Caffeic acid

Papers

Effects Of Nutritional Antioxidants On AAPH- Or AGEs-induced Oxidative Stress In Human SW872 Liposarcoma Cells. Roche, M., et al. Cell Biol. Toxicol. 25, 635-44, (2009)

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Inhibition Of Shiga Toxin 2 (Stx2) In Apple Juices And Its Resistance To Pasteurization. Rasooly, R., et al. J. Food Sci. 75, M296-301, (2010)

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Synthesis and antiinflammatory activity of coumarin derivatives. Christos A Kontogiorgis et al J. Med. Chem. 48, 6400-8, (2005)

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Structure-activity relationships of 1'S-1'-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages. Hisashi Matsuda et al Bioorg. Med. Chem. Lett. 15, 1949-53, (2005)

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Synthesis and biological evaluation of 1,3-diphenylprop-2-yn-1-ones as dual inhibitors of cyclooxygenases and lipoxygenases. P N Praveen Rao et al Bioorg. Med. Chem. Lett. 15, 4842-5, (2005)

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Collagenase inhibitory quinic acid esters from Ipomoea pes-caprae. Fumihiro Teramachi et al J. Nat. Prod. 68, 794-6, (2005)

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Synthesis and structure-activity relationship studies of 1,3-diarylprop-2-yn-1-ones: dual inhibitors of cyclooxygenases and lipoxygenases. P N Praveen Rao et al J. Med. Chem. 49, 1668-83, (2006)

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Chroman/catechol hybrids: synthesis and evaluation of their activity against oxidative stress induced cellular damage. Maria Koufaki et al J. Med. Chem. 49, 300-6, (2006)

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Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase. Sabrina Okombi et al Bioorg. Med. Chem. Lett. 16, 2252-5, (2006)

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Hispidin analogs from the mushroom Inonotus xeranticus and their free radical scavenging activity. In-Kyoung Lee et al Bioorg. Med. Chem. Lett. 16, 2376-9, (2006)

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Free radical scavengers from the medicinal mushroom Inonotus xeranticus and their proposed biogenesis. In-Kyoung Lee et al Bioorg. Med. Chem. Lett. 16, 5621-4, (2006)

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Synthesis and free radical scavenging activity of a novel metabolite from the fungus Colletotrichum gloeosporioides. Marienca Femenía-Ríos et al Bioorg. Med. Chem. Lett. 16, 5836-9, (2006)

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Phenolic glycosides with antioxidant activity from the stem bark of Populus davidiana. Xinfeng Zhang et al J. Nat. Prod. 69, 1370-3, (2006)

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Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus. Hyoung Ja Kim et al J. Nat. Prod. 69, 600-3, (2006)

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Design, synthesis, and discovery of stilbene derivatives based on lithospermic acid B as potent protein tyrosine phosphatase 1B inhibitors. Mankil Jung et al Bioorg. Med. Chem. Lett. 17, 4481-6, (2007)

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Synthesis and anti-inflammatory activity of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives. Francesco Epifano et al Bioorg. Med. Chem. Lett. 17, 5709-14, (2007)

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Synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues. Asunción Burguete et al Bioorg. Med. Chem. Lett. 17, 6439-43, (2007)

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New antioxidant polyphenols from the medicinal mushroom Inonotus obliquus. In-Kyoung Lee et al Bioorg. Med. Chem. Lett. 17, 6678-81, (2007)

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Highly oxygenated and unsaturated metabolites providing a diversity of hispidin class antioxidants in the medicinal mushrooms Inonotus and Phellinus. In-Kyoung Lee et al Bioorg. Med. Chem. 15, 3309-14, (2007)

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The structure-activity relationship of the series of non-peptide small antagonists for p56lck SH2 domain. See-Hyoung Park et al Bioorg. Med. Chem. 15, 3938-50, (2007)

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Synthesis of diverse analogues of Oenostacin and their antibacterial activities. Vandana Srivastava et al Bioorg. Med. Chem. 15, 518-25, (2007)

