin time, activated partial thromboplastin time and thrombin time) in vitro, most compounds demonstrated excellent activities to promote blood coagulation. Among the studied series, compounds N1, N4, N5 and W5 exhibited a significant coagulation activity. Further studies indicated that compound N5 (IC50 = 1.87 μmol/L) displayed the most suitable efficacy of promoting platelet aggregation than the clinically used haemostatic drug etamsylate (IC50 = 46.22 μmol/L). Furthermore, the relationship between the functional groups of the compounds and the corresponding blood coagulant activity was explored in this study.
- Nong, Wenqian,Zhao, Anran,Wei, Jinrui,Lin, Xiao,Wang, Lisheng,Lin, Cuiwu
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supporting information
p. 4506 - 4511
(2017/09/12)
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- Easy Access to Quinolin-2(1 H)-ones via a One-Pot Tandem Oxa-Michael-Aldol Sequence
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An efficient strategy for the synthesis of a variety of quinolin-2(1 H)-one derivatives has been developed. The reaction proceeded from cinnamide derivatives via a tandem reaction in the presence of NaOH to afford the corresponding 2- quinolin-2(1 H)-one derivatives in good to excellent yields.
- Jarrige, Lucie,Merad, Jeremy,Zaied, Siwar,Blanchard, Florent,Masson, Géraldine
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supporting information
p. 1724 - 1728
(2017/10/06)
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- P-coumaroyl malate derivatives of the Pandanus amaryllifolius leaf and their isomerization
-
A novel p-coumaroyl dimethyl malate (1) was isolated from the Pandanus amaryllifolius leaf in addition to three known analogs of p-coumaroyl dimethyl malate (2-4), and their structures were elucidated by analysis of the spectroscopic data. The p-coumaroyl malate derivatives were isolated as a mixture of E and Z isomers. To determine the cause of isomerization, the p-coumaroyl malate isolated in this study was synthesized. We concluded that the Z isomer might be an artifact generated from the E isomer through purification steps.
- Suzuki, Ryuichiro,Kan, Shu,Sugita, Yoshiaki,Shirataki, Yoshiaki
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p. 1191 - 1194
(2018/05/23)
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- Synthesis of p-coumaroylquinic acids and analysis of their interconversion
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The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (?)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-O-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure.
- Gutiérrez Ortiz, Anggy Lusanna,Berti, Federico,Navarini, Luciano,Monteiro, Angelo,Resmini, Marina,Forzato, Cristina
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p. 419 - 427
(2017/03/23)
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- P-coumaroyl malate derivatives of the Pandanus amaryllifolius leaf and their isomerization
-
A novel p-coumaroyl dimethyl malate (1) was isolated from the Pandanus amaryllifolius leaf in addition to three known analogs of p-coumaroyl dimethyl malate (2-4), and their structures were elucidated by analysis of the spectroscopic data. The p-coumaroyl malate derivatives were isolated as a mixture of E and Z isomers. To determine the cause of isomerization, the p-coumaroyl malate isolated in this study was synthesized. We concluded that the Z isomer might be an artifact generated from the E isomer through purification steps.
- Suzuki, Ryuichiro,Kan, Shu,Sugita, Yoshiaki,Shirataki, Yoshiaki
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p. 1191 - 1194
(2017/12/26)
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- Design, synthesis, and biological evaluation of novel Tempol derivatives as effective antitumor agents
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Two series of novel Tempol derivatives T1–T6 based on the piperidine nitroxide Tempol and phenolic acids were designed and synthesized, and their biological evaluation is also described. The chemical structure was verified by HRMS, IR, and EPR analysis. The antitumor activity was tested against two tumor cell lines (A549 and Hela cells). Simultaneously, HK-2 cells were selected to investigate cytotoxicity and selectivity of synthetic compounds to the normal cells. The antioxidant property was also studied by DPPH radical scavenging assay and hydrogen peroxide-induced cell injury assay. The results demonstrated that most of the Tempol derivatives exhibited more active antioxidant activity than Tempol, and all synthesized Tempol derivatives exhibited more potent antitumor activity than Tempol. Among them, compound T6 displayed the highest antitumor activity (IC50?=?29.4?μg/mL for A549 cells; IC50?=?16.2?μg/mL for Hela cells). The results indicated that T6 exhibited efficient antitumor performance, having the potential of being excellent antitumor agents for cancer treatment.
