- Mixed Monolayers for the Design of Structured Surfaces To Induce Oriented 3-D Crystallization
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Mixed monolayers containing two different amphiphiles C19H39CONHCH2CH2CO2H(A) and C19H39CONH2(B) were designed in order to form a two-dimensional (2-D) crystalline solid solution in which the A-type molecules form domains within the sea of B-type molecules.A "continuous" 2-D arrangement of the aliphatic chains was expected, driven by the amide hydrogen bonding requirement; a tendency for the formation of the embeded A-type domains should be provided by the interactions between the -CH2CH2CO2H head group moieties.The mixed monolayers served to promote the oriented nucleation of silver propionate 3-D crystals attached at the monolayer-solution interface.Only the A-type domains induced silver propionate crystallization whereas the B-type domains were essentially inert.The mixed A + B monolayers were found to be efficient nucleators down to a 1:10 molar ratio, providing proof for the existence of A-type domains.Additional information such as the structure and ion-binding properties of the mixed monolayers was furnished by specular X-ray reflectivity and grazing incidence X-ray diffraction using synchrotron radiation.
- Weissbuch, I.,Majewski, J.,Kjaer, K.,Als-Nielsen, J.,Lahav, M.,Leiserowitz, L.
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Read Online
- Catalyst for synthesizing acyl chloride compounds and application thereof
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The invention relates to a catalyst for synthesizing an acyl chloride compound and application of the catalyst. The structural formula is as shown in the specification, and in the formula, R is alkali of which the carbon atom number is 1-12. The catalyst is capable of effectively increasing the product yield, improving the production efficiency and lowering the production cost of acyl chloride, and has wide application prospects. The invention further provides a method for synthesizing acyl chloride with the catalyst.
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Paragraph 0078-0082
(2020/10/20)
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- ANTIVIRAL PRODRUGS AND NANOFORMULATIONS THEREOF
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The present invention provides prodrugs and methods of use thereof.
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Page/Page column 36; 39
(2020/05/28)
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- Synthesis of New Lipophilic Cyclopentafullerenes from Long-Chain Alka-2,3-dienoates
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Abstract: Long-chain alka-2,3-dienoates were synthesized via the Wittig reaction fromthe corresponding fatty acids, and the subsequent triphenylphosphine-catalyzed[3+2]-cycloaddition to fullerene C60 afforded newlipophilic cyclopentafullerenes.
- Biglova, Yu. N.,Mukhametyanova, A. F.,Nugumanov, T. R.,Sakhautdinov, I. M.
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p. 1191 - 1195
(2020/10/02)
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- Synthesis of glycerolipids containing simple linear acyl chains or aromatic rings and evaluation of their Mincle signaling activity
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Mincle, expressed in activated phagocytes, recognizes the lipid ligand to activate the innate immune system. We have synthesized glycerol derivatives possessing simple alkyl chains or aromatic rings and elucidated their structure-activity relationships us
- Matsumaru, Takanori,Ikeno, Risa,Shuchi, Yusuke,Iwamatsu, Toshiki,Tadokoro, Takashi,Yamasaki, Sho,Fujimoto, Yukari,Furukawa, Atsushi,Maenaka, Katsumi
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supporting information
p. 711 - 714
(2019/02/06)
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- SUGAR FATTY ACID ESTER AND OIL GELLING AGENT
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PROBLEM TO BE SOLVED: To provide a compound that can gel various oils. SOLUTION: The present invention provides a compound containing 1,5-anhydro-D-glucitol fatty acid ester, represented by formula (1), or 1,5-anhydro-D-mannitol fatty acid ester, and a gelling agent containing the compound. (R1 independently represent an acyl group derived from a C10, 11 or 13-22 linear saturated fatty acid). SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0029; 0042; 0054
(2019/07/29)
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- Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration
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N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.
- Lin, Hua,Long, Jonathan Z.,Roche, Alexander M.,Svensson, Katrin J.,Dou, Florence Y.,Chang, Mi Ra,Strutzenberg, Timothy,Ruiz, Claudia,Cameron, Michael D.,Novick, Scott J.,Berdan, Charles A.,Louie, Sharon M.,Nomura, Daniel K.,Spiegelman, Bruce M.,Griffin, Patrick R.,Kamenecka, Theodore M.