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Synthesis and pharmacochemical evaluation of novel aryl-acetic acid inhibitors of lipoxygenase, antioxidants, and anti-inflammatory agents. E Pontiki et al Bioorg. Med. Chem. 15, 5819-27, (2007)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Synthesis and antiviral properties of some polyphenols related to Salvia genus. Clémence Queffélec et al Bioorg. Med. Chem. Lett. 18, 4736-40, (2008)

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Synthesis of celecoxib analogs that possess a N-hydroxypyrid-2(1H)one 5-lipoxygenase pharmacophore: biological evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity. Morshed Alam Chowdhury et al Bioorg. Med. Chem. Lett. 18, 6138-41, (2008)

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Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines. Chun-nian Xia et al Bioorg. Med. Chem. Lett. 18, 6553-7, (2008)

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New polyphenols active on beta-amyloid aggregation. Céline Rivière et al Bioorg. Med. Chem. Lett. 18, 828-31, (2008)

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Inhibition of 15-lipoxygenase-catalysed oxygenation of arachidonic acid by substituted benzoic acids. Wendy R Russell et al Bioorg. Med. Chem. 16, 4589-93, (2008)

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Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages. Koji Uwai et al Bioorg. Med. Chem. 16, 7795-803, (2008)

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Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus. Susanne Vogel et al J. Nat. Prod. 71, 1237-41, (2008)

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Synthesis of celecoxib analogues possessing a N-difluoromethyl-1,2-dihydropyrid-2-one 5-lipoxygenase pharmacophore: biological evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity. Morshed A Chowdhury et al J. Med. Chem. 52, 1525-9, (2009)

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Synthesis and 5-lipoxygenase inhibitory activity of new cinnamoyl and caffeoyl clusters. Jérémie Doiron et al Bioorg. Med. Chem. Lett. 19, 1118-21, (2009)

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Synthesis of hydroxycoumarins and hydroxybenzo[f]- or [h]coumarins as lipid peroxidation inhibitors. Theodoros Symeonidis et al Bioorg. Med. Chem. Lett. 19, 1139-42, (2009)

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Synthesis and biological evaluation of quinic acid derivatives as anti-inflammatory agents. Kui Zeng et al Bioorg. Med. Chem. Lett. 19, 5458-60, (2009)

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Synthesis of 1-(methanesulfonyl- and aminosulfonylphenyl)acetylenes that possess a 2-(N-difluoromethyl-1,2-dihydropyridin-2-one) pharmacophore: evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity. Morshed Alam Chowdhury et al Bioorg. Med. Chem. Lett. 19, 584-8, (2009)

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Synthesis of modified homo-N-nucleosides from the reactions of mesityl nitrile oxide with 9-allylpurines and their influence on lipid peroxidation and thrombin inhibition. Andreas Thalassitis et al Bioorg. Med. Chem. Lett. 19, 6433-6, (2009)

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Synthesis and biological evaluation of salicylic acid and N-acetyl-2-carboxybenzenesulfonamide regioisomers possessing a N-difluoromethyl-1,2-dihydropyrid-2-one pharmacophore: dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity. Morshed A Chowdhury et al Bioorg. Med. Chem. Lett. 19, 6855-61, (2009)

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COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans. Ericsson David Coy et al Bioorg. Med. Chem. Lett. 19, 6922-5, (2009)

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p-Terphenyls from the fruiting bodies of Paxillus curtisii and their antioxidant properties. In-Kyoung Lee et al Bioorg. Med. Chem. 17, 4674-80, (2009)

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Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies. Gamze Bora-Tatar et al Bioorg. Med. Chem. 17, 5219-28, (2009)

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Urea and carbamate derivatives of primaquine: synthesis, cytostatic and antioxidant activities. M Simunovi? et al Bioorg. Med. Chem. 17, 5605-13, (2009)

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Natural and synthetic 2'-hydroxy-chalcones and aurones: synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity. Anastasia Detsi et al Bioorg. Med. Chem. 17, 8073-85, (2009)

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New insights into the antioxidant activity of hydroxycinnamic acids: Synthesis and physicochemical characterization of novel halogenated derivatives. Alexandra Gaspar et al Eur. J. Med. Chem. 44, 2092-9, (2009)

