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Artículos de revistas sobre el tema "Cinnamic ester"

Autor: Grafiati

Publicado: 4 de junio de 2021

Última modificación: 12 de febrero de 2022

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1

Tian, Yuxin, Weirui Liu, Yi Lu, Yan Wang, Xiaoyi Chen, Shaojuan Bai, Yicheng Zhao et al. "Naturally Occurring Cinnamic Acid Sugar Ester Derivatives". Molecules 21, n.º 10 (24 de octubre de 2016): 1402. http://dx.doi.org/10.3390/molecules21101402.

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2

Pálinkó, I. "Hydrogen-bonding interactions in the crystalline-phase structures of cinnamic acid derivatives". Acta Crystallographica Section B Structural Science 55, n.º 2 (1 de abril de 1999): 216–20. http://dx.doi.org/10.1107/s0108768198011823.

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Secondary interactions responsible for the crystalline-phase structures of various cinnamic acids and cinnamic acid esters drawn from the Cambridge Structural Database were studied with the help of the Cerius package implemented on an SGI workstation. Primarily hydrogen-bonding interactions were sought, but deviation from planarity was also measured. For the acids, the main structural feature is the strong hydrogen bonding between the carboxyl groups. The dimers are interconnected by C—H...O intermolecular hydrogen bonds. In most cases the C atom of the C—H unit was a member of the aromatic ring. Intramolecular (olefinic) C—H...O bonds were found to be frequent, fixing synperiplanar and antiperiplanar C=C—C=O conformations with about the same abundance in the acids and exclusively synperiplanar conformations in the esters. The carbonyl group of the ester is always involved in C—H...O hydrogen bonding. Here, the C atom of the C—H unit was either a member of the aromatic ring or the olefinic group, or was attached to the alcoholic O atom of the ester group. The β-phenyl and the carboxyl or the ester groups are almost coplanar. The crystals have a layered structure and in the most frequent parallel arrangement the phenyl groups are offset by varing amounts (but always to a small extent) in neighbouring layers. The common hydrogen bonds are mostly within a layer.

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3

Galabov, Angel S., Lubomira Nikolaeva, Daniela Todorova y Tsenka Milkova. "Antiviral Activity of Cholesteryl Esters of Cinnamic Acid Derivatives". Zeitschrift für Naturforschung C 53, n.º 9-10 (1 de octubre de 1998): 883–87. http://dx.doi.org/10.1515/znc-1998-9-1017.

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Cholesteryl 3”,4”-dimethoxycinnamate (7) and a new synthesized o-coumaroyl ester of 3β- (2’-hydroxyethoxy)-cholest-5-en (13) exhibited a marked activity against poliovirus type 1 (Mahoney). Compound 7 showed an approximately 20-fold greater selectivity in its antiviral activity than compound 13. These compounds were selected from thirteen steryl esters of cinnamic acid derivatives through an in vitro antiviral screening against viruses belonging to taxonomic groups with causative agents of important human infectious diseases to which chemotherapy is indicated, i.e. Picornaviridae, Orthomyxoviridae, Paramyxoviridae and Herpesviridae.

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4

Pizzo, Salvatore V., Denise Turner, Ned A. Porter y Steven L. Gonias. "Evaluation of p-Amidinophenyl Esters as Potential Antithrombotic Agents". Thrombosis and Haemostasis 56, n.º 03 (1986): 387–90. http://dx.doi.org/10.1055/s-0038-1661688.

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SummaryThree p-amidinophenyl esters have been synthesized and characterized as irreversible inhibitors of the vitamin-K dependent proteinases; factors IXa, Xa and thrombin (Turner et al. [4])+. In the present report we describe the in vitro and in vivo effects of these agents on standard coagulation tests in vitro and in blood from animals treated with the compounds. At a concentration of 500 μM, the three esters increased the activated partial thromboplastin time (PTT) of pooled human plasma 3 to 5-fold. The prothrombin time increased 1.4 to 3.7-fold under similar conditions. The p-amidinophenyl ester of cinnamic acid (CINN) showed the most pronounced effect on both assays. This ester also is the best inhibitor of human factors IXa and Xa, while the p-amidinophenyl ester of benzoic acid (BENZ) is a slightly better α-thrombin inhibitor (4). The effect of these esters on the thrombin clotting time correlated with in vitro kinetic measurements of α-thrombin inhibition rates. Both BENZ and CINN increased the assay endpoint more than 6-fold. The three esters also were studied using mouse plasma. A comparable effect on the PTT was noted. Intravenous administration of 300 αl of 1 mM CINN as a single bolus in mice caused a 2.3-fold increase in the PTT which remained 1.2-fold normal 2 h later. The BENZ and a-methyl-cinnamic acid (MECINN) esters were somewhat less effective as predicted from their in vitro effect on the PTT. This investigation and previous studies indicate that these compounds demonstrate low toxicity at therapeutic levels. It is concluded that the p-amidinophenyl esters may be useful in antithrombotic therapy.

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5

Redasani, Vivekkumar K., Amol B. Shinde y Sanjay J. Surana. "Anti-Inflammatory and Gastroprotective Evaluation of Prodrugs of Piroxicam". Ulcers 2014 (26 de agosto de 2014): 1–4. http://dx.doi.org/10.1155/2014/729754.