- Sun, Xiao-Liang,Wang, Shi-Yu,Qi, Zhi-Min,Wan, Ning,Zhang, Bang-Le,He, Wei
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p. 7659 - 7673
(2016/09/20)
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- MELANIN GENERATION INHIBITOR AND WHITENING AGENT
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PROBLEM TO BE SOLVED: To provide a melanin generation inhibitor and a whitening agent that are excellent in whitening effect and also excellent in safety and temporal stability. SOLUTION: The invention provides a melanin generation inhibitor containing a compound represented by formula [1] as an active ingredient, a whitening agent, as well as a melanin generation inhibiting method and a whitening method by applying such agents to the skin. (R1, R2, R4, and R5 are each independently H, a hydroxyl group, an alkyl group of C1-4, or -O-C(=O)R6; R6 is an alkyl group of C1-4; R3 is H, an alkyl group of C1-4, or -C(=O)R7; and R7 is an alkyl group of C1-8.) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0077
(2017/04/20)
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- Design, Synthesis and Pharmacological Evaluation of Novel Piperlongumine derivatives as Potential Antiplatelet Aggregation Candidate
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A series of novel piperlongumine derivatives (4a-i, 6a-i) were designed and synthesized. The inhibitory activities of platelet aggregation induced by ADP and AA in vitro have been evaluated by bron turbidimetry and liver microsomal incubated assay. The assay results show that compounds 4e and 6e exhibited remarkable potency to that of the positive control piplartine and aspirin.
- Wang, Yujun,Wang, Jie,Li, Jiaming,Zhang, Yanchun,Huang, Weijun,Zuo, Jian,Liu, Huicai,Xie, Di,Zhu, Panhu
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p. 833 - 840
(2016/05/19)
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- α-Glucosidase inhibitory activities of phenolic acid amides with l-amino acid moiety
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α-Glucosidase inhibitors can effectively control postprandial hyperglycemia. In this study, a series of phenolic acids with the l-amino acid moiety were synthesized and their inhibitory activities against α-glucosidase from Saccharomyces cerevisiae (EC 3.
- Liu, Bin,Ma, Ji-Mei,Chen, Hang-Wei,Li, Zi-Long,Sun, Lin-Hao,Zeng, Zhen,Jiang, Hong
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p. 50837 - 50845
(2016/06/09)
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- Novel hybrid compounds of ascorbic acid and para-coumaric acid and compositions for skin whitening and wrinkle improvement comprising thereof
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The present invention relates to a hybrid compound of ascorbic acid with para-coumaric acid, and a composition for whitening skin and improving wrinkles comprising the same. More particularly, the present invention relates to a multi-functional cosmetic a
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-
Paragraph 0069; 0070
(2017/06/02)
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- Synthesis of Piperlongumine Analogues and Discovery of Nuclear Factor Erythroid 2-Related Factor 2 (Nrf2) Activators as Potential Neuroprotective Agents
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The cellular antioxidant system plays key roles in blocking or retarding the pathogenesis of adult neurodegenerative disorders as elevated oxidative stress has been implicated in the pathophysiology of such diseases. Molecules with the ability in enhancing the antioxidant defense thus are promising candidates as neuroprotective agents. We reported herein the synthesis of piperlongumine analogues and evaluation of their cytoprotection against hydrogen peroxide- and 6-hydroxydopamine-induced neuronal cell oxidative damage in the neuron-like PC12 cells. The structure-activity relationship was delineated after the cytotoxicity and protection screening. Two compounds (4 and 5) displayed low cytotoxicity and confer potent protection of PC12 cells from the oxidative injury via upregulation of a panel of cellular antioxidant molecules. Genetically silencing the transcription factor Nrf2, a master regulator of the cellular stress responses, suppresses the cytoprotection, indicating the critical involvement of Nrf2 for the cellular action of compounds 4 and 5 in PC12 cells.
