Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies @article{Pontiki2014NovelCA, title={Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies}, author={E. Pontiki and D. Hadjipavlou … Cinnamic acid esters and their derivatives are widely distributed in plants including cereals, legumes, oilseeds, fruits, vegetables and tea or coffee beverages[]. Narasimhan B, Belsare D, Pharande D, Mourya V, Dhake A (2004) Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations. Through steps of rational metabolic engineering, we engineered the yeast Saccharomyces cerevisiae as a microbial host to produce trans-cinnamic acid derivatives cinnamaldehyde, cinnamyl alcohol, and hydrocinnamyl alcohol A thesis submitted for the fulfillment of the requirements of the university of Khartoum for Master degree [7] Rolando F. Pellón Centro de Quimica Farmacéutica , P.O. 2017 Jun;101(12):4883-4893. doi: 10.1007/s00253-017-8220-x. Synthetic Communications: … Chemically, cinnamic acid has three main functional groups: first is the Several simple phenolic compounds such as cinnamic acid, p-coumaric acid, ferulic acid, caffeic acid, chlorgenic acid, and rosmarinic acid belong to this class. : Synthesis and radical scavenging activity of cinnamic acid esters 69 conditions [19-22] and as well as green esterification procedures [23-27]. Also the h ydroxylated cinnamic acid derivatives m-coumaric acid ( 13 ) (34% inhi bition at 50 µ M) and caffeic acid ( 7 ) (18% inhibition at 50 µ M) were only weak inhibitors of th e enzyme. Cinnamic acid and its ester derivatives are widely distributed in plants including cereals, legumes, oilseeds, fruits, vegetables and tea or coffee beverages. The naturally occurring cinnamic acid derivatives, p-coumaric acid 1, caffeic acid 2 and ferulic acid 3 , are small phenolic compounds found in fruits, vegetables and flowers (Figure 1) 1 or, as their esters, in essential oils, resins and balsams. N‐(4‐Chlorophenyl)‐2‐chlorocinnamamide proved to be the most active compound against M. gypseum and T. rubrum , while N‐(3‐chlorophenyl) … Aseries of new derivatives 1-11 of cinnamic acid have been synthesized by a facile procedure for esterification based on using of DCC as a coupling agent, DMAP and solvent system methylene chloride. Synthesis of Cinnamic Acid Derivatives Using Ethanol as Solvent or Microwave Assisted Method. Due to the common occurrence in plants and the low toxicity for humans, animals and environment [ 6 , 7 ], cinnamic acid derivatives have … Compound 4ii proved to be the most potent LOX … Hydroxycinnamic acid derivatives are important class of polyphenolic compounds originated from the Mavolanate-Shikimate biosynthesis pathways in plants. By comparison, cinnamic acid 1a was a poor substrate and showed no conversion to the reduced product 1b at pH 7.0 (Entry 1, Table I). 4, 06120 Halle/Saale, Germany cinnamic acid derivatives. (2003). A number of cinnamic acid derivatives have been synthesised from commercially available aromatic aldehydes and propanedioic acid in a water-insoluble ionic liquid (1-butyl-3-methylimidazolium hexafluorophosphate, [bmim]PF 6) in high yields in the presence of small catalytic amounts of piperidine. In order to further explore the biological activities of this family of compounds, a series of cinnamic acid amide and ester derivatives were synthesized (Fig. 1), and the structure– activity relationships (SARs The antioxidant activity of four derivatives of benzoic acid was systematically compared with the activity of the four homologous derivatives of cinnamic acid. They have reported two derivatives of cinnamic acid i.e. The couples of compounds differed for the kind of aromatic substitution (p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy). Eur J Med Chem 39(10):827–834. Among the tested compounds, 4-hydroxycinnamic acid (l-phenylalanine methyl ester) amide (1) and 3,4 Synthesis, Crystallization Studies, and in vitro Characterization of Cinnamic Acid Derivatives as SmHDAC8 Inhibitors for the Treatment of Schistosomiasis Theresa Bayer Institute of Pharmacy, Martin Luther University of Halle-Wittenberg, Wolfgang-Langenbeck-Str. An Improved Synthesis of ( E )-Cinnamic Acid Derivatives via the