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Therapeutically potential prodrugs of piroxicam were synthesized by effective masking of enolic hydroxyl group through generation of ester congeners. The reaction facilitated using N,N′-dicyclohexylcarbodiimide coupled with acetic acid, benzoic acid, p-toluic acid, m-toluic acid, and cinnamic acid. Synthesized prodrugs were characterized for confirmation of the said structures. The modification of piroxicam showed better anti-inflammatory activity as evoked by all prodrugs. Interestingly, compound 3e, cinnamic acid ester prodrug, depicted 75 percent inhibition of rat paw edema as compared to 56 percent for parent piroxicam at 6 h of study. The present work proves the applicability not only with increased anti-inflammatory activity, but also with marked attenuation in ulcerogenicity. Novel prodrug 3e, cinnamic acid derivative, was found to be the least ulcerogenic having ulcer index of 0.67 as compared to parent drug piroxicam with 2.67.

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6

DellaGreca, Marina, Lucio Previtera, Raffaella Purcaro y Armando Zarrelli. "Cinnamic Ester Derivatives fromOxalis pes-caprae(Bermuda Buttercup)#". Journal of Natural Products 70, n.º 10 (octubre de 2007): 1664–67. http://dx.doi.org/10.1021/np0702786.

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7

Barontini, Maurizio, Roberta Bernini, Isabella Carastro, Patrizia Gentili y Annalisa Romani. "Synthesis and DPPH radical scavenging activity of novel compounds obtained from tyrosol and cinnamic acid derivatives". New J. Chem. 38, n.º 2 (2014): 809–16. http://dx.doi.org/10.1039/c3nj01180a.

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8

Sheng, Zhaojun, Siyuan Ge, Ximing Xu, Yan Zhang, Panpan Wu, Kun Zhang, Xuetao Xu, Chen Li, Denggao Zhao y Xiaowen Tang. "Correction: design, synthesis and evaluation of cinnamic acid ester derivatives as mushroom tyrosinase inhibitors". MedChemComm 9, n.º 5 (2018): 897. http://dx.doi.org/10.1039/c8md90024h.

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9

Marín-Zamora, María Elisa, Francisco Rojas-Melgarejo, Francisco García-Cánovas y Pedro Antonio García-Ruiz. "Cinnamic ester ofD-sorbitol for immobilization of mushroom tyrosinase". Journal of Chemical Technology & Biotechnology 80, n.º 12 (2005): 1356–64. http://dx.doi.org/10.1002/jctb.1334.

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10

Wang, Rui, Wei Yang, Yiqing Fan, Wim Dehaen, Yang Li, Huijing Li, Wei Wang, Qingxuan Zheng y Qiyong Huai. "Design and synthesis of the novel oleanolic acid-cinnamic acid ester derivatives and glycyrrhetinic acid-cinnamic acid ester derivatives with cytotoxic properties". Bioorganic Chemistry 88 (julio de 2019): 102951. http://dx.doi.org/10.1016/j.bioorg.2019.102951.

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11

Muñoz, Orlando, Raúl C. Peña, Enrique Ureta, Gloria Montenegro y Barbara N. Timmermann. "Propolis from Chilean Matorral Hives". Zeitschrift für Naturforschung C 56, n.º 3-4 (1 de abril de 2001): 269–72. http://dx.doi.org/10.1515/znc-2001-3-416.

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Abstract Viscidone (0.5%), vanillin, 3',4'-(methylendioxy)acetophenone, 3-ethoxy-4-methoxybenz-aldehyde, cinnamic acid, 3-methoxy-4-hydroxymethyl ester were isolated from propolis of hives from Cuncumen. This is the first report on propolis composition of an arid and a Mediterranean type climate area.

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12

Du, Hua, Ye Wang, Xiaojiang Hao, Chun Li, Youliang Peng, Jihua Wang, Hao Liu y Ligang Zhou. "Antimicrobial Phenolic Compounds from Anabasis Aphylla L". Natural Product Communications 4, n.º 3 (marzo de 2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400314.

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Bioassay-guided fractionation of an ethyl acetate extract from the aerial parts of Anabasis aphylla, a Chenopodiaceous species widely distributed in the northwest of China, led to the isolation of six phenolic compounds, which were identified by means of spectrometric analysis as 1-(2-hydroxy-4,6-dimethoxyphenyl)-ethanone (1), 3,4-dihydroxy cinnamic acid tetracosyl ester (2), 4-hydroxy-3-methoxy benzoic acid (3), 2-hydroxy benzoic acid (4), 3,4-dihydroxy cinnamic acid methyl ester (5) and 4-hydroxy benzoic acid pentadecane ester (6). These compounds were further screened for their minimum inhibitory concentration (MIC) and median inhibitory concentration (IC50) by use of the microdilution-MTT assay for antimicrobial activity against one Gram-positive bacterium ( Bacillus subtilis), three Gram-negative bacteria ( Agrobacterium tumefaciens, Pseudomonas lachrymans, and Xanthomonas vesicatoria), and one yeast ( Candida albicans). Apart from compound 6, which had no activity against any of the tested microorganisms, the other compounds showed selective inhibitory activity. This is the first report on the antimicrobial activity of the phenolic compounds isolated from A. aphylla. The obtained results provide promising baseline information for the potential use of the extract and some isolated compounds from this plant as antimicrobial agents to control plant and animal diseases.

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13

Alotaibi, Adullah, Godwin U. Ebiloma, Roderick Williams, Ibrahim A. Alfayez, Manal J. Natto, Sameah Alenezi, Weam Siheri et al. "Activity of Compounds from Temperate Propolis against Trypanosoma brucei and Leishmania mexicana". Molecules 26, n.º 13 (26 de junio de 2021): 3912. http://dx.doi.org/10.3390/molecules26133912.