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QSAR study of antioxidant activity of wine polyphenols. Vesna Rastija et al Eur. J. Med. Chem. 44, 400-8, (2009)

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Antinociceptive properties of caffeic acid derivatives in mice. Fátima de Campos Buzzi et al Eur. J. Med. Chem. 44, 4596-602, (2009)

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Synthesis and anti-inflammatory evaluation of novel angularly or linearly fused coumarins. Theodoros Symeonidis et al Eur. J. Med. Chem. 44, 5012-7, (2009)

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Chemical constituents from the aerial parts of Artemisia minor. Zhi-Zhou He et al J. Nat. Prod. 72, 1198-201, (2009)

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Composition of the fresh leaves and stems of Melissa officinalis and evaluation of skin irritation in a reconstituted human epidermis model. Teresa Mencherini et al J. Nat. Prod. 72, 1512-5, (2009)

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Molecular docking and ligand specificity in fragment-based inhibitor discovery. Yu Chen et al Nat. Chem. Biol. 5, 358-64, (2009)

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Pharmacophore modeling and virtual screening for designing potential 5-lipoxygenase inhibitors. P Aparoy et al Bioorg. Med. Chem. Lett. 20, 1013-8, (2010)

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Synthesis and biological evaluation of N-difluoromethyl-1,2-dihydropyrid-2-one acetic acid regioisomers: dual inhibitors of cyclooxygenases and 5-lipoxygenase. Gang Yu et al Bioorg. Med. Chem. Lett. 20, 2168-73, (2010)

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Antioxidative activities of histidine containing caffeic acid-dipeptides. Hyo-Suk Seo et al Bioorg. Med. Chem. Lett. 20, 4266-72, (2010)

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Phenylacetic acid regioisomers possessing a N-difluoromethyl-1,2-dihydropyrid-2-one pharmacophore: evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity. Gang Yu et al Bioorg. Med. Chem. Lett. 20, 896-902, (2010)

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Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes. Hiroko Tani et al Bioorg. Med. Chem. 18, 151-7, (2010)

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Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Alessio Innocenti et al Bioorg. Med. Chem. 18, 2159-64, (2010)

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Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties. Fernanda M F Roleira et al Bioorg. Med. Chem. 18, 5816-25, (2010)

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Does conjugation of antioxidants improve their antioxidative/anti-inflammatory potential? Dimitra Hadjipavlou-Litina et al Bioorg. Med. Chem. 18, 8204-17, (2010)

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Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials. Jie Fu et al Eur. J. Med. Chem. 45, 2638-43, (2010)

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Syntheses and evaluation of the antioxidant activity of acitretin analogs with amide bond(s) in the polyene spacer. Dimitra Hadjipavlou-Litina et al Eur. J. Med. Chem. 45, 298-310, (2010)

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Synthesis and biological screening of some novel amidocarbamate derivatives of ketoprofen. Prasanta Kumar Sahoo et al Eur. J. Med. Chem. 45, 3162-8, (2010)

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Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives. Maria Ispikoudi et al Eur. J. Med. Chem. 45, 5635-45, (2010)

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Alkaloids from the bark of Guatteria hispida and their evaluation as antioxidant and antimicrobial agents. Emmanoel Vilaça Costa et al J. Nat. Prod. 73, 1180-3, (2010)

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An efficient and economical MTT assay for determining the antioxidant activity of plant natural product extracts and pure compounds. Yunbao Liu et al J. Nat. Prod. 73, 1193-5, (2010)

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Hepatoprotective constituents from the roots and stems of Erycibe hainanesis. Shuang Song et al J. Nat. Prod. 73, 177-84, (2010)

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Caffeic acid esters and lignans from Piper sanguineispicum. Billy Joel Cabanillas et al J. Nat. Prod. 73, 1884-90, (2010)

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Phenolic constituents of the aerial parts of Cimicifuga simplex and Cimicifuga japonica. Atsufumi Iwanaga et al J. Nat. Prod. 73, 609-12, (2010)

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Curcumin recognizes a unique binding site of tubulin. Soumyananda Chakraborti et al J. Med. Chem. 54, 6183-96, (2011)