- Peng, Shoujiao,Zhang, Baoxin,Meng, Xianke,Yao, Juan,Fang, Jianguo
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p. 5242 - 5255
(2015/08/03)
-
- Synthesis and biological evaluation of curcuminoid derivatives
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Many curcuminoid derivatives have been reported to have multiple biological activities. The aim of this study was to improve the biological activity of curcuminoids by synthesizing 16 new derivatives which combined cinnamic acids with curcuminoids, and we also analyzed the structure-activity relationship of the new compounds. Almost all the new compounds showed encouraging activity, especially compound 7g. It had much better antioxidant activity than curcuminoids and Vitamin C (VC), and also had the most significant antibacterial activity, which was 5-folder better than ampicillin (one of the best marketed antibiotics) with a minimum inhibitory concentration (MIC) of 0.5 μg/mL against Gram-positive cocci (Staphylococcus aureus and Streptococcus viridans) as well as Escherichia coli and 0.6 μg/mL against Enterobacter cloacae. Compound 7g also showed the greatest anticancer activity with a much lower IC50, which was 0.51 μM against MCF-7, 0.58 μM against HepG-2, 0.63 μM against LX-2, and 0.79 μM against 3T3. The results suggest that these compounds have promising potential as candidates for the treatment of cancer and thus further studies are warranted.
- Feng, Ling,Li, Yang,Song, Zhi-Fang,Li, Hui-Jing,Huai, Qi-Yong
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p. 873 - 881
(2016/02/03)
-
- Design, synthesis and cytotoxic evaluation of novel imatinib amide derivatives that target Abl kinase
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Novel imatinib amide derivatives (a1-28, b1-9) were synthesized and evaluated for their biological activities. All compounds were characterized by 1H NMR, MS and elemental analysis. Among all the derivatives, compounds a4, a10, a21, b1 and b2 displayed the most significant ability of inhibiting K562 cell proliferation with the IC50 values of 0.67, 0.66, 0.65, 0.59 and 0.62 μM, respectively, indicating that these compounds were potent inhibitors of Bcr-Abl in leukemic K562 cells, comparable to the reference compound imatinib. Molecular docking study was performed to position compounds a21 and b1 into the active site of Abl to determine the probable binding modes
- Yao, Ri-Sheng,Guan, Qiu-Xiang,Lu, Xiao-Qin,Ruan, Ban-Feng
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-
- METHOD OF PRODUCING BENZOIC ACID
-
PROBLEM TO BE SOLVED: To provide a novel synthesis method in the production of a benzoic acid and an industrially suitable production method using main materials derived from nonfossil resources. SOLUTION: This invention provides a method of producing a benzoic acid represented by formula (II), comprising the step of the ozonation of a compound represented by formula (I). COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0061; 0062; 0063; 0064
(2017/01/02)
-
- Synthesis and DPPH radical scavenging activity of novel compounds obtained from tyrosol and cinnamic acid derivatives
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Tyrosol, a naturally occurring phenolic compound poorly attractive as an antioxidant because of its weak efficacy, was used as starting material to obtain novel compounds. The synthesis is based on a trifluoroacetic acid-mediated hydroarylation of cinnamic esters with tyrosol to produce 4-aryl-3,4-dihydrocoumarins, molecules of biological interest, followed by a basic hydrolysis to give the corresponding ring opening products. Unreported mechanistic investigations confirmed that the first step resulted from an electrophilic aromatic substitution and an intramolecular transesterification. Final products exhibited DPPH radical scavenging activity significantly higher than tyrosol.
