140-10-3Relevant articles and documents
CINNAMAMIDE DERIVATIVES FROM CLAUSENA LANSIUM
Lin, Jer-Huei
, p. 621 - 622 (1989)
From the ether extract of the seeds of Clausena lansium, three new amide derivatives have been isolated, and their structures elucidated by chemical and spectroscopic methods.They were shown to be N-cis-styryl-cinnamamide, N-methyl-N-cis-styryl-cinnamamide and N-methyl-N-phenethyl-cinnamamide, which we have named lansiumamides A, B and C, respectively.In addition, a known amide, lansamide-I was identified. - Keywords: Clausena lansium; Rutaceae; cinnamamide; lansiumamides; lansamide-I; cinnamic acid derivative.
Batatins I and II, ester-type dimers of acylated pentasaccharides from the resin glycosides of sweet potato
Escalante-Sanchez, Edgar,Pereda-Miranda, Rogelio
, p. 1029 - 1034 (2007)
Batatins I (1) and II (2), two ester-type dimers of acylated pentasaccharides, have been isolated by recycling HPLC from the hexane-soluble extract of sweet potato (Ipomoea batatas var. batatas). The structures were elucidated by a combination of high-resolution NMR spectroscopy and mass spectrometry. Complete analysis and unambiguous assignments of the 1H and 13C NMR spectra of 1 and 2 were achieved by 2D shift correlation measurements. The glycosidic acid forming each branched pentasaccharide monomelic unit was confirmed as simonic acid B. Three different fatty acids esterify this core at the same positions in both batatins: C-2 on the second rhamnose unit and C-4 and C-2 (or C-3) on the third rhamnose moiety. The acylating residues were identified as (+)-(2S)-methylbutanoic, dodecanoic (lauric), and cinnamic acids. The site of lactonization by the aglycon in unit A was placed at C-3 of the second saccharide. The position for the ester linkage for monomelic unit B on the macrocylic unit A was identified as C-3 of the terminal rhamnose?. Through spectroscopic simulation of these complex oligosaccharides, the chemical shifts and coupling constants were deduced for the overlapped proton resonances with a non-first-order resolution. The experimental NMR spectroscopic values registered for batatinoside I (3), a new polyacylated macroyclic pentasaccharide also isolated from this plant, were used as the starting point for spectral simulation of 1 and 2. Both polymers 1 and 2 represent dimers of compound 3.
Alkylacylimidazoles in Claisen–Schmidt and Knoevenagel Condensations
Mei, X.,Ning, J.,Quan, H.,She, D.,Wang, L.,Wang, Zh.
, p. 1462 - 1467 (2020)
Abstract: Alkylacylimidazoles were shown to be good reagents for Claisen–Schmidt and Knoevenagel-like condensations. The Claisen–Schmidt condensation of N-acetylimidazole with benzaldehyde followed by acidification with HCl gave cinnamic acid. The Knoevenagel-like condensation of N-(acetoacetyl)imidazole with hydrated aldehydes resulted in a fast and efficient formation of β-hydroxyketones. The studied reactions provide a new and general synthetic approach to cinnamic acid derivatives and β-hydroxyketones, as well as a new application field of alkylacylimidazoles.
An Equilibrium Study of the Conversion of L-Phenylalanine to trans-Cinnamic Acid and Ammonia
Tewari, Yadu B.,Gajewsi, Ewa,Goldberg, Robert N.
, p. 904 - 909 (1987)
The thermodynamics of the enzymatic conversion (L-phenylalanine ammonia-lyase) of aqueous L-phenylalanine to trans-cinnamic acid and ammonia has been investigated by using high-performance liquid chromatography (HPLC).The reaction was carried out in 0.1 M Tris/HCl buffer containing ammonium chloride over the pH range 7.0-7.7, at ionic strength from 1.0 to 2.1 mol kg-1, and over the temperature range 285-316 K.Analysis of the HPLC data using an estimated heat capacity change of 50 J mol-1 K-1 and an ion-size parameter of 1.6 mol-1/2 kg1/2 leads to an equilibrium constant of 1.16 +/- 0.3 mol kg-1 and an enthalpy change of 24.8 +/- 2.0 kJ mol-1 at 298.15 K for the process L-phenylalanine+/-(aq) = trans-cinnamic acid-(aq) + NH4+(aq).The use of these thermodynamic parameters in an equilibrium model for this system allows for the prediction of values of the apparent equilibrium constant as a function of pH, temperature, and composition and also of the effect of these parameters on the optimal product yield of L-phenylalanine during its manufacture from trans-cinnamic acid and ammonia.The available thermochemical data for this generic type of reaction can be rationalized in terms of a scheme which views the entropy changes for related processes to be comparable and then attributes differences in Gibbs energy changes to differences in enthalpy changes which can be influenced by effects such as resonance stabilization of the double bonds which are formed.