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Ethanolic extracts of samples of temperate zone propolis, four from the UK and one from Poland, were tested against three Trypanosoma brucei strains and displayed EC50 values < 20 µg/mL. The extracts were fractionated, from which 12 compounds and one two-component mixture were isolated, and characterized by NMR and high-resolution mass spectrometry, as 3-acetoxypinobanksin, tectochrysin, kaempferol, pinocembrin, 4′-methoxykaempferol, galangin, chrysin, apigenin, pinostrobin, cinnamic acid, coumaric acid, cinnamyl ester/coumaric acid benzyl ester (mixture), 4′,7-dimethoxykaempferol, and naringenin 4′,7-dimethyl ether. The isolated compounds were tested against drug-sensitive and drug-resistant strains of T. brucei and Leishmania mexicana, with the highest activities ≤ 15 µM. The most active compounds against T. brucei were naringenin 4′,7 dimethyl ether and 4′methoxy kaempferol with activity of 15–20 µM against the three T. brucei strains. The most active compounds against L. mexicana were 4′,7-dimethoxykaempferol and the coumaric acid ester mixture, with EC50 values of 12.9 ± 3.7 µM and 13.1 ± 1.0 µM. No loss of activity was found with the diamidine- and arsenical-resistant or phenanthridine-resistant T. brucei strains, or the miltefosine-resistant L. mexicana strain; no clear structure activity relationship was observed for the isolated compounds. Temperate propolis yields multiple compounds with anti-kinetoplastid activity.

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14

Ruan, Ban-Feng, Wei-Wei Ge, Hui-Jie Cheng, Hua-Jian Xu, Qing-Shan Li y Xin-Hua Liu. "Resveratrol-based cinnamic ester hybrids: synthesis, characterization, and anti-inflammatory activity". Journal of Enzyme Inhibition and Medicinal Chemistry 32, n.º 1 (1 de enero de 2017): 1282–90. http://dx.doi.org/10.1080/14756366.2017.1381090.

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15

Oufensou, Safa, Stefano Casalini, Virgilio Balmas, Paola Carta, Wiem Chtioui, Maria A. Dettori, Davide Fabbri, Quirico Migheli y Giovanna Delogu. "Prenylated Trans-Cinnamic Esters and Ethers against Clinical Fusarium spp.: Repositioning of Natural Compounds in Antimicrobial Discovery". Molecules 26, n.º 3 (27 de enero de 2021): 658. http://dx.doi.org/10.3390/molecules26030658.

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Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1–3, ten prenylated derivatives (coded 4–13) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3′-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4–13, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62–250 µM and 7.8–125 µM, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.

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16

Nishikubo, Tadatomi, Atsushi Kameyama, Nobuyuki Hayashi y Riou Nakagome. "Synthesis of a new photoreactive polyester by addition reaction of bisepoxide with f-truxiloyl chloride and chemical modification of this polymer". High Performance Polymers 7, n.º 3 (junio de 1995): 245–54. http://dx.doi.org/10.1088/0954-0083/7/3/001.

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A new reactive polyester (P-I) containing a cyclobutane ring in the main chain and a pendant chloromethyl group in the side chain was synthesized successfully by the addition reaction of diglycidyl ether of bisphenol A (DGEBA) with fi-truxiloyl chloride (TC). The addition reaction of DGEBA with TC proceeded smoothly to give P-1 with a relatively high molecular weight using quaternary onium salts or a crown ether complex as catalysts at 90-C for 15 h. However, the reaction did not occur without a catalyst. Substitution reactions of the obtained P-I with (4-dimethy Iamino)cinnamic acid (MACA), [(4-dimethylamino)-a-cyano]cinnamic acid (MACCA) and (4-dimethylamino4'-hydroxy)chalcone (MACH) were carried out to synthesize certain new multifunctiqnal photosensitive polymers with positive-working groups in the main chain and negative-working groups in the side chains. The reaction of P-I with MACA proceeded very smoothly with 99% conversion to form the corresponding polymer (P-2a) using 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) as a base in DMF. The reaction with MACCA gave the corresponding polymer (P-2b) containing a pendant [(4-dimethylamino)-a-cyano]cinnamJc ester moiety with 26% conversion. The reaction with MIACH produced the corresponding polymer (P-2c) containing a pendant (4-dimethy]amino)chalcone ether moiety with 32% conversion. Photochernical reaction of the thus-obtained P-2a-c was also performed in the film state.

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17

Lin, Zhiqing, Wanling Xia, Renyi Liu, Shaohua Jiang y Zhiqiang Ma. "Synthesis of Cinnamic Acid-Coumarin Ester Analogs and Inhibition of Tyrosinase Activity". Chinese Journal of Organic Chemistry 40, n.º 9 (2020): 2980. http://dx.doi.org/10.6023/cjoc202005006.

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18

Do, Thi Quynh, Bich Ngan Truong, Huong Doan Thi Mai, Thuy Linh Nguyen, Van Hung Nguyen, Hai Dang Nguyen, Tien Dat Nguyen et al. "New dianthramide and cinnamic ester glucosides from the roots of Aconitum carmichaelii". Journal of Asian Natural Products Research 21, n.º 6 (30 de marzo de 2018): 507–15. http://dx.doi.org/10.1080/10286020.2018.1454436.

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19

Xu, Cang-Cang, Ting Deng, Meng-Lin Fan, Wen-Bo Lv, Ji-Hua Liu y Bo-Yang Yu. "Synthesis and in vitro antitumor evaluation of dihydroartemisinin-cinnamic acid ester derivatives". European Journal of Medicinal Chemistry 107 (enero de 2016): 192–203. http://dx.doi.org/10.1016/j.ejmech.2015.11.003.