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Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition. Toshiyuki Takahashi et al Bioorg. Med. Chem. Lett. 21, 1983-6, (2011)

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Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A). J P D van Veldhoven et al Bioorg. Med. Chem. Lett. 21, 2736-9, (2011)

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Thrombin inhibitors with lipid peroxidation and lipoxygenase inhibitory activities. Miloš Ili? et al Bioorg. Med. Chem. Lett. 21, 4705-9, (2011)

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Dual effects of caffeoyl-amino acidyl-hydroxamic acid as an antioxidant and depigmenting agent. Seon-Yeong Kwak et al Bioorg. Med. Chem. Lett. 21, 5155-8, (2011)

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Fatty acids as natural specific inhibitors of the proto-oncogenic protein Shp2. Dongping Liu et al Bioorg. Med. Chem. Lett. 21, 6833-7, (2011)

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Syntheses and characterization of nimesulide derivatives for dual enzyme inhibitors of both cyclooxygenase-1/2 and 5-lipoxygenase. Yue Li et al Bioorg. Med. Chem. 19, 2074-83, (2011)

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Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage. Hnin Thanda Aung et al Bioorg. Med. Chem. 19, 2392-6, (2011)

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Synthesis, in silico docking experiments of new 2-pyrrolidinone derivatives and study of their anti-inflammatory activity. Panagiota Moutevelis-Minakakis et al Bioorg. Med. Chem. 19, 2888-902, (2011)

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Benzenepolycarboxylic acids with potential anti-hemorrhagic properties and structure-activity relationships. Hnin Thanda Aung et al Bioorg. Med. Chem. 19, 7000-2, (2011)

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Design, synthesis and pharmacobiological evaluation of novel acrylic acid derivatives acting as lipoxygenase and cyclooxygenase-1 inhibitors with antioxidant and anti-inflammatory activities. Eleni Pontiki et al Eur. J. Med. Chem. 46, 191-200, (2011)

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Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates. Jose C J M D S Menezes et al Eur. J. Med. Chem. 46, 773-7, (2011)

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Discovery of estrogen receptor ? modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells. Li Liu et al Bioorg. Med. Chem. Lett. 22, 154-63, (2012)

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Design, synthesis and evaluation of caffeic acid phenethyl ester-based inhibitors targeting a selectivity pocket in the active site of human aldo-keto reductase 1B10. Midori Soda et al Eur. J. Med. Chem. 48, 321-9, (2012)

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Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities. Vertuani Silvia et al Eur. J. Med. Chem. 50, 383-92, (2012)

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New losartan-hydrocaffeic acid hybrids as antihypertensive-antioxidant dual drugs: Ester, amide and amine linkers. Gonzalo García et al Eur. J. Med. Chem. 50, 90-101, (2012)

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Selective inhibition of 5-lipoxygenase by natural compounds isolated from Chinese plants Artemisia rubripes Nakai. Koshihara, Y., et al. FEBS Lett. 158, 41-44, (1983)

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Caffeic acid is a selective inhibitor for leukotriene biosynthesis. Koshihara, Y., et al. Biochim. Biophys. Acta 792, 92-97, (1984)

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Prooxidant activity of caffeic acid, dietary non-flavonoid phenolic acid, on Cu2+-induced low density lipoprotein oxidation. Yamanaka N. FEBS Lett. 405, 186-190, (1997)

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In vitro and in vivo reversible and irreversible inhibition of rat glutathione S-transferase isoenzymes by caffeic acid and its 2-S-glutathionyl conjugate. Ploemen, J.H., et al. Food Chem. Toxicol. 31, 475-482, (1993)

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Structure-activity relationship of caffeic acid analogues on xanthine oxidase inhibition. Chan, W.S., et al. Anticancer Res. 15, 703-707, (1995)

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Merck 14,1635

Beil. 10,IV,1776

FT-IR 2 (2), 2643:B / FT-IR 1 (2), 184:D / FT-NMR 1 (2), 1058:B / IR-Spectra (2), 836:F / IR-Spectra (3), 955:E / NMR-Reference 2 (2), 181:C / RegBook 1 (2), 1779:D / Sigma FT-IR 1 (2), 358:A / Structure Index 1, 284:D:2