- Temperature stability and photodimerization kinetics of β-cinnamic acid and comparison to its α-polymorph as studied by solid-state NMR spectroscopy techniques and DFT calculations
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Photoreactions of the α- and β-polymorphs of trans-cinnamic acid were studied by 13C CPMAS solid-state nuclear magnetic resonance spectroscopy, and the reactants and products were spectroscopically characterized in detail. Chemical shifts and c
- Fonseca,Hayes,Bluemich,Bertmer
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Read Online
- Transient states in [2 + 2] photodimerization of cinnamic acid: Correlation of solid-state NMR and X-ray analysis
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13C-CPMAS and other solid-state NMR methods have been applied to monitor the solid-state reactions of trans-cinnamic acid derivatives, which are the pioneer and model compounds in the field of topochemistry previously studied by X-ray diffracti
- Khan, Mujeeb,Brunklaus, Gunther,Enkelmann, Volker,Spiess, Hans-Wolfgang
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- CYCLOBUTANE-1, 3-DIACID BUILDING BLOCKS
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A method of making polymers utilizes cyclobutane-1,3-diacid (CBDA) molecules as polymer building blocks includes and linker molecules with a non-reactive R group and at least two reactive X groups used to create chemically stable polymers of CBDA. The resulting polymers are thermally, photochemically, and chemically stable.
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Paragraph 0078; 0087; 0088
(2019/01/16)
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- SAR studies on truxillic acid mono esters as a new class of antinociceptive agents targeting fatty acid binding proteins
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Fatty acid binding proteins (FABPs) serve as critical modulators of endocannabinoid signaling by facilitating the intracellular transport of anandamide and whose inhibition potentiates anandamide signaling. Our previous work has identified a novel small-m
- Yan, Su,Elmes, Matthew W.,Tong, Simon,Hu, Kongzhen,Awwa, Monaf,Teng, Gary Y.H.,Jing, Yunrong,Freitag, Matthew,Gan, Qianwen,Clement, Timothy,Wei, Longfei,Sweeney, Joseph M.,Joseph, Olivia M.,Che, Joyce,Carbonetti, Gregory S.,Wang, Liqun,Bogdan, Diane M.,Falcone, Jerome,Smietalo, Norbert,Zhou, Yuchen,Ralph, Brian,Hsu, Hao-Chi,Li, Huilin,Rizzo, Robert C.,Deutsch, Dale G.,Kaczocha, Martin,Ojima, Iwao
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p. 233 - 252
(2018/05/28)
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- Template-stereocontrolled [2 + 2] photoreactions directed by surface recognition on hydrophilic functionalized carbon materials
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Supramolecular assistance of the regioselective synthesis of single dimers from [2 + 2] photoreactions surface-directed by multivalent H-bonding exo-templates based on hydrophilic carbon materials (HCMs) is highlighted for the first time. Supramolecular p
- Ortega, Gabriela,Brice?o, Alexander
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p. 2932 - 2939
(2018/06/04)
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- The Antinociceptive Agent SBFI-26 Binds to Anandamide Transporters FABP5 and FABP7 at Two Different Sites
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Human FABP5 and FABP7 are intracellular endocannabinoid transporters. SBFI-26 is an α-truxillic acid 1-naphthyl monoester that competitively inhibits the activities of FABP5 and FABP7 and produces antinociceptive and anti-inflammatory effects in mice. The
- Hsu, Hao-Chi,Tong, Simon,Zhou, Yuchen,Elmes, Matthew W.,Yan, Su,Kaczocha, Martin,Deutsch, Dale G.,Rizzo, Robert C.,Ojima, Iwao,Li, Huilin
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p. 3454 - 3462
(2017/07/17)
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- α-TRUXILLIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF
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The present invention provides a compound, and method of inhibiting the activity of a Fatty Acid Binding Protein (FABP) comprising contacting the FABP with a compound, said compound having the structure : Formula (I)
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Page/Page column 54-55
(2017/09/27)
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- α-AND γ-TRUXILLIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF
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The present invention provides a compound, and method of inhibiting the activity of a Fatty Acid Binding Protein (FABP) comprising contacting the FABP with a compound, having the structure: Formula (I).