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20

Purwaningsih, Yuliana, Mighfar Syukur y Ungsari Rizki Eka Purwanto. "Sonochemical Synthesis of Ethyl Cinnamate". JKPK (Jurnal Kimia dan Pendidikan Kimia) 5, n.º 1 (30 de abril de 2020): 1. http://dx.doi.org/10.20961/jkpk.v5i1.35525.

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<p>This research aimed to determine the yield of ethyl cinnamate synthesized by the sonochemical method and its potency as a sunscreen agent. Ethyl cinnamate was synthesized from cinnamic acid and ethanol with concentrated sulfuric acid as catalysts assisted by ultrasonic waves. The Identification of compounds was carried out by infrared spectrophotometry and gas chromatography-mass spectroscopy. Synthesis of ethyl cinnamate resulted in the form of clear yellow liquid with a fragrant aroma of a cinnamon ester with a 96.61% yield. Identification by an infrared spectrophotometer showed many functional groups of ethyl cinnamate. Identification by GC-MS was given a relative abundance of 98.96%. The product of synthesis had SPF number 4.769 at 10 ppm used Mansur Equation. Based on this research, it concluded that it has potential as a sunscreen agent. The sonochemical method provides an excellent yield of ethyl cinnamate.</p>

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21

Rao, A. Sridhar, J. Shankara Chary y M. Anand Rao. "Ceric Ammonium Nitrate Oxidation of Cinnamic Ester Derivatives for the Synthesis of Benzaldehydes". Asian Journal of Chemistry 25, n.º 18 (2013): 10182–84. http://dx.doi.org/10.14233/ajchem.2013.15224.

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22

Sheng, Zhaojun, Siyuan Ge, Ximing Xu, Yan Zhang, Panpan Wu, Kun Zhang, Xuetao Xu, Chen Li, Denggao Zhao y Xiaowen Tang. "Design, synthesis and evaluation of cinnamic acid ester derivatives as mushroom tyrosinase inhibitors". MedChemComm 9, n.º 5 (2018): 853–61. http://dx.doi.org/10.1039/c8md00099a.

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23

Palermo, Valeria, Diego M. Ruiz, Juan C. Autino, Patricia G. Vázquez y Gustavo P. Romanelli. "Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst". Pure and Applied Chemistry 84, n.º 3 (21 de octubre de 2011): 529–40. http://dx.doi.org/10.1351/pac-con-11-06-05.

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A convenient chlorine-free procedure for the direct esterification of cinnamic acids with phenols is described. The method does not require stoichiometric activation of the carboxyl group with thionyl chloride or condensing reagents. The methodology is very simple, environmentally friendly, and high-yielding for both electron-releasing and -withdrawing substituted phenols. The Keggin heteropoly acids H3PMo12O40 and H4SiMo12O40 were employed as catalyst in simple bulk form. The effects of temperature, reaction time, and amount of the catalyst used on the ester yield were checked. Suitable conditions for the reaction include a 1:1 molar ratio of reactants and a 1 mmol % of catalyst to reactant ratio. Seventeen aryl cinnamates were obtained, yields ranged from 80 to 91 % for most of the esters. The catalyst was shown to be reusable for at least four times without any appreciable loss of its activity.

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24

Van, Nguyen Thi Hong, Tran Hong Quang, Nguyen Xuan Cuong, Nguyen The Dung, Chau Van Minh y Phan Van Kiem. "Chemical Constituents of the Fruits of Gleditschia Australis Hemsl". Natural Product Communications 4, n.º 2 (febrero de 2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400209.

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From the methanolic extract of the fruits of Gleditschia australis Hemsl., a new flavonoid derivative 3″- O-menthiafoloylisovitexin (1) and a new carbohydrate ester of cinnamic acid 1- O- E-cinnamoyl-[2- O- E-cinnamoyl-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside] (2) have been isolated along with four known compounds, 1- O- E-cinnamoyl-[3- O- E-cirmamoyl-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside], isovitexin, luteolin, and quercetin. Their structures were elucidated on the basis of physical and spectroscopic evidence.

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25

Staniland, Samantha, Tommaso Angelini, Ahir Pushpanath, Amin Bornadel, Elina Siirola, Serena Bisagni, Antonio Zanotti-Gerosa y Beatriz Domínguez. "Biocatalytic Reduction of Activated Cinnamic Acid Derivatives : Asymmetric reduction of C=C double bonds using Johnson Matthey enzymes". Johnson Matthey Technology Review 64, n.º 4 (1 de octubre de 2020): 529–36. http://dx.doi.org/10.1595/205651320x16001815466116.

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The asymmetric reduction of C=C double bonds is a sought-after chemical transformation to obtain chiral molecules used in the synthesis of fine chemicals. Biocatalytic C=C double bond reduction is a particularly interesting transformation complementary to more established chemocatalytic methods. The enzymes capable of catalysing this reaction are called ene-reductases (ENEs). For the reaction to take place, ENEs need an electron withdrawing group (EWG) in conjugation with the double bond. Especially favourable EWGs are carbonyls and nitro groups; other EWGs, such as carboxylic acids, esters or nitriles, often give poor results. In this work, a substrate engineering strategy is proposed whereby a simple transformation of the carboxylic acid into a fluorinated ester or a cyclic imide allows to increase the ability of ENEs to reduce the conjugated double bond. Up to complete conversion of the substrates tested was observed with enzymes ENE-105 and *ENE-69.