- Barontini, Maurizio,Bernini, Roberta,Carastro, Isabella,Gentili, Patrizia,Romani, Annalisa
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p. 809 - 816
(2014/02/14)
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- Synthesis and in vitro biological evaluation of hybrids from tetrahydro-β-carboline and hydroxylcinnamic acid as antitumor carcinoma agents
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Novel hybrids 8a-j and 9a-j were designed and synthesized by coupling the carboxyl group of hydroxylcinnamic acids with tetrahydro-β-carboline alkaloids which were linked with different substituted nitrogen-containing heterocycles at the positions-N9, and
- Lin, Ying,Xia, Xuanping,Yao, Rongxin,Ni, Li,Hu, Jie,Guo, Wenjian,Zhu, Baoling
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p. 343 - 349
(2014/04/17)
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- Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases
-
The present study reports the synthesis of cinnamide derivatives and their biological activity as inhibitors of both cholinesterases and anticancer agents. Controlled inhibition of brain acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) may slow neurodegeneration in Alzheimer's diseases (AD). The anticholinesterase activity of phenylcinnamide derivatives was determined against Electric Eel acetylcholinesterase (EeAChE) and horse serum butyrylcholinesterase (hBChE) and some of the compounds appeared as moderately potent inhibitors of EeAChE and hBChE. The compound 3-(2-(Benzyloxy)phenyl)-N- (3,4,5-trimethoxyphenyl)acrylamide (3i) showed maximum activity against EeAChE with an IC50 0.29 ± 0.21 μM whereas 3-(2-chloro-6- nitrophenyl)-N-(3,4,5-trimethoxyphenyl)acrylamide (3k) was proved to be the most potent inhibitor of hBChE having IC50 1.18 ± 1.31 μM. To better understand the enzyme-inhibitor interaction of the most active compounds toward cholinesterases, molecular modelling studies were carried out on high-resolution crystallographic structures. The anticancer effects of synthesized compounds were also evaluated against cancer cell line (lung carcinoma). The compounds may be useful leads for the design of a new class of anticancer drugs for the treatment of cancer and cholinesterase inhibitors for Alzheimer's disease (AD).
- Saeed, Aamer,Mahesar, Parvez Ali,Zaib, Sumera,Khan, Muhammad Siraj,Matin, Abdul,Shahid, Mohammad,Iqbal, Jamshed
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-
- Performances of CN-columns for the analysis of γ-oryzanol and its p-coumarate and caffeate derivatives by normal phase HPLC and a validated method of quantitation
-
γ-Oryzanol is an important phytochemical used in pharmaceutical, alimentary and cosmetic preparations. The present article, for the first time, discloses the performances of NP-HPLC in separating γ-oryzanol components and develops a validated method for i
- D'Ambrosio, Michele
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p. 2079 - 2088
(2013/06/26)
-
- Photosensitive compound and its photosensitive polymer
-
The invention is to provide a photosensitive compound suitable for a photoalignment method, a photosensitive polymer prepared from the compound, a photoaligning agent by using the compound and a liquid crystal alignment film prepared from the photoaligning agent. A photosensitive compound represented by formula (1): in formula (1), Y1 is a divalent group represented by formula (2-1) or (2-2); A1 is 1,4-phenylene or 1,4-cyclohexylene; Z1 is a single bond, —COO— or —OCO—; R1 and R2 are each independently hydrogen, fluorine or alkyl having 1 to 5 carbons; Q1 is independently a single bond or alkylene having 1 to 12 carbons; and n is 0 or 1. In formulas (2-1) and (2-2), W1 and W2 are each independently hydrogen, alkyl having 1 to 3 carbons or alkoxy having 1 to 3 carbons.
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Page/Page column 36; 37
(2013/06/05)
-
- Synthesis of inulin esters of phenylcarboxylic acids
-
Inulin esters were synthesized containing residues of ferulic, p-hydroxycinnamic, and vanillic acids with a maximum degree of substitution of 1.1. The inulin acylation was carried out with chlorides of 4-acetoxy derivatives of the corresponding hydroxyphenylcarboxylic acids in a heterogenic water-organic environment. The removal of the protecting acetyl group at the phenol hydroxyl was carried out by treating with pyrrolidine or ammonium acetate. The solubility of the esters obtained was evaluated.