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Page/Page column 66
(2014/02/15)
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- Novel photolabile diblock copolymers bearing truxillic acid derivative junctions
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Amphiphilic diblock copolymers, poly(ethylene glycol)-block-poly(acrylate), bearing truxillic acid derivatives at the junction point between the two blocks are described. The truxillic acid junction can be selectively cut by UV light, leading to a disassembly of the nano-objects made by self-assembly of the amphiphilic copolymers in water.
- Yang, Hong,Jia, Lin,Wang, Zhifei,Di-Cicco, Aurelie,Levy, Daniel,Keller, Patrick
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scheme or table
p. 159 - 165
(2012/01/30)
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- The interaction of Cinnamic acids with 60Co gamma radiation
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In the interest of expanding our knowledge of the interaction of cinnamic acid and its derivatives with ionizing radiation, (E)-cinnamic acid and several of its chlorinated and brominated derivatives were exposed to 60Co gamma radiation. Dimer yields were estimated from integration of the proton NMR signals of the irradiated material. (E)-Cinnamic acid itself is relatively unreactive. The largest yield of dimer was obtained with p-bromocinnamic acid where exposure to a dose of 116 megarads led to a 24% yield.
- Njus, Jeffrey M.,Sae-Lim, Chantana,Sandman, Daniel J.
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- Templating photodimerization of trans-cinnamic acids with cucurbit[8]uril and γ-cyclodextrin
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(Chemical Equation Presented) Cucurbit[8]uril and γ-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with trans-cinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state.
- Pattabiraman, Mahesh,Natarajan, Arunkumar,Kaanumalle, Lakshmi S.,Ramamurthy
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p. 529 - 532
(2007/10/03)
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- Anti-inflammatory activities of α-truxillic acid derivatives and their monomer components
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The anti-inflammatory activities of α-truxillic acid (1) and 4,4′-dihydroxy-α-truxillic acid (2) as well as their monomer components (E)-cinnamic acid (3) and (E)-p-coumaric acid (4) were evaluated in the formalin test. α-Truxillic acid (1) and its deriva
- Chi, Yu-Ming,Nakamura, Motoyuki,Yoshizawa, Toyokichi,Zhao, Xi-Ying,Yan, Wen-Mei,Hashimoto, Fumio,Kinjo, Junei,Nohara, Toshihiro,Sakurada, Shinobu
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p. 1776 - 1778
(2007/10/03)
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- Radiation-induced reactions via the lowest excited states in cinnamic acid crystals
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Radiation-induced reactions of cinnamic acid derivatives have been examined and compared with photoreactions in the crystalline state; all the reaction products were exactly the same as those of the photoreactions, indicating that the reactions proceed only via the lowest excited state to give [2 + 2] cycloadducts, E/Z isomerization products, or starting molecules.
- Maekawa, Yasunari,Inaba, Tomonori,Hobo, Hiroki,Narita, Tadashi,Koshikawa, Hiroshi,Moon, Seongyun,Kato, Jun,Yoshida, Masaru
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p. 2088 - 2089
(2007/10/03)
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- Structure-antinociceptive activity studies of incarvillateine, a monoterpene alkaloid from Incarvillea sinensis
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Incarvillateine (1), a new monoterpene alkaloid carrying a characteristic cyclobutane ring, has been found to show significant antinociceptive activity in a formalin-induced pain model in mice. To investigate the correlation between its structure and anti
- Nakamura,Chi,Yan,Yonezawa,Nakasugi,Yoshizawa,Hashimoto,Kinjo,Nohara,Sakurada
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p. 114 - 117
(2007/10/03)
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- Photodimerization of trans-Cinnamic Acid in a Bilayer of Dimethyldioctadecylammonium Bromide
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The photochemistry of trans-cinnamic acid (trans-1) was studied in a cast film of dimethyldioctadecylammonium bromide (2), deposited from aqueous dispersions as a crystalline solid by the spontaneous vaporization of water. UV irradiation of the cast film resulted in a highly selective formation of the syn-Head-to-Head dimer, suggesting a parallel orientation of trans-1 within a bilayer film. Analyses with X-ray diffraction, differential scanning calorimetry, and IR spectra revealed the formation of a bilayer structure of 2 in which the molecules of trans-1 are dissolved to interact with 2 of the polar head groups. The photoreactivity of trans-1 in the cast film was found to be dramatically suppressed by heating at 40-60 °C, which is attributed to an improvement in the crystallinity of the bilayer.