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26

Saez, J. J. Sanchez, M. D. Herce Garraleta y T. Balea Otero. "Identification of cinnamic acid ethyl ester and 4-vinylphenol in off-flavour olive oils". Analytica Chimica Acta 247, n.º 2 (julio de 1991): 295–97. http://dx.doi.org/10.1016/s0003-2670(00)83825-8.

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27

P Simatupang, Dedi, Nora Susanti y Jamalum Purba. "Stability of Styrax benzoin extract and fraction with the addition of glycerol and tween 80". Jurnal Pendidikan Kimia 13, n.º 2 (1 de agosto de 2021): 143–50. http://dx.doi.org/10.24114/jpkim.v13i2.26986.

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This research to decide the consequences of expanding the steadiness of the concentrate and part of incense with the expansion of glycerol and tween 80 by contrasting the reference tests of frankincense separates available. The technique utilized in this examination depends on the expansion of glycerol and tween 80, just as directing boundaries of consistency, organoleptic, pH and investigation of substance content of concentrates and parts with GC-MS instruments. The outcomes got in this investigation demonstrate the actual properties of the concentrate and part of the incense sap as a thick fluid, earthy red and has an unmistakable fragrant smell. The consistency got from the thickness test was 277.68 Cp. In the meantime, the thickness estimation consequences of the reference test acquired a consistency worth of 326.54 cP. What's more, has a pH scope of 4.0-5.5. The fundamental synthetic parts of the extraction results and the isoprophyl part of styrax benzoin and the reference part of the reference styrax benzoin remove dependent on the consequences of the investigation discovered 6 mixtures that share practically speaking, in particular Benzoic corrosive, Vanillin, trans-Cinnamic corrosive, (Z) - Cinnamyl benzoate, 2-Propenoic corrosive , 3-phenyl-, phenylmethyl ester, (E) - and Cinnamyl cinnamate. Keywords: Styrax benzoin, Glycerol, Extract stability, Tween 80, Fractionation

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28

Saleh, Na’il, Muna S. Bufaroosha, Ziad Moussa, Rukayat Bojesomo, Hebah Al-Amodi y Asia Al-Ahdal. "Encapsulation of Cinnamic Acid by Cucurbit[7]uril for Enhancing Photoisomerization". Molecules 25, n.º 16 (14 de agosto de 2020): 3702. http://dx.doi.org/10.3390/molecules25163702.

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Cis- or Z-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas the E-form is inactive. Herein, we describe the encapsulation of E-CA by cucurbit[7]uril (CB7) and show that photoisomerization reactions can be more efficiently controlled in aqueous solutions by utilizing this supramolecular approach. Measurements of UV–visible absorption and proton NMR spectra at different pH values confirm that E-CA and its methyl ester, methyl-E-cinnamate (MC), form stronger 1:1 host–guest complexes with CB7 compared to cucurbit[8]uril (CB8) or three cyclodextrins (α-, β-, and γ-CD). Irradiation of (300 nm) UV light to an aqueous solution of the CB7-bound E isomers induces E to Z photoisomerization and the dissociation of the complex. When the same solution is irradiated by (254 nm) UV light, Z to E conformational changes of the unbound Z isomers are observed and are accompanied by restoring the host–guest complex formation.

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29

Gany, Abdul Wadud Bin Pichai y Preeti Shrivastava. "Biofuel Synthesis from Cinnamic Acid Ester Derivatives Using Moringa oleifera Seed Extract: A Sustainable Energy". Journal of Green Science and Technology 2, n.º 1 (1 de diciembre de 2015): 56–61. http://dx.doi.org/10.1166/jgst.2015.1041.

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30

Meng, XuanLin, Yang Li, Chongchong Lu, Man Zhao, Ming Li, ShaoLi Wang, ChangBao Zhao et al. "Purification and antioxidant capacity analysis of anthocyanin glucoside cinnamic ester isomers from Solanum nigrum fruits". Journal of Separation Science 43, n.º 12 (25 de mayo de 2020): 2311–20. http://dx.doi.org/10.1002/jssc.201901289.

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31

LU Dong-wei, WU Xiao-yu, XIE Xian, YU Kai-li y LIN Cui-wu. "Synthesis of Two Cinnamic Oxime Ester Derivatives and Their Interaction Mechanism with Human Serum Albumin". Chinese Journal of Luminescence 38, n.º 3 (2017): 402–12. http://dx.doi.org/10.3788/fgxb20173803.0402.

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32

Marín-Zamora, María Elisa, Francisco Rojas-Melgarejo, Francisco García-Cánovas y Pedro Antonio García-Ruiz. "Direct immobilization of tyrosinase enzyme from natural mushrooms (Agaricus bisporus) on d-sorbitol cinnamic ester". Journal of Biotechnology 126, n.º 3 (10 de noviembre de 2006): 295–303. http://dx.doi.org/10.1016/j.jbiotec.2006.04.024.

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33

Silva, Rayanne H. N., Ana C. M. Andrade, Diego F. Nóbrega, Ricardo D. de Castro, Hilzeth L. F. Pessôa, Nidhi Rani y Damião P. de Sousa. "Antimicrobial Activity of 4-Chlorocinnamic Acid Derivatives". BioMed Research International 2019 (23 de abril de 2019): 1–13. http://dx.doi.org/10.1155/2019/3941242.