Highly regioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated N-acylbenzotriazoles
Zou, Xuefei,Wang, Xiaoxia,Cheng, Cungui,Kong, Lichun,Mao, Hui
, p. 3767 - 3771 (2006)
The Friedel-Crafts alkylation rather than acylation of indoles was realized with α,β-unsaturated acylbenzotriazoles catalyzed by samarium(III) iodide under reflux in anhydrous THF. The reaction was highly regioselective, and a series of new 3-substituted indole derivatives were obtained in moderate to good yields with the potential to be further transformed into various indole derivatives due to the presence of active acylbenzotriazole moiety.
Nakamura,Kikuchi
, p. 1977,1980 (1968)
"Fishing and hunting"-selective immobilization of a recombinant phenylalanine ammonia-lyase from fermentation media
Sánta-Bell, Evelin,Molnár, Zsófia,Varga, Andrea,Nagy, Flóra,Hornyánszky, Gábor,Paizs, Csaba,Balogh-Weiser, Diána,Poppe, László
, (2019)
This article overviews the numerous immobilization methods available for various biocatalysts such as whole-cells, cell fragments, lysates or enzymes which do not require preliminary enzyme purification and introduces an advanced approach avoiding the costly and time consuming downstream processes required by immobilization of purified enzyme-based biocatalysts (such as enzyme purification by chromatographic methods and dialysis). Our approach is based on silica shell coated magnetic nanoparticles as solid carriers decorated with mixed functions having either coordinative binding ability (a metal ion complexed by a chelator anchored to the surface) or covalent bond-forming ability (an epoxide attached to the surface via a proper linker) enabling a single operation enrichment and immobilization of a recombinant phenylalanine ammonia-lyase from parsley fused to a polyhistidine affinity tag.
C-C-VERKNUEPFUNG VON ALKENEN MIT CO2 AN NICKEL(0); HERSTELLUNG VON ZIMTSAEURE AUS STYROL
Hoberg, Heinz,Peres, Yolande,Milchereit, Armin
, p. C38 - C40 (1986)
Styrene undergose a 1/1 oxidative coupling reaction with CO2 and (Lig)Ni0 systems to give two oxanickelacyclopentanones.Depending on the temperature the formation of cinnamic acid is observed in high yield.
Epoxide and hydroperoxide derived from naturally cinnamaldehyde and its Schiff base derivatives
Elgendy, Eman M.,Khayyat, Suzan A.
, p. 6571 - 6574 (2014)
Thermal and photo epoxidation, photooxygenation reactions of cinnamaldehyde may be useful tool for the design of drugs to act as potent chemopreventation and anticancer agents. trans-Cinnamaldehyde was isolated from essential oil of cinnamon ( Cinnamonum verum). It was subjected to oxidation reactions either photochemically with hydrogen peroxide or thermally with 3-chloro-peroxybenzoic acid. Schiff base derivative was synthesized through condensation reaction with aniline. It subjected to photooxidation reaction in the presence of tetraphenylporphin as singlet oxygen sensitizer. photochemically oxidation reaction gave the corresponding epoxy derivative together with cis-isomerisation. Whereas, thermally oxidation reaction resulted the corresponding epoxy derivative together with cinnamic acid. In addition, photooxidation reaction of Schiff base derivative led to 1-phenyl-3-phenyliminopropen-1-yl hydroperoxide through endoperoxide derivative. The primary tested of hydroperoxide derivative showed a moderate degree of DNA degradation. trans-Cinnamaldehyde and its derivatives can act as antioxidants. They were trapped the reactive oxygen species (ROS) to give the intermediated epoxides and hydroperoxide derivatives, which could be alkylated or damage DNA, proteins and other biological species
Cinnamic acid derivatives via heck reaction in an aqueous-biphasic catalytic system with easy catalyst-product separation
Jagtap,Deshpande
, p. 8633 - 8637 (2013)
A true biphasic [aqueous-organic] system for the coupling of water soluble sodium acrylate with different aryl halides for the synthesis of cinnamic acid derivatives has been developed, employing palladium catalysts that is soluble in organic phase. Amongst them, palladacycle was found to be stable in presence of water and could be recycled for four times with no loss in the activity. Such a system facilitates easy recycle of catalyst and also the removal of the salts from the catalyst phase, ensuring high activity with respect to cumulative turn over number (TON) and turn over frequency (TOF). The reaction was facilitated by organic as well as inorganic bases. The efficiency of the catalyst, role of organic/inorganic bases on the activity is reported.