- Nakamura, Tomotaka,Takagi, Katsuhiko,Sawaki, Yasuhiko
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p. 909 - 914
(2007/10/03)
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- Photodimerization of cinnamic acids controlled by molecular assemblies of surfactant amine N-oxides
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UV irradiation of cinnamic acids 1 involving a complex with surfactant amine N-oxides (CnDAO, n = 12, 14 and 16) as vesicles in water leads to the formation of cyclodimers (i.e. β-, δ-truxinic and/or α-truxillic acids ?). Decreasing the molar ratios of 1 to CnDAO causes the vesicles to transform into rod-like micelles and the yield of the cyclodimers decreases. The addition of HCl or NaOH to aqueous solutions of 1 and CnDAO brings about sharp changes in the self-assembly structures from vesicles to micro emulsions or rod-like micelles, accompanied by a change in product distribution in the photolysis of the complex 1. Upon addition of photoinactive carboxylic acids, phenylpropionic and palmitic acids to the 1 and C16DAO system, the rod-like micelles change into vesicles by formation of a complex with C16DAO leading to the observation of a dilution effect in the photodimerization upon addition of phenylpropionic acid. However, no dilution effect is observed for the palmitic acid. This is found to be attributable to the difference in degrees of mixing of 1 with the acids in the vesicles. These results show that photodimerization of 1 incorporated in CnDAO is controlled by a variety of molecular assemblies, i.e. rod-like micelles and homogeneous or heterogeneous vesicles.
- Nakamura, Tomotaka,Takagi, Katsuhiko,Itoh, Mariko,Fujita, Kaori,Katsu, Hiroyuki,Imae, Toyoko,Sawaki, Yasuhiko
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p. 2751 - 2755
(2007/10/03)
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- Photochemical cyclodimerization of cinnmamic acids included in surfactant amine oxides
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Photocyclodimerization of unsubstituted and p-methoxy substituted cinnamic acids incorporated in micelles, vesicles or microemulsions formed by dodecyl-(C12DAO) and hexadecyl-dimethylamine oxides (C16DAO) has been studied in water. The dimerization proceeds in the vesicle much more efficiently than in the micelles with preferable formation of head-to-head dimers. The photoreactivity and the stereochemistry of cyclodimers are affected by structural change of the molecular aggregates.
- Takagi,Nakamura,Katsu,Itoh,Sawaki,Imae
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p. 135 - 138
(2007/10/03)
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- New Host Family Based on Small-Ring Compounds
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Three- and four-membered ring compounds with functional groups and bulky substituents have proved to be a rewarding new source of inclusion hosts.These hosts form clathrates with a variety of uncharged organic molecules ranging from protic dipolar to apolar compounds (168 different inclusion species).Formation and selectivity depend in a systematic manner on structural parameters of the host, such as the nature, number, and position of functional groups, the substituents, and ring size.X-ray structure analyses of two inclusion compounds 12121; = 9.782 (1), b = 11.376 (1), c = 17.603 (1) Angstroem; Z = 4. 17*MeCN (1:1): Pbcn; a = 12.314 (1), b = 16.074 (1), c = 12.938 (1) Angstroem; Z = 4> and of a free host molecule 1; a = 7.339 (2), b = 11.657 (4), c = 9.149 (3) Angstroem; β = 110.070; Z = 2> are reported, revealing the building principles of the new clathrate family.The structures exhibit linear chains of inter-/intramolecular H bridges between carboxylic groups in the free host 1 and H-bridge aggregation of host and guest molecules in infinite helical chains for the 1*t-BuOH (1:1) inclusion.In 17*MeCN (1:1), the guest molecules are tightly enclosed by the host framework without further specific interactions.