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supporting information
p. 3224 - 3230
(2018/04/23)
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- Alkyl chain elongation and acyl group effects in a series of Eu/Tb complexes with hexadentate π-electronic skeletons and their enhanced luminescence in solutions
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Five Eu complexes with long alkyl chain groups, abbreviated as EuLCx ("x" indicates the number of methylene groups: x = 8, 12, 14, 18, and 22), were synthesized to evaluate their structural and luminescence properties in chloroform. The mother helicate Eu complex, EuL, which has two bipyridine moieties bridged by an ethylenediamine, has been previously reported. A reduced form in which the azomethine groups of L also coordinated to the Eu ion, EuLH, was newly prepared. EuLH also adopts a helicate molecular structure based on single crystal X-ray structural analysis. The amine hydrogens of the bridging ethylenediamine of LH are active sites for substitution and were exchanged with five different alkyl chains to form EuLCx. Luminescence band positions and shapes of EuLCx in chloroform were completely identical, with a quantum yield of 37.1 ± 1.2 and a lifetime of around 1.25 ms. This indicates that the environments surrounding the Eu ion in the various complexes are all similar. Luminescence quantum yields of TbLH and TbLC18 are also strengthened, 48.7% in acetonitrile and 55% in chloroform, respectively. Potential energy surfaces were also described by using density functional theory, suggesting the possibility of a 1:2 complex of Eu and the ligand as a main luminescent species in solutions. This 1:2 complexation forms Eu-oxygen coordination using acyl groups. It indicates that the acyl group modification results in a different structure from the mother complexes.
- Ogata, Shuhei,Goto, Naoto,Sakurai, Shoya,Ishii, Ayumi,Hatanaka, Miho,Yoshihara, Koushi,Tanabe, Ryota,Kayano, Kyosuke,Magaribuchi, Ryo,Goto, Kenta,Hasegawa, Miki
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p. 7135 - 7143
(2018/06/04)
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- IMMUNOSTIMULATING AGENT
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The present invention aims to provide an immunostimulating agent superior in an immunostimulatory effect, particularly a compound useful as a vaccine adjuvant, a pharmaceutical composition containing the compound, a vaccine containing the compound and an antigen. An immunostimulating agent containing at least one kind of a compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a salt thereof.
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Paragraph 1642-1645
(2018/11/21)
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- IMMUNOSTIMULATING AGENT
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The present invention aims to provide an immunostimulating agent superior in an immunostimulatory effect, particularly a compound useful as a vaccine adjuvant, a pharmaceutical composition containing the compound, a vaccine containing the compound and an
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Paragraph 0196
(2017/05/21)
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- Electrospray ionization and collision induced dissociation mass spectrometry of primary fatty acid amides
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Primary fatty acid amides are a group of bioactive lipids that have been linked with a variety of biological processes such as sleep regulation and modulation of monoaminergic systems. As novel forms of these molecules continue to be discovered, more emphasis will be placed on selective, trace detection. Currently, there is no published experimental determination of collision induced dissociation of PFAMs. A select group of PFAM standards, 12 to 22 length carbon chains, were directly infused into an electrospray ionization source Quadrupole Time of Flight Mass Spectrometer. All standards were monitored in positive mode using the [M + H]+ peak. Mass Hunter Qualitative Analysis software was used to calculate empirical formulas of the product ions. All PFAMs showed losses of 14 m/z indicative of an acyl chain, while the monounsaturated group displayed neutral losses corresponding to H2O and NH3. The resulting spectra were used to propose fragmentation mechanisms. Isotopically labeled PFAMs were used to validate the proposed mechanisms. Patterns of saturated versus unsaturated standards were distinctive, allowing for simple differentiation. This determination will allow for fast, qualitative identification of PFAMs. Additionally, it will provide a method development tool for selection of unique product ions when analyzed in multiple reaction monitoring mode.
- Divito, Erin B.,Davic, Andrew P.,Johnson, Mitchell E.,Cascio, Michael
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experimental part
p. 2388 - 2394
(2012/07/27)
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- Palladium-catalyzed reduction of acid chlorides to aldehydes with hydrosilanes
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An efficient synthesis of aldehydes from acid chlorides with hydrosilanes as a reducing agent in the presence of a palladium catalyst has been achieved. A simple mixture of commercially available Pd(dba)2 and Mes 3P as a catalyst realized the reduction of various acid chlorides including aliphatic acid chlorides and a, P-unsaturated acid chlorides to the corresponding aldehydes in good to high yields under mild reaction conditions. Georg Thieme Verlag Stuttgart ? New York.