- Torlopov,Udoratina,Kuchin
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p. 702 - 706
(2013/07/19)
-
- Synthesis and antitumor activity of lapathoside D and its analogs
-
Phenylpropanoid sucrose esters are important class of plant-derived natural products and have greater potential to be leads for new drugs because of their structural diversity and broad-array of pharmacological and biological activities. Regio- and chemo-
- Panda, Parthasarathi,Appalashetti, Manjuvani,Natarajan, Meenubharathi,Chan-Park, Mary B.,Venkatraman, Subbu S.,Judeh, Zaher M.A.
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supporting information; experimental part
p. 1 - 12
(2012/08/08)
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- Simultaneous analysis of free phytosterols/phytostanols and intact phytosteryl/phytostanyl fatty acid and phenolic acid esters in cereals
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An approach based on solid-phase extraction for the effective separation of free phytosterols/phytostanols and phytosteryl/phytostanyl fatty acid and phenolic acid esters from cereal lipids was developed. The ester conjugates were analyzed in their intact
- Esche, Rebecca,Barnsteiner, Andreas,Scholz, Birgit,Engel, Karl-Heinz
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experimental part
p. 5330 - 5339
(2012/09/07)
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- MOLECULARLY IMPRINTED POLYMERS
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The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.
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- β-alanine-DBU: A highly efficient catalytic system for knoevenagel-doebner reaction under mild conditions
-
A mild and efficient Knoevenagel-Doebner reaction from malonic acid and a wide range of aldehydes was catalyzed by a catalytic system consisting of β-alanine and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), affording the corresponding (E)-α,β-unsaturated carboxylic acids in good to excellent yields and with high stereoselectivity. The advantage of the method is that the reaction could proceed smoothly at ambient temperature so that it can tolerate a variety of functional groups and avoid unnecessary side reactions. Copyright
- Zhu, Lingjian,Lei, Ning,Miao, Zhenyuan,Sheng, Chunquan,Zhuang, Chunlin,Yao, Jianzhong,Zhang, Wannian
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experimental part
p. 139 - 143
(2012/03/09)
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- Monoamine oxidase inhibition by selected anilide derivatives
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A series of anilide derivatives were synthesized and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The most potent inhibitors among the derivatives that were initially evaluated were (2E)-N-(3-chlorophenyl)-3-phenylprop-2-enamide (2c) and (2E)-N-(3-bromophenyl)- 3-phenylprop-2-enamide (2d) with IC50 values of 0.53 μM and 0.45 μM, respectively. These derivatives exhibited reversible and selective inhibition of MAO-B with binding affinities 37 fold higher for MAO-B than for MAO-A. Analysis of the possible binding interactions of these inhibitors with active site models of human MAO-A and -B led to the design of phenolic and benzonitrile derivatives of 2c and 2d. Among these were (2E)-N-(3-chlorophenyl)- 3-(4-hydroxyphenyl)prop-2-enamide (7c) and (2E)-N-(3-bromophenyl)-3-(4- hydroxyphenyl)prop-2-enamide (7d) which inhibited MAO-B selectively and reversibly with IC50 values of 0.032 μM and 0.026 μM, respectively. These inhibitors were at least 14 fold more potent than 2c and 2d. This study concludes that N,3-diphenylprop-2-enamide is a suitable scaffold for the design of selective MAO-B inhibitors and structural modifications to enhance the binding affinities of the inhibitors for the MAO-B active site include substitution with halogens on the N-phenyl ring and substitution with hydroxyl and nitrile functional groups on the para and meta positions, respectively, of the C3 phenyl ring. Possible binding modes of these structures within the MAO-B active site are proposed with the emphasis on the interactions of the inhibitor halogens and the hydroxyl and nitrile functional groups with active site residues and water molecules.