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The microbial resistance of fungi and bacteria is currently considered a major public health problem. Esters derived from cinnamic acid have a broad spectrum of pharmacological properties that include antimicrobial activity. In this study, a collection of structurally related 4-chlorocinnamic acid esters was prepared using Fischer esterification reactions, alkyl or aryl halide esterification, and Mitsunobu and Steglich reactions. All of the esters were submitted to antimicrobial tests against strains of the species Candida albicans, Candida glabrata, Candida krusei, Candida guilliermondii, Pseudomonas aeruginosa, and Staphylococcus aureus. The compounds also were subjected to molecular docking study with the enzyme 14α-demethylase. Twelve esters derived from 4-chlorocinnamic acid were obtained, with yields varying from 26.3% to 97.6%, three of which were unpublished. The ester methyl 4-chlorocinnamate (1) presented activity against S. aureus at the highest concentration tested. In the antifungal evaluation, all of the esters were bioactive, but methoxyethyl 4-chlorocinnamate (4) and perillyl 4-chlorocinnamate (11) were the most potent (MIC = 0.13 and 0.024 μmol/mL, respectively). The data of molecular docking suggested that all the compounds present good affinity towards the active site related to antifungal activity. Therefore, the esters tested may be inhibitors of the enzyme 14α-demethylase. In addition, the results demonstrate that substituents of short alkyl chains with presence of heteroatom, such as oxygen, or those with a perillyl type terpenic substructure promote better antifungal profiles.

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34

Lombardo-Earl, Galia, Rubén Roman-Ramos, Alejandro Zamilpa, Maribel Herrera-Ruiz, Gabriela Rosas-Salgado, Jaime Tortoriello y Enrique Jiménez-Ferrer. "Extracts and Fractions from Edible Roots ofSechium edule(Jacq.) Sw. with Antihypertensive Activity". Evidence-Based Complementary and Alternative Medicine 2014 (2014): 1–9. http://dx.doi.org/10.1155/2014/594326.

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Sechium eduleis traditionally used in Mexico as a therapeutic resource against renal diseases and to control high blood pressure. The purpose of this work is to evaluate the antihypertensive effect of the hydroalcoholic extract obtained from the roots of this plant, including its fractions and subfractions, on different hypertension models induced with angiotensin II (AG II). The hydroalcoholic extract was tested on anin vitrostudy of isolated aorta rings denuded of endothelial cells, using AG II as the agonist; this assay proved the vasorelaxant effect of this extract. Vagotomized rats were administered different doses of AG II as well as the Hydroalcoholic extract, which reduced blood pressure in 30 mmHg approximately; subsequently this extract was separated into two fractions (acetone and methanol) which were evaluated in the acute hypertension mouse model induced with AG II, where the acetone fraction was identified as the most effective one and was subsequently subfractioned using an open chromatographic column packed with silica gel. The subfractions were also evaluated in the acute hypertension model. Finally, the extract, fraction, and active subfraction were analyzed by MS-PDA-HPLC, identifying cinnamic derivative compounds like cinnamic acid methyl ester.

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35

Bhattacharya, Aditya, Pushpendra Mani Shukla y Biswajit Maji. "Fe(OTf) 3 -catalysed Friedel–Crafts reaction of benzenoid arenes with α,β-unsaturated carbonyl compounds: easy access to 1,1-diarylalkanes". Royal Society Open Science 4, n.º 10 (octubre de 2017): 170748. http://dx.doi.org/10.1098/rsos.170748.

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A simple and efficient method for the synthesis of 1,1-diarylalkanes via the Friedel–Crafts-type alkylation reaction of electron-rich arenes with cinnamic acid ester derivatives or chalcones is reported. Iron triflate has been found to be the best catalyst for the Friedel–Crafts-type alkylation reaction with α,β-unsaturated carbonyl compounds. This reaction afforded β,β-diaryl carbonyl compounds in good yields (65–93%) and with excellent regioselectivities. Remarkably, this method is also compatible with a variety of indoles to provide 3-indolyl-aryl carbonyl compounds in excellent yields. Great efforts have been made to deduce a plausible reaction mechanism based on isotopic labelling experiments.

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36

Nakamura, Seikou, Jiang Liu, Souichi Nakashima, Keiko Ogawa, Takashi Ueda, Eri Onishi, Kiwako Kurooka et al. "Structure of a Coumaric Acid Analogue with a Monoterpene Moiety from the Flowers of Osmanthus fragrans var. aurantiacus and Evaluation of Cinnamic Acid Analogues as Nitric Oxide Production and Degranulation Inhibitors". Natural Product Communications 11, n.º 8 (agosto de 2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100824.

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A coumaric acid analogue with a monoterpene moiety named floraosmanol A (1) was isolated from the flowers of Osmanthus fragrans var. aurantiacus. The chemical structure was elucidated on the basis of chemical and physicochemical evidence. Floraosmanol A (1) significantly inhibited nitric oxide (NO) production in lipopolysaccharide- (LPS) activated RAW264.7 macrophages and the release of β-hexosaminidase as a marker of degranulation from rat basophile leukemia (RBL-2H3) cells. In addition, several cinnamic acid analogues were conjugated with geraniol and 3-methyl-2-buten-1-ol through an ester linkage. The inhibitory effects on NO production and the release of β-hexosaminidase of the synthesized compounds were examined for structure-activity relationships.

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37

Körtvélyesi, T. y I. Pálinkó. "Modeling hydrogen bonding interactions in α-substituted cinnamic acid ester derivatives by semiempirical quantum chemical calculations". Journal of Molecular Structure: THEOCHEM 531, n.º 1-3 (octubre de 2000): 99–103. http://dx.doi.org/10.1016/s0166-1280(00)00436-x.