- Fujihara, Tetsuaki,Cong, Cong,Iwai, Tomohiro,Terao, Jun,Tsuji, Yasushi
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supporting information
p. 2389 - 2392
(2013/07/19)
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- Synthesis and biological evaluation of novel aliphatic amido-quaternary ammonium salts for anticancer chemotherapy: Part i
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We synthesized novel aliphatic amido-quaternary ammonium salts in an effort to discover anticancer agents that increase Ras homolog gene family, member B, (RhoB) levels. These compounds exert anti-proliferative activities against several human cancer cell types. Seventeen compounds, varying in aliphatic carbon chain length and N-substituents, were synthesized and their biological activities were evaluated. Of these 17 compounds, compound 3i emerged as the most promising anticancer compound by promoting apoptosis through the RhoB mediated pathway. Potent biological activities observed for these novel aliphatic amido-quaternary ammonium salt analogues support their potential as anticancer, chemotherapeutic agents.
- Yang, Jee Sun,Song, Doona,Lee, Boah,Ko, Won Jin,Park, Song-Kyu,Won, Misun,Lee, Kiho,Kim, Hwan Mook,Han, Gyoonhee
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experimental part
p. 2861 - 2866
(2011/06/27)
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- HETEROCYCLIC COMPOUNDS CONTAINING NITROGEN ATOMS OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME FOR TREATMENT OF CANCER
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The present invention relates to new heterocyclic compounds containing nitrogen atoms or pharmaceutically acceptable salts thereof, a process for the preparation thereof, and a pharmaceutical composition comprising the same for treatment of cancer. The compounds according to the present invention induce DNA damage due to reactive oxygen species to activate c-abl and p53, induce RhoB to generate apoptosis, and induce cell death by down-regulating Bcl2 involved in cell survival, which is generated by dysregulated signals via the mitochondria pathway, thereby inhibiting tumor cell growth and inducing apoptosis. Accordingly, the composition according to the present invention can be used to treat cancer.
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Page/Page column 7
(2010/06/19)
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- Creatine-fatty acids
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The present invention describes compounds produced from a creatine molecule and a fatty acid molecule. The compounds being in the form of creatine-fatty compounds bound by an amide linkage, or mixtures thereof produced by reacting creatine or derivatives thereof with an appropriate fatty acid in the presence of dichloromethane and a pyridine catalyst, previously reacted with a thionyl halide. The administration of such molecules provides supplemental creatine with enhanced bioavailability and the additional benefits conferred by the specific fatty acid.
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Page/Page column 9
(2008/06/13)
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- NEW HETEROCYCLIC COMPOUNDS CONTAINING NITROGEN ATOMS OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME FOR TREATMENT OF CANCER
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The present invention relates to new heterocyclic compounds containing nitrogen atoms or pharmaceutically acceptable salts thereof, a process for the preparation thereof, and a phar? maceutical composition comprising the same for treatment of cancer. The compounds according to the present invention induce DNA damage due to reactive oxygen species to activate c-abl and p53, induce RhoB to generate apoptosis, and induce cell death by down-regulating Bcl2 involved in cell survival, which is generated by dysregulated signals via the mitochondria pathway, thereby inhibiting tumor cell growth and inducing apoptosis. Accordingly, the composition according to the present invention can be used to treat cancer.
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Page/Page column 13
(2008/06/13)
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- CREATINE-FATTY ACIDS
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The present invention describes compounds produced from a creatine molecule and a fatty acid molecule. The compounds being in the form of creatine-fatty compounds bound by an amide linkage, or mixtures thereof produced by reacting creatine or derivatives thereof with an appropriate fatty acid in the presence of dichloromethane and a pyridine catalyst, previously reacted with a thionyl halide. The administration of such molecules provides supplemental creatine with enhanced bioavailability and the additional benefits conferred by the specific fatty acid. Formula (I)
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Page/Page column 9-10
(2008/12/08)
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- A general and stereoselective route to α- or β- galactosphingolipids via a common four-carbon building block
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(Chemical Equation Presented) A general synthetic strategy toward α- or β-galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O- (4-methoxybenzyl)butane-1,2,4-triol is described. The key steps for the installation of the main lipid chain are either a diasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids with variations in the structure of the sphingoid base. In particular, three α-GalCer-related compounds have been synthesized and evaluated for their ability to activate CD1d-restricted T-cells.