- Legoabe, Lesetja,Kruger, Johann,Petzer, Anél,Bergh, Jacobus J.,Petzer, Jacobus P.
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experimental part
p. 5162 - 5174
(2011/11/29)
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- Dimeric cinnamoylamide derivatives as inhibitors of melanogenesis
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Dimeric cinnamoylamide derivatives were synthetized and tested as inhibitors of tyrosinase activity and melanin formation. The most active dimeric cinnamoylamide derivatives was dimeric compound of p-coumaric acid (compound 1) that inhibited tyrosinase ac
- Criton, Marc,Le Mellay-Hamon, Veronique
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p. 420 - 425
(2013/01/10)
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- Synthesis of some phenylpropanoid glycosides (PPGs) and their acetylcholinesterase/xanthine oxidase inhibitory activities
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In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.
- Li, Xiao-Dong,Kang, Shuai-Tao,Li, Guo-Yu,Li, Xian,Wang, Jin-Hui
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p. 3580 - 3596
(2011/07/07)
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- Biosynthesis of vanillin via ferulic acid in vanilla planifolia
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14C-Labeled phenylalanine, 4-coumaric acid, 4- hydroxybenzaldehyde, 4-hydroxybenzyl alcohol, ferulic acid, and methionine were applied to disks of green vanilla pods 3 and 6 months after pollination (immature and mature pods), and the conversion of these compounds to vanillin or glucovanillin was investigated. In mature green vanilla pods, radioactivities of 11, 15, 29, and 24% from 14C-labeled phenylalanine, 4-coumaric acid, ferulic acid, and methionine, respectively, were incorporated into glucovanillin within 24 h. In the incorporation processes of methionine and phenylalanine into glucovanillin, some of the 14C labels were also trapped by the unlabeled ferulic acid. However, 14C-labeled 4-hydroxybenzaldehyde and 4-hydroxybenzyl alcohol were not converted to glucovanillin. On the other hand, in immature green vanilla pods radioactivities of the above six compounds were not incorporated into glucovanillin. Although 4-coumaric acid, ferulic acid, 4-hydroxybenzaldehyde, and 4-hydroxybenzyl alcohol were converted to the respective glucose esters or glucosides and vanillin was converted to glucovanillin, their conversions were believed to be from the detoxication of the aglycones. These results suggest that the biosynthetic pathway for vanillin is 4-coumaric acid → → ferulic acid → → vanillin → glucovanillin in mature vanilla pods.
- Neglshi, Osamu,Sugiura, Kenji,Negishi, Yukiko
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experimental part
p. 9956 - 9961
(2010/08/05)
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- Amide-containing diketoacids as HIV-1 integrase inhibitors: Synthesis, structure-activity relationship analysis, and biological activity
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HIV-1 integrase, which catalyzes the integration of the viral genome into the cellular chromosome, is an essential enzyme for retroviral replication, and represents an attractive and validated target in the development of therapeutics against AIDS. In this paper, 17 amide-containing novel diketoacids were designed and synthesized, and their ability to inhibit HIV-1 integrase was tested. The structure-activity relationships were also analyzed.
- Li, Hongcai,Wang, Chao,Sanchez, Tino,Tan, Yanmei,Jiang, Chunying,Neamati, Nouri,Zhao, Guisen
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experimental part
p. 2913 - 2919
(2009/09/06)
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- Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone
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SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors.
- Kiviranta, Paeivi H.,Salo, Heikki S.,Leppaenen, Jukka,Rinne, Valtteri M.,Kyrylenko, Sergiy,Kuusisto, Erkki,Suuronen, Tiina,Salminen, Antero,Poso, Antti,Lahtela-Kakkonen, Maija,Wallen, Erik A.A.