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38

Kovačević, Ivana, Mirjana Popsavin, Goran Benedeković, Jelena Kesić, Vesna Kojić, Dimitar Jakimov, Tatjana Srdić-Rajić, Gordana Bogdanović, Vladimir Divjaković y Velimir Popsavin. "Synthesis and in vitro antitumour activity of crassalactone D, its stereoisomers and novel cinnamic ester derivatives". European Journal of Medicinal Chemistry 134 (julio de 2017): 293–303. http://dx.doi.org/10.1016/j.ejmech.2017.03.088.

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39

Qian, Yong, Hong-Jia Zhang, Hao Zhang, Chen Xu, Jing Zhao y Hai-Liang Zhu. "Synthesis, molecular modeling, and biological evaluation of cinnamic acid metronidazole ester derivatives as novel anticancer agents". Bioorganic & Medicinal Chemistry 18, n.º 14 (julio de 2010): 4991–96. http://dx.doi.org/10.1016/j.bmc.2010.06.003.

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40

Perez-Castillo, Yunierkis, Tamires C. Lima, Alana R. Ferreira, Cecília R. Silva, Rosana S. Campos, João B. A. Neto, Hemerson I. F. Magalhães, Bruno C. Cavalcanti, Hélio V. N. Júnior y Damião P. de Sousa. "Bioactivity and Molecular Docking Studies of Derivatives from Cinnamic and Benzoic Acids". BioMed Research International 2020 (27 de mayo de 2020): 1–13. http://dx.doi.org/10.1155/2020/6345429.

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Over the last decade, there has been a dramatic increase in the prevalence and gravity of systemic fungal diseases. This study aimed therefore at evaluating the antifungal potential of ester derivatives of benzoic and cinnamic acids from three Candida species. The compounds were prepared via Fischer esterification, and the antifungal assay was performed by the microdilution method in 96-well microplates for determining the minimal inhibitory concentrations (MICs). The findings of the antifungal tests revealed that the analogue compound methyl ferulate, methyl o-coumarate, and methyl biphenyl-3-carboxylate displayed an interesting antifungal activity against all Candida strains tested, with MIC values of 31.25-62.5, 62.5-125, and 62.5 μg/ml, respectively. A preliminary Structure-Activity Relationship study of benzoic and cinnamic acid derivatives has led to the recognition of some important structural requirements for antifungal activity. The results of molecular docking indicate that the presence of the enoate moiety along with hydroxyl and one methoxy substitution in the phenyl ring has a positive effect on the bioactivity of compound 7 against Candida albicans. These observations further support the hypothesis that the antifungal activity of compound 7 could be due to its binding to multiple targets, specifically to QR, TS, and ST-PK. Additional experiments are required in the future to test this hypothesis and to propose novel compounds with improved antifungal activity.

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41

Ashraf, Zaman, Daeyoung Kim, Sung-Yum Seo y Sung Kwon Kang. "Synthesis and crystal structures of the potential tyrosinase inhibitorsN-(4-acetylphenyl)-2-chloroacetamide and 2-(4-acetylanilino)-2-oxoethyl cinnamate". Acta Crystallographica Section C Structural Chemistry 72, n.º 2 (13 de enero de 2016): 94–98. http://dx.doi.org/10.1107/s205322961502433x.

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Substituted benzoic acid and cinnamic acid esters are of interest as tyrosinase inhibitors and the development of such inhibitors may help in diminishing many dermatological disorders. The tyrosinase enzyme has also been linked to Parkinson's disease. In view of hydroxylated compounds having ester and amide functionalities to potentially inhibit tyrosinase, we herein report the synthesis and crystal structures of two amide-based derivatives, namelyN-(4-acetylphenyl)-2-chloroacetamide, C10H10ClNO2, (I), and 2-(4-acetylanilino)-2-oxoethyl cinnamate, C19H17NO4, (II). In compound (I), the acetylphenyl ring and the N—(C=O)—C unit of the acetamide group are almost coplanar, with a dihedral angle of 7.39 (18)°. Instead of esterification, a cheaper and more efficient synthetic method has been developed for the preparation of compound (II). The molecular geometry of compound (II) is a V-shape. The acetamide and cinnamate groups are almost planar, with mean deviations of 0.088 and 0.046 Å, respectively; the dihedral angle between these groups is 77.39 (7)°. The carbonyl O atoms are positionedsynandantito the amide carbonyl O atom. In the crystals of (I) and (II), N—H...O, C—H...O and C—H...π interactions link the molecules into a three-dimensional network.

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42

Kiss, J. T., K. Felföldi, T. Körtvélyesi y I. Pálinkó. "Hydrogen bonding interactions in α-substituted cinnamic acid ester derivatives studied by FT–IR spectroscopy and calculations". Vibrational Spectroscopy 22, n.º 1-2 (febrero de 2000): 63–73. http://dx.doi.org/10.1016/s0924-2031(99)00054-5.

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43

Mohamed, Mona A., Madeha R. Mammoud y Heiko Hayen. "Evaluation of Antinociceptive and Anti-Inflammatory Activities of a New Triterpene Saponin from Bauhinia variegata Leaves". Zeitschrift für Naturforschung C 64, n.º 11-12 (1 de diciembre de 2009): 798–808. http://dx.doi.org/10.1515/znc-2009-11-1208.

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A new triterpene saponin, named as 23-hydroxy-3α-[O-α-L-1C4-rhamnopyranosyl-(1´´4´)- O-α-L-4C1-arabinopyranosyl-oxy]olean-12-en-28-oic acid O-α-L-1C4-rhamnopyranosyl- (1´´´´´→4´´´´)-O-β-D-4C1-glucopyranosyl-(1´´´´→6´´´)-O-β-D-4C1-glucopyranosyl ester (9), was isolated from the leaves of Bauhinia variegata Linn. In addition, six flavonoid compounds along with two cinnamic acid derivatives were isolated and identified based on their chromatographic properties, and chemical and spectral data (ESI-high resolution-MSn, 1H NMR, 13C NMR, 1H-1H COSY, HSQC, and HMBC). Compound 9 was found to be nontoxic (LD50) and to have significant anti-inflammatory and antinociceptive activities. It also showed a slight antischistosomal activity.