- Matto, Pamela,Modica, Emilia,Franchini, Laura,Facciotti, Federica,Mori, Lucia,De Libero, Gennaro,Lombardi, Grazia,Fallarini, Silvia,Panza, Luigi,Compostella, Federica,Ronchetti, Fiamma
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p. 7757 - 7760
(2008/02/13)
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- Immunomodulatory α-galactoglycosphingolipids: Synthesis of 2′-fluoro-2′-deoxy-α-galactosylceramide and an evaluation of its immunostimulating properties
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In the framework of a project to assess the immunomodulating properties of α-galactosyl glycosphingolipids, the total synthesis of 1-O-(2-fluoro-2-deoxy-α-D-galactopyranosyl)-2-docosanoylamino-1,3, 4-octadecanetriol (1), a 2′-fluoro analogue of the immunostimulating α-galactoglycosphingolipids, was accomplished. The glycosidation reaction of the azido precursor of sphingosine was performed using the Mukaiyama glycosidation reaction. The stimulation of mouse splenocyte proliferation by the 2′-fluoro analogue was highly reduced compared to that of the α-galactoglycosphingolipids, thereby confirming that a free galactose 2-OH group is essential for the immunostimulatory activity. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
- Barbieri, Lucia,Costantino, Valeria,Fattorusso, Ernesto,Mangoni, Alfonso,Basilico, Nicoletta,Mondani, Monica,Taramelli, Donatella
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p. 3279 - 3285
(2007/10/03)
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- Immunomodulatory α-Galactoglycosphingolipids: Synthesis of a 2′-O-Methyl-α-Gal-GSL and Evaluation of Its Immunostimulating Capacity
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The total synthesis of 1-2-docosanoylamino-O-(2-O-methyl-α -D-galactopyranosyl)-1,3,4-octadecanetriol (2), a 2′-methoxy analog of the immunostimulating α-galactoglycosphingolipid 1, is reported. Stereoselective α-glycosylation of the azido precursor of sp
- Barbieri, Lucia,Costantino, Valeria,Fattorusso, Ernesto,Mangoni, Alfonso,Aru, Elisabetta,Parapini, Silvia,Taramelli, Donatella
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p. 468 - 473
(2007/10/03)
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- Immunomodulating glycosphingolipids: An efficient synthesis of a 2′-deoxy-α-galactosyl-GSL
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A new and efficient approach to the total synthesis of 2′-deoxy-α-galactosyl glycosphingolipids was accomplished. Commercially available 3,4,6-tri-O-acetylgalactal was used as the chiral starting material for both the sugar and phytosphingosine building blocks required for the synthesis of 1-O-(2-deoxy-α-D-galactopyranosyl)-2-docosanoylamino-1,3, 4-octadecanetriol. The key step of the synthetic strategy was the stereoselective α-glycosidation of the azido precursor of sphingosine.
- Costantino, Valeria,Fattorusso, Ernesto,Imperatore, Concetta,Mangoni, Alfonso
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p. 369 - 375
(2007/10/03)
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- Synthesis of Sphingosines, 11 - Convenient Synthesis of Phytosphingosine and Sphinganine from D-Galactal and D-Arabitol
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3,4,6-Tri-O-benzyl-D-galactal (3) was directly converted into 3,4,6-tri-O-benzyl-2-deoxy-D-galactose (5).Wittig reaction of 5 with alkyltriphenylphosphonium salts in the presence of n-butyllithium as the base afforded olefins 6a, b which could be readily transformed into phytosphingosines 1a, b via different routes; (i) at first group introduction and then double bond and protective group removal, and azido group generation via hydrogenation; (ii) 2-O-mesylation, then double bond and benzyl group removal via hydrogenation, and finally nitrogen introduction; (iii) selective double bond hydrogenation, then nitrogen introduction, and finally benzyl group removal and amino group generation via hydrogenation.Wittig reaction of 5 with alkyltriphenylphosphonium salt in the presence of potassium tert-butoxide as the base afforded diene 7a which proved to be a convenient precursor for sphinganine syntheses; thus, 2-O-mesylation, then double bond and benzyl group removal via hydrogenation and 1,3-O-acetylation, and finally nitrogen introduction and de-O-acetylation afforded 23a.Based on the convenient transformation of D-arabitol into the 1,3-O-benzylidene derivative 25 a further phytosphingosine synthesis is outlined. - Key Words: Phytosphingosine / Sphinganine / Galactal / 2-Deoxy-D-galactose / D-Arabitol / Carbohydrates
- Wild, Robert,Schmidt, Richard R.