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p. 8054 - 8062
(2008/12/23)
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- Affinity purification and characterization of a key enzyme responsible for circadian rhythmic control of nyctinasty in Lespedeza cuneata L
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The synthesis of an affinity gel aimed at leaf-opening factor β-glucosidase (LOFG) and affinity purification of LOFG is presented. A gluconamidine-based β-glucosidase inhibitor was used as the ligand of the affinity gel. β-Glucosidase exhibiting an activi
- Kato, Eisuke,Sasaki, Takehiko,Ueda, Minoru
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p. 4600 - 4616
(2008/09/21)
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- N-(3-(4-Hydroxyphenyl)-propenoyl)-amino acid tryptamides as SIRT2 inhibitors
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A series of N-(3-(4-hydroxyphenyl)-propenoyl)-amino acid tryptamides was based on a previously reported new SIRT2 inhibitor from our group, and it was designed to study if the molecular size of the compound could be reduced. The most potent compounds, N-(3-(4-hydroxyphenyl)-propenoyl)-2-aminoisobutyric acid tryptamide and N-(3-(4-hydroxyphenyl)-propenoyl)-l-alanine tryptamide, were equipotent, 30% smaller in molecular weight, and slightly more selective (SIRT2/SIRT1) than the parent compound.
- Kiviranta, Paeivi H.,Leppaenen, Jukka,Rinne, Valtteri M.,Suuronen, Tiina,Kyrylenko, Olga,Kyrylenko, Sergiy,Kuusisto, Erkki,Tervo, Anu J.,Jaervinen, Tomi,Salminen, Antero,Poso, Antti,Wallen, Erik A.A.
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p. 2448 - 2451
(2008/02/03)
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- SPHINGOSINE KINASE INHIBITORS AND METHODS OF THEIR USE
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The invention relates to compounds, pharmaceutical compositions thereof, and methods for inhibiting sphingosine kinase and for treating or preventing hyperproliferative disease, inflammatory disease, or angiogenic disease,
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Page/Page column 34
(2010/11/25)
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- Quantitative analysis of N-phenylpropenoyl-L-amino acids in roasted coffee and cocoa powder by means of a stable isotope dilution assay
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Since recent reports on the role of N-phenylpropenoyl-L-amino acids as powerful antioxidants and key contributors to the astringent taste of cocoa nibs, there is an increasing interest in the concentrations of these phytochemicals in plant-derived foods.
- Stark, Timo,Justus, Helene,Hofmann, Thomas
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p. 2859 - 2867
(2007/10/03)
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- Chavicol formation in sweet basil (Ocimum basilicum): Cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction
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Propenyl- and allyl-phenols, such as methylchavicol, p-anol and eugenol, have gained importance as flavoring agents and also as putative precursors in the biosynthesis of 9,9′-deoxygenated lignans, many of which have potential medicinal applications. In spite of several decades of investigation, however, the complete biosynthetic pathway to a propenyl/allylphenol had not yet been reported. We have subjected a Thai basil variety accumulating relatively large amounts of the simplest volatile allylphenol, methylchavicol, to in vivo administration of radiolabeled precursors and assays of protein preparations in vitro. Through these experiments, the biosynthesis of chavicol was shown to occur via the phenylpropanoid pathway to p-coumaryl alcohol. Various possibilities leading to deoxygenation of the latter were examined, including reduction of the side-chain double bond to form p-dihydrocoumaryl alcohol, followed by dehydration to afford chavicol, as well as formation of p-methoxycinnamyl alcohol, with further side-chain modification to afford methylchavicol. A third possibility studied was activation of the side-chain alcohol of p-coumaryl alcohol, e.g. via esterification, to form a more facile leaving group via reductive elimination. The latter was shown to be the case using p-coumaryl esters as potential substrates for a NAD(P)H-dependent reductase to afford chavicol, which is then O-methylated to afford methylchavicol. The Royal Society of Chemistry 2006.
- Vassao, Daniel G.,Gang, David R.,Koeduka, Takao,Jackson, Brenda,Pichersky, Eran,Davin, Laurence B.,Lewis, Norman G.
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p. 2733 - 2744
(2008/10/09)
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