A new cyclododeca[d]oxazole derivative from Streptomyces spp. CIBYL1
Pu, Xiang,Li, Guangzhou,Yang, Tao,Li, Guoyou,Yi, Jinhai,Zhang, Guolin,Luo, Yinggang
, p. 603 - 608 (2013)
A novel secondary metabolite, N-trans-cinnamoyl 2-amino-3a,4,5,6,7,8,9,10, 11,12,13,13a-dodecahydrocyclododeca[d]oxazole (1), was isolated from Streptomyces spp. CIBYL1, along with five known compounds, pimprinine (2), (3R,4S,5R,6R)-3,4,5,6-tetrahydro-4-hydroxy-3,5,6-trimethyl-2H-pyran-2-one (3), indolyl-3-carboxylic acid (4), 2-phenylacetamide (5) and di(1H-pyrrol-2-yl) methanone (6). The structures of these metabolites were elucidated on the basis of extensive analysis of spectroscopic data, including OR, IR, HRMS, 1D and 2D NMR data and chemical derivation.
Transcriptome-wide identification and characterization of Ornithogalum saundersiae phenylalanine ammonia lyase gene family
Wang, Zhi-Biao,Chen, Xi,Wang, Wei,Cheng, Ke-Di,Kong, Jian-Qiang
, p. 27159 - 27175 (2014)
OSW-1 is a promising antitumor glycoside present in the Ornithogalum saundersiae plant. Biosynthesis of the p-methoxybenzoyl group on the disaccharide moiety of OSW-1 is known to take place biochemically by phenylpropanoid biosynthetic pathway, but molecular biological characterization of related genes has been insufficient. Phenylalanine ammonia lyase (PAL, EC 4.3.1.24), which catalyzes the deamination of l-phenylalanine to yield trans-cinnamic acid, plays a key role in phenylpropanoid metabolism. Thus, the study on the characterization of the genes involved in the OSW-1 biosynthetic pathway, particularly the well-documented genes such as PAL, is essential to further the understanding of the biosynthesis of OSW-1. Here, transcriptomic sequencing of O. saundersiae was performed to speed up the identification of a large number of genes related to OSW-1 biosynthesis. De novo assembly of the transcriptome sequence provided 210733 contigs, 104, 180 unigenes, and four unigenes showing high similarities with PALs. Two full-length cDNAs encoding PALs (OsaPAL2 and OsaPAL62) from O. saundersiae were cloned using sequence information from these four unigenes. The PAL and tyrosine ammonia lyase (TAL) activities of recombinant OsaPAL proteins were unambiguously determined by HPLC with UV and MS detection as well as by NMR spectroscopy. Subsequently, a series of site-directed mutants were generated with the aim of improving enzyme activity and investigating the importance of particular residues in determining substrate selectivity. The results reveal that the Phe-to-His mutants, i.e., OsaPAL2F134H and OsaPAL62F128H, exhibited higher TAL activity than the corresponding wild types, providing direct evidence that the Phe residue is responsible for substrate specificity. Mutagenesis studies also demonstrated that the Thr-to-Ser mutants, i.e., OsaPAL2T196S and OsaPAL62T194S, showed significantly higher substrate affinity than the wild types. Furthermore, the Gly-to-Ala mutants, i.e., OsaPAL2G209A and OsaPAL62G207A, showed higher PAL and TAL activities. These findings provide further insight into the genes responsible for OSW-1 biosynthesis and will facilitate the future application of OsaPALs in synthetic biology.
Supported nanosized palladium on superparamagnetic composite microspheres as an efficient catalyst for Heck reaction
Yuan, Dingzhong,Zhang, Qiuyu,Dou, Jinbo
, p. 606 - 610 (2010)
A magnetically separable palladium catalyst has been easily synthesized by immobilizing palladium nanoparticles on the surface of superparamagnetic composite microspheres. It can promote Heck cross-coupling reactions efficiently without an inert atmosphere. The novel catalyst can be conveniently recovered by applying a permanent magnet externally and reused at least six times without significant loss of its catalytic activity.