Claisen–Schmidt Condensation. doi: 10.1016/j.ejmech.2004.06.013 CrossRef Google Scholar using Novozym 435 as a catalyst. … Meanwhile, α-glucosidase inhibitor class of derivatives of cinnamic acid synthesized compounds are p-methoxy cinnamic acid and p-methoxyethyl cinnamate. Synthesis, molecular modeling and biological evaluation of cinnamic acid derivatives with pyrazole moieties as novel anticancer agents Wei-Ming Zhang , † ab Man Xing , † ab Ting-Ting Zhao , ab Yu-Jia Ren , ab Xian-Hui Yang , ab Yu-Shun Yang , ab Peng-Cheng Lv * ab and Hai-Liang Zhu * ab BACKGROUND Principle: The reaction between aromatic aldehyde and an aliphatic anhydride capable of providing an ‘active methylene‘ moiety in the … SD0500023 Synthesis of 2-phenyl- and 2,3-diphenyl-quinolin-4-carboxylic acid derivatives By Sana Adam Elhadi (B. Ed. It is used in the manufacture of methyl, ethyl, and benzyl esters for perfume industry. In 1890, Rainer Ludwig Claisen described the synthesis of ethyl cinnamate via the reaction of ethyl acetate with benzaldehyde in the presence of sodium as base. In the present study, simple cinnamic acids were synthesized by Knoevenagel condensation reactions and evaluated for the above biological activities. The structures of all the newly cinnamic acid and its derivatives, current improvement efforts with entrapping into solid and liquid particles are highlighted. No Z Y Formula * Rf Clog P ** R M # (±SD) Mp C Yield% 1i C16H11NO2 0.74 a 3.20 −0.895 (0e Cinnamic acids have been identified as interesting compounds with antioxidant, anti-inflammatory and cytotoxic properties. Cinnamic acid was first synthesized by the base-catalysed condensation of acetyl chloride and benzaldehyde, followed by hydrolysis of the acid chloride product. The antioxidant activity was … Enzymatic Synthesis of Enantiopure α‐ and β‐Amino Acids by Phenylalanine Aminomutase‐Catalysed Amination of Cinnamic Acid Derivatives Bian Wu Department of Biochemistry, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG … Enzymatic Synthesis of Cinnamic Acid Derivatives Enzymatic Synthesis of Cinnamic Acid Derivatives Lee, Gia-Sheu; Widjaja, Arief; Ju, Yi-Hsu 2006-01-24 00:00:00 Using Novozym 435 as catalyst, the syntheses of ethyl ferulate (EF) from ferulic acid (4-hydroxy 3-methoxy cinnamic acid) and ethanol, … María L. Salum, Lucia M. Itovich, Rosa Erra‐Balsells, Z‐sinapinic acid: the change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI‐MS analysis, Journal of Mass10.1002/jms48 10) Due to their common occurrence in plants and their low toxicity, 11,12) M. Chochkova et al. Today we make some Trans-cinnamic acid from benzaldehyde and malonic acid. Cinnamic acid (3-phenylpropenoic or phenylacrylic acid) and its derivatives occur naturally in a number of plants. A series of cinnamic acid derivatives were synthesized and their biological abilities on lipoprotein metabolism were examined. Synthesis of Cinnamic Acid Ester Derivatives: To a stirred solution of 2 (1 g, 4.2 mmol) in MDC (25 ml) was added DCC (6.3 mmol) in MDC (5 ml) and stirred for about 15 min at rt. Various amide derivatives of o‐chlorocinnamic acid, p‐nitrocinnamic acid, and cinnamic acid were prepared and tested for antifungal activity against four organisms. Chemical structures, physicochemical and reaction data of cinnamic acid derivatives 1–4. Synthesis of two derivatives by using enzymatic method has been carried out by Lee at al. De novo biosynthesis of trans-cinnamic acid derivatives in Saccharomyces cerevisiae Appl Microbiol Biotechnol. Synthesis of cinnamic acids. Synthesis of cinnamic acid and its six derivatives has been done by employing Knoevenagel reaction. Chem.) 2 Cinnamic acid, an important intermediate in the The pKa of cinnamic acid 1a is 4.4 and therefore, at pH 7.0, the carboxylic acid should Epub 2017 Mar 29. Cinnamic acid is used in the flavors, synthetic indigo and certain pharmaceuticals. Considering the importance of phenolic compounds, e.g Semantic Scholar extracted view of "Synthesis of ( Z )-- bromostyrenes from cinnamic acid derivatives through debrominative decarboxylation of dibromoaryl propanoic acids using KF / Al 2 O 3" by R. Hosseinzadeh et al. the synthesis of ethyl ferulate Table 1.