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p. 755 - 764
(2007/10/02)
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- Sphingosine and Phytosphingosine from D-Threose Synthesis of a 4-Keto-Ceramide
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Reaction of 2,4-O-benzylidene-D-threose 3 with tetradecyl magnesium bromide furnished D-arabino- and L-xylo-octadecane-1,2,3,4-tetrols 5a,x.Regioselective oxidation of the 4-OH group gave 4-keto-D-erythro-derivative 6 which can be reduced with acetaldehyde in a SmI2-catalyzed Tishtshenko reaction to afford exclusively 5a.Regioselective 2-O-mesylation of 5a ( -> 7a) and then acid catalyzed debenzylation afforded exclusively 2-O-mesyl-tetrol 9a.Reaction with NaN3 and ensuing azide reduction furnished D-ribo-C18-phytosphingosine (2) in high overall yield.Treatment of 2-O-mesyl derivatives 7a,x with NaN3 and then with 4-nitrobenzenesulfonyl chloride in pyridine afforded 11r,l.Elimination with DBU or, alternatively, by treatment with phenylselenide and then with H2O2, gave known 1,3-O-benzylidene protected azidosphingosine 14, which can be readily converted into sphingosine (1).Transformation of 2 into ceramide 15, selective 1,3-O-silyl protection, oxidation of the 4-OH group ( -> 17) and then desilylation afforded the 4-keto ceramide 18 found in a marine sponge.Reduction of 17 offers a convenient possibility for radioactive labelling of ceramides with tritium.
- Wild, Robert,Schmidt, Richard R.
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p. 2195 - 2208
(2007/10/02)
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- LIGHT EMITTING LANGMUIR-BLODGETT FILMS
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Langmuir-Blodgett films of europium tri-behenate, behenamido benzoate, 2-(4'-dodecylbenzoyl)benzoate-palmitate (1:1) mixture (EDBB/P) and 2-(4'-eicosoxybenzoyl)benzoate-arachidate (1:1) mixture were prepared and their UV absorption and photoluminescent properties were compared with solutions.Fluorescence intensities of LB films of EDBB/P were greatly enhanced by both effects of the large absorption of excitation light and the efficient energy transfer from organic to Eu(3+) ion.This enhancement is due to the preferable molecular alignment of LB films.
- Sugai, Kiyomi,Miyata, Seizo,Watanabe, Toshiyuki,Okamoto, Yoshiyuki
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p. 271 - 276
(2007/10/02)
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- N-acyl peptide, processes for their preparation and pharmaceutical compositions thereof
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N-acylpeptides are disclosed of the formula: STR1 wherein R1 is alkanoyloxy or alkenoyloxy; R2 is alkyl or alkenyl; R3 and R4 are each lower alkyl, hydroxy(lower)alkyl, ar(lower)alkyl, esterified carboxy(lower)alkyl, carboxy(lower)alkyl, protected amino(lower)alkyl or amino(lower)alkyl; R5 is hydrogen, hydroxy(lower)alkyl, protected amino(lower)alkyl, amino(lower)alkyl, carboxy(lower)alkyl or esterified carboxy(lower)alkyl; R6 is carboxy, esterified carboxy or sulfo(lower)alkyl; A1, A2 and A3 are each bond or lower alkylene; and m and n are each an integer of 0 or 1; or its pharmaceutically acceptable salt. These compounds have anti-complementary activity and fibrinolytic activity, and are useful as therapeutic agents for immune-complex diseases or autoimmune diseases such as nephritis, rheumatic diseases, systemic lupus erythematosus, etc. and thrombosis such as cerebral apoplexy, coronary insufficiency, pulmonary embolism, etc.
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- Type II Photochemistry of Ketones in Liquid Crystalline Solvents. The Influence of Ordered Media on Biradical Dynamics
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The Norrish type II photochemistry of five alkylphenones, PhCO(CH2)nH (1a, n=4; 1b, n=10; 1c, n=17; 1d, n=19; 1e, n=21), 10-nonadecanone (2), and 2-undecanone (3) was studied in the isotopic, smetic, and solid phases of n-butyl stearate.The ratio of elimination-to-cyclization products for ketones 1c-e and 2 exhibits a strong phase dependence with a 7-8-fold increase in the smectic phase relative to the isotropic phase.The ratio of isomeric cyclobutanols from 2 shows a similar change.Further increases in the elimination-to-cyclization ratio are observed for 1d in the solid phase.The product ratios for ketones 1a, 1b, and 3 are the same in all the phase studied.Transient absorption studies on the intermediate 1,4-biradical produced from laser flash photolysis of 1d yield lifetimes of 64 +/- 5 and 70 +/- 5 ns in the isotopic and smectic phases, respectively.These results are explaned in terms of the structures of the various phases of n-butyl stearate and the accepted behavior of Norrish type II biradicals.
- Hrovat, David A.,Liu, Jerry H.,Turro, Nicholas J.,Weiss, Richard G.
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p. 7033 - 7037
(2007/10/02)
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