Castro,Stephens
, p. 4358,4359-4362 (1964)
Revised mechanism and improved methodology for the Perkin condensation. Resuscitation of the mechanism involving benzal acetate and the improbability of the enolate of acetic anhydride
Chandrasekhar, Sosale,Karri, Phaneendrasai
, p. 2249 - 2251 (2006)
The Perkin condensation most likely occurs via the initial formation of a gem-diacetate from the aromatic aldehyde and acetic anhydride reactants. The key reactive nucleophile appears to be the enolate of the gem-diacetate rather than of acetic anhydride. The diacetate from PhCHO may be converted to cinnamic acid under a variety of (relatively) mild basic conditions.
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Bacharach,Brogan
, p. 3333 (1928)
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Macroporous magnetic poly(GMA-EGDMA-DVB) microspheres supported palladium complex as an efficient catalyst for Heck reaction
Yuan, Ding Zhong,Zhang, Qiu Yu,Dou, Jin Bo
, p. 1062 - 1066 (2010)
Macroporous magnetic poly(GMA-EGDMA-DVB) microspheres synthesized by suspension polymerization were used as supports for palladium catalyst. The results showed the novel magnetic catalyst can promote Heck reaction of aryl halides with acrylic acid efficiently without an inert atmosphere. In addition, the novel catalyst can be conveniently recovered by applying an external magnet and reused at least five times without significant loss of its activity.
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Brown,Jankowski
, p. 233 (1966)
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Batatins VIII-XI, glycolipid ester-type dimers from ipomoea batatas
Rosas-Ramírez, Daniel,Pereda-Miranda, Rogelio
, p. 26 - 33 (2015)
Sweet potato (Ipomoea batatas) is native to the tropics of Central and South America, where many varieties have been consumed for more that 5000 years. In developing countries, this crop is a recognized effective food for fighting malnutrition. Purification of the minor lipophilic glicolipids found in the n-hexane-soluble resin glycosides from the white-skinned variety was performed by preparative-scale recycling HPLC. Application of column overload, peak shaving, heart cutting, and recycling techniques permitted the purification of four new oligosaccharide ester-type dimer derivatives of jalapinolic acid, batatins VIII-XI (1-4). The structural characterization of these complex lipo-oligosaccharides was performed through NMR spectroscopy and MS, indicating that batatins VIII-XI (1-4) possess an oligomeric structure consisting of two pentasaccharide units of the known simonic acid B.
Not quite the last word on the Perkin reaction
Edwards, Mark,Rourk, Paul M.,Riby, Philip G.,Mendham, Andrew P.
, p. 7245 - 7252 (2014)
Microwave irradiation does not accelerate the rate of the Perkin reaction carried out under normal atmospheric pressure. Water is an essential yet catalytic reactant for the Perkin reaction to occur. Containment of the Perkin reaction in a sealed vessel improves the yield. Two pressure increases are observed during a 4 h reaction time. An induction period is seen in the Perkin reaction when sodium acetate is used as a base. A re-appraisal of the reaction mechanism is proposed on the basis of these observations. The use of PFA reaction vessels enables the Perkin reaction to occur under aqueous conditions for around 80 reactions/vessel.
Application of the SPE Method to Organic Electrochemistry. XII. Lead Dioxide as a Mediator for Electrooxidation of Cinnamyl Alcohol on Pt-Nafion
Chen, Zhen,Ogumi, Zempachi,Takehara, Zen-ichiro
, p. 1261 - 1267 (1991)
Lead dioxide was examined as a mediator to oxidize cinnamyl alcohol on Pt-Nafion, and was compared with manganese dioxide.Lead dioxide was deposited into Pt-Nafion.The current efficiency for the formation of cinnamaldehyde reached 65percent at room temperature, slightly lower than that in the case of using manganese dioxide.The production of cinnamic acid was more remarkable on Pb,Pt-Nafion than on Mn,Pt-Nafion because of the higher oxidation potential of the former.The mediatory action of both oxides was examined and compared with the activity in chemical oxidation using oxides produced separately.The oxidation of cinnamyl alcohol by lead dioxide was faster than that by the manganese dioxide.Their mediatory action reflected their chemical activity for the oxidation.