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44

Ayaz, F. A., A. Kadioglu y R. Turgut. "Water stress effects on the content of low molecular weight carbohydrates and phenolic acids in Ctenanthe setosa (Rosc.) Eichler". Canadian Journal of Plant Science 80, n.º 2 (1 de abril de 2000): 373–78. http://dx.doi.org/10.4141/p99-005.

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Morphological and biochemical changes in plant cells are known as important events for adaptation to stress. In this study, changes in carbohydrate and phenolic acid concentrations during leaf rolling under water stress were investigated. Leaves of vegetatively propagated Ctenanthe setosa (Rosc.) Eichler plants started to roll after a 28-d water deficit. After approximately 33–35 d, the leaves were tightly rolled. Water stress significantly increased the dry weight of rolled leaves. Low molecular dry weight carbohydrate components identified in unrolled and rolled leaves were fructose, glucose, inositol and sucrose. Leaves of stressed plants tended to accumulate more carbohydrates of low molecular weight. The same sugars (except inositol) were also identified in liquid and crystal forms of exudates, which appeared on the abaxial surface of the leaves during leaf rolling. The phenolic acids identified in unrolled and rolled leaves were from the benzoic group (benzoic, salicylic, 4-hydroxybenzoic, vanillic, 3,4-dihydroxybenzoic, syringic acids), and the cinnamic group (ferulic and caffeic acids both in free and methyl ester form and cis- and trans-p-coumaric acids). All phenolic acid concentrations (except for salicylic acid) in the phenolic group increased in rolled leaves in comparison with unrolled leaves. In the cinnamic group, the amounts of cis- and trans-p-coumaric and caffeic acids were greater in rolled leaves than in unrolled leaves. Key words: Ctenanthe setosa, exudate, crystal, leaf rolling, sugar, phenolic acid

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45

Suh, Junghun, Eunkyeong Yang, Eugene Oh y Seung Soo Yoon. "Imidazole-assisted intramolecular nucleophilic attack of the amide oxygen at ester linkages in aryl or alkyl esters of (Z)-α-(acetylamino)cinnamic acid". Bioorganic Chemistry 17, n.º 2 (junio de 1989): 159–68. http://dx.doi.org/10.1016/0045-2068(89)90016-3.

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46

Suh, Junghun y Sung Min Kim. "Metal ion-assisted intramolecular nucleophilic attack of the amide oxygen at ester linkages in 2-pyridineoxime esters of (Z)-α-(acetylamino)cinnamic acid". Bioorganic Chemistry 17, n.º 2 (junio de 1989): 169–76. http://dx.doi.org/10.1016/0045-2068(89)90017-5.

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47

Vallejo-Becerra, Vanessa, María Elisa Marín-Zamora, Jazmin Magdalena Vásquez-Bahena, Francisco Rojas-Melgarejo, María Eugenia Hidalgo-Lara y Pedro Antonio García-Ruiz. "Immobilization of Recombinant Invertase (re-INVB) from Zymomonas mobilis ond-Sorbitol Cinnamic Ester for Production of Invert Sugar". Journal of Agricultural and Food Chemistry 56, n.º 4 (febrero de 2008): 1392–97. http://dx.doi.org/10.1021/jf072646h.

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48

Morrison, Ian M. y Derek Stewart. "Determination of lignin in the presence of ester-bound substituted cinnamic acids by a modified acetyl bromide procedure". Journal of the Science of Food and Agriculture 69, n.º 2 (octubre de 1995): 151–57. http://dx.doi.org/10.1002/jsfa.2740690204.

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49

Li, Chen-Hui, Wen-Wei Lai, Keh Ying Hsu y Teh-Chou Chang. "Studies on the thermotropic liquid crystalline polymer. VII. Synthesis and properties of photocrosslinkable poly(ether-ester) containing cinnamic group". Journal of Polymer Science Part A: Polymer Chemistry 31, n.º 1 (enero de 1993): 27–34. http://dx.doi.org/10.1002/pola.1993.080310103.

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Salonen, Anneli, Sanna Saarnio y Riitta Julkunen-Tiitto. "Phenolic Compounds of Propolis from the Boreal Coniferous Zone". Journal of Apicultural Science 56, n.º 1 (1 de junio de 2012): 13–22. http://dx.doi.org/10.2478/v10289-012-0002-1.

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Phenolic Compounds of Propolis from the Boreal Coniferous ZoneThe profile of phenolic compounds in 19 propolis samples from different provinces in Finland were analysed for the first time using HPLC-DAD. Nine individual flavonoids (comprising 26% of the identified phenolics), eleven cinnamic acid derivatives (36%), two caffeic acid derivatives (14%), three chlorogenic acid derivatives (14%), and three other phenolic acids (10%) were found in the propolis samples. The compounds found in the largest quantities were methyl-naringenin and caffeic acid phenethyl ester (CAPE). The phenolic profiles of Finnish propolis show marked differences when compared withP. nigraandP. tremuloidespropolis of Central European and Canadian origins. The phenolic compounds found in propolis samples are commonly found in the tree species growing in Finland. Non-metric multidimensional scaling showed that samples were scattered and they did not form clear groups according to the geographical origin or age of the sample.

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