- Weber, Edwin,Hecker, Manfred,Csoeregh, Ingeborg,Czugler, Matyas
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p. 7866 - 7872
(2007/10/02)
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- EFFICIENCY FOR SOLID-STATE PHOTOCYCLIZATION OF 2,4,6-TRIISOPROPYLBENZOPHENONES
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Quantum yields for photocyclization of 2,4,6-triisopropylbenzophenones in the solid state were estimated by using an usual merry-go-round apparatus.The results suggest that the ?,?* excited state is responsible for the reaction.
- Ito, Yoshikatsu,Matsuura, Teruo,Fukuyama, Keiichi
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p. 3087 - 3090
(2007/10/02)
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- PREPARATION OF CHLORO-α-TRUXILLIC ACIDS VIA 3-METHYL-4-NITRO-5-STYRYLISOXAZOLE PHOTODIMERS
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Chloro-α-truxillic acids (3b-e) were prepared by oxidation of the photodimers (2b-e) of 3-methyl-4-nitro-5-chlorostyrylisoxazoles (1b-e).
- Baracchi, Antonella,Chimichi, Stefano,Sio, Francesco De,Donati, Donato,Nesi, Rodolfo,et al.
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p. 2863 - 2870
(2007/10/02)
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- SOLID STATE PHOTODIMERIZATION REACTION OF SOME 3-STYRYLISOXAZOLOPYRIDAZIN-7(6H)-ONES
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The solid state irradiation of the title compounds 4a-b gave two colourless products which were recognized as the corresponding dimers 5a-b.The cyclobutane centrosymetric structure of the dimers was demonstrated by taking into account the spectroscopic da
- Chimichi, Stefano,Ciciani, Giovanna,Piaz, Vittoro Dal,Sio, Francesco De,Sarti-Fantoni, Piero,Torroba, Tomas
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p. 3467 - 3471
(2007/10/02)
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- Pulse Radiolysis and 77 K Matrix γ Irradiation of Dimethyl Truxinates and trans-Methyl Cinnamate in 2-Methyltetrahydrofuran
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One-electron reduction of dimethyl μ-truxinate (μ-DMT), dimethyl β-truxinate (β-DMT), and dimethyl α-truxillate (α-DMT) has been investigated by pulse radiolysis and 77 K matrix γ irradiation of the 2-methyltetrahydrofuran solutions.Cycloreversion of the radical anions formed by an electron attachment to these cyclobutanes was observed in all cases, even at 77 K.The orientation of the cycloreversion was dependent on the stereochemistry of the cyclobutanes, and the selectivity was reasonably explained by a so-called cis effect; the best possible release of steric hindrance decides the primary step of the reaction.In 77 K matrix γ irradiation of α-DMT, an intense IR absorption was found after the photobleaching of trapped electrons with light >690 nm.In other DMTs, the IR absorption band was not observed while the cycloreversion of DMT by mobile electrons occurred.Thus, the IR band in the case of α-DMT was assigned to an associated dimer anion due to the interaction between the radical anion and the neutral molecule pair of trans-methyl cinnamate originally formed by the cycloreversion of α-DMT.The dimer anion was presumed to be oriented in a head-to-tail structure in a solvent cage on the basis of the original configuration of α-DMT.
- Takamuku, Setsuo,Kigawa, Hitoshi,Suematsu, Hiroyuki,Toki, Susumu,Tsumori, Kunihiko,Sakurai, Hiroshi
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p. 1861 - 1865
(2007/10/02)
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- Photocycloaddition in Liquid Ethyl Cinnamate and in Ethyl Cinnamate Glasses. The Photoreaction as a Probe into the Micromorphology of the Solid
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Irradiation of neat liquid ethyl cinnamate at room temperature and of ethyl cinnamate glasses at -80 and -196 deg C produces cyclodimers in high yield.Six of the possible eleven isomers have been identified in the products.Their contributions to the overa
- Egerton, P. L.,Hyde, E. M.,Trigg, J.,Payne, A.,Beynon, P.,et al.
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p. 3859 - 3863
(2007/10/02)
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