Homogeneous chromium(VI)-catalyzed oxidations of allylic alcohols by alkyl hydroperoxides: Influence of the nature of the alkyl group on the product distribution
Riahi, Abdelkhalek,Henin, Francoise,Muzart, Jacques
, p. 2303 - 2306 (1999)
The chromium oxide-catalyzed oxidation of allylic alcohols - R1CH(OH)CR2=CHR3 - by ROOH (R= t-Bu, PhCMe2) affords generally a mixture of R1COCR2=CHR3 and R1CH=CR2COR3. The rate of the reaction and the ratio between the two oxidized compounds both depend on the nature of R. It has been concluded that the oxidative species and the reactive intermediates contain this R group.
Two acylated flavone glucosides from Andrographis serpyllifolia
Damu,Jayaprakasam,Gunasekar,Blond,Bodo
, p. 147 - 151 (1999)
Two new acylated flavone glucosides, skullcapflavone I 2'-O-β-D-(3-E- cinnamoyl)glucopyranoside and skullcapflavone I 2'-Oβ-D-(2-E- cinnamoyl)glucopyranoside, together with skullcapflavone I 2'-O-β-D- glucopyranoside and andrographidine C have been isolated from the whole plant of Andrographis serpyllifolia. Structural elucidation of the glycosides was achieved by various NMR techniques including 1H-1H COSY, HMQC, HMBC and ROESY experiments, FAB-mass spectrometry, acid hydrolysis and saponification.
ADSORPTION AND REACTION OF TRANS-CINNAMONITRILE ON A SILVER SURFACE INVESTIGATED BY RAMAN SPECTROSCOPY
Chun, Hyun Aee,Kim, Myung Soo,Kim, Kwan
, p. 127 - 139 (1990)
Adsorption of trans-cinnamonitrile on the metal surface in silver sol has been investigated by the surface-enhanced Raman scattering technique.The molecule is found to adsorb on the surface via its nitrogen lone pair electrons.In the absence of coadsorbed chloride ions, the molecule is converted to trans-cinnamic acid by a surface reaction.When a small amount of sample is irradiated with a laser, a surface photoreaction of trans-cinnamonitrile is observed.
RUTHENATE ION CATALYSED OXIDATION OF SOME UNSATURATED ALCOHOLS BY ALKALINE HEXACYANOFERRATE(III) ION
Dwivedi, R. K.,Verma, Meena,Kumar, Pradeep,Behari, K.
, p. 815 - 818 (1983)
The kinetics of ruthenate ion catalysed oxidation of allyl alcohol, crotyl alcohol, cinnamyl alcohol and propargyl alcohol by hexacyanoferrate(III) ion in aqueous alkaline media at constant ionic strength indicate no dependence of rate on alkali concentration or ionic strength.The reaction shows first order dependence on ruthenate ion and zero order in hexacyanoferrate(III) ion.The rate of the reaction increases with increase in substrate concentration and shows Michaelis-Menten type of behaviour.The data suggests that the oxidation proceeds via the formation of a complex between an alcohol molecule and ruthenate ion yielding corresponding acids.The reaction has been studied at four different temperatures and thermodynamic parameters have been computed.A plausible mechanism consistent with the experimental results is proposed.
Synthesis, spectroscopic characterization and DNA/HSA binding studies of (phenyl/naphthyl)ethenyl-substituted 1,3,4-oxadiazolyl-1,2,4-oxadiazoles
Mayer, Joao C. P.,Acunha, Thiago V.,Rodrigues, Oscar E. D.,Back, Davi F.,Chaves, Otavio A.,Dornelles, Luciano,Iglesias, Bernardo A.
, p. 471 - 484 (2021/01/11)
Two new series of conjugated arylethenyl-1,3,4-oxadiazolyl-1,2,4-oxadiazoles were obtained and spectroscopically characterized in terms of UV-Vis absorption, fluorescence and interaction with CT-DNA and Human Serum Albumin (HSA) biomolecules. Phenyl- and 1-naphthyl-bearing examples were analysed, and the spectroscopic properties of its substitution series were compared, showing extensive conjugation in all compounds and absorption differences due to both the aryl-ethenyl subunit and substituted phenyl/phenylene at the 1,2,4-oxadiazole side. Strong binding interactions of the obtained compounds with CT-DNA and moderate HSA-association capability were observed spectroscopically, and further docking studies were performed. This journal is
Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
supporting information, p. 5905 - 5908 (2021/06/18)
A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives
Li, Peng-Xiao,Liu, Guo-Yun,Liu, Ren-Min,Liu, Yue,Mu, Wen-Wen,Sun, Ya-Lei,Yang, Jie
, (2022/01/13)
This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3-dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta- of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho- and para-substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.
